Title: Best Hotels Near Jackson Square, Key West from CA $176 | Expedia.ca [Jackson Square Car Rentals](https://expedia.ca/Car-Rentals-In-Jackson-Square.d6249254.Car-Rental-Guide)[Jackson Square Vacations](https://expedia.ca/Jackson-Square-Old-Town-Key-West.d6249254.Vacation-Attraction) ![Jackson Square showing an administrative building and heritage architecture](https://images.trvl-media.com/place/6249254/3cd83d52-098c-4ec4-a79e-e9a5fdfae2bf.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find hotels near Jackson Square, Key West from CA $176 ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Tonight [Oct 25 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6249254&startDate=2025-10-25&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 26 - Oct 27](https://www.expedia.ca/Hotel-Search?regionId=6249254&startDate=2025-10-26&endDate=2025-10-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6249254&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6249254&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Recommended Price (low to high) Distance Star rating ## Top Hotels Close to Jackson Square ![Queen Deluxe ADA](https://images.trvl-media.com/lodging/1000000/810000/809100/809031/3d7c7063.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/810000/809100/809031/6c5261fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/810000/809100/809031/1ae9d542.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mini-refrigerator](https://images.trvl-media.com/lodging/1000000/810000/809100/809031/bc9a86c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Almond Tree Inn Hotel - Adults Only Downtown Key West, 0.6 km from Jackson Square 10/10 Exceptional (1015) "Great place to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bettina CA $230 CA $259 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Key-West-Hotels-Almond-Tree-Inn.h809031.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/810000/809100/809032/5e9e36b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/810000/809100/809032/fbbbecd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/810000/809100/809032/e63ab6d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sundeck](https://images.trvl-media.com/lodging/1000000/810000/809100/809032/a23eab61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Orchid Key Inn - Adults Only Uptown - Upper Duval, 0.6 km from Jackson Square 9.8/10 Exceptional (1018) "It was very safe, clean, beautiful rooms and friendly guests. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pamela CA $220 CA $248 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Key-West-Hotels-Orchid-Key-Inn.h809032.Hotel-Information) ![Signature Apartment, 1 Bedroom, Kitchen, Poolside (Room 17) | Terrace/patio](https://images.trvl-media.com/lodging/20000000/19690000/19681600/19681527/537c4db0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/20000000/19690000/19681600/19681527/c77e5b4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/20000000/19690000/19681600/19681527/a3be95ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/20000000/19690000/19681600/19681527/8b4f5465.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly Old Town Key West, 1.1 km from Jackson Square 9.8/10 Exceptional (121) "Great place to stay always clean an the employees are very respectful " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Charles CA $389 CA $498 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Key-West-Hotels-Alexanders-Gay-And-Lesbian-Guesthouse-Adults-Only.h19681527.Hotel-Information) ![3 outdoor pools, a heated pool, sun loungers](https://images.trvl-media.com/lodging/1000000/530000/529500/529420/641eb7f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, individually decorated, individually furnished](https://images.trvl-media.com/lodging/1000000/530000/529500/529420/4b7856d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Townhome, 1 King Bed w/Sofa bed - Fleming's Veranda 100 (bedroom access via spiral staircase)](https://images.trvl-media.com/lodging/1000000/530000/529500/529420/36b2612a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Townhome, 1 King Bed w/Sofa bed - Parrot's Perch 103](https://images.trvl-media.com/lodging/1000000/530000/529500/529420/a151d564.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ambrosia Key West Old Town Key West, 0.4 km from Jackson Square 9.4/10 Exceptional (1000) "Loved staying here, such a cute place and the location was close to Duval St." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) jodi CA $272 CA $306 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Key-West-Hotels-Ambrosia-Key-West.h529420.Hotel-Information) ![11 Gecko's Garden - Adults Only](https://images.trvl-media.com/lodging/10000000/9690000/9681100/9681053/5a952061.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/10000000/9690000/9681100/9681053/bbaba58e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Poinciana Patio, Pool View, Patio - Adult Only | Terrace/patio](https://images.trvl-media.com/lodging/10000000/9690000/9681100/9681053/a07e6903.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/10000000/9690000/9681100/9681053/a7d26b15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tropical Inn Downtown Key West, 0.4 km from Jackson Square 9.6/10 Exceptional (354) "The continental breakfast is delivered to your room after your request. The pool and hot tub area is quiet and quaint. Beautiful setting. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julie CA $221 CA $284 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Key-West-Hotels-Tropical-Inn.h9681053.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/1000000/910000/900500/900423/d8706fe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/1000000/910000/900500/900423/d8ea2dc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/1000000/910000/900500/900423/586198d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/1000000/910000/900500/900423/9013d891.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Duval House Downtown Key West, 0.4 km from Jackson Square 9.4/10 Exceptional (1028) "Very friendly, good breakfasts, clean rooms " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sandor CA $139 CA $186 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Key-West-Hotels-Duval-House.h900423.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/900000/894100/894030/dc763054.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/900000/894100/894030/14ad35b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/900000/894100/894030/76b4e71a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/1000000/900000/894100/894030/eb0b0d9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Silver Palms Inn Old Town Key West, 0.9 km from Jackson Square 9.4/10 Exceptional (1021) "Great location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Beverly CA $137 CA $249 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Key-West-Hotels-Silver-Palms-Inn.h894030.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154002/1237df6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Queen Room](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154002/f11c2855.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154002/3c897d19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154002/b69fa79e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Garden House Historic Seaport, 0.5 km from Jackson Square 9.2/10 Wonderful (663) "It a small convenient location and walkable to great areas. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Manuel CA $130 CA $176 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Key-West-Hotels-The-Garden-House.h1154002.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/9000000/8660000/8657100/8657021/bc64cbf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/9000000/8660000/8657100/8657021/86679c60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/9000000/8660000/8657100/8657021/663b0ca0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Studio, 1 King Bed (Room 2a)](https://images.trvl-media.com/lodging/9000000/8660000/8657100/8657021/974a1d0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Key West Hotel Historic Seaport, 0.3 km from Jackson Square 9.2/10 Wonderful (500) "My wife and I have come to KeyWest for years, this by far the nicest and affordable with great music and staff. It's our new go to place!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $289 CA $325 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Key-West-Hotels-Casa-325.h8657021.Hotel-Information) ![3 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/10000000/9150000/9148400/9148379/15d13ee3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/10000000/9150000/9148400/9148379/a156943e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/10000000/9150000/9148400/9148379/a383df35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/10000000/9150000/9148400/9148379/e32c81ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Marker Key West Harbor Resort Historic Seaport, 0.7 km from Jackson Square 9.2/10 Wonderful (1032) "Really great hotel !" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Vincent CA $234 CA $352 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Key-West-Hotels-The-Marker-Key-West-Harbor-Resort.h9148379.Hotel-Information) ![3 outdoor pools, open 7:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/7cf7d263.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (Winslet) | Exterior](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/f458d20b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (Truman)](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/33f2b657.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/b5f8742c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Winslow's Bungalows - Key West Historic Inns Old Town Key West, 0.8 km from Jackson Square 9.2/10 Wonderful (1016) "Great place. 2nd time here and will definitely go back." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cynthia CA $226 CA $325 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Key-West-Hotels-Kimpton-Winslows-Bungalows.h529611.Hotel-Information) ![3 restaurants, breakfast, lunch, dinner served; Caribbean cuisine](https://images.trvl-media.com/lodging/1000000/10000/3900/3853/a3b28d11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/10000/3900/3853/173674da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, beach towels](https://images.trvl-media.com/lodging/1000000/10000/3900/3853/e0f768ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/10000/3900/3853/c8d74747.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Concha Key West, Autograph Collection Historic Seaport, 0.2 km from Jackson Square 9.0/10 Wonderful (239) "Perfect place to stay in key west " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ashley CA $279 CA $361 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Key-West-Hotels-Crowne-Plaza-Key-West-La-Concha.h3853.Hotel-Information) ![Queen Suite #6, Full Kitchen, Ground Floor, Pool View, Private Bathroom | Room amenity](https://images.trvl-media.com/lodging/1000000/980000/975000/974964/23dd109e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Queen Studio #5, Full Kitchen, Ground Floor, Pool View, Private Bathroom](https://images.trvl-media.com/lodging/1000000/980000/975000/974964/6e53f964.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Queen Studio #4, Full Kitchen, Ground Floor, Pool View, Private Bathroom](https://images.trvl-media.com/lodging/1000000/980000/975000/974964/29bede05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Queen Suite #2, Full Kitchen, Ground Floor, Pool View, Private Bathroom | Private kitchen](https://images.trvl-media.com/lodging/1000000/980000/975000/974964/d1702b63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Alexander Palms Court Casa Marina, 1.2 km from Jackson Square 9.2/10 Wonderful (1005) "It was a great place for the price. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kim CA $162 CA $183 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Key-West-Hotels-Alexander-Palms-Court.h974964.Hotel-Information) ![Outdoor pool, open 8:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/2000000/1180000/1171100/1171079/2155599f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Hemingway)](https://images.trvl-media.com/lodging/2000000/1180000/1171100/1171079/70163bf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Hemingway) | Private kitchen](https://images.trvl-media.com/lodging/2000000/1180000/1171100/1171079/4b1c26cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1180000/1171100/1171079/b1b0732e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lighthouse Hotel - Key West Historic Inns Bahama Village, 0.5 km from Jackson Square 9.0/10 Wonderful (811) "Great location and friendly staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alicia CA $279 CA $385 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Key-West-Hotels-Kimpton-Lighthouse-Hotel.h1171079.Hotel-Information) ![Sundeck](https://images.trvl-media.com/lodging/6000000/5710000/5703000/5702955/0d04a670.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, individually decorated](https://images.trvl-media.com/lodging/6000000/5710000/5703000/5702955/f64c5358.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast buffet](https://images.trvl-media.com/lodging/6000000/5710000/5703000/5702955/e9dfd75a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Room w/porch, 1 King Bed - Adult Exclusive | View from room](https://images.trvl-media.com/lodging/6000000/5710000/5703000/5702955/c7a1cb1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seascape Tropical Inn - Adult Exclusive Downtown Key West, 0.5 km from Jackson Square 9.0/10 Wonderful (394) "It is a very good place to stay. The place is close to the main street and essentially you can walk to the best places in town. The parking was my main concern before going to the place, but after the checking-in process, the lady offered me a parking spot like 3 block away which was included in the package. Additionally you can park in front of the place if you find a parking spot. The staff is very sweet, specially the woman behind the desk." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric CA $195 CA $274 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Key-West-Hotels-Seascape-Tropical-Inn.h5702955.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/1000/901/0b72a249.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine, ocean views ](https://images.trvl-media.com/lodging/1000000/10000/1000/901/ea2f021f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/1000000/10000/1000/901/399f6b5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Room, 1 King Bed](https://images.trvl-media.com/lodging/1000000/10000/1000/901/f89b6e1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Centric Key West Resort and Spa Historic Seaport, 0.7 km from Jackson Square 9.0/10 Wonderful (1014) "Location location location is why u stay here. Walking distance to everything, 40 spot for parking is a bit steep but had a great stay. We would stay there again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric CA $258 CA $381 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Key-West-Hotels-Hyatt-Centric-Key-West-Resort-And-Spa.h901.Hotel-Information) ![Studio Suite | Living area](https://images.trvl-media.com/lodging/2000000/1710000/1709300/1709243/365028d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1710000/1709300/1709243/df1f6f71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite | Private kitchen](https://images.trvl-media.com/lodging/2000000/1710000/1709300/1709243/5700cffa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/2000000/1710000/1709300/1709243/9cd0d2ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Eden House Historic Seaport, 0.9 km from Jackson Square 9.0/10 Wonderful (1006) "Front desk staff friendly and helpful. Pool and hot tub perfect temperatures and very clean. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) KATHLEEN CA $236 CA $298 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Key-West-Hotels-Eden-House.h1709243.Hotel-Information) ![Poolside bar](https://images.trvl-media.com/lodging/1000000/530000/529500/529427/c8bd1ef4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Havana Suite w/kitchenette | Garden view](https://images.trvl-media.com/lodging/1000000/530000/529500/529427/6c9ccbbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/530000/529500/529427/244a3627.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Poolside bar](https://images.trvl-media.com/lodging/1000000/530000/529500/529427/8616a4ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Duval Inn Downtown Key West, 0.3 km from Jackson Square 8.6/10 Excellent (705) "Great location, clean comfortable rooms, great staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Raymond CA $177 CA $255 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Key-West-Hotels-Duval-Inn.h529427.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/9000000/8990000/8984500/8984451/83ae09e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/9000000/8990000/8984500/8984451/d3daa4c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/9000000/8990000/8984500/8984451/d9eb9072.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/9000000/8990000/8984500/8984451/b0c5a846.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Southwinds Motel Uptown - Upper Duval, 1.1 km from Jackson Square 8.8/10 Excellent (1211) "Great location, staff was super friendly and always helpful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jonathan CA $202 CA $267 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Key-West-Hotels-Southwinds-Motel.h8984451.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154005/6045323e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe King - Adult Exclusive](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154005/0a9cb96a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154005/328cc87d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe King - Adult Exclusive](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154005/6b5aa480.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Pensione Inn Old Town Key West, 0.9 km from Jackson Square 8.8/10 Excellent (1000) "charming property that is walkable to both the beach and downtown key west!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Milan CA $125 CA $235 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Key-West-Hotels-La-Pensione-Inn-BB.h1154005.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-08&endDate=2025-11-09®ionId=6249254&adults=2&sort=RECOMMENDED&openPlayBack=true) ## Top Jackson Square Hotel Reviews ![Pegasus International Hotel](//images.trvl-media.com/lodging/1000000/980000/977400/977303/81c4c567_y.jpg) ### Pegasus International Hotel 10/10 Excellent "Everything was awesome. Great location. Breakfast was minimal but ok" [](https://expedia.ca/Key-West-Hotels-Pegasus-International-Hotel.h977303.Hotel-Information) ![Duval House](//images.trvl-media.com/lodging/1000000/910000/900500/900423/d8706fe9_y.jpg) ### Duval House 10/10 Excellent "The balcony view was perfect. Its convenient to restaurants and shopping." [](https://expedia.ca/Key-West-Hotels-Duval-House.h900423.Hotel-Information) ![The Reach Key West, Curio Collection by Hilton](//images.trvl-media.com/lodging/1000000/460000/457900/457821/888fac6b_y.jpg) ### The Reach Key West, Curio Collection by Hilton 10/10 Excellent "Ty was the best bartender. He makes the best drinks and very friendly to everyone sitting at the bar. Food was good." [](https://expedia.ca/Key-West-Hotels-The-Reach-Key-West.h457821.Hotel-Information) ![Lighthouse Hotel - Key West Historic Inns](//images.trvl-media.com/lodging/2000000/1180000/1171100/1171079/2155599f_y.jpg) ### Lighthouse Hotel - Key West Historic Inns 10/10 Excellent "My friend and I had an amazing three days in Key West. Lighthouse Inn was a huge contributor to this awesomely positive experience. Rooms were clean and well-stocked with towels. My friend and I would always arrive at the tail end of breakfast. Even so, there was always an ample variety of food available. Every member of the staff was friendly and inviting. The place is located right across the street from The Hemingway House and a few short blocks from the Butterfly Conservatory. If I’m ever at Key West again, you know this is where I’ll be staying. " [](https://expedia.ca/Key-West-Hotels-Kimpton-Lighthouse-Hotel.h1171079.Hotel-Information) ![The Cabana Inn Key West - Adults Only](//images.trvl-media.com/lodging/7000000/6580000/6576700/6576609/98bddc65_y.jpg) ### The Cabana Inn Key West - Adults Only 10/10 Excellent "Great" [](https://expedia.ca/Key-West-Hotels-The-Cabana-Inn-Key-West-Adults-Only.h6576609.Hotel-Information) ![The Southernmost Inn - Adults Only](//images.trvl-media.com/lodging/5000000/4290000/4280800/4280752/2b7e8bad_y.jpg) ### The Southernmost Inn - Adults Only 10/10 Excellent "everyone was helpful" [](https://expedia.ca/Key-West-Hotels-The-Southernmost-Inn-Adults-Only.h4280752.Hotel-Information) ![The Marker Key West Harbor Resort](//images.trvl-media.com/lodging/10000000/9150000/9148400/9148379/15d13ee3_y.jpg) ### The Marker Key West Harbor Resort 10/10 Excellent "The perfect location for a stay in Key West. Easy walking distance to everything you want to do. Love sitting on my balcony overlooking the harbor. I’ve been coming here for several years and staff and accommodations are always excellent " [](https://expedia.ca/Key-West-Hotels-The-Marker-Key-West-Harbor-Resort.h9148379.Hotel-Information) ![Winslow's Bungalows - Key West Historic Inns](//images.trvl-media.com/lodging/1000000/530000/529700/529611/7cf7d263_y.jpg) ### Winslow's Bungalows - Key West Historic Inns 10/10 Excellent "This was an excellent historic inn. The staff was outstanding and super knowledgeable of Key West and its history. Special thanks to Johanny, Sonia, and Keith (at the bar) for making my wife's birthday a memerable stay. The room was clean and the property was well maintained." [](https://expedia.ca/Key-West-Hotels-Kimpton-Winslows-Bungalows.h529611.Hotel-Information) ![Casa Marina Key West, Curio Collection by Hilton](//images.trvl-media.com/lodging/1000000/20000/12400/12346/be8c9450_y.jpg) ### Casa Marina Key West, Curio Collection by Hilton 10/10 Excellent "This hotel is beautiful. Great view from the room. Staff is amazing " [](https://expedia.ca/Key-West-Hotels-Casa-Marina-Key-West.h12346.Hotel-Information) ## Hotels near other Jackson Square attractions [](https://www.expedia.ca/San-Carlos-Institute-Casa-Cuba-Hotels.0-l6068607-0.Travel-Guide-Filter-Hotels) ![KEY WEST, FLORIDA, USA - September 2012: San Carlos institute is a historic Key West building also known as "La casa de Cuba"](https://images.trvl-media.com/place/6068607/ca50f0f1-1b80-49ca-a7a4-8a8b38bfce5d.jpg) ### San Carlos Institute - Casa Cuba You can spend an afternoon exploring the galleries in San Carlos Institute - Casa Cuba during your trip to Key West. Stroll along the area's beautiful beaches or experience its lively festivals. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6068607) [](https://www.expedia.ca/Duval-Street-Hotels.0-l6068616-0.Travel-Guide-Filter-Hotels) ![Duval Street featuring signage](https://images.trvl-media.com/place/6068616/5997ee0c-eca4-415b-b051-99f4d38fbc11.jpg) ### Duval Street 4.5/5 (9,716 reviews) Along one of the southernmost streets in the continental U.S., enjoy a lively area filled with shops, pubs, restaurants and lots of sidewalk acts and vendors. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6068616) [](https://www.expedia.ca/Harry-S-Truman-Little-White-House-Hotels.0-l6068605-0.Travel-Guide-Filter-Hotels) ![Harry S. Truman Little White House showing a house](https://images.trvl-media.com/place/6068605/4f5f7570-d796-4d5a-9a98-d925004bc7d6.jpg) ### Harry S. Truman Little White House 4.4/5 (983 reviews) Visit the winter home of President Harry S. Truman to see where some of America’s most important post-war decisions were made. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6068605) [](https://www.expedia.ca/We-Cycle-Key-West-Hotels.0-l827848417466060800-0.Travel-Guide-Filter-Hotels) ### We Cycle Key West You can search for that perfect souvenir at We Cycle Key West during your trip to Key West. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=827848417466060800) [](https://www.expedia.ca/St-Pauls-Episcopal-Church-Hotels.0-l553248621532652633-0.Travel-Guide-Filter-Hotels) ### St. Paul's Episcopal Church St. Paul's Episcopal Church is just one of the places to see in Key West, so why not enjoy the other things to explore during your travels? Discover the area's lively bars and its lively festivals. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532652633) [](https://www.expedia.ca/Key-West-Film-Society-Hotels.0-l6069263-0.Travel-Guide-Filter-Hotels) ### Key West Film Society You can get tickets for a performance at Key West Film Society during your stay in Key West. In the area, take in the lively festivals and beautiful sunsets. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6069263) [](https://www.expedia.ca/Red-Barn-Theater-Hotels.0-l6069271-0.Travel-Guide-Filter-Hotels) ### Red Barn Theater You can enjoy a show at Red Barn Theater on your trip to Key West. Wander the seaside and beautiful beaches in the area. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6069271) [](https://www.expedia.ca/Hellings-House-Museum-Hotels.0-l801212012409602048-0.Travel-Guide-Filter-Hotels) ### Hellings House Museum You can spend an afternoon exploring the galleries in Hellings House Museum during your trip to Key West. Experience the area's entertainment choices and great live music. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=801212012409602048) ## Find out more about Jackson Square ### Top reasons to visit Jackson Square - **Vibrant Atmosphere:** Jackson Square is alive with energy, featuring lively festivals and breathtaking sunsets that create a unique ambiance. - **Historic Charm:** The square showcases stunning architecture and historic houses, perfect for culture enthusiasts and casual explorers alike. - **Local Attractions:** Enjoy music concerts and leisure activities in the beautiful Jackson Square Park, enhancing your visit. - **Shopping and Dining:** Explore quaint shops and savour local cuisine, making for a delightful culinary experience. - **Family-Friendly Activities:** Engage in excursions highlighting the region’s rich culture, ideal for families and adventure seekers. ### Find great hotels near Jackson Square Discover a range of charming accommodations near Jackson Square in Key West, Florida, perfect for every type of traveller. Whether you seek a romantic getaway, an adventurous stay, or a historic experience, the area offers delightful resorts and bed & breakfasts. With numerous options close to the vibrant square, you'll find the best hotels to suit your needs for a memorable vacation. - **La Concha Key West, Autograph Collection:** A sophisticated 4-star hotel that embodies the spirit of adventure and family-friendly experiences. Situated a mere 161m from Jackson Square, La Concha Key West is perfect for business travellers and families alike. The hotel boasts a variety of adventure sports and recreational activities both onsite and nearby, including windsurfing, sailing, and parasailing. Families will appreciate the thoughtful amenities for children, such as window guards and complimentary cribs. With its blend of professional facilities and family-oriented services, La Concha is a prime choice for those seeking a balanced vacation. - **Opal Key Resort & Marina, Key West:** This 4-star resort is a pet-friendly haven located 483m from Jackson Square. Opal Key Resort & Marina is designed for adventure-seekers, offering an array of outdoor activities such as hiking, fishing, and onsite parasailing and snorkeling. With a welcoming pet policy that allows dogs and service animals, it's an excellent choice for travellers who wish to bring their furry companions along. Guests can indulge in a variety of water-based adventures and enjoy the marina's scenic views, making it a vibrant destination for both relaxation and excitement. - **[Heron House - Adult Only:](https://www.expedia.ca/Key-West-Hotels-Heron-House-Adult-Only.h57730.Hotel-Information)** A charming 3.5-star bed and breakfast located 322m from Jackson Square, Heron House offers an LGBTQIA-friendly atmosphere perfect for adult travellers seeking adventure. This quaint property is affiliated with LGBTQI travel guides and features a range of activities such as surfing, snorkeling, and bicycle rentals nearby. Guests admire the intimate setting, making it an ideal retreat for couples and friends alike. With its focus on inclusivity and adventure, Heron House promises a memorable getaway in the heart of Key West. ### Where to stay near Jackson Square Jackson Square in Key West offers a vibrant mix of tropical charm and historical significance. Stroll through the historic square surrounded by stunning architecture and quaint shops, then venture to nearby Bourbon Street for lively nightlife. Families can enjoy excursions that highlight the area's rich culture and adventures. With its unique atmosphere, Jackson Square serves as a perfect base for exploring the best of Key West and beyond. - **[Key West:](https://www.expedia.ca/Key-West-Hotels.d1187.Travel-Guide-Hotels)** Nestled on an island, Key West is known for its vibrant atmosphere and unique charm. Jackson Square, located in the heart of the city, provides a fantastic starting point for your adventure. With a consistent influx of visitors throughout the year, the best times to visit are January, March, and September, when activities abound. Key West offers a mix of family-friendly attractions, city-themed experiences, and business opportunities. Enjoy shopping at local boutiques, relaxing on picturesque beaches, and exploring the lively streets that come alive with art and culture. - **[Old Town Key West:](https://www.expedia.ca/Old-Town-Key-West-Key-West-Hotels.0-n553248635976481920-0.Travel-Guide-Filter-Hotels)** As a historic neighbourhood, Old Town Key West exudes a laid-back vibe enriched by its cultural heritage. Jackson Square is your gateway to this area, where traveller numbers peak in March and during the summer months of June and July. Visitors flock here for the delightful mix of family-oriented attractions and city experiences. Wander through charming streets lined with shops and cafes, and take in the scenic beauty of nearby beaches. Old Town is a treasure trove of history and leisure, perfect for relaxing strolls and enjoying local cuisine. - **[Key West Historic District:](https://www.expedia.ca/Key-West-Historic-District-Key-West-Hotels.0-n6281809-0.Travel-Guide-Filter-Hotels)** Just 483m from Jackson Square, the Key West Historic District invites you to step back in time. This neighbourhood is popular among visitors year-round, particularly in March and from June to July. It boasts a rich tapestry of history combined with modern amenities, making it ideal for families, business travellers, and history buffs alike. Explore museums, quaint shops, and scenic waterfronts, all while being close to family-friendly beaches. The Historic District is a delightful blend of past and present, providing a unique travel experience. ### Things to do near Jackson Square At Jackson Square in Key West, immerse yourself in vibrant sunsets, lively festivals, and scenic biking. Enjoy your leisure time at local attractions, where you can catch music concerts and relax on the sun terrace. This lively area offers a delightful mix of activities that reflect the unique charm of the region, making it a perfect spot for visitors to unwind and experience the local culture. **Shopping** For a delightful shopping experience in Jackson Square, visit [We Cycle Key West](https://www.expedia.ca/We-Cycle-Key-West-Hotels.0-l827848417466060800-0.Travel-Guide-Filter-Hotels), just 161m away, and [The Kite House](https://www.expedia.ca/The-Kite-House-Hotels.0-l553248621532652628-0.Travel-Guide-Filter-Hotels), located 644m away, for unique gifts and souvenirs. If you're up for a drive, check out the [Big Pine Key Flea Market](https://www.expedia.ca/Big-Pine-Key-Flea-Market-Hotels.0-l553248621533115810-0.Travel-Guide-Filter-Hotels), 46.7km away, for local treasures. **Recreation** Experience the tranquil ambiance at the [Key West Golf Club](https://www.expedia.ca/Key-West-Golf-Club-Hotels.0-l6163814-0.Travel-Guide-Filter-Hotels), located 6.4km from Jackson Square, where lush greens and outdoor sports create a perfect wellness escape. Alternatively, the [MLK Community Pool & Community Center](https://www.expedia.ca/MLK-Community-Pool-Community-Center-Hotels.0-l553248621532652610-0.Travel-Guide-Filter-Hotels), only 805m away, offers a family-friendly atmosphere for swimming and relaxation. **Adventure** At Jackson Square, immerse yourself in vibrant street performances and local art. Explore nearby waters with paddleboarding or kayaking, or indulge in a thrilling sunset sail. Don’t miss the historic architecture and lively atmosphere, making it a perfect spot for adventurous exploration in Key West. **Nightlife** In Jackson Square, the vibrant nightlife includes the [Waterfront Playhouse](https://www.expedia.ca/Waterfront-Playhouse-Hotels.0-l553248621532652609-0.Travel-Guide-Filter-Hotels), 644m away, and the intimate [Red Barn Theater](https://www.expedia.ca/Red-Barn-Theater-Hotels.0-l6069271-0.Travel-Guide-Filter-Hotels), only 322m from the square, both offering rich cultural experiences. For a unique twist, visit the [Key West Burlesque Theater](https://www.expedia.ca/Key-West-Burlesque-Theater-Hotels.0-l553248621532652629-0.Travel-Guide-Filter-Hotels), 1.1km away, for an entertaining evening. *\*Distances are measured in a straight line; actual driving distances may vary depending on the route.* ### Booking tips and Expedia advantages for Jackson Square To save money during your visit to Jackson Square, plan your trip from August to October when hotel rates are lower. Book your accommodation about a month in advance, or check Expedia for last-minute deals. Stay on a Tuesday for the best rates and consider using Expedia's filters to find eco-friendly hotels within your budget. Combine your hotel, flights, and activities for additional savings through package deals. Don't forget to explore free activities in the area to make the most of your trip without breaking the bank. - **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay around Jackson Square are August to October, where the prices are slightly lower. This is in comparison to February to April, where prices are slightly higher. - **The best time to book a hotel:** The cheapest time to book a hotel around Jackson Square is usually 1 month out from when you are planning to stay, though if you're late to the party, have a look at Expedia's last minute deals - the green banner below the hotel's price indicates a discounted rate. - **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay around Jackson Square is Tuesday. The most expensive day to stay around Jackson Square is Friday. - **Find cheap hotels on Expedia:** Utilize Expedia's search tool to refine your preferences, including your budget, desired location, and preferred type of accommodation. For instance, selecting the Eco-certified filter will show you a range of sustainable and environmentally friendly hotels currently available. To find the best prices and deals, simply sort the price filter from lowest to highest. - **Consider bundling your trip:** You can save money by combining your hotel stay at Jackson Square with your flights and activities through an Expedia package. ### Find the best attractions near Jackson Square Jackson Square in Key West offers a vibrant mix of historic houses, lively streets, and a modern square, making it an ideal spot for culture seekers, families, and city explorers alike. Visitors can enjoy the beautiful Jackson Square Park, explore various attractions, and immerse themselves in the local atmosphere. Whether you're strolling through the park or visiting iconic spots, there's something for everyone in this charming area. - **[Duval Street:](https://www.expedia.ca/Duval-Street-Hotels.0-l6068616-0.Travel-Guide-Filter-Hotels)** A vibrant hub of activity, Duval Street is lined with eclectic shops, lively bars, and local eateries. Experience the bustling city vibes while enjoying street performers and a variety of entertainment options. - **[Mallory Square:](https://www.expedia.ca/Mallory-Square-Hotels.0-l501385-0.Travel-Guide-Filter-Hotels)** Known for its stunning sunsets, Mallory Square is a modern square that hosts street performers, artisanal vendors, and live music. The lively atmosphere makes it a perfect spot to unwind and soak in the local culture. - **[Ernest Hemingway Home and Museum:](https://www.expedia.ca/Ernest-Hemingway-Home-And-Museum-Hotels.0-l501376-0.Travel-Guide-Filter-Hotels)** Step back in time at the Ernest Hemingway Home and Museum, where the renowned author lived and wrote. This historic house offers a glimpse into his life and showcases beautiful gardens, adding a rich cultural vibe to your visit. ### Best time to go to Jackson Square The best time to visit Jackson Square is dependant on what kind of holiday you are seeking. August and August are its hottest month on average. At the time of August, visitor numbers are average and weather is mostly sunny. January and January are its coolest month on average. At the time of January, visitor numbers are average and weather is mostly sunny. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | --- | --- | --- | --- | --- | --- | | January | 71.1°F (21.7°C) | No Rain | Mostly Sunny | Average | Average | | January | 71.1°F (21.7°C) | No Rain | Mostly Sunny | Average | Average | | February | 72.1°F (22.3°C) | No Rain | Mostly Sunny | Average | Slightly High | | February | 72.1°F (22.3°C) | No Rain | Mostly Sunny | Average | Slightly High | | March | 73.4°F (23.0°C) | No Rain | Mostly Sunny | Slightly High | Slightly High | | March | 73.4°F (23.0°C) | No Rain | Mostly Sunny | Slightly High | Slightly High | | April | 76.8°F (24.9°C) | No Rain | Mostly Sunny | Average | Slightly High | | April | 76.8°F (24.9°C) | No Rain | Mostly Sunny | Average | Slightly High | | May | 79.3°F (26.3°C) | Light Rain | Mostly Sunny | Average | Average | | May | 79.3°F (26.3°C) | Light Rain | Mostly Sunny | Average | Average | | June | 82.6°F (28.1°C) | Light Rain | Mostly Sunny | Slightly High | Average | | June | 82.6°F (28.1°C) | Light Rain | Mostly Sunny | Slightly High | Average | | July | 84.0°F (28.9°C) | Light Rain | Mostly Sunny | Slightly High | Average | | July | 84.0°F (28.9°C) | Light Rain | Mostly Sunny | Slightly High | Average | | August | 84.4°F (29.1°C) | Light Rain | Mostly Sunny | Average | Slightly Low | | August | 84.4°F (29.1°C) | Light Rain | Mostly Sunny | Average | Slightly Low | | September | 83.7°F (28.7°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | | September | 83.7°F (28.7°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | | October | 80.8°F (27.1°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | | October | 80.8°F (27.1°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | | November | 76.6°F (24.8°C) | Light Rain | Mostly Sunny | Slightly Low | Average | | November | 76.6°F (24.8°C) | Light Rain | Mostly Sunny | Slightly Low | Average | | December | 73.9°F (23.3°C) | No Rain | Mostly Sunny | Average | Average | | December | 73.9°F (23.3°C) | No Rain | Mostly Sunny | Average | Average | ### The nearest major airports for your trip to Jackson Square Travelling to Jackson Square in Key West, Florida, is convenient with Key West International Airport ([EYW](https://www.expedia.ca/Key-West-Intl-Airport-Hotels.0-aEYW-0.Travel-Guide-Filter-Hotels)), situated 4.8km away. Nearby accommodations include the luxurious [Casa Marina Key West](https://www.expedia.ca/Key-West-Hotels-Casa-Marina-Key-West.h12346.Hotel-Information), a 5-star resort 3.2km from the airport. Margaritaville Beach House and Havana Cabana, both 4-star hotels, are only 1.6km away. For those considering Marathon Airport ([MTH](https://www.expedia.ca/Florida-Keys-Marathon-Airport-Hotels.0-aMTH-0.Travel-Guide-Filter-Hotels)), located 78.9km from Jackson Square, [Isla Bella Beach Resort & Spa](https://www.expedia.ca/Marathon-Hotels-Isla-Bella-Beach-Resort-Spa.h24101706.Hotel-Information), a 4.5-star hotel, is 6.4km away, while Tranquility Bay Beachfront Hotel is just 4.8km from the airport. Transportation services are readily available from these hotels to the respective airports. ## Frequently asked questions ### What are the top-rated hotels near Jackson Square? > Discovering the top-rated hotels near Jackson Square in Key West is an exciting journey toward finding your perfect getaway. > > > > [Almond Tree Inn Hotel - Adults Only](https://www.expedia.ca/Key-West-Hotels-Almond-Tree-Inn.h809031.Hotel-Information) > > > > Almond Tree Inn Hotel is an inviting adults-only retreat located just a 10-minute walk from Jackson Square. With an impressive review rating of 10, this 3.5-star hotel ensures a memorable stay with amenities like an outdoor pool, hot tub, and a beautiful terrace to relax. Guests appreciate the complimentary breakfast, designer toiletries, and the option for nearby windsurfing and snorkeling. The hotel also features electric car charging stations and is designed with an elegant Art Deco hotel style, making it a unique choice for travellers. > > > > [The Gardens Hotel](https://www.expedia.ca/Key-West-Hotels-The-Gardens-Hotel.h20796.Hotel-Information) > > > > The Gardens Hotel, only a 5-minute stroll from Jackson Square, boasts a remarkable review rating of 9.8 and a 4.0-star rating. This hotel offers a lush garden setting and a charming outdoor pool, perfect for unwinding after a day of exploring. Guests can enjoy complimentary cooked breakfasts and relax in spacious rooms featuring Egyptian cotton sheets. Unique amenities like in-room private pools and a yoga class on-site ensure travellers have a tranquil and rejuvenating experience. > > > > [Orchid Key Inn - Adults Only](https://www.expedia.ca/Key-West-Hotels-Orchid-Key-Inn.h809032.Hotel-Information) > > > > Orchid Key Inn is a delightful adults-only hotel, situated just 9 minutes from Jackson Square, rated an impressive 9.8 by travellers. This 3.5-star hotel offers a blend of comfort and style, featuring an outdoor pool with sun loungers and a private hot tub for a more intimate experience. Guests enjoy complimentary breakfasts and have access to nearby kayaking and snorkeling adventures. The presence of designer toiletries and a concierge service adds to the overall appeal, making it a lovely choice for visitors to Key West. ### What hotels are within walking distance to Jackson Square? > Discover a selection of top-rated hotels just a short stroll from Jackson Square, perfect for your Key West getaway. > > > > [Almond Tree Inn Hotel - Adults Only](https://www.expedia.ca/Key-West-Hotels-Almond-Tree-Inn.h809031.Hotel-Information) > > > > Almond Tree Inn Hotel is an inviting 3.5-star accommodation located just a 10-minute walk from Jackson Square. Rated 10 by travellers, this adults-only retreat features an outdoor pool surrounded by sun loungers, perfect for a leisurely day in the sun. Guests can enjoy complimentary daily breakfast and relax in the hot tub after a day of exploring. With amenities like Egyptian cotton sheets and a terrace, it offers a cozy ambiance for a memorable stay. > > > > [The Gardens Hotel](https://www.expedia.ca/Key-West-Hotels-The-Gardens-Hotel.h20796.Hotel-Information) > > > > The Gardens Hotel, a charming 4-star hotel, is located only 5 minutes on foot from Jackson Square, with a stellar review rating of 9.8. This boutique hotel features a beautiful outdoor pool and a garden view restaurant, perfect for dining al fresco. Guests can indulge in complimentary cooked breakfast and unwind with yoga classes on-site. The hotel's unique layout and lush landscaping provide a tranquil oasis amidst the vibrant Key West atmosphere. > > > > [Orchid Key Inn - Adults Only](https://www.expedia.ca/Key-West-Hotels-Orchid-Key-Inn.h809032.Hotel-Information) > > > > Orchid Key Inn, rated 9.8 by travellers, offers a delightful stay just 9 minutes from Jackson Square. This 3.5-star adults-only hotel features an outdoor pool and a relaxing hot tub, creating an ideal environment for unwinding. Guests can enjoy free breakfast daily and take advantage of the nearby beach activities, including snorkeling and kayaking. With its art deco design and premium bedding, it provides a chic and comfortable retreat. ### How much is a hotel near Jackson Square? > Staying near Jackson Square is a treat, with plenty of hotels from CA $176 offering incredible amenities. If you're leaning toward a little luxury, prices can rise, especially in peak season. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays. ### What are the most popular family-friendly hotels near Jackson Square? > For families looking for top-rated hotels near Jackson Square, Key West offers some fantastic options that cater to both comfort and fun. > > > > [Margaritaville Beach House Key West](https://www.expedia.ca/Key-West-Hotels-Barbary-Beach-House-Key-West.h48713884.Hotel-Information) > > > > Margaritaville Beach House Key West, a 4-star hotel just 4.7 km from Jackson Square, welcomes families with open arms. Rated 8.8 by travellers, this hotel offers a range of family-friendly amenities including a pool accessible to all, a kitchenette for in-room meals, and toys to keep children entertained. Guests can also enjoy the nearby beach, outdoor activities like kayaking and snorkeling, and the comfort of daily housekeeping. > > > > [Blue Flamingo Resort Key West](https://www.expedia.ca/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.Hotel-Information) > > > > Blue Flamingo Resort Key West is a charming 4-star hotel located 6.0 km from Jackson Square, a review rating of 7.8 by travellers. This family-friendly resort features connecting rooms and an arcade game room, providing endless entertainment for kids. Guests can also relax by the outdoor pool, enjoy snacks from the poolside bar, and take advantage of the onsite picnic area. > > > > [Hyatt Centric Key West Resort and Spa](https://www.expedia.ca/Key-West-Hotels-Hyatt-Centric-Key-West-Resort-And-Spa.h901.Hotel-Information) > > > > Hyatt Centric Key West Resort and Spa is a luxurious 4-star option just a 12-minute walk from Jackson Square, with an impressive travellers' rating of 9.0. This family-friendly resort offers amenities such as a pool with accessible features and kids' meals at the onsite restaurant. Guests can unwind with spa services, enjoy beach access, and enjoy various water sports, making it a perfect getaway for families. ### Which hotels near Jackson Square offer the best views? > Explore the best hotels near Jackson Square that not only offer comfort but also stunning views for your Key West adventure. > > > > [The Gardens Hotel](https://www.expedia.ca/Key-West-Hotels-The-Gardens-Hotel.h20796.Hotel-Information) > > > > The Gardens Hotel is a top-rated 4-star hotel with a remarkable review rating of 9.8, located just a 5-minute walk from Jackson Square. This charming hotel features a beautiful garden view and offers a complimentary breakfast, an outdoor pool, and unique amenities like in-room massages. Guests appreciate the tranquil atmosphere and close nearby the vibrant sights of Key West, making it an ideal retreat. > > > > [Hyatt Centric Key West Resort and Spa](https://www.expedia.ca/Key-West-Hotels-Hyatt-Centric-Key-West-Resort-And-Spa.h901.Hotel-Information) > > > > Hyatt Centric Key West Resort and Spa, rated 9.0 by travellers, is a 4-star gem located just a 12-minute walk from Jackson Square. Guests can indulge in ocean views from their furnished balconies while enjoying amenities like a full-service spa and an outdoor pool. The beach is nearby, and there's a restaurant offering ocean views, making it a perfect choice for those seeking relaxation and picturesque scenery. > > > > [Casa Marina Key West, Curio Collection by Hilton](https://www.expedia.ca/Key-West-Hotels-Casa-Marina-Key-West.h12346.Hotel-Information) > > > > Casa Marina Key West, Curio Collection by Hilton boasts an impressive review rating of 8.4 and is situated 2.1 km from Jackson Square. This 4-star resort features an ocean view and offers a stunning beachfront location. Guests can enjoy a full-service spa, outdoor pool, and a variety of water sports such as sailing and kayaking, ensuring a delightful stay with breathtaking views at every turn. ### What are the best affordable hotels near Jackson Square? > Finding the best affordable hotels near Jackson Square offers travellers a wonderful opportunity to explore this vibrant area without breaking the bank. > > > > [The Grand Guesthouse](https://www.expedia.ca/Key-West-Hotels-The-Grand-Guesthouse.h1798025.Hotel-Information) > > > > The Grand Guesthouse is situated 1.9 km from Jackson Square and offers a cozy escape with a great traveler rating score of 9.6. This hotel features free continental breakfast and WiFi, along with free parking, making it a practical choice for travellers. Enjoy the terrace, garden, and convenient access to nearby historical sites and beautiful beaches, perfect for a relaxing getaway. > > > > [Simonton Court Historic Inn & Cottages](https://www.expedia.ca/Key-West-Hotels-Simonton-Court-Historic-Inn-Guesthouse.h37900084.Hotel-Information) > > > > Simonton Court Historic Inn & Cottages is a charming option just a 7-minute walk from Jackson Square. Rated by travellers with an impressive 9.8, this inn offers free continental breakfast and WiFi, making it a great choice for budget-conscious travellers. Guests can also enjoy the outdoor pool, terrace, and nearby marina for kayaking and boat tours, ensuring a delightful stay in Key West. > > > > [LA TE DA Hotel - Adults Only](https://www.expedia.ca/Key-West-Hotels-LA-TE-DA-Hotel-Adults-Only.h18312548.Hotel-Information) > > > > LA TE DA Hotel - Adults Only, located 12 minutes on foot from Jackson Square, boasts a stellar review rating of 9.8. This adults-only venue provides free WiFi and toiletries for a straightforward experience. Guests can unwind by the outdoor pool or take advantage of the nearby beach and marina for snorkeling and sailing adventures, making it an ideal retreat for couples. ### What are the best boutique hotels near Jackson Square? > Discover the charm of boutique hotels near Jackson Square, perfect for travellers seeking a top-rated stay in Key West. > > > > [Artist House Key West](https://www.expedia.ca/Key-West-Hotels-Artist-House-Key-West.h2480462.Hotel-Information) > > > > Artist House Key West, a 3.5-star boutique hotel, offers an exceptional experience just a 5-minute walk from Jackson Square, with an impressive review rating of 9.8 by travellers. Guests can indulge in complimentary daily breakfast and enjoy amenities such as a hot tub and concierge service. The hotel also provides easy access to nearby beach activities including snorkeling and kayaking, ensuring a delightful stay in this vibrant location. > > > > [Weatherstation Inn](https://www.expedia.ca/Key-West-Hotels-Weatherstation-Inn.h1749434.Hotel-Information) > > > > Weatherstation Inn is another fantastic boutique option, located only 5 minutes from Jackson Square and rated 9.4 by travellers. This charming inn features an outdoor pool and a terrace, providing perfect spots to relax. Guests can enjoy a complimentary continental breakfast and enjoy nearby water activities like snorkeling and sailing. The inn's adults-only policy offers a serene escape for couples looking to unwind. > > > > [The Inn on Fleming](https://www.expedia.ca/Key-West-Hotels-The-Inn-On-Fleming.h1501593.Hotel-Information) > > > > The Inn on Fleming, a 3.5-star boutique hotel, is situated 12 minutes from Jackson Square and boasts a review rating of 9.4 from travellers. This inviting inn features a refreshing outdoor pool and complimentary breakfast, making it an ideal choice for a relaxing stay. Guests can easily explore nearby attractions and enjoy activities such as windsurfing and boat tours, all while basking in the unique charm of Key West. ### Are there any hotels with pools close to Jackson Square? > For travellers seeking a refreshing stay near Jackson Square, these hotels with pools offer the perfect blend of comfort and convenience. > > > > [Blue Flamingo Resort Key West](https://www.expedia.ca/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.Hotel-Information) > > > > Blue Flamingo Resort Key West is situated 6.0 km from Jackson Square and offers a delightful outdoor pool experience with sun loungers and cabanas for relaxation. Rated 7.8 by travellers, this 4-star hotel also features a poolside bar, fitness facilities nearby, and a complimentary shuttle service for local attractions. Guests can enjoy spacious rooms equipped with kitchenettes, ensuring a comfy stay. > > > > [Pier House Resort & Spa](https://www.expedia.ca/Key-West-Hotels-Pier-House-Resort-Spa.h19307.Hotel-Information) > > > > Located a mere 10-minute stroll from Jackson Square, Pier House Resort & Spa is a luxurious 4-star resort with a captivating outdoor pool featuring sun loungers and poolside service. Rated 9.0 by travellers, it offers an array of amenities including a full-service spa, beachfront dining, and complimentary beach towels. Guests can unwind in elegantly furnished rooms and enjoy a range of wellness treatments for a truly relaxing getaway. > > > > [Southernmost Beach Resort and Guesthouses](https://www.expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) > > > > Just a short 15-minute walk from Jackson Square, Southernmost Beach Resort and Guesthouses is a 4-star gem that boasts a beautiful outdoor pool with cabanas and a poolside bar. With an impressive review rating of 8.6, this resort offers travellers beach access, a full-service spa, and on-site dining options with ocean views. Families will appreciate the free cribs and kid-friendly amenities available. ### What are the best pet-friendly hotels near Jackson Square? > Discover the best pet-friendly hotels near Jackson Square, offering top-rated stays where you and your furry friends can enjoy the vibrant atmosphere of Key West. > > > > [The Gardens Hotel](https://www.expedia.ca/Key-West-Hotels-The-Gardens-Hotel.h20796.Hotel-Information) > > > > The Gardens Hotel is a charming 4-star retreat just a 5-minute walk from Jackson Square, an impressive 9.8 travellers' rating. This pet-friendly haven welcomes your dogs and provides essential amenities like food and water bowls. Guests can also indulge in a relaxing outdoor pool, free breakfast, and serene garden views, ensuring a delightful stay in a picturesque setting. > > > > [Artist House Key West](https://www.expedia.ca/Key-West-Hotels-Artist-House-Key-West.h2480462.Hotel-Information) > > > > Artist House Key West, rated 9.8 by travellers, is a delightful 3.5-star hotel located only 5 minutes from Jackson Square. This inviting hotel welcomes pets and offers amenities such as food and water bowls for your furry companions. Guests can enjoy a complimentary buffet breakfast, relax in the hot tub, and explore nearby kayaking and snorkeling activities, making it a perfect choice for a memorable getaway. > > > > [The Garden House](https://expedia.ca/Key-West-hotels-The-Garden-House.h1154002.Hotel-information) > > > > The Garden House, a cozy 3-star hotel situated 8 minutes from Jackson Square, has a great traveler rating score of 9.2. This pet-friendly accommodation allows dogs and provides food and water bowls for your pets. Guests can unwind by the outdoor pool, enjoy free breakfast, and explore the nearby historical district, making it an ideal base for discovering the beauty of Key West. ### Can I book a fully refundable hotel close to Jackson Square? > Most bookings on Expedia are refundable if canceled within 24-48 hours of arrival, though this depends on the hotel's individual cancellation policy, which you should check in your booking confirmation. If free cancellation is available, you can cancel directly through your Expedia account by going to "My Trips" and selecting your reservation. To find fully refundable hotel options, simply enter "Jackson Square", set your travel dates, and use the "Fully refundable" filter under "Deals & Discounts" on the results page. Alternatively, explore [deals with free cancellation](https://www.expedia.ca/deals/free-cancellation) options on Expedia. ### Can I find Expedia discounts for hotels near Jackson Square? > Sign in to your account to unlock instant savings and access Member Prices on Expedia. 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