Title: Book the Best Hotels with POOL in Downtown Key West in 2026 | Expedia.ca [Downtown Key West Travel Guide](https://expedia.ca/Key-West-Downtown-Key-West.dx553248635976470405)[Flights to Key West](https://expedia.ca/Cheap-Flights-To-Key-West.d1187.Travel-Guide-Flights)[Things to do in Key West](https://expedia.ca/Things-To-Do-In-Key-West.d1187.Travel-Guide-Activities)[Downtown Key West Car Rentals](https://expedia.ca/Car-Rentals-In-Downtown-Key-West.d553248635976470405.Car-Rental-Guide)[Downtown Key West Vacations](https://expedia.ca/Downtown-Key-West.d553248635976470405.Destination-Travel-Guides) ![Ernest Hemingway Home and Museum featuring heritage elements and a house](https://images.trvl-media.com/place/501376/3b4c31fa-338d-424b-aa0f-482ad359d16a.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Downtown Key West, FL from CA $239 - ![](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 availability on Downtown Key West Hotels with a Pool Tonight [Dec 13 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976470405&startDate=2025-12-13&endDate=2025-12-14&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 14 - Dec 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976470405&startDate=2025-12-14&endDate=2025-12-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976470405&startDate=2025-12-19&endDate=2025-12-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976470405&startDate=2025-12-26&endDate=2025-12-28&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Downtown Key West hotels with a pool ![Courtyard](https://images.trvl-media.com/lodging/1000000/910000/900500/900423/9013d891.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment (Adults Only) | Private kitchen](https://images.trvl-media.com/lodging/1000000/910000/900500/900423/4c7ce9b2.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) ![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) ### Duval House [](https://www.expedia.ca/Key-West-Hotels-Duval-House.h900423.Hotel-Information) Old Town Key West 9.4/10 Exceptional (1006) "I loved this place the location was absolutely perfect " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Frank CA $186 CA $239 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Key-West-Hotels-Duval-House.h900423.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/57800/57730/04396af1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/60000/57800/57730/ee4555f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Tropical King](https://images.trvl-media.com/lodging/1000000/60000/57800/57730/84d1a4db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/57800/57730/705cf1b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heron House - Adult Only [](https://www.expedia.ca/Key-West-Hotels-Heron-House-Adult-Only.h57730.Hotel-Information) Old Town Key West 9.0/10 Wonderful (1135) "Loved the setup of the hotel and great location! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rachel CA $176 CA $244 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Key-West-Hotels-Heron-House-Adult-Only.h57730.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/10000000/9690000/9681100/9681053/a7d26b15.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/10000000/9690000/9681100/9681053/8a130c0e.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) ![Front of property](https://images.trvl-media.com/lodging/10000000/9690000/9681100/9681053/7db4678b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tropical Inn [](https://www.expedia.ca/Key-West-Hotels-Tropical-Inn.h9681053.Hotel-Information) Old Town Key West 9.6/10 Exceptional (363) "The place was excellent and the service amazing " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Janae CA $236 CA $300 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Key-West-Hotels-Tropical-Inn.h9681053.Hotel-Information) ![Street view](https://images.trvl-media.com/lodging/1000000/980000/977400/977303/6177b123.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Executive Room, 1 King Bed](https://images.trvl-media.com/lodging/1000000/980000/977400/977303/32852f35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/980000/977400/977303/3eb8f6b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sundeck](https://images.trvl-media.com/lodging/1000000/980000/977400/977303/3f1bd6fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pegasus International Hotel [](https://www.expedia.ca/Key-West-Hotels-Pegasus-International-Hotel.h977303.Hotel-Information) Old Town Key West 8.2/10 Very good (1002) "Wonderful place to stay right in the heart of Key West. The pool and deck area are nice and cozy for a relaxing time. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel CA $199 CA $294 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Key-West-Hotels-Pegasus-International-Hotel.h977303.Hotel-Information) ![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) ![Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/1000000/810000/809100/809031/e3570c6a.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) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/810000/809100/809031/1ae9d542.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Almond Tree Inn Hotel - Adults Only [](https://www.expedia.ca/Key-West-Hotels-Almond-Tree-Inn.h809031.Hotel-Information) Old Town Key West 10/10 Exceptional (1000) "Very nice & peaceful with a wonderful staff. Our second time staying here" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sandra CA $311 CA $350 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Key-West-Hotels-Almond-Tree-Inn.h809031.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/4000000/3930000/3924900/3924835/872463e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite](https://images.trvl-media.com/lodging/4000000/3930000/3924900/3924835/7c366980.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage, 2 Bedrooms (Royal Poinciana) | Terrace/patio](https://images.trvl-media.com/lodging/4000000/3930000/3924900/3924835/069168f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3930000/3924900/3924835/894f1440.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Paradise Inn Key West - Adults Only [](https://www.expedia.ca/Key-West-Hotels-Paradise-Inn-Key-West-Adults-Only.h3924835.Hotel-Information) Old Town Key West 9.2/10 Wonderful (1002) "Cozy place right near everything " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph [](https://www.expedia.ca/Key-West-Hotels-Paradise-Inn-Key-West-Adults-Only.h3924835.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/7000000/6580000/6576700/6576609/cf7f237d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cabana Cottage](https://images.trvl-media.com/lodging/7000000/6580000/6576700/6576609/75209084.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/7000000/6580000/6576700/6576609/98bddc65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite](https://images.trvl-media.com/lodging/7000000/6580000/6576700/6576609/a5da01ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Cabana Inn Key West - Adults Only [](https://www.expedia.ca/Key-West-Hotels-The-Cabana-Inn-Key-West-Adults-Only.h6576609.Hotel-Information) Old Town Key West 8.8/10 Excellent (1002) "Rooms are clean, staff was friendly and pool was refreshing. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wendy [](https://www.expedia.ca/Key-West-Hotels-The-Cabana-Inn-Key-West-Adults-Only.h6576609.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 Room,w/balcony. 1 King Bed](https://images.trvl-media.com/lodging/1000000/530000/529500/529427/f9abeb6a.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) ![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 [](https://www.expedia.ca/Key-West-Hotels-Duval-Inn.h529427.Hotel-Information) Old Town Key West 8.6/10 Excellent (716) "Property was clean and perfect location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tracy [](https://www.expedia.ca/Key-West-Hotels-Duval-Inn.h529427.Hotel-Information) ![Paris | Garden view](https://images.trvl-media.com/lodging/20000000/19700000/19690200/19690128/8c863e97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Paris | Room amenity](https://images.trvl-media.com/lodging/20000000/19700000/19690200/19690128/1f2841e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Madrid | Room amenity](https://images.trvl-media.com/lodging/20000000/19700000/19690200/19690128/60225d19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/20000000/19700000/19690200/19690128/c8d43f54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Andrews Inn & Garden Cottages [](https://www.expedia.ca/Key-West-Hotels-Andrews-Inn-Garden-Cottages.h19690128.Hotel-Information) Old Town Key West 9.0/10 Wonderful (265) "Easy to access and a peaceful place. I’ll definitely come back." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica CA $356 CA $432 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Key-West-Hotels-Andrews-Inn-Garden-Cottages.h19690128.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/3000000/2240000/2232000/2231933/7e102845.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2240000/2232000/2231933/a17d99e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/3000000/2240000/2232000/2231933/e6b2a42c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/3000000/2240000/2232000/2231933/b83c4cbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Coco Plum Inn [](https://www.expedia.ca/Key-West-Hotels-Coco-Plum-Inn.h2231933.Hotel-Information) Old Town Key West 9.6/10 Exceptional (464) "It was a lovely day at the Cocoa plum inn. The location was perfect and the grounds were cleanz, staffl was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Diane CA $222 CA $250 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Key-West-Hotels-Coco-Plum-Inn.h2231933.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=2025-12-28&endDate=2025-12-29®ionId=553248635976470405&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Downtown Key West Hotel Reviews ![Beachside Resort & Residences](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/290b242a_y.jpg) ### Beachside Resort & Residences 10/10 Excellent "The pool beach area was clean, water in pool and hot tub clean and warm Shuttle to Duvall street was very convent and helpful to get to shopping / dinning area " [](https://expedia.ca/Key-West-Hotels-Key-West-Marriott-Beachside-Hotel.h25865.Hotel-Information) ![Heron House - Adult Only](https://images.trvl-media.com/lodging/1000000/60000/57800/57730/04396af1_y.jpg) ### Heron House - Adult Only 10/10 Excellent "Yes" [](https://expedia.ca/Key-West-Hotels-Heron-House-Adult-Only.h57730.Hotel-Information) ![Paradise Inn Key West - Adults Only](https://images.trvl-media.com/lodging/4000000/3930000/3924900/3924835/069168f1_y.jpg) ### Paradise Inn Key West - Adults Only 10/10 Excellent "Staff was amazing! Pool was warm and everything was beautiful " [](https://expedia.ca/Key-West-Hotels-Paradise-Inn-Key-West-Adults-Only.h3924835.Hotel-Information) ![Blue Flamingo Resort Key West](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/c4b850d1_y.jpg) ### Blue Flamingo Resort Key West 10/10 Excellent "They went the extra mile! Was a lovely stay" [](https://expedia.ca/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.Hotel-Information) ![Oceans Edge Key West Resort, Hotel & Marina](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/f7424907_y.jpg) ### Oceans Edge Key West Resort, Hotel & Marina 10/10 Excellent "Rooms were beautiful" [](https://expedia.ca/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.Hotel-Information) ![Southernmost Beach Resort and Guesthouses](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/026f10af_y.jpg) ### Southernmost Beach Resort and Guesthouses 10/10 Excellent "Beautiful room and amazing reception staff of Annette, Sara, Jody and Richardo. They were very accommodating. " [](https://expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) ![Wicker Guesthouse](https://images.trvl-media.com/lodging/11000000/10980000/10974500/10974431/f74278e9_y.jpg) ### Wicker Guesthouse 10/10 Excellent "cool place, good vibe, great view of the parades on Duval St" [](https://expedia.ca/Key-West-Hotels-Wicker-Guesthouse.h10974431.Hotel-Information) ![DoubleTree Resort by Hilton Grand Key - Key West](https://images.trvl-media.com/lodging/1000000/480000/470900/470834/cefb5fc2_y.jpg) ### DoubleTree Resort by Hilton Grand Key - Key West 10/10 Excellent "Our Birthday Club recently stayed at the resort while in town celebrating our Sister Audrey's 60th Birthday. The resort staff were very friendly and accommodating. The front desk team were helpful, the shuttle drivers were friendly and went the extra mile to make sure we got to our destinations, the pool area was beautiful, we felt like we were on a resort in the Caribbean. The bar staff were nice and fun and the breakfast buffet was delicious and had lots of variety. The wait staff were super nice and attentive. I almost forgot, the famous warm cookies did not disappoint!! Lastly, our balcony with the pool view was spacious, had a ceiling fan and provided a great view of the resort courtyard and pool. Overall, our stay was great. We would recommend this resort to others. " [](https://expedia.ca/Key-West-Hotels-DoubleTree-Resort-By-Hilton-Grand-Key-Key-West.h470834.Hotel-Information) ![The Gardens Hotel](https://images.trvl-media.com/lodging/1000000/30000/20800/20796/424c57d6_y.jpg) ### The Gardens Hotel 10/10 Excellent "Excellent stay. Friendly, welcoming staff. Clean, comfortable room. Nice breakfast. Great location one block from Duvall. " [](https://expedia.ca/Key-West-Hotels-The-Gardens-Hotel.h20796.Hotel-Information) ## Frequently asked questions ### What's it like visiting Downtown Key West? ### What are some hotels with pools in Downtown Key West? ### How many pool hotels are there in Downtown Key West? ### What is there to see and do in Downtown Key West? ## Explore a world of travel with Expedia - Lodging - More ways to book - [Adults Only Resorts & in Bahama Village ](https://www.expedia.ca/Bahama-Village-Key-West-Hotels-Adults-Only-Resorts.0-n553248621533115696-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [All Inclusive Resorts and in Bahama Village ](https://www.expedia.ca/Bahama-Village-Key-West-Hotels-All-Inclusive-Hotel.0-n553248621533115696-0-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Bahama Village ](https://www.expedia.ca/Bahama-Village-Key-West-Hotels-Beach-Hotel.0-n553248621533115696-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Bahama Village ](https://www.expedia.ca/Bahama-Village-Key-West-Hotels-Boutique-Hotel.0-n553248621533115696-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - 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