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) ![](https://images.trvl-media.com/place/501376/3b4c31fa-338d-424b-aa0f-482ad359d16a.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [Feb 6 - Feb 7](https://www.expedia.ca/Hotel-Search?regionId=553248635976470405&startDate=2026-02-06&endDate=2026-02-07&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 7 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976470405&startDate=2026-02-07&endDate=2026-02-08&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976470405&startDate=2026-02-06&endDate=2026-02-08&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976470405&startDate=2026-02-13&endDate=2026-02-15&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) ![Property grounds](https://images.trvl-media.com/lodging/1000000/910000/900500/900423/9ce49b35.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 Duplex 2 bedrooms 25 ft Balcony (Adults Only) | Living area](https://images.trvl-media.com/lodging/1000000/910000/900500/900423/83acfbb4.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 (1,003 reviews) - Soothing heated pool in the heart of Key West creates an inviting oasis amid tropical gardens at this bed and breakfast. CA $410 CA $491 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Key-West-Hotels-Duval-House.h900423.Hotel-Information) ![In-room safe, individually decorated, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/60000/57800/57730/6eb12223.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/57800/57730/c435c8cd.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) ![Porch](https://images.trvl-media.com/lodging/1000000/60000/57800/57730/3e2c6b2d.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 (1,144 reviews) - Dive into a rejuvenating outdoor pool sanctuary nestled within lush garden surroundings for a serene Key West getaway. CA $365 CA $462 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Key-West-Hotels-Heron-House-Adult-Only.h57730.Hotel-Information) ![Cabana King, Accessible | Outdoor spa tub](https://images.trvl-media.com/lodging/7000000/6580000/6576700/6576609/7de720ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite](https://images.trvl-media.com/lodging/7000000/6580000/6576700/6576609/8cc28f4a.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) ### 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 (1,005 reviews) - Splash into vibrant Key West relaxation with 24-hour access to a pristine pool and hot tub sanctuary. CA $431 CA $546 total includes taxes & fees Feb 8 - Feb 9 [](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 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/1000000/530000/529500/529427/0655c71e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/530000/529500/529427/d0e113c4.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 (735 reviews) CA $499 CA $631 total includes taxes & fees Mar 9 - Mar 10 [](https://www.expedia.ca/Key-West-Hotels-Duval-Inn.h529427.Hotel-Information) ![Sports facility](https://images.trvl-media.com/lodging/10000000/9690000/9681100/9681053/34315005.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/10000000/9690000/9681100/9681053/3a20de4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/10000000/9690000/9681100/9681053/4d274a0e.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) ### Tropical Inn [](https://www.expedia.ca/Key-West-Hotels-Tropical-Inn.h9681053.Hotel-Information) Old Town Key West 9.6/10 Exceptional (373 reviews) [](https://www.expedia.ca/Key-West-Hotels-Tropical-Inn.h9681053.Hotel-Information) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/810000/809100/809031/cb58ce3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/1000000/810000/809100/809031/37c4e4c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/810000/809100/809031/b1b91ecd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/810000/809100/809031/f9d7e75f.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 (1,002 reviews) CA $513 CA $577 total includes taxes & fees Feb 10 - Feb 11 [](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) ![Exterior](https://images.trvl-media.com/lodging/4000000/3930000/3924900/3924835/d1b7d1bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage, 2 Bedrooms (Royal Poinciana) | Living area](https://images.trvl-media.com/lodging/4000000/3930000/3924900/3924835/bab228c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/4000000/3930000/3924900/3924835/e882a768.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 (1,001 reviews) - Dreamy poolside escape awaits in this Key West oasis with outdoor pool and hot tub paradise. [](https://www.expedia.ca/Key-West-Hotels-Paradise-Inn-Key-West-Adults-Only.h3924835.Hotel-Information) ![Sundeck](https://images.trvl-media.com/lodging/1000000/980000/977400/977303/580edbc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/980000/977400/977303/4a65a2a9.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) ![Street view](https://images.trvl-media.com/lodging/1000000/980000/977400/977303/6177b123.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 (1,008 reviews) - Dive into aquatic bliss at this Art Deco hotel with a rooftop pool offering prime people-watching in the heart of Key West. CA $433 CA $556 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Key-West-Hotels-Pegasus-International-Hotel.h977303.Hotel-Information) ![In-room safe, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/37000000/36270000/36267500/36267409/b7bda456.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One Bedroom Loft Villa](https://images.trvl-media.com/lodging/37000000/36270000/36267500/36267409/142a13b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Check-in/check-out kiosk](https://images.trvl-media.com/lodging/37000000/36270000/36267500/36267409/8458c4ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Self parking (USD 15.00 per night)](https://images.trvl-media.com/lodging/37000000/36270000/36267500/36267409/d36051aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Key West Villas [](https://www.expedia.ca/Key-West-Hotels-Villas-Key-West.h36267409.Hotel-Information) Old Town Key West 9.8/10 Exceptional (251 reviews) [](https://www.expedia.ca/Key-West-Hotels-Villas-Key-West.h36267409.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/77000000/76590000/76587300/76587216/2945a17b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/77000000/76590000/76587300/76587216/5afe806a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76590000/76587300/76587216/72f139d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/77000000/76590000/76587300/76587216/e7443421.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Poolside King Room Steps from Duval! [](https://www.expedia.ca/Key-West-Hotels-Poolside-King-Room.h76587216.Hotel-Information) Old Town Key West 10/10 Exceptional (1 review) CA $682 CA $864 total includes taxes & fees Feb 16 - Feb 17 [](https://www.expedia.ca/Key-West-Hotels-Poolside-King-Room.h76587216.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=2026-02-20&endDate=2026-02-21®ionId=553248635976470405&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at hotels with a pool in Downtown Key West Breakfast included 4 stars Ocean view 5 stars Hot tub ## Top Downtown Key West Hotel Reviews ![Pegasus International Hotel](https://images.trvl-media.com/lodging/1000000/980000/977400/977303/81c4c567_y.jpg) ### Pegasus International Hotel 10/10 Excellent "Overall hotel has been refurbished and freshened up." [](https://expedia.ca/Key-West-Hotels-Pegasus-International-Hotel.h977303.Hotel-Information) ![Parrot Key Hotel & Villas](https://images.trvl-media.com/lodging/1000000/30000/24700/24615/67735d0c_y.jpg) ### Parrot Key Hotel & Villas 10/10 Excellent "This is my second time staying at the Parrot Key. Love the hotel. Beautiful property & rooms, plus the staff is always accommodating & pleasant. The hotels location is also great, just a five to eight minute drive to Duval. I would highly recommend staying there. " [](https://expedia.ca/Key-West-Hotels-Parrot-Key-Hotel-Villas.h24615.Hotel-Information) ![Hyatt Vacation Club at Beach House, Key West](https://images.trvl-media.com/lodging/1000000/860000/858000/857962/fc0a2a7e_y.jpg) ### Hyatt Vacation Club at Beach House, Key West 10/10 Excellent "It was a great experience and the room was amazing would definitely come back here on our next vacation " [](https://expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Beach-House.h857962.Hotel-Information) ![Almond Tree Inn Hotel - Adults Only](https://images.trvl-media.com/lodging/1000000/810000/809100/809031/3d7c7063_y.jpg) ### Almond Tree Inn Hotel - Adults Only 10/10 Excellent "Excellent hotel in a great location just off Duval Street. The staff were very attentive, rooms clean. " [](https://expedia.ca/Key-West-Hotels-Almond-Tree-Inn.h809031.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 "The room was very nice and homey feeling. The staff was very nice. We enjoyed breakfast lunch and diner at the restaurant the Waite staff was very friendly and food was good. We enjoyed the shuttle that is offered the drivers were knowledgeable about the island and history. Jeffery was the best. We would definitely stay there again. " [](https://expedia.ca/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.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 "Everything was great" [](https://expedia.ca/Key-West-Hotels-Heron-House-Adult-Only.h57730.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 "Flawless." [](https://expedia.ca/Key-West-Hotels-DoubleTree-Resort-By-Hilton-Grand-Key-Key-West.h470834.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 "Great property! We had a junior suite and it was extremely spacious. The staff was very nice and the free shuttle to Duval St was a great perk. My only complaint was that nobody, but nobody told you to make a reservation for the free shuttle. I talked to multiple people at the front desk, concierge and on the phone… not one word about making a reservation. We saw countless people deal with that same situation. Kinda frustrating getting told you can’t get on the shuttle when you’ve been waiting for up to an hour. " [](https://expedia.ca/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.Hotel-Information) ![The Perry Hotel & Marina Key West](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/e4eb7fd5_y.jpg) ### The Perry Hotel & Marina Key West 10/10 Excellent "The Perry Hotel was a great experience. Traveled with a friend and stayed in a Mangrove room. Rooms were clean and well cared for. Pool and outside area is clean too. Although outside of downtown, there is a free shuttle that takes you downtown. If you are planning a specific time to go into town, you should ask if the shuttle is typically busy or not. It is first come first serve. Restaurants are great for breakfast or lunch when you arrive. It was a great quiet place to stay with the benefit of being on the water and being able to walk around the docks. Some excursions go out from the marinas as well. " [](https://expedia.ca/Key-West-Hotels-The-Perry-Hotel-Marina-Key-West.h17313680.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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