Title: Book the Best Hotels with POOL in Key West Historic District in 2026 | Expedia.ca [Key West Historic District Travel Guide](https://expedia.ca/Key-West-Key-West-Historic-District.dx6281809)[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)[Key West Historic District Car Rentals](https://expedia.ca/Car-Rentals-In-Key-West-Historic-District.d6281809.Car-Rental-Guide)[Key West Historic District Vacations](https://expedia.ca/Key-West-Historic-District.d6281809.Destination-Travel-Guides) ![Audubon House and Tropical Gardens featuring a house](https://images.trvl-media.com/place/6068599/e22dc889-0174-435e-9d9b-302d362fd045.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Key West Historic District, FL from CA $305 - ![](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 Key West Historic District Hotels with a Pool Tonight [Dec 29 - Dec 30](https://www.expedia.ca/Hotel-Search?regionId=6281809&startDate=2025-12-29&endDate=2025-12-30&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 30 - Dec 31](https://www.expedia.ca/Hotel-Search?regionId=6281809&startDate=2025-12-30&endDate=2025-12-31&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6281809&startDate=2026-01-02&endDate=2026-01-04&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=6281809&startDate=2026-01-09&endDate=2026-01-11&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Key West Historic District hotels with a pool ![Outdoor spa tub](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/77f11bb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![NYAH Private Balcony Room 6 Single Beds | Balcony view](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/a350e3cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/eb10500d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Quadruple Room](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/070a211a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NYAH Key West - Adults Only [](https://www.expedia.ca/Key-West-Hotels-NYAH-Key-West-Adults-Only.h7500588.Hotel-Information) Key West Historic District 8.0/10 Very good (1003) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Venkata Durga Phanindra Reddy [](https://www.expedia.ca/Key-West-Hotels-NYAH-Key-West-Adults-Only.h7500588.Hotel-Information) ![3 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/026f10af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor wedding area](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/4eda9d17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine, beach views ](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/8f43a3d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fountain](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/b4576547.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Southernmost Beach Resort and Guesthouses [](https://www.expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) Old Town Key West 8.8/10 Excellent (2958) "Wonderful stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elisa CA $404 CA $554 total includes taxes & fees Jan 13 - Jan 14, 2026 [](https://www.expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) ![Courtyard](https://images.trvl-media.com/lodging/1000000/910000/900500/900423/9013d891.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) ![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) ### Duval House [](https://www.expedia.ca/Key-West-Hotels-Duval-House.h900423.Hotel-Information) Old Town Key West 9.4/10 Exceptional (1003) "Great place! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $340 CA $412 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Key-West-Hotels-Duval-House.h900423.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) ![Mini Suite, 1 King Bed, Accessible](https://images.trvl-media.com/lodging/4000000/3930000/3924900/3924835/70d203b0.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) ### 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 (1006) "Great stay! Close to Duval Street." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Manuel CA $442 CA $559 total includes taxes & fees Jan 15 - Jan 16, 2026 [](https://www.expedia.ca/Key-West-Hotels-Paradise-Inn-Key-West-Adults-Only.h3924835.Hotel-Information) ![Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/910000/902100/902014/4d24feec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/910000/902100/902014/8717bede.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/1000000/910000/902100/902014/769f8ec7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/1000000/910000/902100/902014/b2259b66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heron House Court - Adult Only [](https://www.expedia.ca/Key-West-Hotels-Heron-House-Court-Adult-Only.h902014.Hotel-Information) Key West Historic District 9.0/10 Wonderful (1003) "Great staff, very friendly. Oerfect location, short walk to Duval, but far enough to get sleep. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chandler CA $229 CA $305 total includes taxes & fees Jan 19 - Jan 20, 2026 [](https://www.expedia.ca/Key-West-Hotels-Heron-House-Court-Adult-Only.h902014.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/58000000/57740000/57737100/57737081/5cbc0ea9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/58000000/57740000/57737100/57737081/1809a710.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/58000000/57740000/57737100/57737081/967dbb83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/58000000/57740000/57737100/57737081/1739e347.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### CORTEZ \~ Adults Only, King Room w/Pool View at Azul Mansion! [](https://www.expedia.ca/Key-West-Hotels-CORTEZ-Adults-Only.h57737081.Hotel-Information) Old Town Key West 9.6/10 Exceptional (144) "Great property. Lots of thoughtful amenities. Management friendly and responsive. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Diane V. CA $168 CA $402 total includes taxes & fees Jan 8 - Jan 9, 2026 [](https://www.expedia.ca/Key-West-Hotels-CORTEZ-Adults-Only.h57737081.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/57800/57730/c435c8cd.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 (1140) "Clean room and staff was great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul CA $294 CA $380 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Key-West-Hotels-Heron-House-Adult-Only.h57730.Hotel-Information) ![Room, Non Smoking, Private Bathroom](https://images.trvl-media.com/lodging/1000000/530000/529300/529277/657b5047.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Non Smoking, Private Bathroom | Bathroom](https://images.trvl-media.com/lodging/1000000/530000/529300/529277/8dc2c8b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/530000/529300/529277/1e7ddd15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/530000/529300/529277/81aa846c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Authors of Key West Guest House [](https://www.expedia.ca/Key-West-Hotels-Authors-Of-Key-West-Guest-House.h529277.Hotel-Information) Old Town Key West 9.0/10 Wonderful (1003) "Everyone was awesome and the rooms and pool was great also" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary CA $282 CA $317 total includes taxes & fees Jan 12 - Jan 13, 2026 [](https://www.expedia.ca/Key-West-Hotels-Authors-Of-Key-West-Guest-House.h529277.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) ![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) ![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) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/900000/894100/894030/14ad35b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Silver Palms Inn [](https://www.expedia.ca/Key-West-Hotels-Silver-Palms-Inn.h894030.Hotel-Information) Old Town Key West 9.4/10 Exceptional (1005) "Very friendly staff, directly in City Center. " ![Germany](https://a.travel-assets.com/egds/marks/flags/de.svg) Philip CA $331 CA $465 total includes taxes & fees Jan 19 - Jan 20, 2026 [](https://www.expedia.ca/Key-West-Hotels-Silver-Palms-Inn.h894030.Hotel-Information) ![View from room](https://images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/137c65ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/6cf9bef0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/3ac97dbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/f2c5f58d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Opal Key Resort & Marina, Key West [](https://www.expedia.ca/Key-West-Hotels-Opal-Key-Resort-Marina.h17442701.Hotel-Information) Old Town Key West 9.2/10 Wonderful (1029) "Our stay was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard CA $573 CA $698 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Key-West-Hotels-Opal-Key-Resort-Marina.h17442701.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=2026-01-12&endDate=2026-01-13®ionId=6281809&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Key West Historic District Hotel Reviews ![Southwinds Motel](https://images.trvl-media.com/lodging/9000000/8990000/8984500/8984451/83ae09e3_y.jpg) ### Southwinds Motel 10/10 Excellent "This hotel is very old but clean and comfortable. The people are very nice and helpful. The location is very close to the beach and southernmost point marker." [](https://expedia.ca/Key-West-Hotels-Southwinds-Motel.h8984451.Hotel-Information) ![The Palms Hotel](https://images.trvl-media.com/lodging/1000000/60000/57700/57655/70e7ac88_y.jpg) ### The Palms Hotel 10/10 Excellent "Welcoming and walking distance from everything! Will come back " [](https://expedia.ca/Key-West-Hotels-The-Palms-Hotel.h57655.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 "Bed was not so great rest was" [](https://expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) ![Pier House Resort & Spa](https://images.trvl-media.com/lodging/1000000/20000/19400/19307/c9267f77_y.jpg) ### Pier House Resort & Spa 10/10 Excellent "The best " [](https://expedia.ca/Key-West-Hotels-Pier-House-Resort-Spa.h19307.Hotel-Information) ![The Reach Key West, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/460000/457900/457821/888fac6b_y.jpg) ### The Reach Key West, Curio Collection by Hilton 10/10 Excellent "Hotel was beautiful. My view from my balcony was fantastic. The staff were really friendly " [](https://expedia.ca/Key-West-Hotels-The-Reach-Key-West.h457821.Hotel-Information) ![NYAH Key West - Adults Only](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/77f11bb4_y.jpg) ### NYAH Key West - Adults Only 10/10 Excellent "Great staff. Close to everything. " [](https://expedia.ca/Key-West-Hotels-NYAH-Key-West-Adults-Only.h7500588.Hotel-Information) ![Silver Palms Inn](https://images.trvl-media.com/lodging/1000000/900000/894100/894030/dc763054_y.jpg) ### Silver Palms Inn 10/10 Excellent "Clean rooms with a balcony, nice stuff 24/7, all you need is here like a pool with pool towels, breakfast, parking inc parking for rented bikes. " [](https://expedia.ca/Key-West-Hotels-Silver-Palms-Inn.h894030.Hotel-Information) ![Opal Key Resort & Marina, Key West](https://images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/f2c5f58d_y.jpg) ### Opal Key Resort & Marina, Key West 10/10 Excellent "Great location. Staff is very friendly." [](https://expedia.ca/Key-West-Hotels-Opal-Key-Resort-Marina.h17442701.Hotel-Information) ![La Concha Key West, Autograph Collection](https://images.trvl-media.com/lodging/1000000/10000/3900/3853/aebf156d_y.jpg) ### La Concha Key West, Autograph Collection 10/10 Excellent "The rooms were clean! Bathroom" [](https://expedia.ca/Key-West-Hotels-Crowne-Plaza-Key-West-La-Concha.h3853.Hotel-Information) ## Frequently asked questions ### What's it like visiting Key West Historic District? ### What are some accommodations with pools in Key West Historic District? ### How many hotels with pools will I find in Key West Historic District? ### What is there to see and do in Key West Historic District? ## Explore a world of travel with Expedia - Lodging - More ways to book - [Cheap Hotels in Bahia Honda Key ](https://www.expedia.ca/Bahia-Honda-Key-Hotels-Cheap-Hotels.0-0-d553248635083902001-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Bahia Honda Key ](https://www.expedia.ca/Bahia-Honda-Key-Hotels-Luxury-Hotel.0-0-d553248635083902001-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Flamingo ](https://www.expedia.ca/Flamingo-Hotels-Adults-Only-Resorts.0-0-d553248635074842070-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Flamingo ](https://www.expedia.ca/Flamingo-Hotels-Beach-Hotel.0-0-d553248635074842070-tBeachHotel.Travel-Guide-Filter-Hotels) - 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