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) ![](https://images.trvl-media.com/place/6068599/e22dc889-0174-435e-9d9b-302d362fd045.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6068599/e22dc889-0174-435e-9d9b-302d362fd045.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 Key West Historic District Hotels with a Pool Tonight [Mar 30 - Mar 31](https://www.expedia.ca/Hotel-Search?regionId=6281809&startDate=2026-03-30&endDate=2026-03-31&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 31 - Apr 1](https://www.expedia.ca/Hotel-Search?regionId=6281809&startDate=2026-03-31&endDate=2026-04-01&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=6281809&startDate=2026-04-03&endDate=2026-04-05&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=6281809&startDate=2026-04-10&endDate=2026-04-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Key West Historic District hotels with a pool ![Outdoor pool, free cabanas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/16700/16682/a299c4a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/16700/16682/05980c06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Minibar, in-room safe, individually decorated, individually furnished](https://images.trvl-media.com/lodging/1000000/20000/16700/16682/fc1e65ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/16700/16682/048e43bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ocean Key Resort - A Noble House Resort [](https://www.expedia.ca/Key-West-Hotels-Ocean-Key-Resort-A-Noble-House-Resort.h16682.Hotel-Information) Key West Historic District 9.2/10 Wonderful (1,002 reviews) "Staff was great. Rooms were spotless. Best location in Key West." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew CA $613 CA $797 total includes taxes & fees Apr 13 - Apr 14 [](https://www.expedia.ca/Key-West-Hotels-Ocean-Key-Resort-A-Noble-House-Resort.h16682.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/1000000/910000/902100/902014/f02c0a2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/910000/902100/902014/617f7c8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/910000/902100/902014/002755fd.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) ### 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 (1,002 reviews) "Had a wonderful stay with friendly and helpful staff!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $222 CA $298 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Key-West-Hotels-Heron-House-Court-Adult-Only.h902014.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) ![Premium Room, 1 King Bed, Ocean View](https://images.trvl-media.com/lodging/1000000/10000/1000/901/8f0e07a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sports facility](https://images.trvl-media.com/lodging/1000000/10000/1000/901/c028e7a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Room, 1 King Bed, Ocean View | Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/1000/901/c6f4724b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Centric Key West Resort and Spa [](https://www.expedia.ca/Key-West-Hotels-Hyatt-Centric-Key-West-Resort-And-Spa.h901.Hotel-Information) Key West Historic District 9.0/10 Wonderful (1,000 reviews) "Great views and great combo of sunning areas with lots of available chairs, at the pool, on the dock, and in the two separate sand areas. Also really cool that there was direct access to the ocean to swim and right next to (steps away from) a small public beach. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $478 CA $635 total includes taxes & fees Apr 20 - Apr 21 [](https://www.expedia.ca/Key-West-Hotels-Hyatt-Centric-Key-West-Resort-And-Spa.h901.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/bd916166.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/1b169515.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/4caaa3f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Oceanfront Walkout Suite - King | View from room](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/14292c62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casa Marina Key West, Curio Collection by Hilton [](https://www.expedia.ca/Key-West-Hotels-Casa-Marina-Key-West.h12346.Hotel-Information) Old Town Key West 8.4/10 Very good (594 reviews) "Waterfront property in a quiet part of Key West " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Calin CA $718 CA $901 total includes taxes & fees Apr 13 - Apr 14 [](https://www.expedia.ca/Key-West-Hotels-Casa-Marina-Key-West.h12346.Hotel-Information) ![View from room](https://images.trvl-media.com/lodging/1000000/460000/457900/457821/48229e5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/460000/457900/457821/370c9c8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/460000/457900/457821/305680b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/460000/457900/457821/w2520h3836x0y4-c7128b29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Reach Key West, Curio Collection by Hilton [](https://www.expedia.ca/Key-West-Hotels-The-Reach-Key-West.h457821.Hotel-Information) Old Town Key West 8.6/10 Excellent (1,002 reviews) "Clean rooms and great staff " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Enid CA $497 CA $653 total includes taxes & fees Apr 27 - Apr 28 [](https://www.expedia.ca/Key-West-Hotels-The-Reach-Key-West.h457821.Hotel-Information) ![Courtyard](https://images.trvl-media.com/lodging/111000000/110490000/110488200/110488130/f6fb7a5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Studio Suite, 1 King Bed, Garden View, Ground Floor](https://images.trvl-media.com/lodging/111000000/110490000/110488200/110488130/d35b4a4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/111000000/110490000/110488200/110488130/ba6b4821.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/111000000/110490000/110488200/110488130/581dcd5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Douglas House - Adults Only [](https://www.expedia.ca/Key-West-Hotels-Douglas-House.h110488130.Hotel-Information) Old Town Key West 9.6/10 Exceptional (336 reviews) "Great quiet location, short walk to all major points of interest. Friendly staff and excellent amenities " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tsvetelina CA $296 CA $366 total includes taxes & fees Apr 12 - Apr 13 [](https://www.expedia.ca/Key-West-Hotels-Douglas-House.h110488130.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/57800/57730/e213aee6.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 (1,128 reviews) "Great location and great accommodation " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) robert CA $248 CA $328 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Key-West-Hotels-Heron-House-Adult-Only.h57730.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154002/d5932f21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room | Property entrance](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154002/d2f1234b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cozy King ](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154002/998684c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154002/71c648b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Garden House [](https://www.expedia.ca/Key-West-Hotels-The-Garden-House.h1154002.Hotel-Information) Key West Historic District 9.2/10 Wonderful (690 reviews) "Room was spotless, breakfast by the pool is a plus, host is always attentive to making everything right!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $333 CA $404 total includes taxes & fees Mar 31 - Apr 1 [](https://www.expedia.ca/Key-West-Hotels-The-Garden-House.h1154002.Hotel-Information) ![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) ![Free continental breakfast](https://images.trvl-media.com/lodging/20000000/19690000/19681600/19681527/76203247.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Studio Suite, 1 King Bed with Sofa bed, Accessible, Refrigerator & Microwave](https://images.trvl-media.com/lodging/20000000/19690000/19681600/19681527/02245218.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Suite, 1 King Bed with Sofa bed, Patio, Garden Area (Room 16) | Living area](https://images.trvl-media.com/lodging/20000000/19690000/19681600/19681527/1c17a8d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly [](https://www.expedia.ca/Key-West-Hotels-Alexanders-Gay-And-Lesbian-Guesthouse-Adults-Only.h19681527.Hotel-Information) Old Town Key West 9.8/10 Exceptional (142 reviews) "Staff very courteous and friendly, public spaces lovely." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul CA $411 CA $523 total includes taxes & fees Mar 31 - Apr 1 [](https://www.expedia.ca/Key-West-Hotels-Alexanders-Gay-And-Lesbian-Guesthouse-Adults-Only.h19681527.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/2000000/1710000/1709300/1709243/3b5db670.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Loft | Living area](https://images.trvl-media.com/lodging/2000000/1710000/1709300/1709243/2227d69d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite | Living area](https://images.trvl-media.com/lodging/2000000/1710000/1709300/1709243/7143a78a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite | Terrace/patio](https://images.trvl-media.com/lodging/2000000/1710000/1709300/1709243/6df6fc13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Eden House [](https://www.expedia.ca/Key-West-Hotels-Eden-House.h1709243.Hotel-Information) Key West Historic District 9.0/10 Wonderful (1,004 reviews) "The staff and guests were amazing. We will definitely be booking another stay there!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shannon CA $382 CA $482 total includes taxes & fees Apr 2 - Apr 3 [](https://www.expedia.ca/Key-West-Hotels-Eden-House.h1709243.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=2026-04-13&endDate=2026-04-14®ionId=6281809&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at hotels with a pool in Key West Historic District Breakfast included 4 stars 5 stars Hot tub Spa ## Top Key West Historic District Hotel Reviews ![Eden House](https://images.trvl-media.com/lodging/2000000/1710000/1709300/1709243/6df6fc13_y.jpg) ### Eden House 10/10 Excellent "It was great overall" [](https://expedia.ca/Key-West-Hotels-Eden-House.h1709243.Hotel-Information) ![Duval House](https://images.trvl-media.com/lodging/1000000/910000/900500/900423/9ce49b35_y.jpg) ### Duval House 8/10 Good "Breakfast menu great and staff were wonderful" [](https://expedia.ca/Key-West-Hotels-Duval-House.h900423.Hotel-Information) ![Pier House Resort & Spa](https://images.trvl-media.com/lodging/1000000/20000/19400/19307/c9267f77_y.jpg) ### Pier House Resort & Spa 2/10 Terrible "Booked a twin queen bed suite for this stay and was told it was a garden view only to discover it was a view of the parking lot. Then there was a significant water leak which flooded our room while we were out for a walk and soaked our suitcases. The repair man came while we were having dinner, however, when we returned the leak was starting to pool water in our room again. The hotel offered to switch us to a standard room and a $200 refund which I felt was rich when we had booked a suite. We weren’t interested, so thankfully Expedia issued a full refund and we drove back to Miami late that evening. " [](https://expedia.ca/Key-West-Hotels-Pier-House-Resort-Spa.h19307.Hotel-Information) ![Winslow's Bungalows - Key West Historic Inns](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/b5f8742c_y.jpg) ### Winslow's Bungalows - Key West Historic Inns 10/10 Excellent "Excellent choice for our 3 night stay. The property is beautiful, the bungalows are charming and the staff is friendly. The daily breakfast options are fresh and beautiful displayed. The property is quiet and is within walking distance to shops, historic places, and many restaurants. I give this property an A+" [](https://expedia.ca/Key-West-Hotels-Kimpton-Winslows-Bungalows.h529611.Hotel-Information) ![The Reach Key West, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/460000/457900/457821/bc3021c3_y.jpg) ### The Reach Key West, Curio Collection by Hilton 8/10 Good "The beach was perfect except when a wedding was going on it was limited and no warnings for this. There was only 1 waitress fir beach and pool orders. Also waitress didnt even knowledge us over 10 when we tried to go for breakfast so we left . The culture is wonderful except wasnt informed roosters would wake u at 4am so earplugs would have been nice . Other than that It was beautiful and enjoyable" [](https://expedia.ca/Key-West-Hotels-The-Reach-Key-West.h457821.Hotel-Information) ![Heron House Court - Adult Only](https://images.trvl-media.com/lodging/1000000/910000/902100/902014/f02c0a2a_y.jpg) ### Heron House Court - Adult Only 8/10 Good "Roman was GREAT!! Parking terrible. Once you get a parking spot, you do not want to leave until you have to. Have to walk 2 blocks and more to find a place to eat. If elderly like us, hard to get around. Very clean. Seem to be safe area. Old town charm." [](https://expedia.ca/Key-West-Hotels-Heron-House-Court-Adult-Only.h902014.Hotel-Information) ![Casa Marina Key West, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/14292c62_y.jpg) ### Casa Marina Key West, Curio Collection by Hilton 8/10 Good "Waterfront property in a quiet part of Key West " [](https://expedia.ca/Key-West-Hotels-Casa-Marina-Key-West.h12346.Hotel-Information) ![The Cabana Inn Key West - Adults Only](https://images.trvl-media.com/lodging/7000000/6580000/6576700/6576609/4d2c753c_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) ![NYAH Key West - Adults Only](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/8af6b0ce_y.jpg) ### NYAH Key West - Adults Only 6/10 Okay "The shared room with strangers. Not worth it " [](https://expedia.ca/Key-West-Hotels-NYAH-Key-West-Adults-Only.h7500588.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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