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 [Apr 2 - Apr 3](https://www.expedia.ca/Hotel-Search?regionId=6281809&startDate=2026-04-02&endDate=2026-04-03&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Apr 3 - Apr 4](https://www.expedia.ca/Hotel-Search?regionId=6281809&startDate=2026-04-03&endDate=2026-04-04&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 ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/bd916166.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/1b169515.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/12400/12346/7df2a82d.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 (597 reviews) - Crystal blue waters beckon from private beach paradise with 2 outdoor pools and a luxurious beachside bar. CA $637 CA $810 total includes taxes & fees Apr 15 - Apr 16 [](https://www.expedia.ca/Key-West-Hotels-Casa-Marina-Key-West.h12346.Hotel-Information) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/20000/16700/16682/2317df22.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/16700/16682/05980c06.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) - Float in the outdoor pool with Key West sunset views, poolside loungers, and bar service for luxury. CA $565 CA $743 total includes taxes & fees Apr 21 - Apr 22 [](https://www.expedia.ca/Key-West-Hotels-Ocean-Key-Resort-A-Noble-House-Resort.h16682.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 | Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/1000/901/c6f4724b.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/cd7c9771.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) ### 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 (1,002 reviews) CA $475 CA $631 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) ![Porch](https://images.trvl-media.com/lodging/1000000/910000/902100/902014/f02c0a2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Tropical King](https://images.trvl-media.com/lodging/1000000/910000/902100/902014/7d668ce0.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) ![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 (1,011 reviews) - Escape to a sun-soaked paradise with a peaceful outdoor pool, just steps from Duval Street and Hemingway's historic home. CA $269 CA $351 total includes taxes & fees Apr 13 - Apr 14 [](https://www.expedia.ca/Key-West-Hotels-Heron-House-Court-Adult-Only.h902014.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) ![Daily buffet breakfast for a fee](https://images.trvl-media.com/lodging/1000000/460000/457900/457821/98c792a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch, dinner, brunch served; local cuisine ](https://images.trvl-media.com/lodging/1000000/460000/457900/457821/9f3b5b61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/1000000/460000/457900/457821/1fd13a40.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 (1,000 reviews) - Beachfront pool paradise with private loungers and poolside bar service at this Key West resort. CA $450 CA $600 total includes taxes & fees May 3 - May 4 [](https://www.expedia.ca/Key-West-Hotels-The-Reach-Key-West.h457821.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) ![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) ![Garden](https://images.trvl-media.com/lodging/1000000/910000/900500/900423/1fc21e10.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 (1,016 reviews) - Soothing heated pool in the heart of Key West creates an inviting oasis amid tropical gardens at this bed and breakfast. CA $345 CA $419 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Key-West-Hotels-Duval-House.h900423.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) ![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) ![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) ### Douglas House - Adults Only [](https://www.expedia.ca/Key-West-Hotels-Douglas-House.h110488130.Hotel-Information) Old Town Key West 9.6/10 Exceptional (338 reviews) - Tropical poolside sanctuary just steps from Duval Street offers a heated outdoor pool surrounded by lush gardens and privacy. CA $295 CA $365 total includes taxes & fees Apr 13 - Apr 14 [](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) ![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) ![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 (1,126 reviews) - Dive into a rejuvenating outdoor pool sanctuary nestled within lush garden surroundings for a serene Key West getaway. CA $267 CA $349 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Key-West-Hotels-Heron-House-Adult-Only.h57730.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) ![View from room](https://images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/360a1c60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/841e73b6.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/18000000/17450000/17442800/17442701/0acd853b.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 (1,073 reviews) CA $484 CA $599 total includes taxes & fees Apr 19 - Apr 20 [](https://www.expedia.ca/Key-West-Hotels-Opal-Key-Resort-Marina.h17442701.Hotel-Information) ![Building design](https://images.trvl-media.com/lodging/5000000/4290000/4280800/4280752/a8250942.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4290000/4280800/4280752/34b65216.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/5000000/4290000/4280800/4280752/f1874592.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/5000000/4290000/4280800/4280752/f4becc1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Southernmost Inn - Adults Only [](https://www.expedia.ca/Key-West-Hotels-The-Southernmost-Inn-Adults-Only.h4280752.Hotel-Information) Old Town Key West 8.4/10 Very good (1,290 reviews) - Dive into azure bliss at this Key West adults-only retreat with two pristine pools, hot tub sanctuary, and poolside loungers. CA $374 CA $484 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Key-West-Hotels-The-Southernmost-Inn-Adults-Only.h4280752.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=2026-04-16&endDate=2026-04-17®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 ![Opal Key Resort & Marina, Key West](https://images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/360a1c60_y.jpg) ### Opal Key Resort & Marina, Key West 10/10 Excellent "Perfection " [](https://expedia.ca/Key-West-Hotels-Opal-Key-Resort-Marina.h17442701.Hotel-Information) ![The Southernmost Inn - Adults Only](https://images.trvl-media.com/lodging/5000000/4290000/4280800/4280752/a8250942_y.jpg) ### The Southernmost Inn - Adults Only 10/10 Excellent "Only a half block off upper Duval and a five minute walk to the beach! Very near great restaurants and bars with live entertainment! " [](https://expedia.ca/Key-West-Hotels-The-Southernmost-Inn-Adults-Only.h4280752.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 10/10 Excellent "The rooms need some painting around windows, doorstrim, etc. They and bathroom are spacious. Would stay again." [](https://expedia.ca/Key-West-Hotels-Heron-House-Court-Adult-Only.h902014.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 "My husband and I had a spectacular time at this resort. Looking forward to coming back real soon! The food and location were perfect!" [](https://expedia.ca/Key-West-Hotels-Pier-House-Resort-Spa.h19307.Hotel-Information) ![Duval House](https://images.trvl-media.com/lodging/1000000/910000/900500/900423/9ce49b35_y.jpg) ### Duval House 10/10 Excellent "Very accommodating. Very friendly. Excellent facilities, breakfast, pool. Will definitely stay again!!" [](https://expedia.ca/Key-West-Hotels-Duval-House.h900423.Hotel-Information) ![Southernmost Beach Resort and Guesthouses](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/546caf1e_y.jpg) ### Southernmost Beach Resort and Guesthouses 10/10 Excellent "Clean and very friendly staff. Beach view adequate for side of building. Great breakfast variety. Overall, enjoyable experience. " [](https://expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) ![The Marker Key West Harbor Resort](https://images.trvl-media.com/lodging/10000000/9150000/9148400/9148379/821176b1_y.jpg) ### The Marker Key West Harbor Resort 8/10 Good "We stayed at the Marker for our anniversary in a Harbor View room. Room was very nice and we looked out over a marina and had a nice balcony to sit out and enjoy a glass of wine. Breakfast was good at the bar by the pool but not great. Staff very friendly and helpful. Good enough fitness room to get a decent workout in but no universal machines. Close enough to walk to just about anything you need. If you do stay in the Herbirview room be aware that the Schooner Bar across the path plays music til around 11 am or later each night and you can hear it from your room though it’s muffled. The first night we were there the band playing was way too loud and I could hear the words of the songs inside my room while the door was closed. But if you want a very nice hotel with 3 pools and attentive staff in a great location whilst having the Key West vibe all around you the Marker is very good. " [](https://expedia.ca/Key-West-Hotels-The-Marker-Key-West-Harbor-Resort.h9148379.Hotel-Information) ![Southwinds Motel](https://images.trvl-media.com/lodging/9000000/8990000/8984500/8984451/45887e0a_y.jpg) ### Southwinds Motel 10/10 Excellent "My husband and I had a great time. The staff was friendly, this is a great location for the price. The Tipsy Rooster was fantastic, the drinks and music were perfect. We will be back" [](https://expedia.ca/Key-West-Hotels-Southwinds-Motel.h8984451.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 "Second time we have stayed here.Staff is excellent, accommodating. The property is very well maintained and a great location." [](https://expedia.ca/Key-West-Hotels-Kimpton-Winslows-Bungalows.h529611.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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