Title: Book the Best Hotels with POOL in Old Town Key West in 2026 | Expedia.ca [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)[Old Town Key West Car Rentals](https://expedia.ca/Car-Rentals-In-Old-Town-Key-West.d553248635976481920.Car-Rental-Guide)[Old Town Key West Vacations](https://expedia.ca/Old-Town-Key-West.d553248635976481920.Destination-Travel-Guides) ![Key West Lighthouse and Keeper\'s Quarters Museum featuring a lighthouse](https://images.trvl-media.com/place/501383/0a79f1bb-7c8b-43da-830f-8c77ccf8ffbb.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Old Town Key West, FL from CA $194 - ![](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 Old Town Key West Hotels with a Pool Tonight [Dec 12 - Dec 13](https://www.expedia.ca/Hotel-Search?regionId=553248635976481920&startDate=2025-12-12&endDate=2025-12-13&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 13 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976481920&startDate=2025-12-13&endDate=2025-12-14&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976481920&startDate=2025-12-12&endDate=2025-12-14&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976481920&startDate=2025-12-19&endDate=2025-12-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Old Town Key West hotels with a pool ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/57800/57730/04396af1.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/57800/57730/705cf1b1.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) ### 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 (1132) "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 14 - Dec 15 [](https://www.expedia.ca/Key-West-Hotels-Heron-House-Adult-Only.h57730.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) ![Suite, 1 King Bed with Sofa bed (ADULT ONLY)](https://images.trvl-media.com/lodging/5000000/4290000/4280800/4280752/ee1be58b.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) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/5000000/4290000/4280800/4280752/db77bb38.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 8.2/10 Very good (1204) "Great rooms, clean great friendly staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ryan CA $164 CA $246 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Key-West-Hotels-The-Southernmost-Inn-Adults-Only.h4280752.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) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/900000/894100/894030/14ad35b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/900000/894100/894030/f9b09089.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) ### Silver Palms Inn [](https://www.expedia.ca/Key-West-Hotels-Silver-Palms-Inn.h894030.Hotel-Information) Old Town Key West 9.4/10 Exceptional (1018) "We had a wonderful stay and it was a convenient location for all the activities along Duval Street. The room was clean & comfortable with a great breakfast." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susanne CA $185 CA $301 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Key-West-Hotels-Silver-Palms-Inn.h894030.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) ![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) ![Garden](https://images.trvl-media.com/lodging/1000000/910000/900500/900423/d8ea2dc3.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) ![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) ![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) ![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) ![3 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/69828d6c.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 (2919) "Great stay with an actual beach which is rare in Key West. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $284 CA $420 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.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) ![Exterior](https://images.trvl-media.com/lodging/58000000/57740000/57737100/57737081/1739e347.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker](https://images.trvl-media.com/lodging/58000000/57740000/57737100/57737081/38d0f336.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) ### 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 (143) "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 $135 CA $362 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Key-West-Hotels-CORTEZ-Adults-Only.h57737081.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/530000/529300/529277/66df4261.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 (1000) "This guest house was excellent, breakfast was decent, had everything you needed." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) David CA $173 CA $194 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Key-West-Hotels-Authors-Of-Key-West-Guest-House.h529277.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) ![Garden](https://images.trvl-media.com/lodging/10000000/9690000/9681100/9681053/bbaba58e.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) ![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) ### 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) ![Exterior](https://images.trvl-media.com/lodging/111000000/110490000/110488200/110488130/46602c80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Apartment, 1 Queen Bed, City View, Annex Building | Private kitchen](https://images.trvl-media.com/lodging/111000000/110490000/110488200/110488130/c002f8c1.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) ![Exterior](https://images.trvl-media.com/lodging/111000000/110490000/110488200/110488130/ba6b4821.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Douglas House [](https://www.expedia.ca/Key-West-Hotels-Douglas-House.h110488130.Hotel-Information) Old Town Key West 9.6/10 Exceptional (222) "Very clean room, loved the location!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey Ray CA $189 CA $234 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Key-West-Hotels-Douglas-House.h110488130.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) ![Exterior](https://images.trvl-media.com/lodging/18000000/17450000/17442800/17442701/acfeb5a7.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 (1019) "Our stay was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard CA $357 CA $456 total includes taxes & fees Dec 17 - Dec 18 [](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=2025-12-26&endDate=2025-12-27®ionId=553248635976481920&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Price trends for hotels in Old Town Key West | Less expensive | More expensive | This month | Next month | | -------------- | -------------- | ---------- | ---------- | | August | February | CA $454 | CA $568 | | Month | Price | | --------- | ------- | | January | CA $568 | | February | CA $653 | | March | CA $602 | | April | CA $575 | | May | CA $462 | | June | CA $397 | | July | CA $380 | | August | CA $319 | | September | CA $323 | | October | CA $379 | | November | CA $415 | | December | CA $454 | Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed hotels in Old Town Key West. Select dates and complete search for nightly totals inclusive of taxes and fees. ## Top Old Town Key West Hotel Reviews ![The Palms Hotel](https://images.trvl-media.com/lodging/1000000/60000/57700/57655/70e7ac88_y.jpg) ### The Palms Hotel 10/10 Excellent "Everything was great!" [](https://expedia.ca/Key-West-Hotels-The-Palms-Hotel.h57655.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) ![Lighthouse Hotel - Key West Historic Inns](https://images.trvl-media.com/lodging/2000000/1180000/1171100/1171079/2155599f_y.jpg) ### Lighthouse Hotel - Key West Historic Inns 10/10 Excellent "Was beautiful property! Second time staying there and Loved breakfast and swinging egg chairs were awesome! Everyone was very helpful and super nice. We will be back! " [](https://expedia.ca/Key-West-Hotels-Kimpton-Lighthouse-Hotel.h1171079.Hotel-Information) ![Southwinds Motel](https://images.trvl-media.com/lodging/9000000/8990000/8984500/8984451/83ae09e3_y.jpg) ### Southwinds Motel 10/10 Excellent "Really sweet little place with fantastic beach access. The beach is a block away but the hotel provides free towels and long chairs with umbrellas. Nice cuban deli across the street. Close to Duval but without its busy-ness. " [](https://expedia.ca/Key-West-Hotels-Southwinds-Motel.h8984451.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 "Great view, amazing room and friendly staff" [](https://expedia.ca/Key-West-Hotels-The-Reach-Key-West.h457821.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) ![The Southernmost Inn - Adults Only](https://images.trvl-media.com/lodging/5000000/4290000/4280800/4280752/2b7e8bad_y.jpg) ### The Southernmost Inn - Adults Only 10/10 Excellent "Great little Gem for sure. " [](https://expedia.ca/Key-West-Hotels-The-Southernmost-Inn-Adults-Only.h4280752.Hotel-Information) ![Ella's Cottages - Key West Historic Inns](https://images.trvl-media.com/lodging/1000000/870000/863200/863188/deb4f031_y.jpg) ### Ella's Cottages - Key West Historic Inns 10/10 Excellent "Breakfast on the porch every morning was a great start to our days" [](https://expedia.ca/Key-West-Hotels-Kimpton-Ellas-Cottages.h863188.Hotel-Information) ## Frequently asked questions ### What's it like visiting Old Town Key West? ### What are some hotels with pools in Old Town Key West? ### How many pool hotels are there in Old Town Key West? ### What is there to see and do in Old Town Key West? ## 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) - 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