Title: The Best Hotels with a Pool in Cudjoe Key from $188 in 2026 | Expedia.com [Cudjoe Key Travel Guide](https://expedia.com/Cudjoe-Key.dx3000430966)[Hotels in Cudjoe Key](https://expedia.com/Cudjoe-Key-Hotels.d3000430966.Travel-Guide-Hotels)[Vacation Rentals in Cudjoe Key](https://expedia.com/Cudjoe-Key-Vacation-Rentals.d3000430966.Travel-Guide-VacationRentals)[Flights to Cudjoe Key](https://expedia.com/Cheap-Flights-To-Cudjoe-Key.d3000430966.Travel-Guide-Flights)[Things to do in Cudjoe Key](https://expedia.com/Things-To-Do-In-Cudjoe-Key.d3000430966.Travel-Guide-Activities)[Car Rentals in Cudjoe Key](https://expedia.com/Car-Rentals-In-Cudjoe-Key.d3000430966.Car-Rental-Guide)[Cudjoe Key Vacation Packages](https://expedia.com/Cudjoe-Key.d3000430966.Destination-Travel-Guides) ![Venture Out in Cudjoe Key, Florida Keys. ](https://images.trvl-media.com/place/3000430966/daf5ff89-9933-4bcf-aacf-f9b64b3fe505.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/3000430966/daf5ff89-9933-4bcf-aacf-f9b64b3fe505.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Upfront pricing Our total price for your stay includes taxes and fees - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save 10% or more on over 100,000 hotels worldwide with Member Prices [Learn about One Key](https://www.expedia.com/welcome-one-key) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Cudjoe Key Hotels with a Pool Tonight [Mar 3 - Mar 4](https://www.expedia.com/Hotel-Search?regionId=3000430966&startDate=2026-03-03&endDate=2026-03-04&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 4 - Mar 5](https://www.expedia.com/Hotel-Search?regionId=3000430966&startDate=2026-03-04&endDate=2026-03-05&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 6 - Mar 8](https://www.expedia.com/Hotel-Search?regionId=3000430966&startDate=2026-03-06&endDate=2026-03-08&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=3000430966&startDate=2026-03-13&endDate=2026-03-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Cudjoe Key hotels with a pool ![Exterior](https://images.trvl-media.com/lodging/70000000/69810000/69809300/69809218/d227c1d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/70000000/69810000/69809300/69809218/c4c56e7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sport court](https://images.trvl-media.com/lodging/70000000/69810000/69809300/69809218/ea553f5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/70000000/69810000/69809300/69809218/3942591a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Canal front lot only. No house or RV. You need to bring your RV. [](https://www.expedia.com/Summerland-Key-Hotels-Canal-Front-RV-Lot-Quick-Access-To-Atlantic-Ocean-Or-Gulf.h69809218.Hotel-Information) Cudjoe Key 10/10 Exceptional (2 reviews) $169 nightly $188 total Mar 31 - Apr 1 Total with taxes and fees [](https://www.expedia.com/Summerland-Key-Hotels-Canal-Front-RV-Lot-Quick-Access-To-Atlantic-Ocean-Or-Gulf.h69809218.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/74000000/73240000/73238600/73238505/925121e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/74000000/73240000/73238600/73238505/ce4bddc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/74000000/73240000/73238600/73238505/db40386c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73240000/73238600/73238505/4d3ccae9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West [](https://www.expedia.com/Summerland-Key-Hotels-Old-Florida-Style.h73238505.Hotel-Information) Cudjoe Key 9.0/10 Wonderful (56 reviews) $413 nightly $458 total Mar 11 - Mar 12 Total with taxes and fees [](https://www.expedia.com/Summerland-Key-Hotels-Old-Florida-Style.h73238505.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/34000000/33570000/33564800/33564734/f4a6c5c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33570000/33564800/33564734/a7df710a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33570000/33564800/33564734/070ba9c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/34000000/33570000/33564800/33564734/ef0fcc3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private Oceanfront Cottage with dockage, pool just minutes to Key West! [](https://www.expedia.com/Summerland-Key-Hotels-Private-Oceanfront-Cottage-With-Dockage.h33564734.Hotel-Information) Cudjoe Key 8.6/10 Excellent (165 reviews) $317 nightly $351 total Mar 12 - Mar 13 Total with taxes and fees [](https://www.expedia.com/Summerland-Key-Hotels-Private-Oceanfront-Cottage-With-Dockage.h33564734.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/34000000/33560000/33557700/33557696/012c9f08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33560000/33557700/33557696/caa3fc2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/34000000/33560000/33557700/33557696/3b42facf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33560000/33557700/33557696/e1365b54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quaint cottage, pool, dockage just minutes to Key West! [](https://www.expedia.com/Summerland-Key-Hotels-Quaint-Cottage.h33557696.Hotel-Information) Cudjoe Key 9.0/10 Wonderful (150 reviews) $398 nightly $441 total Mar 10 - Mar 11 Total with taxes and fees [](https://www.expedia.com/Summerland-Key-Hotels-Quaint-Cottage.h33557696.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/1020b125.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/080e8cfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/6bfc69e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/5f412538.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### $$ SAVE BIG $$ MARCH! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS! [](https://www.expedia.com/Cudjoe-Key-Hotels-Ocean-Paradise-AT-Venture-OUT-4-Bikes-2-2-Person-Kayaks.h44556643.Hotel-Information) Cudjoe Key 9.8/10 Exceptional (85 reviews) $445 nightly $494 total Mar 5 - Mar 6 Total with taxes and fees [](https://www.expedia.com/Cudjoe-Key-Hotels-Ocean-Paradise-AT-Venture-OUT-4-Bikes-2-2-Person-Kayaks.h44556643.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/112000000/111540000/111535500/111535402/w2641h1530x1y4-f00b5aa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/112000000/111540000/111535500/111535402/w2720h1531x0y0-d54bbbc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Villa, Ocean View | Garden view](https://images.trvl-media.com/lodging/112000000/111540000/111535500/111535402/w1153h1530x0y2-2909ca24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Villa, Ocean View | 4 bedrooms, individually decorated, individually furnished](https://images.trvl-media.com/lodging/112000000/111540000/111535500/111535402/w2304h1532x8y4-86de2f42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Atlantic View Luxury Villa with Pool [](https://www.expedia.com/Summerland-Key-Hotels-Atlantic-View-Luxury-Villa-With-Pool.h111535402.Hotel-Information) Summerland Key 10/10 Exceptional (1 review) - Private plunge pool paradise unfolds with Atlantic views and 7 outdoor oases for sun-drenched days. $975 nightly $1,097 total Mar 15 - Mar 16 Total with taxes and fees [](https://www.expedia.com/Summerland-Key-Hotels-Atlantic-View-Luxury-Villa-With-Pool.h111535402.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/117000000/116670000/116667100/116667062/8bf693c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/117000000/116670000/116667100/116667062/d1732c67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116670000/116667100/116667062/09f11ae8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, table tennis, books](https://images.trvl-media.com/lodging/117000000/116670000/116667100/116667062/627e8283.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access [](https://www.expedia.com/Summerland-Key-Hotels-Planktons-Palace-Cozy-2BR-Getaway-In-Oceanfront-Resort-Community-With-Patio-Island-Vibes.h116667062.Hotel-Information) Cudjoe Key 10/10 Exceptional (1 review) $553 nightly $614 total Mar 4 - Mar 5 Total with taxes and fees [](https://www.expedia.com/Summerland-Key-Hotels-Planktons-Palace-Cozy-2BR-Getaway-In-Oceanfront-Resort-Community-With-Patio-Island-Vibes.h116667062.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/62000000/61590000/61585200/61585151/4681bad1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/62000000/61590000/61585200/61585151/16e13244.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/62000000/61590000/61585200/61585151/bce2dd72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/62000000/61590000/61585200/61585151/94e4b670.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Canal front, dockage, 2 bedroom, 2 bath [](https://www.expedia.com/Summerland-Key-Hotels-Canal-Front.h61585151.Hotel-Information) Cudjoe Key 9.0/10 Wonderful (93 reviews) $445 nightly $493 total Mar 9 - Mar 10 Total with taxes and fees [](https://www.expedia.com/Summerland-Key-Hotels-Canal-Front.h61585151.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/105000000/104880000/104875300/104875207/ce42ac53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/105000000/104880000/104875300/104875207/6ca864aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/105000000/104880000/104875300/104875207/2f62f857.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/105000000/104880000/104875300/104875207/20868446.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Endless Summer Hideaway - lot 181 [](https://www.expedia.com/Summerland-Key-Hotels-Endless-Summer-Hideaway-Lot-181.h104875207.Hotel-Information) Cudjoe Key $272 nightly $293 total Mar 4 - Mar 5 Total with taxes and fees [](https://www.expedia.com/Summerland-Key-Hotels-Endless-Summer-Hideaway-Lot-181.h104875207.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/32000000/31900000/31892500/31892418/7a3fc564.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/32000000/31900000/31892500/31892418/6a3c7406.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/32000000/31900000/31892500/31892418/39a5429b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/32000000/31900000/31892500/31892418/98e9c6b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Home [](https://www.expedia.com/Cudjoe-Key-Hotels-Waterfront-Home.h31892418.Hotel-Information) Cudjoe Key 8.6/10 Excellent (178 reviews) $438 nightly $486 total Mar 11 - Mar 12 Total with taxes and fees [](https://www.expedia.com/Cudjoe-Key-Hotels-Waterfront-Home.h31892418.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.com/Hotel-Search?startDate=2026-03-17&endDate=2026-03-18®ionId=3000430966&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at hotels with a pool in Cudjoe Key Breakfast included 4 stars 5 stars Hot tub Spa ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=AFFINITY_SPRING_PROMO_3000430966) ## Top Cudjoe Key Hotel Reviews ![Ibis Bay Beach Resort](https://images.trvl-media.com/lodging/5000000/4220000/4218900/4218809/4a09d86c_y.jpg) ### Ibis Bay Beach Resort 8/10 Good "Room was unique with tile floors but necessary with the beach right out front! Everyone we met was amazing and so kind! Will be staying again! The tortoises were a nice bonus! " [](https://expedia.com/Key-West-Hotels-Ibis-Bay-Beach-Resort.h4218809.Hotel-Information) ![Hilton Garden Inn Key West / The Keys Collection](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/449c6937_y.jpg) ### Hilton Garden Inn Key West / The Keys Collection 10/10 Excellent "Friendly staff. Nice room and pool " [](https://expedia.com/Key-West-Hotels-Hilton-Garden-Inn-Key-West.h1376.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 8/10 Good "Breakfast was good, room was clean, stafff was excellent." [](https://expedia.com/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.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 nice. We had a view of the marina, which was fun to watch the boats. All the pools seemed very nice. It was cold and rainy when we were there, but the property is nice and the shuttle bus to Key West is super convenient." [](https://expedia.com/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.Hotel-Information) ![Hampton Inn Key West FL](https://images.trvl-media.com/lodging/1000000/20000/15800/15720/4075e8ff_y.jpg) ### Hampton Inn Key West FL 10/10 Excellent "Awesome place nice pool great tiki bar great view of ocean" [](https://expedia.com/Key-West-Hotels-Hampton-Inn-Key-West-FL.h15720.Hotel-Information) ![Beachside Resort & Residences](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/290b242a_y.jpg) ### Beachside Resort & Residences 10/10 Excellent "I absolutely loved this place. The reviews were mixed. I read negative comments about the cleanliness. I had no issues with that. I read negative reviews about the pool and poor mgmt of the grounds. Again, I saw no issues with that. I also read negative reviews saying they felt unsafe at the resort. I was a single female traveling alone. I came and went all hours of the day and evening. I was never afraid. This was a wonderful resort, with amazing staff and caretakers. The grounds were beautiful kept, they worked in the every day. The onsite restaurant was delicious, and the Chicken Walk (pool bar) was delightful. They had water activities onsite. Sunset cruises, sandbar trips, lighted glass bottom night kayaking, fishing. I will definitely stay here again anytime I’m in Key West. " [](https://expedia.com/Key-West-Hotels-Key-West-Marriott-Beachside-Hotel.h25865.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 "The 4 pools were outstanding! Plan to spend some time there if you enjoy relaxing, swimming or sunbathing. " [](https://expedia.com/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 "Stayed there for 5 nights and it was very pleasant!" [](https://expedia.com/Key-West-Hotels-Hyatt-Vacation-Club-At-Beach-House.h857962.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 8/10 Good "Nice room, food good but not great, a little expensive for food" [](https://expedia.com/Key-West-Hotels-The-Perry-Hotel-Marina-Key-West.h17313680.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - [Fishing Resorts & in Lower Keys ](https://www.expedia.com/Lower-Keys-Hotels-Fishing-Hotels.0-0-d553248621593965863-tFishingHotels.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Lower Keys ](https://www.expedia.com/Lower-Keys-Hotels-Cheap-Hotels.0-0-d553248621593965863-tCheapHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Lower Keys ](https://www.expedia.com/Lower-Keys-Hotels-Pet-Friendly-Hotel.0-0-d553248621593965863-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - 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