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) ![Dining](https://images.trvl-media.com/lodging/70000000/69810000/69809300/69809218/61a8a4c0.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) ### 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) ![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) ![Beach nearby](https://images.trvl-media.com/lodging/74000000/73240000/73238600/73238505/8649ed7b.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) ![Beach](https://images.trvl-media.com/lodging/34000000/33570000/33564800/33564734/ef0fcc3f.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) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33570000/33564800/33564734/4231ea78.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) ![Marina](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/7f597dff.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) ![Exterior](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/6bfc69e0.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) ![Exterior](https://images.trvl-media.com/lodging/112000000/111540000/111535500/111535402/w2722h1530x2y6-b30f2be4.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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/117000000/116670000/116667100/116667062/d1732c67.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) $556 nightly $617 total Mar 9 - Mar 10 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) ![Outdoor dining](https://images.trvl-media.com/lodging/62000000/61590000/61585200/61585151/94e4b670.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) ### Canal front, dockage, 2 bedroom, 2 bath [](https://www.expedia.com/Summerland-Key-Hotels-Canal-Front.h61585151.Hotel-Information) Cudjoe Key 8.8/10 Excellent (94 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/105000000/104880000/104875300/104875207/2f62f857.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) ![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 5 - Mar 6 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) ![Terrace/patio](https://images.trvl-media.com/lodging/32000000/31900000/31892500/31892418/78df4af0.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) ![Dining](https://images.trvl-media.com/lodging/32000000/31900000/31892500/31892418/39a5429b.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) $437 nightly $485 total Mar 12 - Mar 13 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=2026-03-18&endDate=2026-03-19®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 ![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 8/10 Good "Pool area very nice, plenty of lounge chairs and towels. Elevators were not working during entire stay which was an inconvenience. Assistance with luggage was provided upon request as we were unable to carry heavy suitcases up and down stairs. " [](https://expedia.com/Key-West-Hotels-Hilton-Garden-Inn-Key-West.h1376.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 "View was awesome! " [](https://expedia.com/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.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 10/10 Excellent "Fantastic property with amazing staff and amenities. Jayme and Mitch were fanastically hospitable and supported all of our needs at checkin and beyond. Free shuttles available on the hour (didn't use) make it easy and cheap to get into the heart of the action with the chill vibes of Stock Island a welcome retreat. Ubers are never more than a few minutes away and some solid restaurant options allow for staying away from the hustle and bustle if needed. Would stay again and highly recommend!" [](https://expedia.com/Key-West-Hotels-The-Perry-Hotel-Marina-Key-West.h17313680.Hotel-Information) ![Hampton Inn Key West FL](https://images.trvl-media.com/lodging/1000000/20000/15800/15720/046434c3_y.jpg) ### Hampton Inn Key West FL 8/10 Good "I reserved an ocean view room and, while we could see the ocean, I thought it would be more like the picture featuring the hotel with the pool included. We had a busy road to look at in front of the ocean and there is no beach." [](https://expedia.com/Key-West-Hotels-Hampton-Inn-Key-West-FL.h15720.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 10/10 Excellent "Wonderful place to stay. Very accommodating for pets " [](https://expedia.com/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.Hotel-Information) ![Ibis Bay Beach Resort](https://images.trvl-media.com/lodging/5000000/4220000/4218900/4218809/4a09d86c_y.jpg) ### Ibis Bay Beach Resort 8/10 Good "Poolside seating was wery good" [](https://expedia.com/Key-West-Hotels-Ibis-Bay-Beach-Resort.h4218809.Hotel-Information) ![Hyatt Vacation Club at Windward Pointe, Key West](https://images.trvl-media.com/lodging/1000000/870000/868700/868697/481a771e_y.jpg) ### Hyatt Vacation Club at Windward Pointe, Key West 10/10 Excellent "Great place with awesome views!" [](https://expedia.com/Key-West-Hotels-Hyatt-Vacation-Club-At-Windward-Pointe.h868697.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!" 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