Title: The Best Hotels with a Pool in Cudjoe Key from $158 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 [Feb 12 - Feb 13](https://www.expedia.com/Hotel-Search?regionId=3000430966&startDate=2026-02-12&endDate=2026-02-13&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 13 - Feb 14](https://www.expedia.com/Hotel-Search?regionId=3000430966&startDate=2026-02-13&endDate=2026-02-14&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 13 - Feb 15](https://www.expedia.com/Hotel-Search?regionId=3000430966&startDate=2026-02-13&endDate=2026-02-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 20 - Feb 22](https://www.expedia.com/Hotel-Search?regionId=3000430966&startDate=2026-02-20&endDate=2026-02-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Cudjoe Key hotels with a pool ![Pool](https://images.trvl-media.com/lodging/34000000/33570000/33566300/33566283/fa9fff97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33570000/33566300/33566283/00d423f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33570000/33566300/33566283/fcb4c32a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/34000000/33570000/33566300/33566283/f3c522ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage with swimming pool and dockage, just minutes to Key West! [](https://www.expedia.com/Summerland-Key-Hotels-Cottage-With-Swimming-Pool-And-Dockage.h33566283.Hotel-Information) Cudjoe Key 9.0/10 Wonderful (166 reviews) "Everything was there that I needed. Very nice area for my dog." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Terry $292 nightly $324 total Feb 15 - Feb 16 Total with taxes and fees [](https://www.expedia.com/Summerland-Key-Hotels-Cottage-With-Swimming-Pool-And-Dockage.h33566283.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) ![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 8.8/10 Excellent (55 reviews) "Clean rooms, clear guidelines, completely no contact experience without facing any trouble." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Raj $413 nightly $458 total Feb 18 - Feb 19 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/33000000/32670000/32660400/32660303/d56a9a80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![LED TV, DVD player, table tennis, books](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/787fb31a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/9c267ac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/9e0e4056.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SAVE BIG $$FEBRUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS [](https://www.expedia.com/Cudjoe-Key-Hotels-Waterfront-Paradise-AT-Venture-Out4-Bikes-2-2-Seat-Kayaks-King-Queen-Beds.h32660303.Hotel-Information) Cudjoe Key 9.4/10 Exceptional (104 reviews) "Great location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Davian k. $446 nightly $495 total Feb 25 - Feb 26 Total with taxes and fees [](https://www.expedia.com/Cudjoe-Key-Hotels-Waterfront-Paradise-AT-Venture-Out4-Bikes-2-2-Seat-Kayaks-King-Queen-Beds.h32660303.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) ![Property grounds](https://images.trvl-media.com/lodging/32000000/31900000/31892500/31892418/98e9c6b6.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) ![Terrace/patio](https://images.trvl-media.com/lodging/32000000/31900000/31892500/31892418/78df4af0.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) "Great location if you bring a boat. Secure location. Venture Out is a nice community. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Georgiana V. $429 nightly $477 total Feb 22 - Feb 23 Total with taxes and fees [](https://www.expedia.com/Cudjoe-Key-Hotels-Waterfront-Home.h31892418.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 | 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) ![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) ### 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) "We were here for a night and it was great. A nice rustic feel on a big property, with good view. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Preetam $975 nightly $1,097 total Feb 22 - Feb 23 Total with taxes and fees [](https://www.expedia.com/Summerland-Key-Hotels-Atlantic-View-Luxury-Villa-With-Pool.h111535402.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/35000000/34330000/34324000/34323967/7fa52371.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34330000/34324000/34323967/60a3d49e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach towels](https://images.trvl-media.com/lodging/35000000/34330000/34324000/34323967/f6d4e696.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/35000000/34330000/34324000/34323967/bfb5dd99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relax by Florida Keys Beaches, just a 7-min drive away [](https://www.expedia.com/Cudjoe-Key-Hotels-Waterfront-Fresh-Cozy-2-Bedroom-35seawall.h34323967.Hotel-Information) Cudjoe Key 9.8/10 Exceptional (201 reviews) "The cottage was clean and the location was nice and quiet. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jaconica B. $556 nightly $617 total Feb 27 - Feb 28 Total with taxes and fees [](https://www.expedia.com/Cudjoe-Key-Hotels-Waterfront-Fresh-Cozy-2-Bedroom-35seawall.h34323967.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 $274 nightly $295 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/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) ![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) ![Outdoor dining](https://images.trvl-media.com/lodging/117000000/116670000/116667100/116667062/35103395.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 $556 nightly $617 total Feb 27 - Feb 28 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) ![A heated pool](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/08f26cef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/5fa1ecc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/6db1494c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/75d37db8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West [](https://www.expedia.com/Summerland-Key-Hotels-Updated-2BR2BA-Venture-Out-Home-W-Pool-Access.h120816897.Hotel-Information) Cudjoe Key $606 nightly $673 total Mar 3 - Mar 4 Total with taxes and fees [](https://www.expedia.com/Summerland-Key-Hotels-Updated-2BR2BA-Venture-Out-Home-W-Pool-Access.h120816897.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/106000000/105240000/105238300/105238265/6b5c5ac3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105240000/105238300/105238265/548e5f5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105240000/105238300/105238265/8235caf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/106000000/105240000/105238300/105238265/42e04085.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seabreeze Escape WF RV Lot 489 [](https://www.expedia.com/Summerland-Key-Hotels-Seabreeze-Escape-WF-RV-Lot-489.h105238265.Hotel-Information) Cudjoe Key 8.0/10 Very Good (1 review) $274 nightly $295 total Mar 3 - Mar 4 Total with taxes and fees [](https://www.expedia.com/Summerland-Key-Hotels-Seabreeze-Escape-WF-RV-Lot-489.h105238265.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=2026-02-26&endDate=2026-02-27®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 Ocean view 5 stars Hot tub ![](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) ## Hotels with pools and ocean views in Cudjoe Key ![Interior](https://images.trvl-media.com/lodging/35000000/34330000/34324000/34323967/7fa52371.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34330000/34324000/34323967/60a3d49e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach towels](https://images.trvl-media.com/lodging/35000000/34330000/34324000/34323967/f6d4e696.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/35000000/34330000/34324000/34323967/bfb5dd99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relax by Florida Keys Beaches, just a 7-min drive away [](https://www.expedia.com/Cudjoe-Key-Hotels-Waterfront-Fresh-Cozy-2-Bedroom-35seawall.h34323967.Hotel-Information) Cudjoe Key 9.8/10 Exceptional (201) $556 nightly $617 total Feb 27 - Feb 28 Total with taxes and fees [](https://www.expedia.com/Cudjoe-Key-Hotels-Waterfront-Fresh-Cozy-2-Bedroom-35seawall.h34323967.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) ![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) ![Outdoor dining](https://images.trvl-media.com/lodging/117000000/116670000/116667100/116667062/35103395.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 $556 nightly $617 total Feb 27 - Feb 28 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) ![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 | 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) ![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 | 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) ### 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) $975 nightly $1,097 total Feb 22 - Feb 23 Total with taxes and fees [](https://www.expedia.com/Summerland-Key-Hotels-Atlantic-View-Luxury-Villa-With-Pool.h111535402.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/104000000/103540000/103537700/103537636/e3bc7bba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/104000000/103540000/103537700/103537636/fc5e8fb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/104000000/103540000/103537700/103537636/c8330712.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/104000000/103540000/103537700/103537636/056b8deb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Endless Ocean Views - RV589 [](https://www.expedia.com/Summerland-Key-Hotels-Endless-Ocean-Views-RV589.h103537636.Hotel-Information) Cudjoe Key $293 nightly $317 total Mar 6 - Mar 7 Total with taxes and fees [](https://www.expedia.com/Summerland-Key-Hotels-Endless-Ocean-Views-RV589.h103537636.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/108000000/107120000/107116600/107116554/a01f4162.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107120000/107116600/107116554/w2500h1666x0y1-8de3e595.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, table tennis, books](https://images.trvl-media.com/lodging/108000000/107120000/107116600/107116554/99097ad0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107120000/107116600/107116554/67b94030.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blue Lobster Lodge - Venture Out #543 - Cudjoe Key [](https://www.expedia.com/Summerland-Key-Hotels-Blue-Lobster-Lodge-Venture-Out-543-Cudjoe-Key.h107116554.Hotel-Information) Cudjoe Key 9.2/10 Wonderful (7) $545 nightly $604 total Mar 11 - Mar 12 Total with taxes and fees [](https://www.expedia.com/Summerland-Key-Hotels-Blue-Lobster-Lodge-Venture-Out-543-Cudjoe-Key.h107116554.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/121000000/120870000/120862100/120862073/4c3dc49f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120870000/120862100/120862073/c8d44015.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/121000000/120870000/120862100/120862073/20d90f2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120870000/120862100/120862073/393a2acc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key [](https://www.expedia.com/Summerland-Key-Hotels-Waterfront-2BR2BA-35-Seawall-For-32-Boat-Beautiful-Sunrises-On-Cudjoe-Key.h120862073.Hotel-Information) Cudjoe Key 10/10 Exceptional (1) $708 nightly $786 total Feb 25 - Feb 26 Total with taxes and fees [](https://www.expedia.com/Summerland-Key-Hotels-Waterfront-2BR2BA-35-Seawall-For-32-Boat-Beautiful-Sunrises-On-Cudjoe-Key.h120862073.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/6bfc69e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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/45000000/44560000/44556700/44556643/080e8cfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SAVE BIG $$FEBRUARY! 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 (83) $659 nightly $732 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) ![A heated pool](https://images.trvl-media.com/lodging/125000000/124260000/124259500/124259402/1098ffdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, table tennis, books, stereo](https://images.trvl-media.com/lodging/125000000/124260000/124259500/124259402/104729b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/125000000/124260000/124259500/124259402/93591741.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/125000000/124260000/124259500/124259402/w2500h1666x0y1-ea7b0041.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Florida Keys Waterfront Escape w/35' Seawall & Seconds to Open Water [](https://www.expedia.com/Summerland-Key-Hotels-Florida-Keys-Waterfront-Escape-W35-Seawall-Seconds-To-Open-Water.h124259402.Hotel-Information) Cudjoe Key $671 nightly $745 total Mar 5 - Mar 6 Total with taxes and fees [](https://www.expedia.com/Summerland-Key-Hotels-Florida-Keys-Waterfront-Escape-W35-Seawall-Seconds-To-Open-Water.h124259402.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34010000/34007900/34007879/c3050189.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34010000/34007900/34007879/30086228.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/35000000/34010000/34007900/34007879/b6f371a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/35000000/34010000/34007900/34007879/dc4f2745.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cudjoe Cottages, swimming pool, just 20 miles from Key West [](https://www.expedia.com/Summerland-Key-Hotels-Cudjoe-Cottages.h34007879.Hotel-Information) Cudjoe Key 8.8/10 Excellent (150) $656 nightly $728 total Feb 21 - Feb 22 Total with taxes and fees [](https://www.expedia.com/Summerland-Key-Hotels-Cudjoe-Cottages.h34007879.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/b25eb073.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/e93bd5d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/3835dc3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/df6d7013.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Just 20 miles from Key West! Oceanfront, dockage, swimming pool [](https://www.expedia.com/Summerland-Key-Hotels-Just-20-Miles-From-Key-West-Oceanfront.h33547859.Hotel-Information) Cutthroat Harbor Estates 8.4/10 Very Good (121) $627 nightly $696 total Feb 22 - Feb 23 Total with taxes and fees [](https://www.expedia.com/Summerland-Key-Hotels-Just-20-Miles-From-Key-West-Oceanfront.h33547859.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=2026-02-26&endDate=2026-02-27®ionId=3000430966&adults=2&amenities=POOL&sort=RECOMMENDED&amenities=OCEAN_VIEW&openPlayBack=true) ## Top Cudjoe Key Hotel Reviews ![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 "Everything about this place was great!" [](https://expedia.com/Key-West-Hotels-Hyatt-Vacation-Club-At-Beach-House.h857962.Hotel-Information) ![Beachside Resort & Residences](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/290b242a_y.jpg) ### Beachside Resort & Residences 10/10 Excellent "Clean suite, friendly staff members, a convenient shuttle downtown, a great restaurant, the pool and more! We’d stay there again, in a minute!" [](https://expedia.com/Key-West-Hotels-Key-West-Marriott-Beachside-Hotel.h25865.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 "Room was beautiful and very clean. Concierge so very helpful. The property is relaxing and the view is beautiful " [](https://expedia.com/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.Hotel-Information) ![Ibis Bay Beach Resort](https://images.trvl-media.com/lodging/5000000/4220000/4218900/4218809/4a09d86c_y.jpg) ### Ibis Bay Beach Resort 10/10 Excellent "Clean, nice location, small but nice room" [](https://expedia.com/Key-West-Hotels-Ibis-Bay-Beach-Resort.h4218809.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 "Very nice clean room staff was wonderful." [](https://expedia.com/Key-West-Hotels-Hampton-Inn-Key-West-FL.h15720.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 "Suite was very nice " [](https://expedia.com/Key-West-Hotels-Hilton-Garden-Inn-Key-West.h1376.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 "Beautiful " [](https://expedia.com/Key-West-Hotels-Parrot-Key-Hotel-Villas.h24615.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 "Everything was wonderful. Excellent service, lots of food options right there at the marina. Very pleased. " [](https://expedia.com/Key-West-Hotels-The-Perry-Hotel-Marina-Key-West.h17313680.Hotel-Information) ![Looe Key Reef Resort](https://images.trvl-media.com/lodging/5000000/4760000/4759500/4759500/63d12f01_y.jpg) ### Looe Key Reef Resort 10/10 Excellent "Great place ! Friendly staff " [](https://expedia.com/Ramrod-Key-Hotels-Looe-Key-Reef-Resort.h4759500.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) - [Beach Hotels in Lower Keys ](https://www.expedia.com/Lower-Keys-Hotels-Beach-Hotel.0-0-d553248621593965863-tBeachHotel.Travel-Guide-Filter-Hotels) - [Extended Stay Hotels in Lower Keys ](https://www.expedia.com/Lower-Keys-Hotels-Extended-Stay-Hotels.0-0-d553248621593965863-tExtendedStayHotels.Travel-Guide-Filter-Hotels) - 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