Title: Book the Best Hotels with POOL in Cudjoe Key in 2026 | Expedia.ca [Cudjoe Key Travel Guide](https://expedia.ca/Cudjoe-Key.dx3000430966)[Hotels in Cudjoe Key](https://expedia.ca/Cudjoe-Key-Hotels.d3000430966.Travel-Guide-Hotels)[Vacation Rentals in Cudjoe Key](https://expedia.ca/Cudjoe-Key-Vacation-Rentals.d3000430966.Travel-Guide-VacationRentals)[Flights to Cudjoe Key](https://expedia.ca/Cheap-Flights-To-Cudjoe-Key.d3000430966.Travel-Guide-Flights)[Things to do in Cudjoe Key](https://expedia.ca/Things-To-Do-In-Cudjoe-Key.d3000430966.Travel-Guide-Activities)[Cudjoe Key Car Rentals](https://expedia.ca/Car-Rentals-In-Cudjoe-Key.d3000430966.Car-Rental-Guide)[Cudjoe Key Vacation Packages](https://expedia.ca/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__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 Cudjoe Key Hotels with a Pool Tonight [Feb 14 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=3000430966&startDate=2026-02-14&endDate=2026-02-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 15 - Feb 16](https://www.expedia.ca/Hotel-Search?regionId=3000430966&startDate=2026-02-15&endDate=2026-02-16&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=3000430966&startDate=2026-02-20&endDate=2026-02-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=3000430966&startDate=2026-02-27&endDate=2026-03-01&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) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33570000/33566300/33566283/bc83e7d9.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) ![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) ### Cottage with swimming pool and dockage, just minutes to Key West! [](https://www.expedia.ca/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 [](https://www.expedia.ca/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) ![Beach nearby](https://images.trvl-media.com/lodging/74000000/73240000/73238600/73238505/8649ed7b.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) ### Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West [](https://www.expedia.ca/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 CA $337 CA $621 total includes taxes & fees Feb 18 - Feb 19 [](https://www.expedia.ca/Summerland-Key-Hotels-Old-Florida-Style.h73238505.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) ![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) ### Waterfront Home [](https://www.expedia.ca/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. CA $340 CA $665 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Cudjoe-Key-Hotels-Waterfront-Home.h31892418.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) ![Outdoor dining](https://images.trvl-media.com/lodging/117000000/116670000/116667100/116667062/35103395.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) ### Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access [](https://www.expedia.ca/Summerland-Key-Hotels-Planktons-Palace-Cozy-2BR-Getaway-In-Oceanfront-Resort-Community-With-Patio-Island-Vibes.h116667062.Hotel-Information) Cudjoe Key CA $286 CA $838 total includes taxes & fees Feb 27 - Feb 28 [](https://www.expedia.ca/Summerland-Key-Hotels-Planktons-Palace-Cozy-2BR-Getaway-In-Oceanfront-Resort-Community-With-Patio-Island-Vibes.h116667062.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) ![Deluxe Villa, Ocean View](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/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) ### Atlantic View Luxury Villa with Pool [](https://www.expedia.ca/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 CA $766 CA $1,398 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Summerland-Key-Hotels-Atlantic-View-Luxury-Villa-With-Pool.h111535402.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) ![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) ![Outdoor dining](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/9c267ac9.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) ### SAVE BIG $$FEBRUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS [](https://www.expedia.ca/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. CA $271 CA $680 total includes taxes & fees Feb 25 - Feb 26 [](https://www.expedia.ca/Cudjoe-Key-Hotels-Waterfront-Paradise-AT-Venture-Out4-Bikes-2-2-Seat-Kayaks-King-Queen-Beds.h32660303.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) ![Marina](https://images.trvl-media.com/lodging/105000000/104880000/104875300/104875207/c4e05ae6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Endless Summer Hideaway - lot 181 [](https://www.expedia.ca/Summerland-Key-Hotels-Endless-Summer-Hideaway-Lot-181.h104875207.Hotel-Information) Cudjoe Key CA $231 CA $410 total includes taxes & fees Mar 4 - Mar 5 [](https://www.expedia.ca/Summerland-Key-Hotels-Endless-Summer-Hideaway-Lot-181.h104875207.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) ![Dining](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/75d37db8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/a9f31955.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) ### Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West [](https://www.expedia.ca/Summerland-Key-Hotels-Updated-2BR2BA-Venture-Out-Home-W-Pool-Access.h120816897.Hotel-Information) Cudjoe Key CA $341 CA $916 total includes taxes & fees Mar 3 - Mar 4 [](https://www.expedia.ca/Summerland-Key-Hotels-Updated-2BR2BA-Venture-Out-Home-W-Pool-Access.h120816897.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) ![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) ![Outdoor dining](https://images.trvl-media.com/lodging/108000000/107120000/107116600/107116554/e29d300c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blue Lobster Lodge - Venture Out #543 - Cudjoe Key [](https://www.expedia.ca/Summerland-Key-Hotels-Blue-Lobster-Lodge-Venture-Out-543-Cudjoe-Key.h107116554.Hotel-Information) Cudjoe Key 9.2/10 Wonderful (7 reviews) "Close to Key West. Would stay there again!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) elisa b. CA $272 CA $820 total includes taxes & fees Mar 11 - Mar 12 [](https://www.expedia.ca/Summerland-Key-Hotels-Blue-Lobster-Lodge-Venture-Out-543-Cudjoe-Key.h107116554.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/35000000/34010000/34007900/34007879/30086228.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34010000/34007900/34007879/6fdc38c2.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) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34010000/34007900/34007879/c3050189.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cudjoe Cottages, swimming pool, just 20 miles from Key West [](https://www.expedia.ca/Summerland-Key-Hotels-Cudjoe-Cottages.h34007879.Hotel-Information) Cudjoe Key 8.8/10 Excellent (151 reviews) "Boat access and docking spaces could be improved but overall not terrible. Spent a week here and enjoyed the stay. Quiet decent location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) bryan c. CA $511 CA $993 total includes taxes & fees Feb 21 - Feb 22 [](https://www.expedia.ca/Summerland-Key-Hotels-Cudjoe-Cottages.h34007879.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=2026-03-01&endDate=2026-03-02®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.ca/deals?rfrr=AFFINITY_SPRING_PROMO_3000430966) ## Hotels with pools and ocean views in Cudjoe Key ![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](https://images.trvl-media.com/lodging/112000000/111540000/111535500/111535402/w2304h1532x8y4-86de2f42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### Atlantic View Luxury Villa with Pool [](https://www.expedia.ca/Summerland-Key-Hotels-Atlantic-View-Luxury-Villa-With-Pool.h111535402.Hotel-Information) Summerland Key 10/10 Exceptional (1) CA $766 CA $1,398 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Summerland-Key-Hotels-Atlantic-View-Luxury-Villa-With-Pool.h111535402.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) ![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) ![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) ### SAVE BIG $$FEBRUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS! [](https://www.expedia.ca/Cudjoe-Key-Hotels-Ocean-Paradise-AT-Venture-OUT-4-Bikes-2-2-Person-Kayaks.h44556643.Hotel-Information) Cudjoe Key 9.8/10 Exceptional (83) CA $530 CA $1,008 total includes taxes & fees Mar 5 - Mar 6 [](https://www.expedia.ca/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/117000000/116670000/116667100/116667062/8bf693c2.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) ![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) ### Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access [](https://www.expedia.ca/Summerland-Key-Hotels-Planktons-Palace-Cozy-2BR-Getaway-In-Oceanfront-Resort-Community-With-Patio-Island-Vibes.h116667062.Hotel-Information) Cudjoe Key CA $286 CA $838 total includes taxes & fees Feb 27 - Feb 28 [](https://www.expedia.ca/Summerland-Key-Hotels-Planktons-Palace-Cozy-2BR-Getaway-In-Oceanfront-Resort-Community-With-Patio-Island-Vibes.h116667062.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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34010000/34007900/34007879/6fdc38c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cudjoe Cottages, swimming pool, just 20 miles from Key West [](https://www.expedia.ca/Summerland-Key-Hotels-Cudjoe-Cottages.h34007879.Hotel-Information) Cudjoe Key 8.8/10 Excellent (151) CA $511 CA $993 total includes taxes & fees Feb 21 - Feb 22 [](https://www.expedia.ca/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.ca/Summerland-Key-Hotels-Just-20-Miles-From-Key-West-Oceanfront.h33547859.Hotel-Information) Cutthroat Harbor Estates 8.4/10 Very good (121) CA $477 CA $950 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Summerland-Key-Hotels-Just-20-Miles-From-Key-West-Oceanfront.h33547859.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/58000000/57260000/57259300/57259241/3f698bba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/58000000/57260000/57259300/57259241/fd63c9b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/58000000/57260000/57259300/57259241/84aef88f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/58000000/57260000/57259300/57259241/da1c9823.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West [](https://www.expedia.ca/Summerland-Key-Hotels-Oceanfront-Home-Shared-Swimming-Pool.h57259241.Hotel-Information) Cudjoe Key 8.6/10 Excellent (90) [](https://www.expedia.ca/Summerland-Key-Hotels-Oceanfront-Home-Shared-Swimming-Pool.h57259241.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/124000000/123190000/123180400/123180380/7efc866d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/124000000/123190000/123180400/123180380/eb123bd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/124000000/123190000/123180400/123180380/ad25c145.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, table tennis, books](https://images.trvl-media.com/lodging/124000000/123190000/123180400/123180380/0e91961d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Open-water home with stunning views, 42' seawall for 40' boat, modern updates, large balcony [](https://www.expedia.ca/Summerland-Key-Hotels-Open-Water-Home-With-Stunning-Views.h123180380.Hotel-Information) Cudjoe Key CA $786 CA $1,480 total includes taxes & fees Feb 21 - Feb 22 [](https://www.expedia.ca/Summerland-Key-Hotels-Open-Water-Home-With-Stunning-Views.h123180380.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/126000000/125790000/125783000/125782983/w2499h1666x1y1-23a46351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/126000000/125790000/125783000/125782983/71b92dc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/126000000/125790000/125783000/125782983/e09a63d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/126000000/125790000/125783000/125782983/w2500h1403x0y1-f8c6eb6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Open Water Views | 32' Boat, King Beds, Fish Cleaning Station, Waterfront Escape [](https://www.expedia.ca/Summerland-Key-Hotels-Open-Water-Views-32-Boat.h125782983.Hotel-Information) Cudjoe Key CA $572 CA $1,209 total includes taxes & fees Feb 21 - Feb 22 [](https://www.expedia.ca/Summerland-Key-Hotels-Open-Water-Views-32-Boat.h125782983.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/107000000/106920000/106911800/106911727/83762f00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106920000/106911800/106911727/f8f120c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106920000/106911800/106911727/8ac90ad0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106920000/106911800/106911727/aa364b9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key [](https://www.expedia.ca/Summerland-Key-Hotels-Salty-Breeze-161-Canal-Front-Venture-Out-Home-On-Cudjoe-Key.h106911727.Hotel-Information) Cudjoe Key 9.0/10 Wonderful (7) CA $568 CA $1,205 total includes taxes & fees Mar 7 - Mar 8 [](https://www.expedia.ca/Summerland-Key-Hotels-Salty-Breeze-161-Canal-Front-Venture-Out-Home-On-Cudjoe-Key.h106911727.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/110000000/109980000/109979300/109979224/c532d8a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/110000000/109980000/109979300/109979224/w2500h1734x0y1-423dc0ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, table tennis](https://images.trvl-media.com/lodging/110000000/109980000/109979300/109979224/w2500h1663x0y1-0f893c52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109980000/109979300/109979224/w2500h1664x0y1-e1c3d816.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Post Card Point #319 - Ocean Views! [](https://www.expedia.ca/Summerland-Key-Hotels-Post-Card-Point-319-Ocean-Views.h109979224.Hotel-Information) Cudjoe Key 10/10 Exceptional (52) CA $572 CA $1,276 total includes taxes & fees Feb 28 - Mar 1 [](https://www.expedia.ca/Summerland-Key-Hotels-Post-Card-Point-319-Ocean-Views.h109979224.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=2026-03-01&endDate=2026-03-02®ionId=3000430966&adults=2&amenities=POOL&sort=RECOMMENDED&amenities=OCEAN_VIEW&openPlayBack=true) ## Top Cudjoe Key Hotel Reviews ![Parmer's Resort](https://images.trvl-media.com/lodging/6000000/5570000/5561500/5561465/6492712a_y.jpg) ### Parmer's Resort 10/10 Excellent "Super nice staff and the property is cute, clean and within walking distances." [](https://expedia.ca/Little-Torch-Key-Hotels-Parmers-Resort.h5561465.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 "Room was spotless. Staff friendly and helpful. Onsite bicycle rental. Better for adults. " [](https://expedia.ca/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 10/10 Excellent "Great location. Staff was great. Amenities were convenient. Beautiful property, well maintained. Restaurant staff was great. " [](https://expedia.ca/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 "Great service " [](https://expedia.ca/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 "Everything was great at this resort. Staff was extremely friendly! Had our SuperBowl party by the outdoor bar and the food and drinks were great! Hotel staff were super responsive and would highly recommend!" [](https://expedia.ca/Key-West-Hotels-Parrot-Key-Hotel-Villas.h24615.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.ca/Key-West-Hotels-Key-West-Marriott-Beachside-Hotel.h25865.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 "Great service and experience " [](https://expedia.ca/Key-West-Hotels-The-Perry-Hotel-Marina-Key-West.h17313680.Hotel-Information) ![DoubleTree Resort by Hilton Grand Key - Key West](https://images.trvl-media.com/lodging/1000000/480000/470900/470834/cefb5fc2_y.jpg) ### DoubleTree Resort by Hilton Grand Key - Key West 10/10 Excellent "Very expensive but beautiful " [](https://expedia.ca/Key-West-Hotels-DoubleTree-Resort-By-Hilton-Grand-Key-Key-West.h470834.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 "We had a great stay. Clean and well maintained property. Quiet. We would stay here again. 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