Title: Book the Best Hotels with POOL in Summerland Key in 2025 | Expedia.ca [Summerland Key Travel Guide](https://expedia.ca/Summerland-Key.dx6177802)[Hotels in Summerland Key](https://expedia.ca/Summerland-Key-Hotels.d6177802.Travel-Guide-Hotels)[Vacation Rentals in Summerland Key](https://expedia.ca/Summerland-Key-Vacation-Rentals.d6177802.Travel-Guide-VacationRentals)[Flights to Summerland Key](https://expedia.ca/Cheap-Flights-To-Summerland-Key.d6177802.Travel-Guide-Flights)[Things to do in Summerland Key](https://expedia.ca/Things-To-Do-In-Summerland-Key.d6177802.Travel-Guide-Activities)[Summerland Key Car Rentals](https://expedia.ca/Car-Rentals-In-Summerland-Key.d6177802.Car-Rental-Guide)[Summerland Key Vacation Packages](https://expedia.ca/Summerland-Key.d6177802.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/498000/498234-sugarloaf-key.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Summerland Key, FL from CA $155 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Summerland Key Hotels with a Pool Tonight [Oct 8 - Oct 9](https://www.expedia.ca/Hotel-Search?regionId=6177802&startDate=2025-10-08&endDate=2025-10-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 9 - Oct 10](https://www.expedia.ca/Hotel-Search?regionId=6177802&startDate=2025-10-09&endDate=2025-10-10&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6177802&startDate=2025-10-10&endDate=2025-10-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6177802&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Summerland Key Hotels with a Pool ![Outdoor pool](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/83592c1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/125c52d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/a0504154.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/95d2903e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sugar Loaf Lodge Summerland Key 8.2/10 Very good (1001) "Nice family owned spot. " CA $138 CA $155 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Sugarloaf-Key-Hotels-Sugar-Loaf-Lodge.h3918121.Hotel-Information) ![Dock](https://images.trvl-media.com/lodging/6000000/5570000/5561500/5561465/a69616f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/6000000/5570000/5561500/5561465/9585f19f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Kitchen, Sea Facing | Beach/ocean view](https://images.trvl-media.com/lodging/6000000/5570000/5561500/5561465/6492712a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/6000000/5570000/5561500/5561465/0a8ded52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Parmer's Resort Summerland Key 9.0/10 Wonderful (1000) "Had a wonderful time place is very nice enjoyed ourselves " CA $143 CA $207 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Little-Torch-Key-Hotels-Parmers-Resort.h5561465.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) ![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) ![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 Cudjoe Key 9.0/10 Wonderful (51) "We enjoyed our stay. Place is exactly as described. We really enjoyed the lanai. Wanted somewhere close to Key West and this turned out perfect. Would definitely stay here again. Thanks!" CA $223 CA $487 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Summerland-Key-Hotels-Old-Florida-Style.h73238505.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/5000000/4760000/4759500/4759500/9eff678c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine, pool views ](https://images.trvl-media.com/lodging/5000000/4760000/4759500/4759500/2a9d6b25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room, 2 Queen Beds | Terrace/patio](https://images.trvl-media.com/lodging/5000000/4760000/4759500/4759500/13570c88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4760000/4759500/4759500/63d12f01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Looe Key Reef Resort Summerland Key 7.4/10 Good (1000) "Average stay, old room, friendly staff, quiet" [](https://www.expedia.ca/Ramrod-Key-Hotels-Looe-Key-Reef-Resort.h4759500.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/6e8a6b91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/ec0614f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/88047f08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/10da66f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage with Pool and Dockage, just minutes to Key West Cudjoe Key 9.2/10 Wonderful (154) "Good Fishing, Good local eateries. " CA $209 CA $441 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Summerland-Key-Hotels-Cottage-With-Pool-And-Dockage.h33389096.Hotel-Information) ![Swim-up bar](https://images.trvl-media.com/lodging/112000000/111540000/111535500/111535402/17e19347.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room service - dining](https://images.trvl-media.com/lodging/112000000/111540000/111535500/111535402/5f145d76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/112000000/111540000/111535500/111535402/6f8ffa24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Villa, Ocean View | Private kitchenette](https://images.trvl-media.com/lodging/112000000/111540000/111535500/111535402/c0b097db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Atlantic View Luxury Villa with Pool Summerland Key 10/10 Exceptional (1) "We were here for a night and it was great. A nice rustic feel on a big property, with good view. " CA $589 CA $1,150 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Summerland-Key-Hotels-Atlantic-View-Luxury-Villa-With-Pool.h111535402.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/w1024h630x0y0-e267420a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/d57de0d1.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/f111b153.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) ### WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS Cudjoe Key 9.6/10 Exceptional (98) "The house was very clean. Friendly and quiet location. The hosts were extremely helpful. " CA $194 CA $586 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Cudjoe-Key-Hotels-Waterfront-Paradise-AT-Venture-Out4-Bikes-2-2-Seat-Kayaks-King-Queen-Beds.h32660303.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/28679789.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/8e7ed1a2.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) ### OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS! Cudjoe Key 9.8/10 Exceptional (81) "Great location near Key West. Awesome property, will book again." CA $222 CA $620 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Cudjoe-Key-Hotels-Ocean-Paradise-AT-Venture-OUT-4-Bikes-2-2-Person-Kayaks.h44556643.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/70000000/69810000/69809300/69809218/d227c1d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/70000000/69810000/69809300/69809218/97c0a768.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) ![Marina](https://images.trvl-media.com/lodging/70000000/69810000/69809300/69809218/c4c56e7d.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. Cudjoe Key CA $208 CA $262 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Summerland-Key-Hotels-Canal-Front-RV-Lot-Quick-Access-To-Atlantic-Ocean-Or-Gulf.h69809218.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/108000000/107120000/107116600/107116554/3c8eff21.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107120000/107116600/107116554/e1bc9e10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/108000000/107120000/107116600/107116554/5498fbd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blue Lobster Lodge - Venture Out #543 - Cudjoe Key Cudjoe Key 9.2/10 Wonderful (7) "Close to Key West. Would stay there again!!" CA $264 CA $820 total includes taxes & fees Oct 11 - Oct 12 [](https://www.expedia.ca/Summerland-Key-Hotels-Blue-Lobster-Lodge-Venture-Out-543-Cudjoe-Key.h107116554.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-22&endDate=2025-10-23®ionId=6177802&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Summerland Key Hotel Reviews ![Sugar Loaf Lodge](//images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/95d2903e_y.jpg) ### Sugar Loaf Lodge 10/10 Excellent "Everything was fine even better as it was there for longer " [](https://expedia.ca/Sugarloaf-Key-Hotels-Sugar-Loaf-Lodge.h3918121.Hotel-Information) ![Looe Key Reef Resort](//images.trvl-media.com/lodging/5000000/4760000/4759500/4759500/63d12f01_y.jpg) ### Looe Key Reef Resort 8/10 Good "This is a very REASONABLY priced lodging for the FL Keys so expect simple things. We had a great stay, room was clean, the young gent at the front desk was exceptionally friendly and helpful, ditto at checkout. The beds are comfortable. The shower head had great pressure and the onsite tiki bar is a big plus. There were no plastic cups or coffee maker in the room but there was a microwave and fridge and table with two chairs. The ice machine was not working but there is a quickie mart just next door for that if you needed it. Could the resort be flashier, yes it could but Looe Key Reef Resort offered us a cost effective comfy safe stay in a place where time in the room was not important. We did not use the pool or the dive/snorkle amenities as we came down to fish, but if you wanted that stuff it’s all here. We hope to be back soon." [](https://expedia.ca/Ramrod-Key-Hotels-Looe-Key-Reef-Resort.h4759500.Hotel-Information) ![Parmer's Resort](//images.trvl-media.com/lodging/6000000/5570000/5561500/5561465/6492712a_y.jpg) ### Parmer's Resort 10/10 Excellent "Clean room , many options for guests to do around property. Close to key west and marathon" [](https://expedia.ca/Little-Torch-Key-Hotels-Parmers-Resort.h5561465.Hotel-Information) ## Frequently asked questions ### What's it like visiting Summerland Key? > If lounging next to a pool is your idea of a great vacation, you may want to consider Summerland Key, which has 7 places to stay with pools. During your visit, you can explore attractions like Sugarloaf Beach and Venture Out Keys, and then kick back and relax poolside at one of the accommodations in Summerland Key that guests like for their pools. ### What are some accommodations with pools in Summerland Key? > [Parmer's Resort](https://www.expedia.ca/Little-Torch-Key-Hotels-Parmers-Resort.h5561465.Hotel-Information): Features a private beach, an outdoor pool, and daily. [Sugar Loaf Lodge](https://www.expedia.ca/Sugarloaf-Key-Hotels-Sugar-Loaf-Lodge.h3918121.Hotel-Information): Offers 2 outdoor tennis courts, an outdoor pool, and free self parking. [Looe Key Reef Resort](https://www.expedia.ca/Ramrod-Key-Hotels-Looe-Key-Reef-Resort.h4759500.Hotel-Information): Provides free self parking, an outdoor pool, and complimentary wireless internet access. [Sugarloaf Key Hotel at KOA Resort](https://www.expedia.ca/Sugarloaf-Key-Hotels-Sugarloaf-Key-Hotel.h101135765.Hotel-Information): Features a private beach, an outdoor pool, and a snack bar/deli. [Old Florida Style, wrap around porch, boat basin for dockage, open water](https://www.expedia.ca/Little-Torch-Key-Hotels-Old-Florida-Style.h73238458.Hotel-Information): Features kitchens, a communal pool, and televisions. ### How many hotels with pools will I be able to find in Summerland Key? > Expedia has 7 hotels in Summerland Key for your poolside break. ### What is there to see and do in Summerland Key? > The picturesque setting of Sugarloaf Beach and Venture Out Keys showcase the area's natural beauty. Discover sights such as Upper Sugarloaf Key, Coupon Bight Aquatic Preserve, and Upper Sugarloaf Sound during your stay. ### When is the best time to book a hotel with a pool in Summerland Key? > Taking into account the local weather in Summerland Key is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually August and July with an average temp of 84°F, while the coldest months are January and February with an average of 73°F. 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