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) ![Aerial view of road to Key West with turquoise water and small island, Summerland Key, Florida, United States.](https://images.trvl-media.com/place/6177802/f131c6a4-614b-4692-9e06-db0aca0a1329.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Summerland Key, FL from CA $157 - ![](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 Summerland Key Hotels with a Pool Tonight [Nov 25 - Nov 26](https://www.expedia.ca/Hotel-Search?regionId=6177802&startDate=2025-11-25&endDate=2025-11-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 26 - Nov 27](https://www.expedia.ca/Hotel-Search?regionId=6177802&startDate=2025-11-26&endDate=2025-11-27&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=6177802&startDate=2025-11-28&endDate=2025-11-30&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=6177802&startDate=2025-12-05&endDate=2025-12-07&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Summerland Key Hotels with a Pool ![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) ![Cottage, 2 Bedrooms, Ocean View | Terrace/patio](https://images.trvl-media.com/lodging/6000000/5570000/5561500/5561465/75ac6ed2.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 (1006) "Breakfast options, a heated pool" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ricardo CA $152 CA $217 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Little-Torch-Key-Hotels-Parmers-Resort.h5561465.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/83592c1d.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) ![Balcony](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/a36bdda4.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 (1004) "Tiki hit closed, wish I had known Staff very nice, rooms fine" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $140 CA $157 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Sugarloaf-Key-Hotels-Sugar-Loaf-Lodge.h3918121.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/75000000/74240000/74237000/74236945/00dc7121.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/75000000/74240000/74237000/74236945/cd44e6df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74240000/74237000/74236945/17d08c7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/75000000/74240000/74237000/74236945/13a191dd.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 8.2/10 Very good (48) "Very quiet place close to restaurants of all source we would like to come back and stay in the 3/2 cabin on the water with our grown children" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nathalie F. CA $190 CA $447 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Summerland-Key-Hotels-Old-Florida-Style.h74236945.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) ![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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/8879ca02.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 (159) "Great property,Great location. Will definitely stay there again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roy F. CA $212 CA $447 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Summerland-Key-Hotels-Cottage-With-Pool-And-Dockage.h33389096.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/34000000/33920000/33912100/33912031/6f06ccde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33920000/33912100/33912031/761d8c20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33920000/33912100/33912031/7fe34b71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/34000000/33920000/33912100/33912031/9baadd6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage with Pool and Boat Dockage just minutes to Key West! Cudjoe Key 8.6/10 Excellent (150) "This cottage served our purpose well, very close to our family’s home and was very clean and comfortable for a short stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard S. CA $176 CA $357 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Summerland-Key-Hotels-Cottage-With-Pool-And-Boat-Dockage-Just-Minutes-To-Key-West.h33912031.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) ![Exterior](https://images.trvl-media.com/lodging/5000000/4760000/4759500/4759500/63d12f01.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) ![Breakfast, lunch, dinner served; American cuisine, pool views ](https://images.trvl-media.com/lodging/5000000/4760000/4759500/4759500/974f08a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Looe Key Reef Resort Summerland Key 7.4/10 Good (1003) "Room was really clean and receptionist very friendly. Travelling with my son so had a nice big bed each. Balcony was nice and its only 35 mins to Key West which was oerfect" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Clare CA $247 CA $278 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Ramrod-Key-Hotels-Looe-Key-Reef-Resort.h4759500.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) ![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) ![Outdoor dining](https://images.trvl-media.com/lodging/70000000/69810000/69809300/69809218/75f89a41.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 $210 CA $265 total includes taxes & fees Nov 28 - Nov 29 [](https://www.expedia.ca/Summerland-Key-Hotels-Canal-Front-RV-Lot-Quick-Access-To-Atlantic-Ocean-Or-Gulf.h69809218.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) ![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) ![Interior](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/f2ffe64a.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) ### NOV. & DEC. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS! Cudjoe Key 9.6/10 Exceptional (100) "Great location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Davian k. CA $323 CA $754 total includes taxes & fees Dec 1 - Dec 2 [](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) ![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) ### NOV. & DEC. 50% OFF! OCEANFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS! Cudjoe Key 9.8/10 Exceptional (82) "The place is clean and convenient for anyone wanting to spend time on the water in the keys" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ubaldo G. CA $351 CA $789 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Cudjoe-Key-Hotels-Ocean-Paradise-AT-Venture-OUT-4-Bikes-2-2-Person-Kayaks.h44556643.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/7c5d926a.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) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/b25eb073.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) ### Just 20 miles from Key West! Oceanfront, dockage, swimming pool Cutthroat Harbor Estates 8.4/10 Very good (118) "Great experience " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peyton S. CA $317 CA $760 total includes taxes & fees Nov 28 - Nov 29 [](https://www.expedia.ca/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.ca/Hotel-Search?startDate=2025-12-09&endDate=2025-12-10®ionId=6177802&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AFFINITY_BF_PROMO_6177802) ## Top Summerland 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 "Awesome experience" [](https://expedia.ca/Little-Torch-Key-Hotels-Parmers-Resort.h5561465.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 "Lovely receptionist, very frieindly and helpful. Room very clean. 60 yards from Tiki bar with great live music, bar good and cold beer!!" [](https://expedia.ca/Ramrod-Key-Hotels-Looe-Key-Reef-Resort.h4759500.Hotel-Information) ![Sugar Loaf Lodge](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/95d2903e_y.jpg) ### Sugar Loaf Lodge 10/10 Excellent "…" [](https://expedia.ca/Sugarloaf-Key-Hotels-Sugar-Loaf-Lodge.h3918121.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 Upper Sugarloaf Key and Florida Keys Beaches, 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): Hotel located near Florida Keys Beaches. 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 Upper Sugarloaf Key and Florida Keys Beaches showcase the area's natural beauty. Discover sights such as Venture Out Keys, 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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