Title: The Best Summerland Key Hotels with Pools from $188 - Hotels with indoor pools in Summerland Key, FL | Expedia.com [Summerland Key Travel Guide](https://expedia.com/Summerland-Key.dx6177802)[Hotels in Summerland Key](https://expedia.com/Summerland-Key-Hotels.d6177802.Travel-Guide-Hotels)[Vacation Rentals in Summerland Key](https://expedia.com/Summerland-Key-Vacation-Rentals.d6177802.Travel-Guide-VacationRentals)[Flights to Summerland Key](https://expedia.com/Cheap-Flights-To-Summerland-Key.d6177802.Travel-Guide-Flights)[Things to do in Summerland Key](https://expedia.com/Things-To-Do-In-Summerland-Key.d6177802.Travel-Guide-Activities)[Car Rentals in Summerland Key](https://expedia.com/Car-Rentals-In-Summerland-Key.d6177802.Car-Rental-Guide)[Summerland Key Vacation Packages](https://expedia.com/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) ![](https://images.trvl-media.com/place/6177802/f131c6a4-614b-4692-9e06-db0aca0a1329.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 Summerland Key Hotels with a Pool Tonight [Apr 2 - Apr 3](https://www.expedia.com/Hotel-Search?regionId=6177802&startDate=2026-04-02&endDate=2026-04-03&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Apr 3 - Apr 4](https://www.expedia.com/Hotel-Search?regionId=6177802&startDate=2026-04-03&endDate=2026-04-04&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=6177802&startDate=2026-04-03&endDate=2026-04-05&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=6177802&startDate=2026-04-10&endDate=2026-04-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Summerland Key hotels with a pool ![Private beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/6000000/5570000/5561500/5561465/af3b2788.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dock](https://images.trvl-media.com/lodging/6000000/5570000/5561500/5561465/a69616f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Kitchen, Sea Facing | Individually decorated, individually furnished, iron/ironing board](https://images.trvl-media.com/lodging/6000000/5570000/5561500/5561465/680528cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5570000/5561500/5561465/bc839964.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Parmer's Resort [](https://www.expedia.com/Little-Torch-Key-Hotels-Parmers-Resort.h5561465.Hotel-Information) Summerland Key 9.0/10 Wonderful (1,006 reviews) "Within easy reach of Key West" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peter $238 nightly $268 total Apr 27 - Apr 28 Total with taxes and fees [](https://www.expedia.com/Little-Torch-Key-Hotels-Parmers-Resort.h5561465.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/12041d0c.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) ![Property grounds](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/125c52d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/fe329a14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sugar Loaf Lodge [](https://www.expedia.com/Sugarloaf-Key-Hotels-Sugar-Loaf-Lodge.h3918121.Hotel-Information) Summerland Key 8.2/10 Very Good (1,000 reviews) "good location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert $169 nightly $190 total May 3 - May 4 Total with taxes and fees [](https://www.expedia.com/Sugarloaf-Key-Hotels-Sugar-Loaf-Lodge.h3918121.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) ![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) ![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) ### 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 (57 reviews) "The location was perfect for going in and out of Key West. The house was clean, spacious and comfortable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Josie D. $359 nightly $398 total Apr 3 - Apr 4 Total with taxes and fees [](https://www.expedia.com/Summerland-Key-Hotels-Old-Florida-Style.h73238505.Hotel-Information) ![Outdoor pool, open 7:00 AM to 10:00 PM, 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) ![Sports bar, pool views, open daily](https://images.trvl-media.com/lodging/5000000/4760000/4759500/4759500/17a84140.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![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 [](https://www.expedia.com/Ramrod-Key-Hotels-Looe-Key-Reef-Resort.h4759500.Hotel-Information) Summerland Key 7.6/10 Good (1,010 reviews) "Room was clean and great location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) KHANDAKER MOINUR $217 nightly $245 total May 3 - May 4 Total with taxes and fees [](https://www.expedia.com/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) ![Marina](https://images.trvl-media.com/lodging/70000000/69810000/69809300/69809218/c4c56e7d.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) ![Dining](https://images.trvl-media.com/lodging/70000000/69810000/69809300/69809218/61a8a4c0.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 (3 reviews) "Just as described, a place to park our RV, nice amenities, (extra 125 one time charge, but that was explained ahead of time)" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Larry B. $169 nightly $188 total Apr 30 - May 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) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/84000000/83450000/83440800/83440767/88788395.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/84000000/83450000/83440800/83440767/166b3fd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83450000/83440800/83440767/d142accd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83450000/83440800/83440767/e990b643.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Island Oasis \~ YOUR Paradise awaits in Venture Out Resort! [](https://www.expedia.com/Cudjoe-Key-Hotels-Island-Oasis-YOUR-Paradise-Awaits-In-Venture-Out-Resort.h83440767.Hotel-Information) Cudjoe Key 9.6/10 Exceptional (14 reviews) "The owners were fantastic to deal with and the house was great. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveler $326 nightly $362 total Apr 8 - Apr 9 Total with taxes and fees [](https://www.expedia.com/Cudjoe-Key-Hotels-Island-Oasis-YOUR-Paradise-Awaits-In-Venture-Out-Resort.h83440767.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/45000000/44560000/44556700/44556643/080e8cfe.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 $$$ APRIL! 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 (86 reviews) "The rental was super clean and beautiful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) christopher v. $501 nightly $557 total Apr 3 - Apr 4 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) ![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) ![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) ### 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 (2 reviews) "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 Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Summerland-Key-Hotels-Atlantic-View-Luxury-Villa-With-Pool.h111535402.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) $271 nightly $292 total Apr 3 - Apr 4 Total with taxes and fees [](https://www.expedia.com/Summerland-Key-Hotels-Seabreeze-Escape-WF-RV-Lot-489.h105238265.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) ![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) ### 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 (155 reviews) "Great place with beautiful views, house could use some TLC so the trade out is location and outdoor space with nice yard and very peaceful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peggy H. $629 nightly $698 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/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.com/Hotel-Search?startDate=2026-04-16&endDate=2026-04-17®ionId=6177802&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at hotels with a pool in Summerland Key Breakfast included Hot tub 4 stars 5 stars Spa ## Hotels with pools and hot tubs in Summerland Key ![Exterior](https://images.trvl-media.com/lodging/70000000/69810000/69809300/69809218/d227c1d8.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) ![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) ![Dining](https://images.trvl-media.com/lodging/70000000/69810000/69809300/69809218/61a8a4c0.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 (3) $169 nightly $188 total Apr 30 - May 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) ![Property grounds](https://images.trvl-media.com/lodging/84000000/83450000/83440800/83440767/166b3fd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/84000000/83450000/83440800/83440767/88788395.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83450000/83440800/83440767/d142accd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83450000/83440800/83440767/e990b643.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Island Oasis \~ YOUR Paradise awaits in Venture Out Resort! [](https://www.expedia.com/Cudjoe-Key-Hotels-Island-Oasis-YOUR-Paradise-Awaits-In-Venture-Out-Resort.h83440767.Hotel-Information) Cudjoe Key 9.6/10 Exceptional (14) $326 nightly $362 total Apr 8 - Apr 9 Total with taxes and fees [](https://www.expedia.com/Cudjoe-Key-Hotels-Island-Oasis-YOUR-Paradise-Awaits-In-Venture-Out-Resort.h83440767.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) $271 nightly $292 total Apr 3 - Apr 4 Total with taxes and fees [](https://www.expedia.com/Summerland-Key-Hotels-Seabreeze-Escape-WF-RV-Lot-489.h105238265.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) ![Outdoor dining](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/9c267ac9.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) ![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 $$$ APRIL! 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 (106) $449 nightly $498 total Apr 13 - Apr 14 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) ![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 | 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) ![Exterior](https://images.trvl-media.com/lodging/112000000/111540000/111535500/111535402/w2722h1530x2y6-b30f2be4.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.com/Summerland-Key-Hotels-Atlantic-View-Luxury-Villa-With-Pool.h111535402.Hotel-Information) Summerland Key 10/10 Exceptional (2) $975 nightly $1,097 total Apr 5 - Apr 6 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) ![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) ![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.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) $536 nightly $588 total Apr 11 - Apr 12 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) ![Dining](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/75d37db8.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) ![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.com/Summerland-Key-Hotels-Updated-2BR2BA-Venture-Out-Home-W-Pool-Access.h120816897.Hotel-Information) Cudjoe Key 8.0/10 Very Good (2) $578 nightly $634 total Apr 6 - Apr 7 Total with taxes and fees [](https://www.expedia.com/Summerland-Key-Hotels-Updated-2BR2BA-Venture-Out-Home-W-Pool-Access.h120816897.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) ![Marina](https://images.trvl-media.com/lodging/105000000/104880000/104875300/104875207/c4e05ae6.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) ![Property grounds](https://images.trvl-media.com/lodging/105000000/104880000/104875300/104875207/6ca864aa.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 $269 nightly $290 total Apr 30 - May 1 Total with taxes and fees [](https://www.expedia.com/Summerland-Key-Hotels-Endless-Summer-Hideaway-Lot-181.h104875207.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 $299 nightly $323 total Apr 3 - Apr 4 Total with taxes and fees [](https://www.expedia.com/Summerland-Key-Hotels-Endless-Ocean-Views-RV589.h103537636.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/118000000/117680000/117678200/117678152/50d75af0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/118000000/117680000/117678200/117678152/15b239c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117680000/117678200/117678152/b22a7d78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/118000000/117680000/117678200/117678152/b7dc0f05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key [](https://www.expedia.com/Summerland-Key-Hotels-Charming-2-Bedroom-House-With-WiFi.h117678152.Hotel-Information) Cudjoe Key 10/10 Exceptional (3) $562 nightly $623 total Apr 6 - Apr 7 Total with taxes and fees [](https://www.expedia.com/Summerland-Key-Hotels-Charming-2-Bedroom-House-With-WiFi.h117678152.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=2026-04-16&endDate=2026-04-17®ionId=6177802&adults=2&amenities=POOL&sort=RECOMMENDED&amenities=HOT_TUB&openPlayBack=true) ## Top Summerland Key Hotel Reviews ![Looe Key Reef Resort](https://images.trvl-media.com/lodging/5000000/4760000/4759500/4759500/a7994045_y.jpg) ### Looe Key Reef Resort 10/10 Excellent "Tiki bar on the property was so much fun. Beds were comfortable. " [](https://expedia.com/Ramrod-Key-Hotels-Looe-Key-Reef-Resort.h4759500.Hotel-Information) ![Sugar Loaf Lodge](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/8ae32688_y.jpg) ### Sugar Loaf Lodge 6/10 Okay "Get what you pay for I guess" [](https://expedia.com/Sugarloaf-Key-Hotels-Sugar-Loaf-Lodge.h3918121.Hotel-Information) ![Parmer's Resort](https://images.trvl-media.com/lodging/6000000/5570000/5561500/5561465/bc839964_y.jpg) ### Parmer's Resort 10/10 Excellent "Everything about Parmer’s resort was great! The staff was incredibly kind and helpful, the amenities were fun, the space around rooms were filled with lots of seating and areas to relax. There was a variety of breakfast items as well. " [](https://expedia.com/Little-Torch-Key-Hotels-Parmers-Resort.h5561465.Hotel-Information) ## Frequently asked questions ### What's it like visiting Summerland Key? ### What are some accommodations with pools in Summerland Key? ### How many hotels with pools will I be able to find in Summerland Key? ### What is there to see and do in Summerland Key? ### When is the best time to book a hotel with a pool in Summerland Key? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - [Pet-Friendly Hotels in Ramrod Key ](https://www.expedia.com/Ramrod-Key-Hotels-Pet-Friendly-Hotel.0-0-d6156102-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Hotels with Bars in Ramrod Key ](https://www.expedia.com/Ramrod-Key-Hotels-Bar-Hotel.0-0-d6156102-tBarHotel.Travel-Guide-Filter-Hotels) - [Historic Hotels in Ramrod Key ](https://www.expedia.com/Ramrod-Key-Hotels-Historic-Hotel.0-0-d6156102-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Beach Hotels in Ramrod Key ](https://www.expedia.com/Ramrod-Key-Hotels-Beach-Hotel.0-0-d6156102-tBeachHotel.Travel-Guide-Filter-Hotels) - 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