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 5 - Apr 6](https://www.expedia.com/Hotel-Search?regionId=6177802&startDate=2026-04-05&endDate=2026-04-06&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Apr 6 - Apr 7](https://www.expedia.com/Hotel-Search?regionId=6177802&startDate=2026-04-06&endDate=2026-04-07&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) In two weeks [Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=6177802&startDate=2026-04-17&endDate=2026-04-19&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) ![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) ![Suite, 1 Bedroom, Kitchen, Sea Facing | Living area | TV, books, stereo](https://images.trvl-media.com/lodging/6000000/5570000/5561500/5561465/686b790f.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 (1,005 reviews) - Soak up sun and sea at this coastal oasis with a sparkling pool, private beach, and marina. $217 nightly $244 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) ![Exterior](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/fe329a14.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) ### Sugar Loaf Lodge [](https://www.expedia.com/Sugarloaf-Key-Hotels-Sugar-Loaf-Lodge.h3918121.Hotel-Information) Summerland Key 8.2/10 Very Good (1,003 reviews) - Dive into paradise at this oceanfront retreat with heated pool, marina access, and tennis courts. $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) ![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/5000000/4760000/4759500/4759500/974f08a3.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) ### Looe Key Reef Resort [](https://www.expedia.com/Ramrod-Key-Hotels-Looe-Key-Reef-Resort.h4759500.Hotel-Information) Summerland Key 7.6/10 Good (1,002 reviews) - Sun-dappled pool paradise at Looe Key Reef Resort offers snorkeling adventures nearby. $201 nightly $226 total May 4 - May 5 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) ![Dining](https://images.trvl-media.com/lodging/70000000/69810000/69809300/69809218/61a8a4c0.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) ![Sport court](https://images.trvl-media.com/lodging/70000000/69810000/69809300/69809218/ea553f5e.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) $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) ![Exterior](https://images.trvl-media.com/lodging/84000000/83450000/83440800/83440767/5ff4b852.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) ### 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) $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/34000000/33390000/33389100/33389096/8c6eb102.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) ![Interior](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/29a8f0dd.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 [](https://www.expedia.com/Summerland-Key-Hotels-Cottage-With-Pool-And-Dockage.h33389096.Hotel-Information) Cudjoe Key 9.2/10 Wonderful (165 reviews) $346 nightly $383 total Apr 22 - Apr 23 Total with taxes and fees [](https://www.expedia.com/Summerland-Key-Hotels-Cottage-With-Pool-And-Dockage.h33389096.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/45000000/44560000/44556700/44556643/5f412538.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) ### 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) $449 nightly $498 total Apr 13 - Apr 14 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) ![Exterior detail](https://images.trvl-media.com/lodging/118000000/117680000/117678200/117678152/50d75af0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117680000/117678200/117678152/bb5499e0.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 reviews) $585 nightly $649 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) ![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) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/a9f31955.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 reviews) $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) ![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 | 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/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.com/Summerland-Key-Hotels-Atlantic-View-Luxury-Villa-With-Pool.h111535402.Hotel-Information) Summerland Key 10/10 Exceptional (2 reviews) - Private plunge pool paradise unfolds with Atlantic views and 7 outdoor oases for sun-drenched days. $975 nightly $1,097 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/Summerland-Key-Hotels-Atlantic-View-Luxury-Villa-With-Pool.h111535402.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=2026-04-19&endDate=2026-04-20®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) ![Dining](https://images.trvl-media.com/lodging/70000000/69810000/69809300/69809218/61a8a4c0.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) ![Sport court](https://images.trvl-media.com/lodging/70000000/69810000/69809300/69809218/ea553f5e.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) ![Exterior](https://images.trvl-media.com/lodging/84000000/83450000/83440800/83440767/5ff4b852.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) ### 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) ![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) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/a9f31955.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) ![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/106000000/105240000/105238300/105238265/8235caf5.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) ![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105240000/105238300/105238265/548e5f5d.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) $275 nightly $296 total Apr 6 - Apr 7 Total with taxes and fees [](https://www.expedia.com/Summerland-Key-Hotels-Seabreeze-Escape-WF-RV-Lot-489.h105238265.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) ![Property grounds](https://images.trvl-media.com/lodging/104000000/103540000/103537700/103537636/2c15f130.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) ![Beach](https://images.trvl-media.com/lodging/104000000/103540000/103537700/103537636/fc5e8fb3.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 $303 nightly $327 total Apr 6 - Apr 7 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) ![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117680000/117678200/117678152/bb5499e0.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) $585 nightly $649 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) ![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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/117000000/116670000/116667100/116667062/d1732c67.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) ![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 | 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) ![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 12 - Apr 13 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/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) ![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) ### 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) ![Outdoor dining](https://images.trvl-media.com/lodging/105000000/104880000/104875300/104875207/ce42ac53.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) ![Marina](https://images.trvl-media.com/lodging/105000000/104880000/104875300/104875207/c4e05ae6.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) 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=2026-04-19&endDate=2026-04-20®ionId=6177802&adults=2&amenities=POOL&sort=RECOMMENDED&amenities=HOT_TUB&openPlayBack=true) ## Top Summerland Key Hotel Reviews ![Parmer's Resort](https://images.trvl-media.com/lodging/6000000/5570000/5561500/5561465/bc839964_y.jpg) ### Parmer's Resort 10/10 Excellent "Overall resort is good and near to kiki restaurant , back water, 7 mile bridge , Honda park beach , deer preservation area , staff is friendly , breakfast included and one hour to key west downtown activities " [](https://expedia.com/Little-Torch-Key-Hotels-Parmers-Resort.h5561465.Hotel-Information) ![Looe Key Reef Resort](https://images.trvl-media.com/lodging/5000000/4760000/4759500/4759500/a7994045_y.jpg) ### Looe Key Reef Resort 10/10 Excellent "Great" [](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 10/10 Excellent "We would go back here again, view was amazing. Enjoyed staying there " [](https://expedia.com/Sugarloaf-Key-Hotels-Sugar-Loaf-Lodge.h3918121.Hotel-Information) ![Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security](https://images.trvl-media.com/lodging/20000000/19100000/19092400/19092385/d0245a3c_y.jpg) ### Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security 10/10 Excellent "We enjoyed our stay here with our 2 kids. The pool is awesome and heated to a very comfortable temperature. There are lots of chairs around the pool and places to sit. We liked the variety of common areas around the property and really enjoyed the bicycles. It was too rough for kayaking due to wind but it looks like a great area to kayak. The house is clean and comfortable with every amenity you could need. Some reviews mention aggressive security personnel but we found them to be polite and friendly. I appreciate the extra level of security that keeps the area nice and very family friendly. " [](https://expedia.com/Cudjoe-Key-Hotels-Oceanside-Paradise-Kayaks.h19092385.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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[Enterprise Rental Cars in Cudjoe Key ](https://www.expedia.com/Enterprise-Car-Rentals-In-Cudjoe-Key.d3000430966-c15.Car-Rental-Guide-Suppliers) - [Ramrod Key Vacation Rentals ](https://www.expedia.com/Ramrod-Key-Vacation-Rentals.d6156102.Travel-Guide-VacationRentals) - [Lower Keys Vacation Rentals ](https://www.expedia.com/Lower-Keys-Vacation-Rentals.d553248621593965863.Travel-Guide-VacationRentals) - [Little Torch Key Vacation Rentals ](https://www.expedia.com/Little-Torch-Key-Vacation-Rentals.d177498.Travel-Guide-VacationRentals) - [Cudjoe Key Vacation Rentals ](https://www.expedia.com/Cudjoe-Key-Vacation-Rentals.d3000430966.Travel-Guide-VacationRentals) - [Things to do in Ramrod Key ](https://www.expedia.com/Things-To-Do-In-Ramrod-Key.d6156102.Travel-Guide-Activities) - [Things to do in Cudjoe Key ](https://www.expedia.com/Things-To-Do-In-Cudjoe-Key.d3000430966.Travel-Guide-Activities) - [Things to do in Lower Keys ](https://www.expedia.com/Things-To-Do-In-Lower-Keys.d553248621593965863.Travel-Guide-Activities) - [Things to do in Little Torch Key ](https://www.expedia.com/Things-To-Do-In-Little-Torch-Key.d177498.Travel-Guide-Activities)