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 [Mar 16 - Mar 17](https://www.expedia.com/Hotel-Search?regionId=6177802&startDate=2026-03-16&endDate=2026-03-17&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 17 - Mar 18](https://www.expedia.com/Hotel-Search?regionId=6177802&startDate=2026-03-17&endDate=2026-03-18&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=6177802&startDate=2026-03-20&endDate=2026-03-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=6177802&startDate=2026-03-27&endDate=2026-03-29&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Summerland Key hotels with a pool ![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) ![Exterior](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/8ae32688.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 (1,000 reviews) - Dive into paradise at this oceanfront retreat with heated pool, marina access, and tennis courts. $249 nightly $280 total Mar 19 - Mar 20 Total with taxes and fees [](https://www.expedia.com/Sugarloaf-Key-Hotels-Sugar-Loaf-Lodge.h3918121.Hotel-Information) ![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 | 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) ![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) ### Parmer's Resort [](https://www.expedia.com/Little-Torch-Key-Hotels-Parmers-Resort.h5561465.Hotel-Information) Summerland Key 9.0/10 Wonderful (1,003 reviews) - Soak up sun and sea at this coastal oasis with a sparkling pool, private beach, and marina. $307 nightly $345 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Little-Torch-Key-Hotels-Parmers-Resort.h5561465.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 (1,003 reviews) - Sun-dappled pool paradise at Looe Key Reef Resort offers snorkeling adventures nearby. $207 nightly $233 total Mar 24 - Mar 25 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) ![Sport court](https://images.trvl-media.com/lodging/70000000/69810000/69809300/69809218/ea553f5e.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. [](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 Mar 31 - Apr 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](https://images.trvl-media.com/lodging/72000000/71410000/71402800/71402765/2cf2f4c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71410000/71402800/71402765/6b090d7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/72000000/71410000/71402800/71402765/442d52e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71410000/71402800/71402765/49c68fa8.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.h71402765.Hotel-Information) Cudjoe Key 8.6/10 Excellent (53 reviews) $413 nightly $458 total Mar 21 - Mar 22 Total with taxes and fees [](https://www.expedia.com/Summerland-Key-Hotels-Old-Florida-Style.h71402765.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/133c6194.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/61e6cf8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/41c85b83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/136fc75c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming cottages, dockage, pool, just minutes to Key West [](https://www.expedia.com/Summerland-Key-Hotels-Charming-Cottages.h33548243.Hotel-Information) Cudjoe Key 8.6/10 Excellent (124 reviews) $372 nightly $413 total Mar 20 - Mar 21 Total with taxes and fees [](https://www.expedia.com/Summerland-Key-Hotels-Charming-Cottages.h33548243.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) ![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) ![Dining](https://images.trvl-media.com/lodging/32000000/31900000/31892500/31892418/39a5429b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Home [](https://www.expedia.com/Cudjoe-Key-Hotels-Waterfront-Home.h31892418.Hotel-Information) Cudjoe Key 8.6/10 Excellent (178 reviews) $408 nightly $453 total Mar 20 - Mar 21 Total with taxes and fees [](https://www.expedia.com/Cudjoe-Key-Hotels-Waterfront-Home.h31892418.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) ![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 | 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) ### 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 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Summerland-Key-Hotels-Atlantic-View-Luxury-Villa-With-Pool.h111535402.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/105000000/104880000/104875300/104875207/6ca864aa.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) ![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.com/Summerland-Key-Hotels-Endless-Summer-Hideaway-Lot-181.h104875207.Hotel-Information) Cudjoe Key $270 nightly $291 total Mar 21 - Mar 22 Total with taxes and fees [](https://www.expedia.com/Summerland-Key-Hotels-Endless-Summer-Hideaway-Lot-181.h104875207.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/71000000/70550000/70541400/70541336/6e3c9448.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach towels](https://images.trvl-media.com/lodging/71000000/70550000/70541400/70541336/86d1247e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/71000000/70550000/70541400/70541336/w1282h837x1y0-05f17a6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/71000000/70550000/70541400/70541336/w1284h2247x0y0-fe8bc1e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds! [](https://www.expedia.com/Cudjoe-Key-Hotels-Oceanview-Paradise-AT-Venture-Out4-Bikes-2-2-Seat-Kayaks-King-Queen-Beds.h70541336.Hotel-Information) Cudjoe Key 8.0/10 Very Good (15 reviews) $462 nightly $512 total Mar 20 - Mar 21 Total with taxes and fees [](https://www.expedia.com/Cudjoe-Key-Hotels-Oceanview-Paradise-AT-Venture-Out4-Bikes-2-2-Seat-Kayaks-King-Queen-Beds.h70541336.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=2026-03-31&endDate=2026-04-01®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 ## 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 "Very clean I love the casual style of the resort the breakfast and pool and yoga and common areas. Will definitely go back " [](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 "Pam at reception was very welcoming. We went on a 4hr snorkelling trip through the resort which was first rate. The on-site bar is very handy and has live music. No food being served the 3 nights we were there, but no problem as other restaurants nearby. It was a great place from which to explore the Keys. Only 30-45mins to Key West." [](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 "Very clean and friendly environment. Clerk asked if he could carry our bags upstairs for us as there is no elevator. No coffee in available in the rooms but a fantastic coffee bar in the tiki tabernacle with great a view open till 11:00\. Quiet, peaceful and would do again. " [](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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