Title: The Best Hotels with a Pool in Dredgers Key from $336 in 2026 | Expedia.com [Dredgers Key Travel Guide](https://expedia.com/Dredgers-Key.dx180165)[Hotels in Dredgers Key](https://expedia.com/Dredgers-Key-Hotels.d180165.Travel-Guide-Hotels)[Vacation Rentals in Dredgers Key](https://expedia.com/Dredgers-Key-Vacation-Rentals.d180165.Travel-Guide-VacationRentals)[Flights to Dredgers Key](https://expedia.com/Cheap-Flights-To-Dredgers-Key.d180165.Travel-Guide-Flights)[Car Rentals in Dredgers Key](https://expedia.com/Car-Rentals-In-Dredgers-Key.d180165.Car-Rental-Guide)[Dredgers Key Vacation Packages](https://expedia.com/Dredgers-Key.d180165.Destination-Travel-Guides) ![Sailboat Anchored off coast of Dredger Key Sigsbee - Key West Florida](https://images.trvl-media.com/place/180165/e5da9c05-163f-4610-8c3c-2e059edcacec.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/180165/e5da9c05-163f-4610-8c3c-2e059edcacec.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 Dredgers Key Hotels with a Pool Tonight [Feb 10 - Feb 11](https://www.expedia.com/Hotel-Search?regionId=180165&startDate=2026-02-10&endDate=2026-02-11&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 11 - Feb 12](https://www.expedia.com/Hotel-Search?regionId=180165&startDate=2026-02-11&endDate=2026-02-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 13 - Feb 15](https://www.expedia.com/Hotel-Search?regionId=180165&startDate=2026-02-13&endDate=2026-02-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 20 - Feb 22](https://www.expedia.com/Hotel-Search?regionId=180165&startDate=2026-02-20&endDate=2026-02-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Dredgers 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 (1,005 reviews) "Clean, convenient location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael $299 nightly $336 total Feb 16 - Feb 17 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/34000000/33570000/33566300/33566283/fa9fff97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/34000000/33570000/33566300/33566283/f3c522ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33570000/33566300/33566283/00d423f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33570000/33566300/33566283/bc83e7d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage with swimming pool and dockage, just minutes to Key West! [](https://www.expedia.com/Summerland-Key-Hotels-Cottage-With-Swimming-Pool-And-Dockage.h33566283.Hotel-Information) Cudjoe Key 9.0/10 Wonderful (165 reviews) "Everything was there that I needed. Very nice area for my dog." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Terry $292 nightly $324 total Feb 15 - Feb 16 Total with taxes and fees [](https://www.expedia.com/Summerland-Key-Hotels-Cottage-With-Swimming-Pool-And-Dockage.h33566283.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) ![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 [](https://www.expedia.com/Summerland-Key-Hotels-Old-Florida-Style.h73238505.Hotel-Information) Cudjoe Key 8.8/10 Excellent (55 reviews) "Clean rooms, clear guidelines, completely no contact experience without facing any trouble." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Raj $413 nightly $458 total Feb 18 - Feb 19 Total with taxes and fees [](https://www.expedia.com/Summerland-Key-Hotels-Old-Florida-Style.h73238505.Hotel-Information) ![Courtyard](https://images.trvl-media.com/lodging/111000000/110490000/110488200/110488130/f6fb7a5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/111000000/110490000/110488200/110488130/ba6b4821.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fish Tail Palm Premium King Suite, 1King bed, Large Patio area in Garden, Ground Floor | Individually decorated, individually furnished, iron/ironing board](https://images.trvl-media.com/lodging/111000000/110490000/110488200/110488130/d35b4a4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/111000000/110490000/110488200/110488130/9cfe0bbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Douglas House [](https://www.expedia.com/Key-West-Hotels-Douglas-House.h110488130.Hotel-Information) Old Town Key West 9.6/10 Exceptional (282 reviews) "Great place with a perfect location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brandon $449 nightly $505 total Mar 10 - Mar 11 Total with taxes and fees [](https://www.expedia.com/Key-West-Hotels-Douglas-House.h110488130.Hotel-Information) ![6 outdoor pools, free cabanas, pool umbrellas](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/f7424907.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/5714c59c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, down comforters, in-room safe](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/0fcf571b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/d55ace8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oceans Edge Key West Resort, Hotel & Marina [](https://www.expedia.com/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.Hotel-Information) Stock Island 9.0/10 Wonderful (1,799 reviews) "Good location and service" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Weiling $411 nightly $462 total Mar 9 - Mar 10 Total with taxes and fees [](https://www.expedia.com/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.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/w2722h1530x2y6-b30f2be4.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) ### 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 (1 review) "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 Feb 22 - Feb 23 Total with taxes and fees [](https://www.expedia.com/Summerland-Key-Hotels-Atlantic-View-Luxury-Villa-With-Pool.h111535402.Hotel-Information) ![Food and drink](https://images.trvl-media.com/lodging/49000000/48720000/48713900/48713884/5fd7b8bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/49000000/48720000/48713900/48713884/82d7bf8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, white sand](https://images.trvl-media.com/lodging/49000000/48720000/48713900/48713884/01280e2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/49000000/48720000/48713900/48713884/62b1909b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Margaritaville Beach House Key West [](https://www.expedia.com/Key-West-Hotels-Margaritaville-Beach-House-Key-West.h48713884.Hotel-Information) Key West 8.8/10 Excellent (1,795 reviews) "Clean room, amazing food at the resort, and a courteous staff. Thank you for a great stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) michael $554 nightly $623 total Mar 9 - Mar 10 Total with taxes and fees [](https://www.expedia.com/Key-West-Hotels-Margaritaville-Beach-House-Key-West.h48713884.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/290b242a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Top Floor 1BR Ocean View Condo with Rooftop Balcony | Living area | 50-inch flat-screen TV with satellite channels, TV](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/45254304.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ocean View 3BR Condo with Rooftop Balcony | Balcony](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/a1e6ec60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony view](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/ce510800.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beachside Resort & Residences [](https://www.expedia.com/Key-West-Hotels-Key-West-Marriott-Beachside-Hotel.h25865.Hotel-Information) Key West 8.6/10 Excellent (1,974 reviews) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Timothy $435 nightly $489 total Mar 2 - Mar 3 Total with taxes and fees [](https://www.expedia.com/Key-West-Hotels-Key-West-Marriott-Beachside-Hotel.h25865.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/5000000/4220000/4218900/4218809/53a8339f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; seafood, pool views ](https://images.trvl-media.com/lodging/5000000/4220000/4218900/4218809/e7e2b650.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room, 2 Double Beds, Bay View | Premium bedding, pillowtop beds, individually decorated](https://images.trvl-media.com/lodging/5000000/4220000/4218900/4218809/1c18f751.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/5000000/4220000/4218900/4218809/7ea6251e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ibis Bay Beach Resort [](https://www.expedia.com/Key-West-Hotels-Ibis-Bay-Beach-Resort.h4218809.Hotel-Information) Northside Resort 8.0/10 Very Good (2,082 reviews) "Great ppl that work there! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Evan $390 nightly $439 total Mar 12 - Mar 13 Total with taxes and fees [](https://www.expedia.com/Key-West-Hotels-Ibis-Bay-Beach-Resort.h4218809.Hotel-Information) ![Outdoor pool, open 6:00 AM to 10:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/5c83029c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/4583520b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/eb3fe8a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/4d8ae5b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Key West / The Keys Collection [](https://www.expedia.com/Key-West-Hotels-Hilton-Garden-Inn-Key-West.h1376.Hotel-Information) New Town 8.0/10 Very Good (1,200 reviews) "Great place to stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicole $324 nightly $364 total Feb 12 - Feb 13 Total with taxes and fees [](https://www.expedia.com/Key-West-Hotels-Hilton-Garden-Inn-Key-West.h1376.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=2026-02-25&endDate=2026-02-26®ionId=180165&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at hotels with a pool in Dredgers Key Breakfast included 4 stars Ocean view 5 stars Hot tub ## Top Dredgers Key Hotel Reviews ![Pier House Resort & Spa](https://images.trvl-media.com/lodging/1000000/20000/19400/19307/c9267f77_y.jpg) ### Pier House Resort & Spa 10/10 Excellent "Everything was incredible! Beautiful resort and everyone was so nice" [](https://expedia.com/Key-West-Hotels-Pier-House-Resort-Spa.h19307.Hotel-Information) ![Southernmost Beach Resort and Guesthouses](https://images.trvl-media.com/lodging/1000000/870000/863400/863329/026f10af_y.jpg) ### Southernmost Beach Resort and Guesthouses 10/10 Excellent "This resort is more than we ever expected, located right on the gorgeous beach but also right on Duvall Street! The staff was awesome, the Beach Cafe incredible, delicious drinks and food! We will be back for sure!" [](https://expedia.com/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information) ![Ibis Bay Beach Resort](https://images.trvl-media.com/lodging/5000000/4220000/4218900/4218809/4a09d86c_y.jpg) ### Ibis Bay Beach Resort 10/10 Excellent "Clean, nice location, small but nice room" [](https://expedia.com/Key-West-Hotels-Ibis-Bay-Beach-Resort.h4218809.Hotel-Information) ![Parrot Key Hotel & Villas](https://images.trvl-media.com/lodging/1000000/30000/24700/24615/67735d0c_y.jpg) ### Parrot Key Hotel & Villas 10/10 Excellent "Beautiful " [](https://expedia.com/Key-West-Hotels-Parrot-Key-Hotel-Villas.h24615.Hotel-Information) ![The Perry Hotel & Marina Key West](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/e4eb7fd5_y.jpg) ### The Perry Hotel & Marina Key West 10/10 Excellent "Everything was wonderful. Excellent service, lots of food options right there at the marina. Very pleased. " [](https://expedia.com/Key-West-Hotels-The-Perry-Hotel-Marina-Key-West.h17313680.Hotel-Information) ![Winslow's Bungalows - Key West Historic Inns](https://images.trvl-media.com/lodging/1000000/530000/529700/529611/7cf7d263_y.jpg) ### Winslow's Bungalows - Key West Historic Inns 10/10 Excellent "Room was lovely and comfortable. Grounds were very pretty. Location was easy for walking. Both ladies made check-in and check-out easy. They were also very friendly. " [](https://expedia.com/Key-West-Hotels-Kimpton-Winslows-Bungalows.h529611.Hotel-Information) ![Blue Flamingo Resort Key West](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/c4b850d1_y.jpg) ### Blue Flamingo Resort Key West 10/10 Excellent "Was great time!" [](https://expedia.com/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.Hotel-Information) ![Hyatt Vacation Club at Beach House, Key West](https://images.trvl-media.com/lodging/1000000/860000/858000/857962/fc0a2a7e_y.jpg) ### Hyatt Vacation Club at Beach House, Key West 10/10 Excellent "This place is amazing! The property is beautiful and quiet. The pool area was clean and well cared for. Our room was spacious, very clean and had everything we needed. The staff was kind and always helpful. We would definitely go back. " [](https://expedia.com/Key-West-Hotels-Hyatt-Vacation-Club-At-Beach-House.h857962.Hotel-Information) ![NYAH Key West - Adults Only](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/77f11bb4_y.jpg) ### NYAH Key West - Adults Only 10/10 Excellent "Staff courteous and room was clean." [](https://expedia.com/Key-West-Hotels-NYAH-Key-West-Adults-Only.h7500588.Hotel-Information)