Title: Book the Best Hotels with POOL in Sugarloaf Shores in 2025 | Expedia.ca [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)[Sugarloaf Shores Car Rentals](https://expedia.ca/Car-Rentals-In-Sugarloaf-Shores.d6270983.Car-Rental-Guide)[Sugarloaf Shores Vacations](https://expedia.ca/Sugarloaf-Shores.d6270983.Destination-Travel-Guides) ![Sugarloaf Shores featuring a bay or harbor](https://images.trvl-media.com/place/6270983/44cc35b6-7c5a-4d30-8d33-616900dbf0d6.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Sugarloaf Shores, FL - ![](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 Sugarloaf Shores Hotels with a Pool Tonight [Nov 8 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6270983&startDate=2025-11-08&endDate=2025-11-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 9 - Nov 10](https://www.expedia.ca/Hotel-Search?regionId=6270983&startDate=2025-11-09&endDate=2025-11-10&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6270983&startDate=2025-11-14&endDate=2025-11-16&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=6270983&startDate=2025-11-21&endDate=2025-11-23&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Sugarloaf Shores 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) ![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) ![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) ### Parmer's Resort Summerland Key 9.0/10 Wonderful (1000) "Excellent laid back property. Close to a good restaurant " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jane CA $154 CA $219 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Little-Torch-Key-Hotels-Parmers-Resort.h5561465.Hotel-Information) ![Outdoor pool, open 8:30 AM to 8:00 PM, sun loungers](https://images.trvl-media.com/lodging/18000000/17110000/17102400/17102343/bdbf7145.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 Bedroom Aqua Lodge # 13 Barracuda | Living area](https://images.trvl-media.com/lodging/18000000/17110000/17102400/17102343/92962431.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 Bedroom Aqualodge # 6 Tarpon | Living area](https://images.trvl-media.com/lodging/18000000/17110000/17102400/17102343/dee083de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/18000000/17110000/17102400/17102343/1bf38821.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Old Wooden Bridge Resort and Marina Punta Brisa 8.6/10 Excellent (267) "I love this place!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Greg CA $176 CA $397 total includes taxes & fees Dec 6 - Dec 7 [](https://www.expedia.ca/Big-Pine-Key-Hotels-Old-Wooden-Bridge-Marina.h17102343.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) ![Balcony](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/a36bdda4.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) ![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 Summerland Key 8.2/10 Very good (1000) "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 $139 CA $156 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Sugarloaf-Key-Hotels-Sugar-Loaf-Lodge.h3918121.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) ![Double Room, 2 Queen Beds | Terrace/patio](https://images.trvl-media.com/lodging/5000000/4760000/4759500/4759500/13570c88.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 (1000) "Really cute. Good rooms and good spot." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Clotilde CA $247 CA $278 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Ramrod-Key-Hotels-Looe-Key-Reef-Resort.h4759500.Hotel-Information) ![2 outdoor pools, open 8:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/e4eb7fd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; seafood](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/89147e75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/54c5f4f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/d6618f5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Perry Hotel & Marina Key West Stock Island 9.4/10 Exceptional (1142) "The rooms were very clean the staff was extremely nice and helpful. Would definitely stay here again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard CA $176 CA $277 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Key-West-Hotels-The-Perry-Hotel-Marina-Key-West.h17313680.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) ![Daily continental breakfast (USD 18 per person)](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/3484f3ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/ee750f93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/d5aad7de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Key West / The Keys Collection New Town 8.0/10 Very good (1113) "Everything was wonderful, clean room, great staff, lovely facility" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth A CA $122 CA $177 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Key-West-Hotels-Hilton-Garden-Inn-Key-West.h1376.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/86ab7efa.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) ![View from property](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/15e67a67.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) ### Oceans Edge Key West Resort, Hotel & Marina Stock Island 9.0/10 Wonderful (1730) "Great hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jonathan CA $214 CA $325 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/77f11bb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/2f1f2895.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Quadruple Room](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/070a211a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/8000000/7510000/7500600/7500588/eb10500d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NYAH Key West - Adults Only Key West Historic District 7.8/10 Good (1000) "Clean great staff and perfect pool!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristy CA $134 CA $214 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Key-West-Hotels-NYAH-Key-West-Adults-Only.h7500588.Hotel-Information) ![2 outdoor pools, open 7:00 AM to 11:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/cb0a4c1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Poolside bar](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/5792173a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/44728c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/dcdeb665.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blue Flamingo Resort Key West New Town 8.0/10 Very good (1663) "Great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Aaron CA $142 CA $239 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/49000000/48720000/48713900/48713884/4233d834.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/49000000/48720000/48713900/48713884/5710a846.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) ![Exterior](https://images.trvl-media.com/lodging/49000000/48720000/48713900/48713884/2ac07b2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Margaritaville Beach House Key West Key West 8.8/10 Excellent (1768) "Great place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tracey CA $251 CA $371 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Key-West-Hotels-Margaritaville-Beach-House-Key-West.h48713884.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=2025-11-22&endDate=2025-11-23®ionId=6270983&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Sugarloaf Shores Hotel Reviews ![Casa Marina Key West, Curio Collection by Hilton](//images.trvl-media.com/lodging/1000000/20000/12400/12346/be8c9450_y.jpg) ### Casa Marina Key West, Curio Collection by Hilton 10/10 Excellent "Perfect location. Relaxing" [](https://expedia.ca/Key-West-Hotels-Casa-Marina-Key-West.h12346.Hotel-Information) ![Hyatt Vacation Club at Beach House, Key West](//images.trvl-media.com/lodging/1000000/860000/858000/857962/fc0a2a7e_y.jpg) ### Hyatt Vacation Club at Beach House, Key West 10/10 Excellent "Amazing property" [](https://expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Beach-House.h857962.Hotel-Information) ![Hyatt Vacation Club at Windward Pointe, Key West](//images.trvl-media.com/lodging/1000000/870000/868700/868697/481a771e_y.jpg) ### Hyatt Vacation Club at Windward Pointe, Key West 10/10 Excellent "All very good!" [](https://expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Windward-Pointe.h868697.Hotel-Information) ![Hyatt Centric Key West Resort and Spa](//images.trvl-media.com/lodging/1000000/10000/1000/901/0b72a249_y.jpg) ### Hyatt Centric Key West Resort and Spa 10/10 Excellent "View was amazing, great location and friendly staff" [](https://expedia.ca/Key-West-Hotels-Hyatt-Centric-Key-West-Resort-And-Spa.h901.Hotel-Information) ![The Perry Hotel & Marina Key West](//images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/e4eb7fd5_y.jpg) ### The Perry Hotel & Marina Key West 10/10 Excellent "Clean, out of the busy Key West Center. Very nice property." [](https://expedia.ca/Key-West-Hotels-The-Perry-Hotel-Marina-Key-West.h17313680.Hotel-Information) ![Fairfield Inn and Suites by Marriott Key West](//images.trvl-media.com/lodging/1000000/10000/9000/8946/7b2c8a2c_y.jpg) ### Fairfield Inn and Suites by Marriott Key West 10/10 Excellent "Good room. Great breakfast!" [](https://expedia.ca/Key-West-Hotels-Fairfield-Inn-And-Suites-By-Marriott-Key-West.h8946.Hotel-Information) ![Fairfield Inn & Suites by Marriott Key West at the Keys Collection](//images.trvl-media.com/lodging/1000000/30000/21900/21871/aba770f6_y.jpg) ### Fairfield Inn & Suites by Marriott Key West at the Keys Collection 10/10 Excellent "i had a wonderful relaxing stay here . i cant wait to come back again . the staff was Amazing and courteous and very attentive to my every need . i just love the pool area and having a delightful buffet breakfast . the spacious room was exactly what i needed complete with every amenity you could need or want . can i give a 6th star ? wish i could . smileface. i will be back ! " [](https://expedia.ca/Key-West-Hotels-Fairfield-Inn-Suites-Key-West-At-The-Keys-Collection.h21871.Hotel-Information) ![DoubleTree Resort by Hilton Grand Key - Key West](//images.trvl-media.com/lodging/1000000/480000/470900/470834/be4147fb_y.jpg) ### DoubleTree Resort by Hilton Grand Key - Key West 10/10 Excellent "Nice and clean, very curtious staff. Free Shuttle service was great. Food in restaurant was great. " [](https://expedia.ca/Key-West-Hotels-DoubleTree-Resort-By-Hilton-Grand-Key-Key-West.h470834.Hotel-Information) ![Hilton Garden Inn Key West / The Keys Collection](//images.trvl-media.com/lodging/1000000/10000/1400/1376/5c83029c_y.jpg) ### Hilton Garden Inn Key West / The Keys Collection 10/10 Excellent "Clean, comfortable room. Great breakfast, nice pool. " [](https://expedia.ca/Key-West-Hotels-Hilton-Garden-Inn-Key-West.h1376.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Sugarloaf Shores? > [Oceans Edge Key West Resort, Hotel & Marina](https://www.expedia.ca/Key-West-Hotels-Oceans-Edge-Key-West-Resort.h16202992.Hotel-Information): Hotel located near Smathers Beach. Features complimentary bicycles, 6 outdoor pools, and complimentary wireless internet access. [Blue Flamingo Resort Key West](https://www.expedia.ca/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.Hotel-Information): Hotel located near Smathers Beach. Offers 2 restaurants, 2 outdoor pools, and 2 pool bars. [Beachside Resort & Residences](https://www.expedia.ca/Key-West-Hotels-Key-West-Marriott-Beachside-Hotel.h25865.Hotel-Information): Hotel located near Smathers Beach. Provides a private beach, an outdoor pool, and 2 restaurants. [Southernmost Beach Resort and Guesthouses](https://www.expedia.ca/Key-West-Hotels-Southernmost-Beach-Resort.h863329.Hotel-Information): Hotel steps from South Beach. Features 2 pool bars, 3 outdoor pools, and a full-service spa. [Hilton Garden Inn Key West / The Keys Collection](https://www.expedia.ca/Key-West-Hotels-Hilton-Garden-Inn-Key-West.h1376.Hotel-Information): Hotel located near Smathers Beach. Offers 2 restaurants, a pool, and complimentary wired internet access. ### What is there to see and do in Sugarloaf Shores? > Explore places like Duval Street while you're in the area. 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