Title: Book the Best Hotels with POOL in Breezeswept Beach Estates 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)[Breezeswept Beach Estates Car Rentals](https://expedia.ca/Car-Rentals-In-Breezeswept-Beach-Estates.d553248635976468855.Car-Rental-Guide)[Breezeswept Beach Estates Vacations](https://expedia.ca/Breezeswept-Beach-Estates.d553248635976468855.Destination-Travel-Guides) ![Bahia Honda State Park - Calusa Beach, Florida Keys - tropical beach - USA.](https://images.trvl-media.com/place/553248635976468855/342969f8-bf72-47fd-9555-c44c22f7719e.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Breezeswept Beach Estates, FL from CA $156 - ![](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 Breezeswept Beach Estates Hotels with a Pool Tonight [Nov 20 - Nov 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976468855&startDate=2025-11-20&endDate=2025-11-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 21 - Nov 22](https://www.expedia.ca/Hotel-Search?regionId=553248635976468855&startDate=2025-11-21&endDate=2025-11-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=553248635976468855&startDate=2025-11-21&endDate=2025-11-23&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248635976468855&startDate=2025-11-28&endDate=2025-11-30&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Breezeswept Beach Estates Hotels with a Pool ![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) ![Restaurant](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/95d2903e.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) ### Sugar Loaf Lodge Summerland Key 8.2/10 Very good (1002) "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 $138 CA $156 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Sugarloaf-Key-Hotels-Sugar-Loaf-Lodge.h3918121.Hotel-Information) ![Dock](https://images.trvl-media.com/lodging/6000000/5570000/5561500/5561465/a69616f4.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) ![Suite, 1 Bedroom, Kitchen, Sea Facing | Beach/ocean view](https://images.trvl-media.com/lodging/6000000/5570000/5561500/5561465/6492712a.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) ### Parmer's Resort Summerland Key 9.0/10 Wonderful (1004) "Breakfast options, a heated pool" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ricardo CA $151 CA $216 total includes taxes & fees Dec 2 - Dec 3 [](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) ![New Deluxe Duplex Unit, 1 Queen Bed, Unit C | Private kitchen](https://images.trvl-media.com/lodging/18000000/17110000/17102400/17102343/3b24927e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Old Wooden Bridge Resort and Marina Punta Brisa 8.6/10 Excellent (271) "We will definitely stay here again. Perfect spot to relax. Clean Rooms " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gregory [](https://www.expedia.ca/Big-Pine-Key-Hotels-Old-Wooden-Bridge-Marina.h17102343.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/25000000/24110000/24101800/24101706/3555d599.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast and dinner served](https://images.trvl-media.com/lodging/25000000/24110000/24101800/24101706/9f64224f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/25000000/24110000/24101800/24101706/046d7acc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/25000000/24110000/24101800/24101706/e1765627.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Isla Bella Beach Resort & Spa Marathon 9.2/10 Wonderful (1053) "Rooms and property were very clean . " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica CA $372 CA $505 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Marathon-Hotels-Isla-Bella-Beach-Resort-Spa.h24101706.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/14000000/13210000/13209500/13209442/b9320de6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/14000000/13210000/13209500/13209442/44936e56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, soundproofing, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/14000000/13210000/13209500/13209442/f0cbd748.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/14000000/13210000/13209500/13209442/bf541532.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Knight's Key Suites Marathon 9.0/10 Wonderful (1155) "Room were clean and staff was very helpful " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leonard CA $140 CA $188 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Marathon-Hotels-Captain-Pips-At-Knights-Key-Inn.h13209442.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/75000000/74240000/74237000/74236945/00dc7121.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74240000/74237000/74236945/17d08c7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/75000000/74240000/74237000/74236945/2be7fe30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/75000000/74240000/74237000/74236945/13a191dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West Cudjoe Key 8.2/10 Very good (48) "Very quiet place close to restaurants of all source we would like to come back and stay in the 3/2 cabin on the water with our grown children" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nathalie F. CA $189 CA $444 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Summerland-Key-Hotels-Old-Florida-Style.h74236945.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/w1024h630x0y0-e267420a.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/f111b153.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NOV. & DEC. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS! Cudjoe Key 9.6/10 Exceptional (99) "The house was very clean. Friendly and quiet location. The hosts were extremely helpful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roy F. CA $181 CA $575 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Cudjoe-Key-Hotels-Waterfront-Paradise-AT-Venture-Out4-Bikes-2-2-Seat-Kayaks-King-Queen-Beds.h32660303.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/6e8a6b91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/88047f08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/8879ca02.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) ### Cottage with Pool and Dockage, just minutes to Key West Cudjoe Key 9.2/10 Wonderful (158) "Great property,Great location. Will definitely stay there again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roy F. CA $210 CA $442 total includes taxes & fees Dec 6 - Dec 7 [](https://www.expedia.ca/Summerland-Key-Hotels-Cottage-With-Pool-And-Dockage.h33389096.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/34000000/33920000/33912100/33912031/6f06ccde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33920000/33912100/33912031/761d8c20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33920000/33912100/33912031/7fe34b71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33920000/33912100/33912031/a14e8a95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage with Pool and Boat Dockage just minutes to Key West! Cudjoe Key 8.6/10 Excellent (150) "This cottage served our purpose well, very close to our family’s home and was very clean and comfortable for a short stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard S. CA $175 CA $354 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Summerland-Key-Hotels-Cottage-With-Pool-And-Boat-Dockage-Just-Minutes-To-Key-West.h33912031.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/112000000/111950000/111943400/111943308/1588b31f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/112000000/111950000/111943400/111943308/4b44c88c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111950000/111943400/111943308/b83fa837.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111950000/111943400/111943308/w4096h2519x0y0-7750867f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 🌴 TROPICAL RETREAT 🌴 RV in the Keys Big Pine Key 10/10 Exceptional (2) "Its clean and plenty of room.Outdoor seating is wonderful. Could use a gas grill. But definitely a great place." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) DeeBrett CA $188 CA $459 total includes taxes & fees Nov 22 - Nov 23 [](https://www.expedia.ca/Big-Pine-Key-Hotels-TROPICAL-RETREAT-RV-In-The-Keys.h111943308.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=2025-12-04&endDate=2025-12-05®ionId=553248635976468855&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Breezeswept Beach Estates Hotel Reviews ![Sunshine Key RV Resort & Marina](https://images.trvl-media.com/lodging/7000000/6950000/6940600/6940514/edd108d5_y.jpg) ### Sunshine Key RV Resort & Marina 10/10 Excellent "Excellent place. Clean and welcoming. Perfect for a family weekend." [](https://expedia.ca/Big-Pine-Key-Hotels-Sunshine-Key-RV-Resort-Marina.h6940514.Hotel-Information) ![Parmer's Resort](https://images.trvl-media.com/lodging/6000000/5570000/5561500/5561465/6492712a_y.jpg) ### Parmer's Resort 10/10 Excellent "Awesome experience" [](https://expedia.ca/Little-Torch-Key-Hotels-Parmers-Resort.h5561465.Hotel-Information) ![Old Wooden Bridge Resort and Marina](https://images.trvl-media.com/lodging/18000000/17110000/17102400/17102343/92962431_y.jpg) ### Old Wooden Bridge Resort and Marina 10/10 Excellent "We will definitely stay here again. Perfect spot to relax. Clean Rooms " [](https://expedia.ca/Big-Pine-Key-Hotels-Old-Wooden-Bridge-Marina.h17102343.Hotel-Information) ![Looe Key Reef Resort](https://images.trvl-media.com/lodging/5000000/4760000/4759500/4759500/63d12f01_y.jpg) ### Looe Key Reef Resort 10/10 Excellent "Lovely receptionist, very frieindly and helpful. Room very clean. 60 yards from Tiki bar with great live music, bar good and cold beer!!" [](https://expedia.ca/Ramrod-Key-Hotels-Looe-Key-Reef-Resort.h4759500.Hotel-Information) ![Sugar Loaf Lodge](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/95d2903e_y.jpg) ### Sugar Loaf Lodge 10/10 Excellent "…" [](https://expedia.ca/Sugarloaf-Key-Hotels-Sugar-Loaf-Lodge.h3918121.Hotel-Information) ![Knight's Key Suites](https://images.trvl-media.com/lodging/14000000/13210000/13209500/13209442/5fa8d60e_y.jpg) ### Knight's Key Suites 10/10 Excellent "Room was spotless " [](https://expedia.ca/Marathon-Hotels-Captain-Pips-At-Knights-Key-Inn.h13209442.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Breezeswept Beach Estates? > [Isla Bella Beach Resort & Spa](https://www.expedia.ca/Marathon-Hotels-Isla-Bella-Beach-Resort-Spa.h24101706.Hotel-Information): Hotel located near Sombrero Beach. Features a full-service spa, 5 outdoor pools, and 2 bars. [Old Wooden Bridge Resort and Marina](https://www.expedia.ca/Big-Pine-Key-Hotels-Old-Wooden-Bridge-Marina.h17102343.Hotel-Information): Offers free self parking, an outdoor pool, and complimentary wireless internet access. [Parmer's Resort](https://www.expedia.ca/Little-Torch-Key-Hotels-Parmers-Resort.h5561465.Hotel-Information): Provides a private beach, an outdoor pool, and daily. [Sugar Loaf Lodge](https://www.expedia.ca/Sugarloaf-Key-Hotels-Sugar-Loaf-Lodge.h3918121.Hotel-Information): Hotel located near Florida Keys Beaches. Features 2 outdoor tennis courts, an outdoor pool, and free self parking. [Sugarloaf Key Hotel at KOA Resort](https://www.expedia.ca/Sugarloaf-Key-Hotels-Sugarloaf-Key-Hotel.h101135765.Hotel-Information): Offers a private beach, an outdoor pool, and a snack bar/deli. ### What is there to see and do in Breezeswept Beach Estates? > Make a point to visit attractions like Calusa Beach and Cook Island. 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