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) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Breezeswept Beach Estates, FL from CA $132 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 [Oct 5 - Oct 6](https://www.expedia.ca/Hotel-Search?regionId=553248635976468855&startDate=2025-10-05&endDate=2025-10-06&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 6 - Oct 7](https://www.expedia.ca/Hotel-Search?regionId=553248635976468855&startDate=2025-10-06&endDate=2025-10-07&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976468855&startDate=2025-10-10&endDate=2025-10-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976468855&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Breezeswept Beach Estates Hotels with a Pool ![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) ![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) ![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 (258) "Really I have the best experience and soon I want to go again " CA $103 CA $313 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Big-Pine-Key-Hotels-Old-Wooden-Bridge-Marina.h17102343.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) ![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) ![Mini-fridge, coffee/tea maker](https://images.trvl-media.com/lodging/14000000/13210000/13209500/13209442/d5d22c5a.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 (1148) "Great place " CA $91 CA $132 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Marathon-Hotels-Captain-Pips-At-Knights-Key-Inn.h13209442.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) "Nice family owned spot. " CA $138 CA $155 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Sugarloaf-Key-Hotels-Sugar-Loaf-Lodge.h3918121.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/112000000/111950000/111943400/111943366/45fc9285.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111950000/111943400/111943366/6e677530.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111950000/111943400/111943366/33eb7376.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111950000/111943400/111943366/cc3a1cda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 🌴 TROPICAL RETREAT 🌴 RV IN THE KEYS 🌴 Big Pine Key CA $124 CA $378 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Big-Pine-Key-Hotels-RV-IN-THE-KEYS-INSIDE-OUTSIDE-LIVING.h111943366.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 (1000) "Had a wonderful time place is very nice enjoyed ourselves " CA $162 CA $228 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Little-Torch-Key-Hotels-Parmers-Resort.h5561465.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) ![Interior](https://images.trvl-media.com/lodging/112000000/111950000/111943400/111943308/b83fa837.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/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." CA $124 CA $379 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Big-Pine-Key-Hotels-TROPICAL-RETREAT-RV-In-The-Keys.h111943308.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) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33390000/33389100/33389096/ec0614f8.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) ![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 Cudjoe Key 9.2/10 Wonderful (154) "Good Fishing, Good local eateries. " CA $209 CA $443 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Summerland-Key-Hotels-Cottage-With-Pool-And-Dockage.h33389096.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) ![Breakfast, 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) ![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) ![Exterior](https://images.trvl-media.com/lodging/5000000/4760000/4759500/4759500/63d12f01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Looe Key Reef Resort Summerland Key 7.4/10 Good (1000) "Average stay, old room, friendly staff, quiet" CA $182 CA $205 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Ramrod-Key-Hotels-Looe-Key-Reef-Resort.h4759500.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73240000/73238600/73238505/4d3ccae9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/74000000/73240000/73238600/73238505/25ce0afb.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 9.0/10 Wonderful (51) "We enjoyed our stay. Place is exactly as described. We really enjoyed the lanai. Wanted somewhere close to Key West and this turned out perfect. Would definitely stay here again. Thanks!" CA $223 CA $487 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Summerland-Key-Hotels-Old-Florida-Style.h73238505.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) ![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) ![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) ![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 (1052) "Absolutely beautiful resort!" CA $325 CA $449 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Marathon-Hotels-Isla-Bella-Beach-Resort-Spa.h24101706.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=2025-10-19&endDate=2025-10-20®ionId=553248635976468855&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Breezeswept Beach Estates Hotel Reviews ![Sugar Loaf Lodge](//images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/95d2903e_y.jpg) ### Sugar Loaf Lodge 10/10 Excellent "Everything was fine even better as it was there for longer " [](https://expedia.ca/Sugarloaf-Key-Hotels-Sugar-Loaf-Lodge.h3918121.Hotel-Information) ![Looe Key Reef Resort](//images.trvl-media.com/lodging/5000000/4760000/4759500/4759500/63d12f01_y.jpg) ### Looe Key Reef Resort 8/10 Good "This is a very REASONABLY priced lodging for the FL Keys so expect simple things. We had a great stay, room was clean, the young gent at the front desk was exceptionally friendly and helpful, ditto at checkout. The beds are comfortable. The shower head had great pressure and the onsite tiki bar is a big plus. There were no plastic cups or coffee maker in the room but there was a microwave and fridge and table with two chairs. The ice machine was not working but there is a quickie mart just next door for that if you needed it. Could the resort be flashier, yes it could but Looe Key Reef Resort offered us a cost effective comfy safe stay in a place where time in the room was not important. We did not use the pool or the dive/snorkle amenities as we came down to fish, but if you wanted that stuff it’s all here. We hope to be back soon." [](https://expedia.ca/Ramrod-Key-Hotels-Looe-Key-Reef-Resort.h4759500.Hotel-Information) ![Old Wooden Bridge Resort and Marina](//images.trvl-media.com/lodging/18000000/17110000/17102400/17102343/92962431_y.jpg) ### Old Wooden Bridge Resort and Marina 10/10 Excellent "Really I have the best experience and soon I want to go again " [](https://expedia.ca/Big-Pine-Key-Hotels-Old-Wooden-Bridge-Marina.h17102343.Hotel-Information) ![Parmer's Resort](//images.trvl-media.com/lodging/6000000/5570000/5561500/5561465/6492712a_y.jpg) ### Parmer's Resort 10/10 Excellent "Clean room , many options for guests to do around property. Close to key west and marathon" [](https://expedia.ca/Little-Torch-Key-Hotels-Parmers-Resort.h5561465.Hotel-Information) ![Knight's Key Suites](//images.trvl-media.com/lodging/14000000/13210000/13209500/13209442/5fa8d60e_y.jpg) ### Knight's Key Suites 10/10 Excellent "Great place " [](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. [Parmer's Resort](https://www.expedia.ca/Little-Torch-Key-Hotels-Parmers-Resort.h5561465.Hotel-Information): Offers a private beach, an outdoor pool, and daily. [Old Wooden Bridge Resort and Marina](https://www.expedia.ca/Big-Pine-Key-Hotels-Old-Wooden-Bridge-Marina.h17102343.Hotel-Information): Provides free self parking, an outdoor pool, and complimentary wireless internet access. [Sugar Loaf Lodge](https://www.expedia.ca/Sugarloaf-Key-Hotels-Sugar-Loaf-Lodge.h3918121.Hotel-Information): Features 2 outdoor tennis courts, an outdoor pool, and free self parking. [Looe Key Reef Resort](https://www.expedia.ca/Ramrod-Key-Hotels-Looe-Key-Reef-Resort.h4759500.Hotel-Information): Offers free self parking, an outdoor pool, and complimentary wireless internet access. ### What is there to see and do in Breezeswept Beach Estates? > Make a point to visit attractions like Calusa Beach and Venture Out Keys. 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