Title: Visit Cutthroat Harbor Estates: Best of Cutthroat Harbor Estates, Summerland Key Travel 2025 | Expedia Tourism - Expedia.ca [Hotels in Cutthroat Harbor Estates](https://expedia.ca/Cutthroat-Harbor-Estates-Summerland-Key-Hotels.0-n553248635976481702-0.Travel-Guide-Filter-Hotels)[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)[Cutthroat Harbor Estates Car Rentals](https://expedia.ca/Car-Rentals-In-Cutthroat-Harbor-Estates.d553248635976481702.Car-Rental-Guide)[Cutthroat Harbor Estates Vacations](https://expedia.ca/Cutthroat-Harbor-Estates.d553248635976481702.Destination-Travel-Guides) # Cutthroat Harbor Estates ## Summerland Key ## Visit Cutthroat Harbor Estates Hotels Where to stay * * * * * * ## Cutthroat Harbor Estates Hotel Deals ![Just 20 miles from Key West! Oceanfront, dockage, swimming pool](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/0c89d58b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Just 20 miles from Key West! Oceanfront, dockage, swimming pool Cudjoe Key CA $315 CA $755 total Oct 28 - Oct 29 includes taxes & fees Stay at this vacation home in Summerland Key. Enjoy laundry facilities, patios, and cable/satellite TV service. Our guests praise the property condition in our ... 8.4/10 Very Good! (117 reviews) Property was clean and comfortable. Location was ideal for our visit and the host gave hreat instructions on locating our unit. Its not a 5 star hotel- if thats what you want, this isnt the place. But if you want a clean, comfortable, affordavlble and convenient location. This is it. Cant wait to ... Reviewed on Aug 19, 2025 [](https://expedia.ca/Hotel-Search?startDate=28%2F10%2F2025&endDate=29%2F10%2F2025&selected=33547859&PinnedHotelID=33547859&HadPinnedHotel=true®ionId=553248635976481702) ![Oceans Edge Key West Resort, Hotel & Marina](https://images.trvl-media.com/lodging/17000000/16210000/16203000/16202992/3a4457a0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Oceans Edge Key West Resort, Hotel & Marina 5950 Peninsular Avenue, Key West, FL CA $201 CA $307 total Nov 17 - Nov 18 includes taxes & fees Stay at this 4-star luxury hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the restaurant in our reviews. Popular ... 8.8/10 Excellent! (1,725 reviews) Beautiful setting - great water views. Room was clean and comfortable - pools were great. Reviewed on Oct 24, 2025 [](https://expedia.ca/Hotel-Search?startDate=17%2F11%2F2025&endDate=18%2F11%2F2025&selected=16202992&PinnedHotelID=16202992&HadPinnedHotel=true®ionId=553248635976481702) ![Hilton Garden Inn Key West / The Keys Collection](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/5c83029c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Garden Inn Key West / The Keys Collection 3850 N Roosevelt Blvd, Key West, FL CA $142 CA $199 total Nov 18 - Nov 19 includes taxes & fees Book a stay at this business-friendly hotel in Key West. Enjoy 2 restaurants, breakfast (surcharge), and a free area shuttle. Our guests praise the pool and ... 7.8/10 Good! (1,103 reviews) Our stay at the Hilton Garden Inn Key West was fantastic. The rooms were well appointed, well stocked, and clean. The pool area is beautiful and includes an outdoor bar with great drinks and exceptional staff. The front desk team were all an absolute pleasure to deal with. And the free shuttle to ... Reviewed on Oct 24, 2025 [](https://expedia.ca/Hotel-Search?startDate=18%2F11%2F2025&endDate=19%2F11%2F2025&selected=1376&PinnedHotelID=1376&HadPinnedHotel=true®ionId=553248635976481702) ![Blue Flamingo Resort Key West](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/cb0a4c1e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Blue Flamingo Resort Key West 3820 North Roosevelt Boulevard, Key West, FL CA $125 CA $219 total Oct 28 - Oct 29 includes taxes & fees Stay at this 4-star family-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ... 7.8/10 Good! (1,629 reviews) All great! Reviewed on Oct 24, 2025 [](https://expedia.ca/Hotel-Search?startDate=28%2F10%2F2025&endDate=29%2F10%2F2025&selected=12599231&PinnedHotelID=12599231&HadPinnedHotel=true®ionId=553248635976481702) ![DoubleTree Resort by Hilton Grand Key - Key West](https://images.trvl-media.com/lodging/1000000/480000/470900/470834/be4147fb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### DoubleTree Resort by Hilton Grand Key - Key West 3990 S Roosevelt Blvd, Key West, FL CA $157 CA $223 total Oct 29 - Oct 30 includes taxes & fees Stay at this 4-star business-friendly resort in Key West. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ... 8/10 Very Good! (1,003 reviews) Staff was very helpful reported to front desk that ac unit was not working properly. When we return to hotel they informed us they were going to switch our room and give us a balcony room too Reviewed on Oct 24, 2025 [](https://expedia.ca/Hotel-Search?startDate=29%2F10%2F2025&endDate=30%2F10%2F2025&selected=470834&PinnedHotelID=470834&HadPinnedHotel=true®ionId=553248635976481702) ![Beachside Resort & Residences](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/290b242a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Beachside Resort & Residences 3841 N Roosevelt Blvd, Key West, FL CA $151 CA $241 total Oct 27 - Oct 28 includes taxes & fees Stay at this 3.5-star beach hotel in Key West. Enjoy free WiFi, 2 restaurants, and a private beach. Our guests praise the pool and the helpful staff in our reviews. ... 8.4/10 Very Good! (1,629 reviews) Clean room and convenient parking Reviewed on Oct 23, 2025 [](https://expedia.ca/Hotel-Search?startDate=27%2F10%2F2025&endDate=28%2F10%2F2025&selected=25865&PinnedHotelID=25865&HadPinnedHotel=true®ionId=553248635976481702) [See all 1,413 properties in Cutthroat Harbor Estates](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=27%2F10%2F2025&endDate=28%2F10%2F2025®ionId=553248635976481702) 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. ## Check Cutthroat Harbor Estates hotel availability [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976481702&startDate=2025-10-26&endDate=2025-10-27) [Tonight](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976481702&startDate=2025-10-26&endDate=2025-10-27) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976481702&startDate=2025-10-26&endDate=2025-10-27) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976481702&startDate=2025-10-26&endDate=2025-10-27)[Oct 26 - Oct 27](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976481702&startDate=2025-10-26&endDate=2025-10-27) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976481702&startDate=2025-10-27&endDate=2025-10-28) [Tomorrow night](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976481702&startDate=2025-10-27&endDate=2025-10-28) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976481702&startDate=2025-10-27&endDate=2025-10-28) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976481702&startDate=2025-10-27&endDate=2025-10-28)[Oct 27 - Oct 28](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976481702&startDate=2025-10-27&endDate=2025-10-28) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976481702&startDate=31%2F10%2F2025&endDate=02%2F11%2F2025) [Next weekend](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976481702&startDate=31%2F10%2F2025&endDate=02%2F11%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976481702&startDate=31%2F10%2F2025&endDate=02%2F11%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976481702&startDate=31%2F10%2F2025&endDate=02%2F11%2F2025)[Oct 31 - Nov 2](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635976481702&startDate=31%2F10%2F2025&endDate=02%2F11%2F2025) * * * ### Other neighbourhoods around Cutthroat Harbor Estates ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Cudjoe Gardens When in Cudjoe Gardens, you can plan a visit to Upper Sugarloaf Key and Venture Out Keys, some noteworthy sights in the nearby area. [](https://expedia.ca/Summerland-Key-Cudjoe-Gardens.dx553248635976472640) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Breezeswept Beach Estates While Breezeswept Beach Estates isn't home to many top sights, Newfound Harbor Keys and Cook Island are some notable places to visit nearby. [](https://expedia.ca/Ramrod-Key-Breezeswept-Beach-Estates.dx553248635976468855) ![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/498000/498222-sugarloaf-key.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Sugarloaf Shores While Sugarloaf Shores isn't home to many top sights, Florida Keys Beaches and Sugarloaf Beach are some notable places to visit nearby. [](https://expedia.ca/Sugarloaf-Key-Sugarloaf-Shores.dx6270983) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Bay Point Bay Point might not have many top sights, but Lower Sugarloaf Sound and Sugarloaf Beach are two attractions nearby that you can check out. [](https://expedia.ca/Bay-Point.dx553248635976383913) * * * * * * - [Stays](?pwaLob=wizard-hotel-pwa-v2) - [Packages](?pwaLob=wizard-package-pwa) - [Flights](?pwaLob=wizard-flight-pwa) - [Things to do](?pwaLob=wizard-lx-pwa) - [Cruises](?pwaLob=wizard-cruise-pwa) - [Cars](?pwaLob=wizard-car-pwa) # Cutthroat Harbor Estates ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)