Title: Book the Best Cutthroat Harbor Estates Hotels with Early Check-in in 2026 | 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)[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) ![Bird refuge wildlife background panorama banner of nature landscape ocean birds in Key West, Florida. Animals of the USA.](https://images.trvl-media.com/place/553248635976481702/7efc6f73-bf7b-4c19-9424-6ca3071f1ffe.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with Early Check-in in Cutthroat Harbor Estates, 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 Cutthroat Harbor Estates Hotels with Early Check-in Tonight [Dec 17 - Dec 18](https://www.expedia.ca/Hotel-Search?regionId=553248635976481702&startDate=2025-12-17&endDate=2025-12-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 18 - Dec 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976481702&startDate=2025-12-18&endDate=2025-12-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976481702&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976481702&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Cutthroat Harbor Estates hotels with express check-in ![Exterior](https://images.trvl-media.com/lodging/5000000/4760000/4759500/4759500/63d12f01.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) ![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) ![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) ### Looe Key Reef Resort [](https://www.expedia.ca/Ramrod-Key-Hotels-Looe-Key-Reef-Resort.h4759500.Hotel-Information) Summerland Key 7.4/10 Good (1003) "Was nice roo.s and close to my charter boat captain " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicholas CA $174 CA $195 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Ramrod-Key-Hotels-Looe-Key-Reef-Resort.h4759500.Hotel-Information) ![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) ![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) ### Old Wooden Bridge Resort and Marina [](https://www.expedia.ca/Big-Pine-Key-Hotels-Old-Wooden-Bridge-Marina.h17102343.Hotel-Information) Punta Brisa 8.6/10 Excellent (278) "We loved it here. So beautiful and quiet." ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Mark [](https://www.expedia.ca/Big-Pine-Key-Hotels-Old-Wooden-Bridge-Marina.h17102343.Hotel-Information) ![Outdoor pool, open 7:00 AM to 11:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/1000000/480000/470900/470834/cefb5fc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/480000/470900/470834/c6252245.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 7:00 AM to 11:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/1000000/480000/470900/470834/e235d199.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/480000/470900/470834/6cc1fa14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree Resort by Hilton Grand Key - Key West [](https://www.expedia.ca/Key-West-Hotels-DoubleTree-Resort-By-Hilton-Grand-Key-Key-West.h470834.Hotel-Information) Key West 8.2/10 Very good (1011) "Nice property, comfortable stay - cookies and staff are great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $219 CA $292 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Key-West-Hotels-DoubleTree-Resort-By-Hilton-Grand-Key-Key-West.h470834.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) ![Private beach, white sand, sun loungers, beach towels](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/c23326fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ocean Front 3BR Presidential Suite | Living area](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/d01b8b60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/c646d9fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beachside Resort & Residences [](https://www.expedia.ca/Key-West-Hotels-Key-West-Marriott-Beachside-Hotel.h25865.Hotel-Information) Key West 8.6/10 Excellent (1789) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) james CA $215 CA $312 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Key-West-Hotels-Key-West-Marriott-Beachside-Hotel.h25865.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=2025-12-31&endDate=2026-01-01®ionId=553248635976481702&adults=2&property_amenities_group_explore=express_checkin&sort=RECOMMENDED&openPlayBack=true) ## Top Cutthroat Harbor Estates Hotel Reviews ![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 "." 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