Title: Book the Best Cutthroat Harbor Estates Hotels with FREE WIFI 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 Wifi in Cutthroat Harbor Estates, FL from CA $153 - ![](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 Wifi Tonight [Dec 16 - Dec 17](https://www.expedia.ca/Hotel-Search?regionId=553248635976481702&startDate=2025-12-16&endDate=2025-12-17&adults=2&amenities=WIFI&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 17 - Dec 18](https://www.expedia.ca/Hotel-Search?regionId=553248635976481702&startDate=2025-12-17&endDate=2025-12-18&adults=2&amenities=WIFI&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&amenities=WIFI&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&amenities=WIFI&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Cutthroat Harbor Estates hotels with wifi ![Balcony](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/0c89d58b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/b25eb073.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/3835dc3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/b653e8ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Just 20 miles from Key West! Oceanfront, dockage, swimming pool [](https://www.expedia.ca/Summerland-Key-Hotels-Just-20-Miles-From-Key-West-Oceanfront.h33547859.Hotel-Information) Cutthroat Harbor Estates 8.4/10 Very good (118) "Great experience " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peyton S. CA $310 CA $742 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Summerland-Key-Hotels-Just-20-Miles-From-Key-West-Oceanfront.h33547859.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/8ae32688.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) ![Property grounds](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/125c52d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/fe329a14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sugar Loaf Lodge [](https://www.expedia.ca/Sugarloaf-Key-Hotels-Sugar-Loaf-Lodge.h3918121.Hotel-Information) Summerland Key 8.2/10 Very good (1004) "Great place to stary. Staff was very nice." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) norka CA $136 CA $153 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Sugarloaf-Key-Hotels-Sugar-Loaf-Lodge.h3918121.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/deb8b21f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, individually decorated](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/9e2158b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/bfe6eb86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/948eecb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Perry Hotel & Marina Key West [](https://www.expedia.ca/Key-West-Hotels-The-Perry-Hotel-Marina-Key-West.h17313680.Hotel-Information) Stock Island 9.4/10 Exceptional (1173) "great place to stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) michael CA $179 CA $284 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Key-West-Hotels-The-Perry-Hotel-Marina-Key-West.h17313680.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/c4b850d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Poolside bar](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/ff4257d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gift shop](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/fa09f1b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee shop](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/572146c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blue Flamingo Resort Key West [](https://www.expedia.ca/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.Hotel-Information) New Town 8.0/10 Very good (1772) "Great, friendly staff, nice amenities, easy parking and convenient location " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Caitlyn CA $172 CA $271 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.Hotel-Information) ![Outdoor pool, open 6:00 AM to 10:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/449c6937.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/fe552ece.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/4d8ae5b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/4583520b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Key West / The Keys Collection [](https://www.expedia.ca/Key-West-Hotels-Hilton-Garden-Inn-Key-West.h1376.Hotel-Information) New Town 8.0/10 Very good (1157) "clean room comfortable bed ,pool jacuzzi with bar make us amazing stay this hotel." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shanker CA $178 CA $239 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Key-West-Hotels-Hilton-Garden-Inn-Key-West.h1376.Hotel-Information) ![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/cbb89b9f.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) ![Front of property](https://images.trvl-media.com/lodging/18000000/17110000/17102400/17102343/2ece49e6.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 CA $155 CA $369 total includes taxes & fees Jan 7 - Jan 8, 2026 [](https://www.expedia.ca/Big-Pine-Key-Hotels-Old-Wooden-Bridge-Marina.h17102343.Hotel-Information) ![Karaoke room](https://images.trvl-media.com/lodging/5000000/4760000/4759500/4759500/a7994045.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) ![Bar (on property)](https://images.trvl-media.com/lodging/5000000/4760000/4759500/4759500/17a84140.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 [](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) ![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) ![Garden](https://images.trvl-media.com/lodging/1000000/480000/470900/470834/e83716cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/480000/470900/470834/ffbb5429.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/1000000/480000/470900/470834/af62b69d.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 8.0/10 Very good (1007) "Very very nice stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chloe CA $212 CA $285 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Key-West-Hotels-DoubleTree-Resort-By-Hilton-Grand-Key-Key-West.h470834.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/6000000/5570000/5561500/5561465/bc839964.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dock](https://images.trvl-media.com/lodging/6000000/5570000/5561500/5561465/a69616f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Kitchen, Sea Facing](https://images.trvl-media.com/lodging/6000000/5570000/5561500/5561465/680528cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Kitchen, Sea Facing | Living area](https://images.trvl-media.com/lodging/6000000/5570000/5561500/5561465/686b790f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Parmer's Resort [](https://www.expedia.ca/Little-Torch-Key-Hotels-Parmers-Resort.h5561465.Hotel-Information) Summerland Key 9.0/10 Wonderful (1001) "Room was clean and comfortable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Barbara K CA $185 CA $253 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Little-Torch-Key-Hotels-Parmers-Resort.h5561465.Hotel-Information) ![Ocean View 3BR Condo with Rooftop Balcony | Balcony](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/a1e6ec60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Top Floor 1BR Ocean View Condo with Rooftop Balcony | Living area](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/45254304.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/0ccc9844.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony view](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/ce510800.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 $214 CA $311 total includes taxes & fees Dec 17 - Dec 18 [](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=2025-12-30&endDate=2025-12-31®ionId=553248635976481702&adults=2&amenities=WIFI&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 "." [](https://expedia.ca/Key-West-Hotels-24-North-Hotel-Key-West-Newly-Renovated.h12599231.Hotel-Information) ![DoubleTree Resort by Hilton Grand Key - Key West](https://images.trvl-media.com/lodging/1000000/480000/470900/470834/cefb5fc2_y.jpg) ### DoubleTree Resort by Hilton Grand Key - Key West 10/10 Excellent "shuttle" [](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](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/449c6937_y.jpg) ### Hilton Garden Inn Key West / The Keys Collection 10/10 Excellent "clean room comfortable bed ,pool jacuzzi with bar make us amazing stay this hotel." [](https://expedia.ca/Key-West-Hotels-Hilton-Garden-Inn-Key-West.h1376.Hotel-Information) ![Sugar Loaf Lodge](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/95d2903e_y.jpg) ### Sugar Loaf Lodge 10/10 Excellent "Very nice property. Owner/Staff were fantastic. I love the life-long effort the family has put into the property. View off the deck is great. Free, good, coffee at the Tiki Bar in the mornings. Overall, the mid-century modern aesthetic is awesome in my opinion. All items worked. Ice machine, ice bucket, clean (linens, room, floors, surfaces, bath fixtures) and a farmer's market outside on Wednesdays. Really a great spot with a short drive to Key West. We will return." [](https://expedia.ca/Sugarloaf-Key-Hotels-Sugar-Loaf-Lodge.h3918121.Hotel-Information) ![Beachside Resort & Residences](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/290b242a_y.jpg) ### Beachside Resort & Residences 10/10 Excellent "The pool beach area was clean, water in pool and hot tub clean and warm Shuttle to Duvall street was very convent and helpful to get to shopping / dinning area " [](https://expedia.ca/Key-West-Hotels-Key-West-Marriott-Beachside-Hotel.h25865.Hotel-Information) ![Fairfield Inn & Suites by Marriott Key West at the Keys Collection](https://images.trvl-media.com/lodging/1000000/30000/21900/21871/ca442072_y.jpg) ### Fairfield Inn & Suites by Marriott Key West at the Keys Collection 10/10 Excellent "The check in process went very smoothly " [](https://expedia.ca/Key-West-Hotels-Fairfield-Inn-Suites-Key-West-At-The-Keys-Collection.h21871.Hotel-Information) ![Hampton Inn Key West FL](https://images.trvl-media.com/lodging/1000000/20000/15800/15720/4075e8ff_y.jpg) ### Hampton Inn Key West FL 10/10 Excellent "What i like best was how clean the room was. It had ample space " [](https://expedia.ca/Key-West-Hotels-Hampton-Inn-Key-West-FL.h15720.Hotel-Information) ![Parmer's Resort](https://images.trvl-media.com/lodging/6000000/5570000/5561500/5561465/6492712a_y.jpg) ### Parmer's Resort 10/10 Excellent "Room was clean and comfortable." [](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 had a very nice stay. The room had almost everything we needed. The beds and pillows were comfortable and the inverters cooled us without being noisy. The room was very clean. Only con was the smell of the cleaning product used was very strong. Bonus, we loved seeing the key deer. 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