Title: Book the Best Cutthroat Harbor Estates Scuba Diving 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)[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) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Scuba Diving 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 Scuba Diving Tonight [Oct 28 - Oct 29](https://www.expedia.ca/Hotel-Search?regionId=553248635976481702&startDate=2025-10-28&endDate=2025-10-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 29 - Oct 30](https://www.expedia.ca/Hotel-Search?regionId=553248635976481702&startDate=2025-10-29&endDate=2025-10-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976481702&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635976481702&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Cutthroat Harbor Estates Scuba Diving ![Balcony](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/0c89d58b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/7c5d926a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/e93bd5d2.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) ### Just 20 miles from Key West! Oceanfront, dockage, swimming pool Cutthroat Harbor Estates 8.4/10 Very good (117) "Deer in the front yard, perfect location, clean and friendly " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sara H. CA $315 CA $754 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Summerland-Key-Hotels-Just-20-Miles-From-Key-West-Oceanfront.h33547859.Hotel-Information) ![2 outdoor pools, open 8:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/e4eb7fd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/54c5f4f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/d6618f5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/18000000/17320000/17313700/17313680/8475e5b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Perry Hotel & Marina Key West Stock Island 9.4/10 Exceptional (1134) "Nice stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) SHAMBRE CA $167 CA $266 total includes taxes & fees Oct 30 - Oct 31 [](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/cb0a4c1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Poolside bar](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/5792173a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/44728c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bicycling](https://images.trvl-media.com/lodging/13000000/12600000/12599300/12599231/4a54e511.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blue Flamingo Resort Key West New Town 8.0/10 Very good (1636) "Amazing resort with lovely amenities:)" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wakglene CA $125 CA $219 total includes taxes & fees Oct 30 - Oct 31 [](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/1000000/10000/1400/1376/5c83029c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/ee750f93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/d5aad7de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily continental breakfast (USD 18 per person)](https://images.trvl-media.com/lodging/1000000/10000/1400/1376/3484f3ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Key West / The Keys Collection New Town 7.8/10 Good (1105) "Great location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Johann CA $141 CA $198 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Key-West-Hotels-Hilton-Garden-Inn-Key-West.h1376.Hotel-Information) ![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) ![Cottage, 2 Bedrooms, Ocean View | Terrace/patio](https://images.trvl-media.com/lodging/6000000/5570000/5561500/5561465/75ac6ed2.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) ![Dock](https://images.trvl-media.com/lodging/6000000/5570000/5561500/5561465/a69616f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Parmer's Resort Summerland Key 9.0/10 Wonderful (1005) "Excellent for relaxation " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leismy CA $143 CA $207 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Little-Torch-Key-Hotels-Parmers-Resort.h5561465.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) ![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) ![Balcony view](https://images.trvl-media.com/lodging/1000000/30000/25900/25865/ce510800.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) ### Beachside Resort & Residences Key West 8.6/10 Excellent (1636) "Very cool place to vacation " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gabriel CA $151 CA $241 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Key-West-Hotels-Key-West-Marriott-Beachside-Hotel.h25865.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) ![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) ![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 (263) "I love this place!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Greg CA $126 CA $339 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Big-Pine-Key-Hotels-Old-Wooden-Bridge-Marina.h17102343.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/870000/868700/868697/481a771e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/870000/868700/868697/af5a58cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sport court](https://images.trvl-media.com/lodging/1000000/870000/868700/868697/d5483cf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/870000/868700/868697/07ffbf0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Vacation Club at Windward Pointe, Key West Key West 9.6/10 Exceptional (1036) "Great staff and service " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anthony CA $367 CA $476 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Key-West-Hotels-Hyatt-Vacation-Club-At-Windward-Pointe.h868697.Hotel-Information) ![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) ![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) ![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 Summerland Key 7.4/10 Good (1001) "We enjoyed our three night stay. We dived Looe Key reef every day through their dive shop. Safe shallow diving with excellent storage, easy access and excellent staff. Left the afternoon/evening open to relax or go into town. About 50 minutes from Key West. Recommend car rental for your stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Timothy CA $222 CA $250 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Ramrod-Key-Hotels-Looe-Key-Reef-Resort.h4759500.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/9c267ac9.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) ![Interior](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/f2ffe64a.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) ### OCT. & NOV. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS! Cudjoe Key 9.6/10 Exceptional (98) "Clean place with room for 2 couples. Everything you need." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason W. CA $194 CA $590 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Cudjoe-Key-Hotels-Waterfront-Paradise-AT-Venture-Out4-Bikes-2-2-Seat-Kayaks-King-Queen-Beds.h32660303.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=2025-11-11&endDate=2025-11-12®ionId=553248635976481702&adults=2&recreation_group_explore=scuba_diving_on_site&sort=RECOMMENDED&openPlayBack=true) ## Top Cutthroat Harbor Estates Hotel Reviews ## Explore a world of travel with Expedia - Lodging - More ways to book - [Cheap Hotels in Bahia Honda Key](https://www.expedia.ca/Bahia-Honda-Key-Hotels-Cheap-Hotels.0-0-d553248635083902001-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Bahia Honda Key](https://www.expedia.ca/Bahia-Honda-Key-Hotels-Luxury-Hotel.0-0-d553248635083902001-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Cudjoe Key](https://www.expedia.ca/Cudjoe-Key-Hotels-Beach-Hotel.0-0-d3000430966-tBeachHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Cudjoe Key](https://www.expedia.ca/Cudjoe-Key-Hotels-Cheap-Hotels.0-0-d3000430966-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Free Breakfast in Cudjoe Key](https://www.expedia.ca/Cudjoe-Key-Hotels-Hotels-With-Free-Breakfast.0-0-d3000430966-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) - 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