Top 10 Cutthroat Harbor Estates Hotels of 2026

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Where to stay in Cutthroat Harbor Estates

Find the best Cutthroat Harbor Estates areas for the activities you enjoy most.

Sugarloaf Shores

Though Sugarloaf Shores may not have many top sights, you can venture to the surrounding area to see attractions like Florida Keys Beaches and Sugarloaf Beach.

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Bay Point

While Bay Point may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Lower Sugarloaf Sound and Florida Keys Beaches.

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Cudjoe Gardens

While Cudjoe Gardens may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Upper Sugarloaf Key and Florida Keys Beaches.

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Bahia Honda State Park - Calusa Beach, Florida Keys - tropical beach - USA.

Breezeswept Beach Estates

While there might not be top attractions in Breezeswept Beach Estates, you can explore the larger area and discover places like Venture Out Keys and Munson Island.

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Top Cutthroat Harbor Estates Hotel Reviews

Hyatt Vacation Club at Windward Pointe, Key West

10/10 Excellent

"The room and balcony were fantastic. The pool, grounds, and view of the ocean were lovely. The staff was super welcoming and friendly when we arrived. We enjoyed the close restaurant and walking path right across the street."

Havana Cabana at Key West

10/10 Excellent

"This was such a fun hotel to stay in with an awesome pool and a shuttle to downtown so I didn't have to worry about finding parking. I especially loved the DJ at the pool every day spinning great tropical tunes combined with 80's dance music, and shots at 2PM daily! I wish I had stayed an extra night here because it was so much fun getting a suntan."

Blue Flamingo Resort Key West

6/10 Okay

"The property was clean and nice. They did leave my door unlocked and propped open when cleaning. Thank God nothing was taken. I did have an issue with how they handled the situation. They did offer 3 free drink tickets but I do not drink really. Used one and asked if they could maybe just comp the $16 dollar pizza I had ordered. They did not. Also, I had to email to have the drink removed because it was charged to me. Not a huge deal I just did not like that. It’s not a cheap resort to stay at. They could have handled the situation better in my opinion."

Hampton Inn Key West FL

10/10 Excellent

"We had a wonderful week. Room was great. View of the ocean and the pool. The staff was super friendly and helpful. Breakfast was excellent and had a different variation of hot items like 4 or 5 days in a row. That was a nice surprise. The pool was wonderful with sun and shade options. The Cheekie Hut was great with lots of food and drink options. The shuttle was timely and the drivers friendly. They take you downtown regularly and also to the airport when needed. Highly recommend."

The Laureate Key West

2/10 Terrible

"Their staff was horrible. They have booking procedures that say one thing when booking but then they cancel your booking for procedures not stated on the booking site. I called the property to speak directly to the staff. The first time they said they are unable to update the website to match the current booking process. Then when I called back to adhere to the process they answered while in the middle of a personal conversation and once they realized I was on the phone they hung up. I immediately called back and no one answered my call. HORRIBLE CUSTOMER SERVICE!!! Also, once I got there this location is very far from the best parts of Key West ie Duval Street and Mallory Square Market. Choose another location."

Frequently asked questions

What's it like in Cutthroat Harbor Estates?

Travellers to Summerland Key's Cutthroat Harbor Estates neighbourhood will be sure to enjoy a stay here.

How many hotels are there in Cutthroat Harbor Estates?

Expedia has 69 hotels and other accommodation options in Cutthroat Harbor Estates to choose from, making this an ideal home base for exploring the greater Summerland Key area.

If I need to cancel my hotel reservation in Cutthroat Harbor Estates, will I receive a refund?

Yes! Most hotel bookings are refundable if you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before your scheduled arrival. If your reservation is non-refundable, it might still be possible to cancel it and receive a refund within 24 hours of booking. Add dates, click "Search", then use the filter option "fully refundable" to get the best options available in Cutthroat Harbor Estates.

What are the top things to see and do in Cutthroat Harbor Estates?

A few places to visit in the area around Cutthroat Harbor Estates include Venture Key, Out Key and Venture Out Keys. Crab Key and Pye Key are also worth a visit when you're out sightseeing in Summerland Key.

Hotels in Cutthroat Harbor Estates

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Our top choices for Cutthroat Harbor Estates hotels

Old Wooden Bridge Resort and Marina

Barnacle Resort

Looe Key Reef Resort

Sugar Loaf Lodge

Parmer's Resort

Atlantic View Luxury Villa with Pool

Starlight Serenity - Hideaway w Stunning Views

Beachside Resort & Residences

DoubleTree Resort by Hilton Grand Key - Key West

The Perry Hotel & Marina Key West

Hampton Inn Key West FL

Aqua Lodges at Hurricane Hole Marina

Hyatt Vacation Club at Beach House, Key West

Blue Flamingo Resort Key West

Hyatt Vacation Club at Windward Pointe, Key West

Grand Marina Suite by Brightwild Waterfront

Hilton Garden Inn Key West / The Keys Collection

The Laureate Key West

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

Oceans Edge Key West Resort, Hotel & Marina

Where to stay in Cutthroat Harbor Estates

Sugarloaf Shores

Bay Point

Cudjoe Gardens

Breezeswept Beach Estates

Top Cutthroat Harbor Estates Hotel Reviews

Hyatt Vacation Club at Windward Pointe, Key West

Frequently asked questions

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