Top Cutthroat Harbor Estates Hotels

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Where to stay in Cutthroat Harbor Estates

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

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.

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Cudjoe Gardens

When in Cudjoe Gardens, you can plan a visit to Upper Sugarloaf Key and Florida Keys Beaches, some noteworthy sights in the nearby area.

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Bay Point

Bay Point might not have many top sights, but Lower Sugarloaf Sound and Florida Keys Beaches are two attractions nearby that you can check out.

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

Breezeswept Beach Estates

While Breezeswept Beach Estates isn't home to many top sights, Venture Out Keys and Munson Island are some notable places to visit nearby.

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Top Cutthroat Harbor Estates Hotel Reviews

Blue Flamingo Resort Key West

8/10 Good

"The only bad thing that the resort has is the elevator service was horrible and most of the time not working. They really need to update them"

Hilton Garden Inn Key West / The Keys Collection

8/10 Good

"Checked into room 214 and discovered the ac wasn’t working, called the front desk to inform them. They sent someone up and he took the thermal off the wall and it started working. We left for lunch and came back to change for the beach & the heater was blowing. Ugh once again we’re back to a sweat box. This went on for quite a few hours our first day. It would blow cold then hot. It was annoying to say the least. The fitness center is in the basement & o had no issue using the treadmill & elliptical Pool area was nice and clean. Overall it was a good visit but the heat in the room was sad"

The Perry Hotel & Marina Key West

8/10 Good

"Restaurant staff was hit or miss. You either had a really awesome waiter or a waitress who couldn't be bothered. Breakfast was good but other meals were not the best. Drink was good. Property is beautiful and very well maintained. Host staff was great and friendly. Room had some deferred maintenance issues. Balcony light didn't work, phone didn't work and shower gel and shampoo bottles just say on the ledge of the shower instead of them being on the apparatus to hold them."

Hyatt Vacation Club at Windward Pointe, Key West

10/10 Excellent

"We stayed at the Hyatt Vacation Club at Windward Pointe in Key West and overall had a great experience. The room was spacious, very clean, and had everything we needed for our stay. The property itself was well maintained, relaxing, and a great place to unwind. One thing to note is that the resort is very close to the airport, so there is some airplane noise throughout the day. If that doesn’t bother you too much, it’s absolutely worth staying here. It’s also a little outside the main Duval Street area, about a 15–20 minute ride depending on traffic, and usually around a $25 Uber. For us, that was a fair tradeoff for a quieter, more laid-back property. One thing that could be clearer in the listing is the beach situation. The property is not directly on a beach. Across the street is more of a bulkhead/waterfront area where you’re not really going to lay out or swim. The closest actual beach is about a 15-minute walk away. Overall, we’d definitely stay here again."

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

8/10 Good

"As a business traveler, the Wi-Fi connection is extremely important to me. It is so weak that I can’t even connect to Gmail. I had to use my cellphone hotspot to connect to Gmail. It was strong enough to send a few files that were due in the morning! My work would’ve been late if my hotspot didn’t work. Also, as a business traveler, I don’t use any of the other amenities (including the free breakfast). I think there should be an option for business travelers to opt out of the resort fee and forgo the amenities. Other than that, it’s super close to where I work when I’m there and my room is clean and otherwise adequate. The staff is always super nice."

Frequently asked questions

What's it like in Cutthroat Harbor Estates?

Travelers to Summerland Key's Cutthroat Harbor Estates neighborhood will be sure to enjoy a stay in this neighborhood.

How many hotels will I find in Cutthroat Harbor Estates?

Expedia has 69 hotels and other accommodations 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 reservations are fully refundable as long as you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If you have a non-refundable reservation, you may still be able to cancel and get a refund within a 24-hour period of booking. Add dates, click "Search", then you can filter by "fully refundable" to view the best deals in Cutthroat Harbor Estates.

Where can I learn more about changing or cancelling my trip to Cutthroat Harbor Estates?

For more details about changing or cancelling your trip to Cutthroat Harbor Estates, click here.

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.

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Our top choices for Cutthroat Harbor Estates hotels

Looe Key Reef Resort

Sugar Loaf Lodge

Parmer's Resort

Old Wooden Bridge Resort and Marina

Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Windward Pointe, Key West

Starlight Serenity - Hideaway w Stunning Views

Oceans Edge Key West Resort, Hotel & Marina

Barnacle Resort

Hampton Inn Key West FL

DoubleTree Resort by Hilton Grand Key - Key West

Atlantic View Luxury Villa with Pool

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

Beachside Resort & Residences

Blue Flamingo Resort Key West

Hilton Garden Inn Key West / The Keys Collection

The Fairhaven House at Solaire Lunara Bay

Havana Cabana at Key West

The Laureate Key West

Aqua Lodges at Hurricane Hole Marina

Where to stay in Cutthroat Harbor Estates

Sugarloaf Shores

Cudjoe Gardens

Bay Point

Breezeswept Beach Estates

Top Cutthroat Harbor Estates Hotel Reviews

Blue Flamingo Resort Key West

Frequently asked questions

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