The Best Hotels in Cutthroat Harbor Estates, Summerland Key - 2026 Updated Prices

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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 Cook Island and Big Pine Key Flea Market.

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Top Cutthroat Harbor Estates Hotel Reviews

Hyatt Vacation Club at Windward Pointe, Key West

10/10 Excellent

"Excellent place to be on vacation!"

Beachside Resort & Residences

8/10 Good

"We stayed at the property 9 years ago when it was a Marriott and it seemed like the upkeep of the property was not the greatest. Nothing terible, but just little things like door handles coming off, discoloration of the tile floors, etc. Great property and location, especially with the free shuttle to Duvall St., but the property could use a little bit of a facelift at this point. I also had to get a little testy with the staff about getting a room. Their checkout time is 10 am and their check in time is 4 pm and the property was nowhere near full. When we got ther at 1 pm, it could understand not having a room ready, but when I went back at 4 pm and they said they still did not have a room, I had to throw down and guess what - they had a room available. So the trip got off to kind of an unsteady start. Need more people to clean rooms apparently."

Havana Cabana at Key West

6/10 Okay

"I stayed in a standard room without a balcony, and honestly, it was much smaller than I expected. The room was very dark, with poor lighting, and there wasn’t even a comfortable chair to sit on. The mattresses were not very comfortable and could definitely use an upgrade. Overall, the room felt outdated and could use some renovation. The pool area was nice, spacious, and comfortable, which was probably the best part of the property. The jacuzzi, however, could use some maintenance, as the paint is peeling. One thing that surprised me was that there is no actual restaurant on site—just a food truck. There is also no gym. When it rains, there’s no covered walkway between the lobby, rooms, and pool, so you end up getting wet moving around the hotel. Overall, it wasn’t a terrible stay, but I don’t think the property offers the amenities or comfort I would expect from a resort."

The Laureate Key West

2/10 Terrible

"HORRIBLE! They do not care about their guests at all. I have never been to Key West before and there was a flash flood I am Assuming it was almost 4ft deep and it was me and my daughter. So naturally I wanted off the island and go to marathon. But they would not budge on giving me any of the money back so I could go elsewhere. The manager did not help me and the general manager told me life happens and I was not getting a dime back. So me and my daughter waited for almost 3 hours for the water to go down enough for us to go drive thru it. When we got there there was mold all around the sink and the people in the next room was making noises all night. The walls was paper thin. Spend your money elsewhere where the room is clean and where the staff actually care about the well beings of others. This was probably why the hotel was not busy. I travel a lot and have never dealt with such inhumane individuals. They ruined my experience of Key West and I won’t ever go back to the island or to any of their nasty hotels."

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 70 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.

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Our top choices for Cutthroat Harbor Estates hotels

Looe Key Reef Resort

Sugar Loaf Lodge

Old Wooden Bridge Resort and Marina

Parmer's Resort

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Beach House, Key West

Hampton Inn Key West FL

Starlight Serenity - Hideaway w Stunning Views

Atlantic View Luxury Villa with Pool

Barnacle Resort

DoubleTree Resort by Hilton Grand Key - Key West

Oceans Edge Key West Resort, Hotel & Marina

The Laureate Key West

Blue Flamingo Resort Key West

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

Beachside Resort & Residences

Hilton Garden Inn Key West / The Keys Collection

Springtide House by Brightwild Waterfront Pool

Aqua Lodges at Hurricane Hole Marina

The Perry Hotel & Marina Key West

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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