Top Cutthroat Harbor Estates Hotels

A calm lake with several white birds, including herons and pelicans, on the water's edge.

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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.

A waterfront property with a pool, palm trees, and a building with a white roof.

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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An aerial view of a bridge over turquoise water.

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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An aerial view of a long bridge over turquoise waters with a few vehicles on it.

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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An aerial view of a coastal area with a long bridge connecting two landmasses, clear turquoise waters, and a clear blue sky with scattered clouds.

Breezeswept Beach Estates

While Breezeswept Beach Estates isn't home to many top sights, Cook Island and Big Pine Key Flea Market are some notable places to visit nearby.

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Top Cutthroat Harbor Estates Hotel Reviews

Hilton Garden Inn Key West / The Keys Collection

8/10 Good

"Thank you"

Blue Flamingo Resort Key West

10/10 Excellent

"The grounds are beautiful. One morning I watched them pressure wash around the pool area and they cleaned everything. There was so much to take in and since the grounds are beautiful so many places for photos. The room we stayed in was clean and even though we faced the busy street the noice was not bad at all. Didnt need earplugs. The shuttle to Duval was really nice, just go to the desk first and tell them when you want to leave. We used the bigger pool and it was nice and lots of seating. The staff was really helpful and on our last night we were outside taking pictures for our anniversary when I saw Jose who works at the hotel. He didn't know we were there celebrating our anniversary and he took pictures for us and also had a very nice surprise in our room when we got back. Seriously though we were thrilled he walked by and could take pictures for us. We have stayed at several hotels in key West including one of the sister hotels. Any hotel will fit what you want to experience while you are in Key West but keep this on the top of your list. I read reviews before I booked and I will say they are honest. This is a very good place to stay. One thing not about the hotel but about the beaches. Take a Lyft to smathers beach or Ft. Zachary Taylor. There is a smaller beach people may steal you too. Don't fall for it. Blue Flamingo yes we will like book this hotel again!"

Havana Cabana at Key West

10/10 Excellent

"We arrived to a room change. We booked a king with a balcony and was told that due to circumstances (some said renovations, others roof issues) those rooms were unavailable. To make it right our reaort fees were waived. So the room was ok, the shower drain should have been replaced, but the pool and outside Tiki bar are AMAZING! The complimentary shuttle service to and from the airport and/or Duval street helped with getting around. The shuttle drivers are knowledgeable and shared stories of the island. Our stay included drink vouchers and complimentary breakfast (which we always missed. Lol) and the cigar bar not only had amazing drinks and an amazing bartender, but stunning views of the sunset from their balcony."

Hyatt Vacation Club at Windward Pointe, Key West

10/10 Excellent

"I loved the outdoor area and pool! We utilized the grill area as we had a big party and it was great!! I would have game 5 stars for everything but I was not advised during check in that cleaning staff do not come in daily. I had to call every day for towels (they were delivered quickly) but the old towels and trash were not removed from the room, even after I requested it from the front desk."

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

1. Looe Key Reef Resort

2. Sugar Loaf Lodge

3. Parmer's Resort

4. Old Wooden Bridge Resort and Marina

5. Starlight Serenity - Hideaway w Stunning Views

6. Atlantic View Luxury Villa with Pool

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

8. Hilton Key West Resort & Marina

9. Hampton Inn Key West FL

10. Blue Flamingo Resort Key West

11. The Perry Hotel & Marina Key West

12. DoubleTree Resort by Hilton Grand Key - Key West

13. Beachside Resort & Residences

14. Hilton Garden Inn Key West / The Keys Collection

15. Ocean Front One Bedroom Residence

16. The Laureate Key West

17. Aqua Lodges at Hurricane Hole Marina

18. Coconut Mallory Marina and Resort Condo

19. Havana Cabana at Key West

20. Resort View 1BR Suite With Direct Pool Access

Where to stay in Cutthroat Harbor Estates

Sugarloaf Shores

Cudjoe Gardens

Bay Point

Breezeswept Beach Estates

Top Cutthroat Harbor Estates Hotel Reviews

Hilton Garden Inn Key West / The Keys Collection

Frequently asked questions

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