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

"loved our stay here!"

Hampton Inn Key West FL

8/10 Good

"The property itself is nice, the pool was pretty. Lizards and crabs around. The complimentary breakfast was super nice. They had the works - bacon, sausage, eggs, waffles, it was fire. We liked the room, we had a nice ocean view and patio. The whole free shuttle is kind of a hot mess. To get picked up from downtown, its limited seats and some guests were kind of fighting about it. Hard to get rides with the shuttle. The coconut shrimp at the Cheekie Hut was amazingly delicious."

Blue Flamingo Resort Key West

10/10 Excellent

"What a lovely place to stay. The staff were so friendly and helpful. It was our 40th wedding anniversary and unbeknown to us, our daughter contacted the hotel to let them know. They had left a bottle of wine with a red heart balloon attached and a lovely card in our room. It was such a sweet and kind gesture. The room was immaculate and spacious and well set out; you could tell a lot of thought had gone into it all. There is plenty of facilities too, including 2 pools and outside games for all the family. There’s even a Starbucks on site as well as bars and eateries. We thoroughly enjoyed our stay and would highly recommend it. The free shuttle to and from old town key west is a brilliant idea and we certainly made use of that. Thank you everyone at Blue Flamingo Resort"

Havana Cabana at Key West

10/10 Excellent

"⭐⭐⭐⭐⭐ I booked our stay through Expedia and had a wonderful experience at Havana Cabana! I joined my son, bonus daughter, and grandsons for a fun-filled Key West weekend. The resort has a great tropical vibe, a fantastic pool, and plenty of space for families to relax. The boys had a blast, and watching them make memories together was the highlight of the trip. The staff was friendly, with a huge shoutout to Lana—she was amazing. The rooms were clean, and the shuttle service made getting around Key West easy. Overall, it was a fantastic family getaway, and we would definitely stay here again!"

Beachside Resort & Residences

10/10 Excellent

"2BR Gulf Facing Room was great, room accommodations was great, pool was great, pool staff was great, female event planner was great. Front office requests for water and towels were not as timely as we would have liked. Restaurant was good. We knew in advance that the property was a 10-15 minute drive to Duvall Street and all activities in that area. We spent roughly $60 a day on uber for a family of four for our daily activities. Dry Tortuga National Park requires reservations for the ferry 30-60-90 days out so plan ahead. A couple of restaraunts (other hotel and private) and Starbucks was 10-20 minute walk."

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

Old Wooden Bridge Resort and Marina

Parmer's Resort

Sugar Loaf Lodge

Hilton Garden Inn Key West / The Keys Collection

Barnacle Resort

Hyatt Vacation Club at Windward Pointe, Key West

Starlight Serenity - Hideaway w Stunning Views

DoubleTree Resort by Hilton Grand Key - Key West

Beachside Resort & Residences

The Perry Hotel & Marina Key West

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

The Laureate Key West

Hampton Inn Key West FL

Hyatt Vacation Club at Beach House, Key West

Blue Flamingo Resort Key West

Atlantic View Luxury Villa with Pool

Ocean Front One Bedroom Residence

Aqua Lodges at Hurricane Hole Marina

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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