Cutthroat Harbor Estates Travel Guide
Tourist Guide
Visit Cutthroat Harbor Estates
Popular places to visit
Sugarloaf Beach
Why not spend a lazy afternoon at Sugarloaf Beach during your trip to Summerland Key?
Upper Sugarloaf Key
Commune with nature and explore the great outdoors at Upper Sugarloaf Key during your travels in Summerland Key.
Upper Sugarloaf Sound
Commune with nature and explore the great outdoors at Upper Sugarloaf Sound during your travels in Summerland Key.
Pye Key
Commune with nature and explore the great outdoors at Pye Key during your travels in Summerland Key.
Crab Key
Commune with nature and explore the great outdoors at Crab Key during your travels in Summerland Key.
Squirrel Key
Commune with nature and explore the great outdoors at Squirrel Key during your travels in Summerland Key.
Activities
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Key West Mangrove Kayak Eco Tour
Key West Dolphin & Snorkeling Tour - Small Group
Key West's Island Eco Tour: Sandbar Adventure with Kayaking Tour
Full-Day Trip to Key West from Miami
All-Inclusive Key West Beach Pass with Parasailing, Kayaks, Paddleboards
Our pick of the best Cutthroat Harbor Estates Hotel Deals
Blue Flamingo Resort Key West
"The food was amazing! There was a language barrier for the maid staff, but most were very nice. The last three days the place was overrun by little league baseball players and their families. The lobby was packed with screaming, horseplay all hours and both pools were overcrowded with kids as well. ..."
Reviewed on 22 June 2026
Hilton Garden Inn Key West / The Keys Collection
"it was nice"
Reviewed on 21 June 2026
Beachside Resort & Residences
"One of the reasons we booked this location is that they have elevators…. Nope, elevators do not work!!"
Reviewed on 22 June 2026
Havana Cabana at Key West
"my daughter and and I were there for two days. Everything was exceptional. We love the pool the food trucks and the ability to catch the shuttle. Definitely recommend."
Reviewed on 20 June 2026
DoubleTree Resort by Hilton Grand Key - Key West
"I’m extremely disappointed with my stay this weekend. The room was not clean and the condition of the bedding was unacceptable. The sheets and covers were visibly dirty, which made me question whether the room had been properly cleaned before we arrived. On top of the cleanliness issues, the way ..."
Reviewed on 21 June 2026
Hyatt Vacation Club at Windward Pointe, Key West
"Nice place ,clean, free parking very spacious"
Reviewed on 21 June 2026
Check Cutthroat Harbor Estates hotel availability
Our guide on where to stay in Cutthroat Harbor Estates
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.
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.
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.
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.
