Summerland Key Holidays
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Where to stay in Summerland Key
Cutthroat Harbor Estates
While there might not be top attractions in Cutthroat Harbor Estates, you can explore the larger area and discover places like Venture Key and Venture Out Keys.
Top hotels in Summerland Key
Sugarloaf Key Hotel at KOA Resort
Great property
Reviewed on 18 Mar, 2026
Parmer's Resort
The perfect amount of extra touches makes this property the best place to stay in the lower keys.
Reviewed on 18 Mar, 2026
Looe Key Reef Resort
This is an old hotel that would benefit from many renovations. It is very basic but the beds were comfortable and they try to keep it clean. If you are just looking for a cheap place to lay your head, then this place will do.
Reviewed on 20 Mar, 2026
What to do in Summerland Key
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
Bucket-List Parasailing In Downtown Key West - Highest & Longest Rides
Key West Mangrove Kayak Eco Tour
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
