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 Out Keys and Upper Sugarloaf Key.
Top hotels in Summerland Key
Parmer's Resort
Excellent for relaxation
Reviewed on 26 Oct, 2025
Sugar Loaf Lodge
This was an excellent value for the price - the room was spacious and clean, the property was quiet. There was a beautiful view with a balcony. I could not have been happier with my experience!
Reviewed on 6 Oct, 2025
Looe Key Reef Resort
We enjoyed our three night stay. We dived Looe Key reef every day through their dive shop. Safe shallow diving with excellent storage, easy access and excellent staff. Left the afternoon/evening open to relax or go into town. About 50 minutes from Key West. Recommend car rental for your stay
Reviewed on 17 Oct, 2025
What to do in Summerland Key
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Key West Sunset Cruise & Glass Bottom Eco Tour
* 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.
