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
Looe Key Reef Resort
⭐️⭐️⭐️⭐️⭐️
Reviewed on 25 Jan, 2026
Parmer's Resort
Staff and amenities are great
Reviewed on 25 Jan, 2026
Sugarloaf Key Hotel at KOA Resort
Immaculate Our stay was outstanding. Would recommend 100%
Reviewed on 22 Jan, 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
Historic Key West Old Town Trolley Hop-On Hop-Off 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.
