Summerland Key Holidays
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Where to stay in Summerland Key
Find the best Summerland Key areas and neighborhoods for the activities you enjoy most. Learn more about 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
565 Barry Avenue Summerland Key FL
Fully refundableReserve now, pay when you stay
The price is 2.843.117 ₫ per night from 30 Nov to 1 Dec
2.843.117 ₫
4.059.090 ₫ total
30 Nov - 1 Dec
includes taxes & fees
9/10 Wonderful! (1,008 reviews)
We had a wonderful stay at Parmer's Resort. It was quiet and comfortable. We especially loved all the outdoor areas to sit and enjoy the views.
Reviewed on 23 Nov 2025
Looe Key Reef Resort
27340 Overseas Highway Summerland Key FL
Fully refundableReserve now, pay when you stay
7.4/10 Good! (1,003 reviews)
Room was really clean and receptionist very friendly. Travelling with my son so had a nice big bed each. Balcony was nice and its only 35 mins to Key West which was oerfect
Reviewed on 9 Nov 2025
Sugar Loaf Lodge
17001 Overseas Hwy Summerland Key FL
Fully refundableReserve now, pay when you stay
The price is 2.611.026 ₫ per night from 30 Nov to 1 Dec
2.611.026 ₫
2.937.536 ₫ total
30 Nov - 1 Dec
includes taxes & fees
8/10 Very Good! (1,002 reviews)
View from the room was good. Close to key west too.
Reviewed on 21 Nov 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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