
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 2.926.264 ₫ per night from 31 Aug to 1 Sept
2.926.264 ₫
4.147.638 ₫ total
31 Aug - 1 Sept
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"Relaxing"
Reviewed on 4 Aug 2025

Sugar Loaf Lodge
17001 Overseas Hwy, Summerland Key, FL
Fully refundableReserve now, pay when you stay
The price is 2.595.879 ₫ per night from 17 Aug to 18 Aug
2.595.879 ₫
2.920.495 ₫ total
17 Aug - 18 Aug
includes taxes & fees
8/10 Very Good! (998 reviews)
"It was great"
Reviewed on 27 Jul 2025

Sugarloaf Key Hotel at KOA Resort
251 Co Rd 939, Summerland Key, FL
9.6/10 Exceptional! (420 reviews)
"This was my first time staying at this property. I can only say that it will not be the last. The staff and the property was such an amazing experience. It is family friendly, close proximity to Key West and very quiet and clean. It was such a pleasure to stay there."
Reviewed on 3 Aug 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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