Summerland Key Vacations

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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
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Cutthroat Harbor Estates

While Cutthroat Harbor Estates isn't home to many top sights, Venture Out Keys and Upper Sugarloaf Key are some notable places to visit nearby.

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Find the Best Summerland Key Vacation Packages

Summerland Key Hotel Deals

Parmer's Resort

Parmer's Resort

2.5 out of 5
565 Barry Avenue, Summerland Key, FL
Fully refundableReserve now, pay when you stay
The price is ₩158,745 per night from Nov 19 to Nov 20
₩158,745
₩225,856 total
Nov 19 - Nov 20
includes taxes & fees
9/10 Wonderful! (1,007 reviews)
Everything was excellent 5 stars we stayed at a lot of resorts this was best by far Sue was very helpful and even talked with cleaning staff was so friendly. They ALL go above and beyond. Will be back to our private little getaway.

Reviewed on Oct 30, 2025

Parmer's Resort
Sugar Loaf Lodge

Sugar Loaf Lodge

2.5 out of 5
17001 Overseas Hwy, Summerland Key, FL
Fully refundableReserve now, pay when you stay
The price is ₩142,781 per night from Dec 4 to Dec 5
₩142,781
₩160,636 total
Dec 4 - Dec 5
includes taxes & fees
8/10 Very Good! (998 reviews)
…

Reviewed on Nov 5, 2025

Sugar Loaf Lodge
Looe Key Reef Resort

Looe Key Reef Resort

2.5 out of 5
27340 Overseas Highway, Summerland Key, FL
Fully refundableReserve now, pay when you stay
7.4/10 Good! (1,001 reviews)
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 Oct 17, 2025

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Looe Key Reef Resort
See all 625 properties in Summerland Key
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.