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
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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.

Find hotels in Cutthroat Harbor Estates

Top hotels in Summerland Key

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 S$315 per night from 19 Dec to 20 Dec
S$315
19 Dec - 20 Dec
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
Room was clean and comfortable.

Reviewed on 10 Dec, 2025

Parmer's Resort
Looe Key Reef Resort

Looe Key Reef Resort

2.5 out of 5
27340 Overseas Highway Summerland Key FL
7.4/10 Good! (1,002 reviews)
Second stay here. Best price near Key West. Clean nice rooms. Great tiki, often live music. An authentic Keys experience.

Reviewed on 13 Dec, 2025

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Looe Key Reef Resort
Sugar Loaf Lodge

Sugar Loaf Lodge

2.5 out of 5
17001 Overseas Hwy Summerland Key FL
The price is S$144 per night from 19 Dec to 20 Dec
S$144
19 Dec - 20 Dec
includes taxes & fees
8/10 Very Good! (1,001 reviews)
Very nice property. Owner/Staff were fantastic. I love the life-long effort the family has put into the property. View off the deck is great. Free, good, coffee at the Tiki Bar in the mornings. Overall, the mid-century modern aesthetic is awesome in my opinion. All items worked. Ice machine, ice ...

Reviewed on 12 Dec, 2025

Sugar Loaf Lodge
See all 617 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.

What to do in Summerland Key

12 hours Day at Key West With Boat Tour and Snorkeling

Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar

S$35
per adult
90% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
Key West Parasailing Downtown

Bucket-List Parasailing In Downtown Key West - Highest & Longest Rides

S$93
per traveller
92% of travellers recommend
Bucket-List Parasailing In Downtown Key West - Highest & Longest Rides
Aboard the trolley in Key West

Historic Key West Old Town Trolley Hop-On Hop-Off Tour

S$79
per adult
86% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
See all activities in Summerland Key

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