Summerland Key, FL

Travel Guide
Sugarloaf Shores showing a house, a sunset and a bay or harbor
Sugarloaf Shores which includes a bay or harbor and a house
Sugarloaf Shores featuring a sunset and tropical scenes
Sugarloaf Shores showing a house, a sunset and a bay or harbor
Sugarloaf Shores which includes a bay or harbor and a house

Where to stay in 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.

Cutthroat Harbor Estates
Sugarloaf Shores featuring a bay or harbor

Sugarloaf Shores

While Sugarloaf Shores isn't home to many top sights, Florida Keys Beaches and Sugarloaf Beach are some notable places to visit nearby.

Sugarloaf Shores
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Cudjoe Gardens

When in Cudjoe Gardens, you can plan a visit to Upper Sugarloaf Key and Venture Out Keys, some noteworthy sights in the nearby area.

Cudjoe Gardens
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Breezeswept Beach Estates

While Breezeswept Beach Estates isn't home to many top sights, Venture Out Keys and Newfound Harbor Keys are some notable places to visit nearby.

Breezeswept Beach Estates
Looe Key Reef Resort
Looe Key Reef Resort
2.5 out of 5
27340 Overseas Highway, Summerland Key, FL
The price is AED 766 per night from Jan 26 to Jan 27
AED 766
AED 862 total
includes taxes & fees
26 Jan - 27 Jan
Stay at this hotel in Summerland Key. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the bar and the helpful staff in our reviews. ...
7.4/10 Good! (1,000 reviews)
"It was a great place nice pool area and the Tiki bar and grill was right next door we ended up staying there for New Year’s Eve and they had excellent entertainment for the evening all in all we will definitely go back there again"

Reviewed on 14 January 2025

Looe Key Reef Resort
Parmer's Resort
Parmer's Resort
2.5 out of 5
565 Barry Avenue, Summerland Key, FL
The price is AED 731 per night from Jan 27 to Jan 28
AED 731
AED 942 total
includes taxes & fees
27 Jan - 28 Jan
Book a stay at this beach motel in Summerland Key. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in ...
8.8/10 Excellent! (1,001 reviews)
"This is an older property, likely developed in the 60’s. We were greeted warmly despite our early arrival. We stayed in a double twin room named “Tuna.” On entering the space there was a strong smell of cleanser. It adjoined two lodging areas on either side. We were able to hear a bit of conversation ..."

Reviewed on 12 January 2025

Parmer's Resort
Sugar Loaf Lodge
Sugar Loaf Lodge
2.5 out of 5
17001 Overseas Hwy, Summerland Key, FL
The price is AED 731 per night from Jan 26 to Jan 27
AED 731
AED 822 total
includes taxes & fees
26 Jan - 27 Jan
Stay at this hotel in Summerland Key. Enjoy free WiFi, free parking, and a marina. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
8/10 Very Good! (998 reviews)
"Everything was good"

Reviewed on 6 January 2025

Sugar Loaf Lodge
See all 586 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.
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
Stay at this cottage in Summerland Key. Enjoy free WiFi, a garden, and patios. Popular attractions Florida Keys Beaches and Upper Sugarloaf Key are located ...
9/10 Wonderful! (40 reviews)
Super comfortable and great location.
"This is our second year at one of these cottages. We love the complex and the location is great to get to many things. The cottage has everything you would need and is very clean. The host has been great to work with."

Reviewed on 19 December 2024

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Direct Oceanfront Cottage-Sunrise View- #2,
Direct Oceanfront Cottage-Sunrise View- #2,
Little Torch Key
Book a stay at this beach cottage in Summerland Key. Enjoy a beach locale, a garden, and patios. Popular attractions Big Pine Key Flea Market and Blue Hole are ...
8.6/10 Excellent! (164 reviews)
great vacation
"It was kind of exciting. the cops showed up on the property and on the next door property to the North, there was a tree of stolen bouys and a stolen crab trap. It was quiet. there was a bit of a flood when it rained but within a day or 2 the water was gone. we had trouble opening the slider on the ..."

Reviewed on 3 January 2025

Direct Oceanfront Cottage-Sunrise View- #2,
Old Florida Style, wrap around porch, boat basin for dockage, open water
Old Florida Style, wrap around porch, boat basin for dockage, open water
Little Torch Key
Stay at this vacation home in Summerland Key. Enjoy a garden, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Big Pine Key Flea Market ...
9.6/10 Exceptional! (63 reviews)
Relaxing
"Just a beautiful location, paradise. Spent mornings in the covered porch, husband loved the lagoon for fishing. We brought kayaks and the kids loved it. The dogs enjoyed the large property as well."

Reviewed on 3 January 2025

Old Florida Style, wrap around porch, boat basin for dockage, open water
See all 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.

Popular places to visit

Upper Sugarloaf Sound

Upper Sugarloaf Sound

Commune with nature and explore the great outdoors at Upper Sugarloaf Sound during your travels in Summerland Key.

Upper Sugarloaf Sound

Sugarloaf Beach

Why not spend a lazy afternoon at Sugarloaf Beach during your trip to Summerland Key?

Sugarloaf Beach

Upper Sugarloaf Key

4/5(21 reviews)

Commune with nature and explore the great outdoors at Upper Sugarloaf Key during your travels in Summerland Key.

Upper Sugarloaf Key

Squirrel Key

Commune with nature and explore the great outdoors at Squirrel Key during your travels in Summerland Key.

Squirrel Key

Venture Key

Commune with nature and explore the great outdoors at Venture Key during your travels in Summerland Key.

Venture Key

Crab Key

Commune with nature and explore the great outdoors at Crab Key during your travels in Summerland Key.

Crab Key