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 Florida Keys Beaches, 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, Cook Island and Newfound Harbor Keys are some notable places to visit nearby.

Breezeswept Beach Estates
Parmer's Resort
Parmer's Resort
2.5 out of 5
565 Barry Avenue, Summerland Key, FL
The price is AED 592 per night from May 12 to May 13
AED 592
AED 786 total
includes taxes & fees
12 May - 13 May
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! (1,003 reviews)
"The pool, the beach, the sun rise, the staff, all 5 out of 5. I have been all over the keys this property is in the middle of all the best islands. One day here one day there. Love it"

Reviewed on 2 May 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 584 per night from May 11 to May 12
AED 584
AED 657 total
includes taxes & fees
11 May - 12 May
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)
"I like it!."

Reviewed on 4 May 2025

Sugar Loaf Lodge
Looe Key Reef Resort
Looe Key Reef Resort
2.5 out of 5
27340 Overseas Highway, Summerland Key, FL
The price is AED 625 per night from May 11 to May 12
AED 625
AED 703 total
includes taxes & fees
11 May - 12 May
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! (1,001 reviews)
"Great alternative choice to Key West. We took the afternoon seaplane to the Dry Tortugas, but didn't want to pay the prices of Key West. Being about 45 minutes north was great. Our trip down the keys was shorter and vice versa, and traveling 45 min after the seaplane ride (with a stop for dinner) ..."

Reviewed on 7 May 2025

Looe Key Reef Resort
See all 591 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.
Cottage with Pool and Boat Dockage just minutes to Key West!
Cottage with Pool and Boat Dockage just minutes to Key West!
Cudjoe Key
Stay at this cottage in Summerland Key. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Florida Keys Beaches and Upper Sugarloaf ...
Cottage
"Cottage worked well for us as we were meeting some friends in Key West and did not want to stay in the city. For those that fish and have a boat, what a great place to stay. We really just needed it for overnight lodging and it was comfortable for that."

Reviewed on 18 April 2025

Cottage with Pool and Boat Dockage just minutes to 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! (174 reviews)
On the Bay
"We loved the location on the bay. Bed was comfortable and bathroom kitchen were clean. This cabin is nice but a little rustic."

Reviewed on 21 April 2025

Direct Oceanfront Cottage-Sunrise View- #2,
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Cudjoe Key
Stay at this vacation home in Summerland Key. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Florida Keys Beaches and Upper Sugarloaf ...
8.8/10 Excellent! (145 reviews)
Family get away
"We had a fantastic stay, lots of room for our kids and even room for our family when they came over. Watched the sunrise on the enclosed deck every morning and evening had a walkway toSit on the water. Definitely recommend this location!!"

Reviewed on 29 April 2025

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
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

Crab Key

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

Crab Key

Squirrel Key

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

Squirrel Key

Pye Key

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

Pye Key