Summerland Key, FL
Travel Guide
Visit Summerland Key
Where to stay in Summerland Key
Cutthroat Harbor Estates
While Cutthroat Harbor Estates isn't home to many top sights, Venture Out Keys and Venture Key are some notable places to visit nearby.
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.
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.
Breezeswept Beach Estates
While Breezeswept Beach Estates isn't home to many top sights, Venture Out Keys and Cook Island are some notable places to visit nearby.
Sugarloaf Key Hotel at KOA Resort
251 Co Rd 939 Summerland Key FL
Stay at this hotel in Summerland Key. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the clean rooms in our reviews. ...
9.8/10 Exceptional! (551 reviews)
Enjoyed our time there
Reviewed on Apr 13, 2026
Parmer's Resort
565 Barry Avenue Summerland Key FL
$207 nightly
The price is $232 total per night from Apr 27 to Apr 28
$232 total
Apr 27 - Apr 28
Total with taxes and fees
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 ...
9/10 Wonderful! (1,016 reviews)
Excellent place for a family getaway.
Reviewed on Apr 13, 2026
Looe Key Reef Resort
27340 Overseas Highway Summerland Key FL
$262 nightly
The price is $295 total per night from May 8 to May 9
$295 total
May 8 - May 9
Total with taxes and fees
Stay at this hotel in Summerland Key. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. ...
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.
Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key FL
Stay at this cottage in Summerland Key. Enjoy laundry facilities, patios, and an in-room coffeemaker. Popular attractions Florida Keys Beaches and Venture Key ...
8.8/10 Excellent! (96 reviews)
The photo shot from above from the outside of the building is abit misleading. The lower building on the left is the apartment and the high building next to it is a large separate home, so you can’t actually see the bay unless you walk to the water edge for a slight bay view. The houses across the ...
Reviewed on Mar 12, 2026
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Cudjoe Key FL
Stay at this cottage in Summerland Key. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Florida Keys Beaches and Upper Sugarloaf Key are ...
8.6/10 Excellent! (166 reviews)
Yes you are on the ocean, yes there are docks, and yes you are centrally located for activities. Cottage was clean but very dated and not well kept. It is not private, we had people walking and driving in and around us throughout the day. We did bring a dog, which is why we liked the private description, ...
Reviewed on Mar 18, 2026
Old Florida Style, wrap around porch, boat basin for dockage, open water
Little Torch Key FL
Stay at this vacation home in Summerland Key. Enjoy a garden, laundry facilities, and an in-room coffeemaker. Popular attractions Big Pine Key Flea Market and ...
9.6/10 Exceptional! (104 reviews)
Great house, great location. Everything was exactly as described.
Reviewed on Mar 30, 2026
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
Sugarloaf Beach
Why not spend a lazy afternoon at Sugarloaf Beach during your trip to Summerland Key?
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 Sound
Commune with nature and explore the great outdoors at Upper Sugarloaf Sound during your travels in Summerland Key.
Venture Key
Commune with nature and explore the great outdoors at Venture Key during your travels in Summerland Key.
Crab Key
Commune with nature and explore the great outdoors at Crab Key during your travels in Summerland Key.
Pye Key
Commune with nature and explore the great outdoors at Pye Key during your travels in Summerland Key.
Things to do
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
$27
per adult
88% of travellers recommend
Key West Dolphin & Snorkeling Tour - Small Group
$135
per adult
100% of travellers recommend
Key West Haunted Tour : Ghosts & Gravestones
$40
per adult
88% of travellers recommend
Key West Sunset Cruise & Glass Bottom Eco Tour
$70
per adult
76% of travellers recommend
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- Upper Sugarloaf Key
- Sugarloaf Beach
- Upper Sugarloaf Sound
- Duval Street
- Mallory Square
- Southernmost Point
- Smathers Beach
- Sombrero Beach
- Fort Zachary Taylor Historic State Park
- Ernest Hemingway Home and Museum
- South Beach
- Seven Mile Bridge
- Florida Keys National Marine Sanctuary
- Clarence S. Higgs Memorial Beach Park
- Key West Butterfly and Nature Conservatory
- Boca Chica Nude Beach
- Stock Island Yacht Club & Marina
- Vaca Key
- Harry S. Truman Little White House
- Key West Lighthouse and Keeper's Quarters Museum
- Key West Golf Club
- Florida Keys Eco - Discovery Center
- Key West Tropical Forest and Botanical Garden