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 Key and Venture Out Keys 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, Cook Island and Newfound Harbor Keys are some notable places to visit nearby.
Looe Key Reef Resort
27340 Overseas Highway Summerland Key FL
$140 nightly
The price is $158 total per night from Jan 29 to Jan 30
$158 total
Jan 29 - Jan 30
Total with taxes and fees
Stay at this hotel in Summerland Key. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.4/10 Good! (1,010 reviews)
⭐️⭐️⭐️⭐️⭐️
Reviewed on Jan 25, 2026
Parmer's Resort
565 Barry Avenue Summerland Key FL
$313 nightly
The price is $352 total per night from Jan 28 to Jan 29
$352 total
Jan 28 - Jan 29
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 ...
8.8/10 Excellent! (1,006 reviews)
Clean room, exceptional customer care, location was fantastic!
Reviewed on Jan 23, 2026
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. ...
9.6/10 Exceptional! (477 reviews)
Immaculate Our stay was outstanding. Would recommend 100%
Reviewed on Jan 22, 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.
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key FL
Stay at this cottage in Summerland Key. Enjoy laundry facilities, patios, and cable/satellite TV service. Popular attractions Florida Keys Beaches and Upper ...
8.2/10 Very Good! (56 reviews)
It was like staying at my Grandmom's house--it was clean but bathroom and kitchen cabinet needed some attention. Still, we were very happy with bungalow 12 and would stay there again.We only stayed overnight but the little pool, beach and fire pit would be quite enjoyable had we stayed longer. Great ...
Reviewed on Jan 22, 2026
Private Secluded Ocean View & Pool Near Key West
Summerland Key FL
Stay at this vacation home in Summerland Key. Enjoy free WiFi, private pools, and a fitness center. Our guests praise the helpful staff in our reviews. Popular ...
8.2/10 Very Good! (99 reviews)
A wonderful time was had by all. Host was very responsive and we had no issues. Beautiful home and views!
Reviewed on Nov 18, 2025
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Cudjoe Key FL
Stay at this vacation home in Summerland Key. Enjoy a garden, laundry facilities, and patios. Popular attractions Florida Keys Beaches and Upper Sugarloaf Key ...
8.8/10 Excellent! (157 reviews)
The home itself does need some updating but overall the home fit our needs. Could have had a better cleaning in some areas, but we will be back to stay in the future.
Reviewed on Jan 4, 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 Sound
Commune with nature and explore the great outdoors at Upper Sugarloaf Sound during your travels in Summerland Key.
Upper Sugarloaf Key
Commune with nature and explore the great outdoors at Upper Sugarloaf 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.
Crab Key
Commune with nature and explore the great outdoors at Crab Key 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.
Things to do
Key West's Island Eco Tour: Sandbar Adventure with Kayaking Tour
$120
per adult
98% of travellers recommend
Guided Night Kayak Adventure Tour in Luminous Lagoon
$90
per adult
86% of travellers recommend
Key West Back-Country Tour with Snorkel - Drive Your Own Boat
$170
per adult
100% of travellers recommend
Explore a world of travel with Expedia
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- Sugarloaf Beach
- Saddlebunch Keys
- Upper Sugarloaf Sound
- Upper Sugarloaf Key
- Duval Street
- Mallory Square
- Smathers Beach
- Southernmost Point
- Sombrero Beach
- Fort Zachary Taylor Historic State Park
- Ernest Hemingway Home and Museum
- South Beach
- Stock Island Yacht Club & Marina
- Key West Butterfly and Nature Conservatory
- Clarence S. Higgs Memorial Beach Park
- Seven Mile Bridge
- Boca Chica Nude Beach
- Florida Keys National Marine Sanctuary
- Vaca Key
- Key West Golf Club
- Harry S. Truman Little White House
- Key West Tropical Forest and Botanical Garden
- Calusa Beach
