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 Upper Sugarloaf 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 Venture Out Keys, some noteworthy sights in the nearby area.
Breezeswept Beach Estates
While Breezeswept Beach Estates isn't home to many top sights, Cook Island and Venture Out Keys are some notable places to visit nearby.
Parmer's Resort
565 Barry Avenue Summerland Key FL
$178 nightly
The price is $200 total per night from Dec 7 to Dec 8
$200 total
Dec 7 - Dec 8
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! (1,012 reviews)
Awesome Experience. Such a fun Atmosphere
Reviewed on Dec 2, 2025
Looe Key Reef Resort
27340 Overseas Highway Summerland Key FL
$146 nightly
The price is $164 total per night from Jan 4 to Jan 5
$164 total
Jan 4 - Jan 5, 2026
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! (1,005 reviews)
It was a clean and affordable room right where I needed one. It has canal access to the Atlantic and I could moor my boat right outside of my room. The Tiki bar does live music and I could hear it inside my room at night so be aware. Nice and accommodating people who like to help.
Reviewed on Dec 1, 2025
Sugar Loaf Lodge
17001 Overseas Hwy Summerland Key FL
$99 nightly
The price is $111 total per night from Dec 7 to Dec 8
$111 total
Dec 7 - Dec 8
Total with taxes and fees
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! (1,006 reviews)
nice water front in the backyard
Reviewed on Nov 26, 2025
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.
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! (98 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
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 cable/satellite TV service. Popular attractions Big Pine Key Flea Market ...
9.6/10 Exceptional! (85 reviews)
This property is fantastic and we highly recommend. Whether bringing your own boat, or renting one from next door from Dawn at Lower Keys Boat Rental - this is the perfect place to stay if you are planning to spend time on the water. There are pros and cons with every rental, so I have listed ours ...
Reviewed on Oct 29, 2025
Cottage with swimming pool and dockage, just minutes to Key West!
Cudjoe Key FL
Stay at this cottage in Summerland Key. Enjoy a garden, laundry facilities, and patios. Popular attractions Florida Keys Beaches and Upper Sugarloaf Key are ...
9/10 Wonderful! (158 reviews)
Everything was there that I needed. Very nice area for my dog.
Reviewed on Nov 14, 2025
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
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.
Sugarloaf Beach
Why not spend a lazy afternoon at Sugarloaf Beach during your trip to Summerland Key?
Crab Key
Commune with nature and explore the great outdoors at Crab Key during your travels in Summerland Key.
Squirrel Key
Commune with nature and explore the great outdoors at Squirrel 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
Guided Night Kayak Adventure Tour in Luminous Lagoon
$90
per adult
86% of travellers recommend
Key West's Island Eco Tour: Sandbar Adventure with Kayaking Tour
$120
per adult
98% of travellers recommend
Key West Back-Country Tour with Snorkel - Drive Your Own Boat
$189
per adult
100% of travellers recommend
Explore a world of travel with Expedia
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- Upper Sugarloaf Key
- Sugarloaf Beach
- Saddlebunch Keys
- Upper Sugarloaf Sound
- Duval Street
- Mallory Square
- Southernmost Point
- Sombrero Beach
- Smathers Beach
- Fort Zachary Taylor Historic State Park
- Ernest Hemingway Home and Museum
- South Beach
- Key West Butterfly and Nature Conservatory
- Stock Island Yacht Club & Marina
- Clarence S. Higgs Memorial Beach Park
- Seven Mile Bridge
- Boca Chica Nude Beach
- Harry S. Truman Little White House
- Key West Golf Club
- Vaca Key
- Florida Keys National Marine Sanctuary
- Key West Lighthouse and Keeper's Quarters Museum
- Key West Tropical Forest and Botanical Garden
- Calusa Beach
