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, Upper Sugarloaf Sound and Florida Keys Beaches are some notable places to visit nearby.
Cudjoe Gardens
When in Cudjoe Gardens, you can plan a visit to Upper Sugarloaf Key and Upper Sugarloaf Sound, 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 12 to Jan 13
$158 total
Jan 12 - Jan 13
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! (1,001 reviews)
Staff was friendly. Room was clean. Furniture a little worn but bed comfortable and clean linens
Reviewed on Jan 8, 2026
Parmer's Resort
565 Barry Avenue Summerland Key FL
$258 nightly
The price is $290 total per night from Jan 11 to Jan 12
$290 total
Jan 11 - Jan 12
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! (1,016 reviews)
Excellent
Reviewed on Jan 5, 2026
Sugar Loaf Lodge
17001 Overseas Hwy Summerland Key FL
$169 nightly
The price is $190 total per night from Jan 11 to Jan 12
$190 total
Jan 11 - Jan 12
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! (1,005 reviews)
The room was spacious well proportioned very clean and friendly staff only drawback was no coffee pot in the room
Reviewed on Jan 1, 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.
Cottage with Pool and Boat 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 ...
8.4/10 Very Good! (154 reviews)
Stayed one night, conveniently located.
Reviewed on Dec 16, 2025
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Cudjoe Key FL
Stay at this vacation home in Summerland Key. Enjoy free WiFi, laundry facilities, and concierge services. Popular attractions Florida Keys Beaches and Venture ...
9.6/10 Exceptional! (40 reviews)
Great place!
Reviewed on Nov 29, 2025
Atlantic View Luxury Villa with Pool
125 Colson Dr Summerland Key FL
Stay at this villa in Summerland Key. Enjoy free WiFi, free parking, and 10 outdoor pools. Popular attractions Florida Keys Beaches and Upper Sugarloaf Key are ...
10/10 Exceptional! (1 review)
We were here for a night and it was great. A nice rustic feel on a big property, with good view.
Reviewed on Jan 28, 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.
Sugarloaf Beach
Why not spend a lazy afternoon at Sugarloaf Beach during your trip to Summerland Key?
Upper Sugarloaf Key
Commune with nature and explore the great outdoors at Upper Sugarloaf 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.
Squirrel Key
Commune with nature and explore the great outdoors at Squirrel 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
$189
per adult
100% of travellers recommend
Explore a world of travel with Expedia
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- Sugarloaf Beach
- Upper Sugarloaf Sound
- Saddlebunch Keys
- Upper Sugarloaf Key
- Duval Street
- Mallory Square
- Smathers Beach
- Southernmost Point
- Sombrero Beach
- Ernest Hemingway Home and Museum
- Fort Zachary Taylor Historic State Park
- South Beach
- Seven Mile Bridge
- Key West Butterfly and Nature Conservatory
- Stock Island Yacht Club & Marina
- Clarence S. Higgs Memorial Beach Park
- Boca Chica Nude Beach
- Key West Golf Club
- Harry S. Truman Little White House
- Vaca Key
- Florida Keys National Marine Sanctuary
- Key West Tropical Forest and Botanical Garden
- Key West Lighthouse and Keeper's Quarters Museum
- Calusa Beach
