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, 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 Crab Key are some notable places to visit nearby.
Looe Key Reef Resort
27340 Overseas Highway Summerland Key FL
Fully refundableReserve now, pay when you stay
$140 nightly
The price is $158 total per night from Jan 5 to Jan 6
$158 total
Jan 5 - Jan 6, 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! (1,001 reviews)
Staff very polite and accommodating.
Reviewed on Dec 21, 2025
Parmer's Resort
565 Barry Avenue Summerland Key FL
Fully refundableReserve now, pay when you stay
$243 nightly
The price is $273 total per night from Jan 5 to Jan 6
$273 total
Jan 5 - Jan 6, 2026
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! (1,000 reviews)
Room was clean and comfortable.
Reviewed on Dec 10, 2025
Sugar Loaf Lodge
17001 Overseas Hwy Summerland Key FL
$199 nightly
The price is $224 total per night from Jan 4 to Jan 5
$224 total
Jan 4 - Jan 5, 2026
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! (999 reviews)
Exceeded expectations. Nothing to complain about. Nice water scenery back of rooms. Spacious parking. Quiet, off road.
Reviewed on Dec 16, 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.
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key FL
Stay at this cottage in Summerland Key. Enjoy a garden, laundry facilities, and cable/satellite TV service. Popular attractions Florida Keys Beaches and Upper ...
8.6/10 Excellent! (73 reviews)
It was a nice location. 30” from Key West.
Reviewed on Nov 21, 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
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
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.
Squirrel Key
Commune with nature and explore the great outdoors at Squirrel 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
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
$81
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
- Upper Sugarloaf Sound
- Upper Sugarloaf Key
- Saddlebunch Keys
- Duval Street
- Mallory Square
- Smathers Beach
- Southernmost Point
- Sombrero Beach
- Fort Zachary Taylor Historic State Park
- Ernest Hemingway Home and Museum
- South Beach
- Seven Mile Bridge
- Stock Island Yacht Club & Marina
- Key West Butterfly and Nature Conservatory
- Clarence S. Higgs Memorial Beach Park
- Boca Chica Nude Beach
- Harry S. Truman Little White House
- Key West Golf Club
- Vaca Key
- Florida Keys National Marine Sanctuary
- Key West Tropical Forest and Botanical Garden
- Key West Lighthouse and Keeper's Quarters Museum
- Calusa Beach
