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 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
$144 nightly
The price is $162 total per night from Dec 14 to Dec 15
$162 total
Dec 14 - Dec 15
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! (1,001 reviews)
Awesome experience
Reviewed on Nov 14, 2025
Sugar Loaf Lodge
17001 Overseas Hwy Summerland Key FL
$99 nightly
The price is $111 total per night from Nov 23 to Nov 24
$111 total
Nov 23 - Nov 24
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! (1,000 reviews)
A very well maintained older facility. Especially enjoyed the high vaulted ceiling on this 2nd floor unit
Reviewed on Nov 17, 2025
Looe Key Reef Resort
27340 Overseas Highway Summerland Key FL
$190 nightly
The price is $213 total per night from Dec 8 to Dec 9
$213 total
Dec 8 - Dec 9
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! (1,000 reviews)
Room was really clean and receptionist very friendly. Travelling with my son so had a nice big bed each. Balcony was nice and its only 35 mins to Key West which was oerfect
Reviewed on Nov 9, 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! (97 reviews)
Great house far enough away from Key West to be quiet and peaceful, and close enough to enjoy the nightlife!
Reviewed on Oct 23, 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
Cudjoe Cottages, swimming pool, just 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! (147 reviews)
great
was a great stay however i think the photos should be updated especially for the dock / boating areas, they are much more run down than the photos show. there were some ants but thats to be expected in an area like this. the tenants before us left dirty dishes in the dish washer. other than that ...
Reviewed on Jul 7, 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
4/5(21 reviews)
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?
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.
Crab Key
Commune with nature and explore the great outdoors at Crab Key during your travels in Summerland Key.
Things to do
Key West Haunted Tour : Ghosts & Gravestones
$40
per adult
86% of travellers recommend
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
84% 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
- 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
- Harry S. Truman Little White House
- Key West Golf Club
- Vaca Key
- Key West Lighthouse and Keeper's Quarters Museum
- Key West Tropical Forest and Botanical Garden
- Florida Keys National Marine Sanctuary
- Calusa Beach
