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.
Bay Point
Bay Point might not have many top sights, but Lower Sugarloaf Sound and Sugarloaf Beach are two attractions nearby that you can check out.
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, Newfound Harbor Keys and Cook Island are some notable places to visit nearby.
Parmer's Resort
565 Barry Avenue, Summerland Key, FL
The price is $178 total per night from Nov 16 to Nov 17
$178 total
per night
Nov 16 - Nov 17
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! (1,005 reviews)
Excellent for relaxation
Reviewed on Oct 26, 2025
Sugar Loaf Lodge
17001 Overseas Hwy, Summerland Key, FL
Fully refundableReserve now, pay when you stay
The price is $111 total per night from Nov 30 to Dec 1
$111 total
per night
Nov 30 - Dec 1
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)
This was an excellent value for the price - the room was spacious and clean, the property was quiet. There was a beautiful view with a balcony. I could not have been happier with my experience!
Reviewed on Oct 6, 2025
Sugarloaf Key Hotel at KOA Resort
251 Co Rd 939, Summerland Key, FL
Stay at this 3-star 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 ...
9.6/10 Exceptional! (448 reviews)
Very clean room, great condition. We loved the layout of the one bedroom. The view from the balcony was stunning! Would recommend.
Reviewed on Oct 27, 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
Stay at this cottage in Summerland Key. Enjoy laundry facilities, patios, and cable/satellite TV service. Popular attractions Upper Sugarloaf Key and Venture ...
8/10 Very Good! (47 reviews)
Great area. Quiet and comfortable
Reviewed on Sep 5, 2025
Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes
Cudjoe Key
Book a stay at this beach vacation home in Summerland Key. Enjoy free WiFi, a beach locale, and laundry facilities. Popular attractions Upper Sugarloaf Key and ...
9.6/10 Exceptional! (230 reviews)
Perfect location for our family with reasonable nearby marina for launching and storing boat trailer.
Reviewed on Oct 20, 2025
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
Cudjoe
Stay at this vacation home in Summerland Key. Enjoy free WiFi, laundry facilities, and tennis courts. Our guests praise the helpful staff in our reviews. Popular ...
9.8/10 Exceptional! (229 reviews)
This is by far the best property we have rented in Venture Out. Everything was amazing, everything was well thought out, super clean, and the extra little thoughtful touches went a long way! We really enjoyed the complimentary pie and the book was very well put together and helpful!
Reviewed on Aug 15, 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
4/5(21 reviews)
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
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
$27
per adult
80% of travellers recommend
Key West Sunset Cruise & Glass Bottom Eco Tour
$64
per adult
74% of travellers recommend
Key West Haunted Tour : Ghosts & Gravestones
$40
per adult
86% of travellers recommend
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- Sugarloaf Beach
- Upper Sugarloaf Key
- Saddlebunch Keys
- Upper Sugarloaf Sound
- Duval Street
- Southernmost Point
- Mallory Square
- Smathers Beach
- Sombrero Beach
- South Beach
- Ernest Hemingway Home and Museum
- Fort Zachary Taylor Historic State Park
- Stock Island Yacht Club & Marina
- Key West Golf Club
- Clarence S. Higgs Memorial Beach Park
- Seven Mile Bridge
- Boca Chica Nude Beach
- Harry S. Truman Little White House
- Key West Butterfly and Nature Conservatory
- Vaca Key
- Florida Keys National Marine Sanctuary
- Key West Lighthouse and Keeper's Quarters Museum
- Florida Keys Eco - Discovery Center
- Calusa Beach