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, Newfound Harbor Keys and Cook Island are some notable places to visit nearby.
Parmer's Resort
565 Barry Avenue, Summerland Key, FL
$158 nightly
The price is $178 total per night from Nov 16 to Nov 17
$178 total
Nov 16 - Nov 17
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! (1,002 reviews)
Excellent service and ammenities. We enjoyed our stay, very personable resort and we took pleasure in getting to know the other patrons at the pool. The Resort is in the perfect central location, we travelled to both Islamorada and Key West a couple of days. A fishing charter picked us up right at ...
Reviewed on Nov 8, 2025
Sugar Loaf Lodge
17001 Overseas Hwy, Summerland Key, FL
$99 nightly
The price is $111 total per night from Nov 30 to Dec 1
$111 total
Nov 30 - Dec 1
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! (998 reviews)
…
Reviewed on Nov 5, 2025
Looe Key Reef Resort
27340 Overseas Highway, Summerland Key, FL
$195 nightly
The price is $219 total per night from Nov 30 to Dec 1
$219 total
Nov 30 - Dec 1
Total with taxes and fees
Stay at this hotel in Summerland Key. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the bar and the helpful staff in our reviews. ...
7.4/10 Good! (1,003 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.
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
Cudjoe Key
Stay at this vacation home in Summerland Key. Enjoy free WiFi, laundry facilities, and concierge services. Popular attractions Venture Key and Out Key are located ...
10/10 Exceptional! (4 reviews)
Excellent stay Quiet clean and comfortable Thank you for making our vacation a fantastic experience
Reviewed on Sep 8, 2025
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Cudjoe Key
Stay at this vacation home in Summerland Key. Enjoy a garden, laundry facilities, and patios. Popular attractions Upper Sugarloaf Key and Venture Out Keys are ...
8.8/10 Excellent! (152 reviews)
Great location , clear communications and listing accuracy. Will be coming back again
Reviewed on Sep 17, 2025
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Cudjoe Key
Stay at this vacation home in Summerland Key. Enjoy free WiFi, laundry facilities, and concierge services. Popular attractions Venture Key and Out Key are located ...
9.6/10 Exceptional! (37 reviews)
This is one of the best rental units in venture out. The location on the canal looking out at the bay is very nice and gets a breeze. The furnishing and layout are great too. Would love to stay here again.
Reviewed on Oct 19, 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
- Key West Butterfly and Nature Conservatory
- Seven Mile Bridge
- 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
- Florida Keys National Marine Sanctuary
- Vaca Key
- Key West Lighthouse and Keeper's Quarters Museum
- Key West Tropical Forest and Botanical Garden
- Calusa Beach
