Summerland Key Travel Guide
Tourist Guide
Visit Summerland Key
Where to stay in Summerland Key
Cutthroat Harbor Estates
While there might not be top attractions in Cutthroat Harbor Estates, you can explore the larger area and discover places like Venture Out Keys and Upper Sugarloaf Key.
Sugarloaf Shores
Though Sugarloaf Shores may not have many top sights, you can venture to the surrounding area to see attractions like Florida Keys Beaches and Sugarloaf Beach.
Cudjoe Gardens
While Cudjoe Gardens may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Upper Sugarloaf Key and Venture Out Keys.
Bay Point
While Bay Point may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Lower Sugarloaf Sound and Sugarloaf Beach.
Breezeswept Beach Estates
While there might not be top attractions in Breezeswept Beach Estates, you can explore the larger area and discover places like Newfound Harbor Keys and Cook Island.
Parmer's Resort
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 8 Nov 2025
Sugar Loaf Lodge
…
Reviewed on 5 Nov 2025
Looe Key Reef Resort
We enjoyed our three night stay. We dived Looe Key reef every day through their dive shop. Safe shallow diving with excellent storage, easy access and excellent staff. Left the afternoon/evening open to relax or go into town. About 50 minutes from Key West. Recommend car rental for your stay
Reviewed on 17 Oct 2025
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
Excellent stay Quiet clean and comfortable Thank you for making our vacation a fantastic experience
Reviewed on 8 Sept 2025
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Great location , clear communications and listing accuracy. Will be coming back again
Reviewed on 17 Sept 2025
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
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 19 Oct 2025
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.
Activities
Key West Sunset Cruise & Glass Bottom Eco Tour
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
