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
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
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Reviewed on Nov 5, 2025

Looe Key Reef Resort
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

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 Sep 8, 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 Sep 17, 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 Oct 19, 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.
Upper Sugarloaf Key
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

Key West's Island Eco Tour: Sandbar Adventure with Kayaking Tour

Guided Night Kayak Adventure Tour in Luminous Lagoon
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- Honeymoon Resorts & in Little Torch Key
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- Resorts in Cudjoe Key
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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





