
Summerland Key Vacations from $497
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Your Summerland Key Vacation
The hassle-free way to experience this interesting city is with a tailor-made Summerland Key vacation package. Base yourself in the neighborhood of Sugarloaf Shores, which is great for families, fishing and views or go someplace else — our package deals are all about you. Cook Island, Big Pine Key Flea Market and Blue Hole are just some of the sights you'll want to see during your trip to Summerland Key. Stop daydreaming and start traveling. Browse the wide range of options on Expedia today and put your Summerland Key vacation plans in motion!
The Latest Summerland Key vacation packages

Henrosa Hotel
Reviewed on Nov 13, 2026

The Retreat Collection at 1 Hotel & Homes South Beach
Reviewed on Jun 22, 2016


Eurostars Winter Haven
Reviewed on Nov 4, 2026

Where to stay in Summerland Key

Cutthroat Harbor Estates
While Cutthroat Harbor Estates isn't home to many top sights, Venture Key and Venture Out Keys are some notable places to visit nearby.
Stay near popular Summerland Key attractions
What to do in Summerland Key

Guided Night Kayak Adventure Tour in Luminous Lagoon
Summerland Key Hotel Deals

Parmer's Resort
"Lovely, quiet spot. Perfect for an anniversary trip."
Reviewed on Nov 14, 2026

Sugarloaf Key Hotel at KOA Resort

Looe Key Reef Resort
Find the Best Summerland Key Vacation Packages
Summerland Key Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Key West Intl. Airport (EYW) |
Max Temp Winter | 75ºF |
Max Temp Summer | 85ºF |
Top Sights | Bahia Honda State Park, Florida Keys Beaches and Calusa Beach |
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Frequently asked questions
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