Summerland Key Vacation Packages
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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!
Top Summerland Key Vacation Deals
Brickell Bay 3505
Reviewed on Apr 14, 2026
Where to stay in Summerland Key
Cutthroat Harbor Estates
While Cutthroat Harbor Estates isn't home to many top sights, Venture Out Keys and Venture Key are some notable places to visit nearby.
Summerland Key Hotel Deals
Parmer's Resort
Wonderful waterfront property with private beach, multiple piers, paddle boards, kayaks, laundry and a great continental breakfast; plus cookies, lemonade and coffee in the afternoon! Great loation at the top of the lower Keys. We'll be back, all the way from Seattle.
Reviewed on May 7, 2026
Sugarloaf Key Hotel at KOA Resort
This hotel is so good and the room is so pretty!
Reviewed on May 8, 2026
Sugar Loaf Lodge
What to do in Summerland Key
