
Summerland Key Holidays from £816
Book a Hotel + Flight or Car together to unlock savings
Your Summerland Key Holiday
The hassle-free way to experience this interesting city is with a tailor-made Summerland Key holiday package. Base yourself in the neighbourhood 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 travelling. Browse the wide range of options on Expedia today and put your Summerland Key holiday plans in motion!
The Latest Summerland Key Holiday Deals


The Shelborne By Proper
Reviewed on 31 May 2025


iCoconutGrove Vacation Rentals
Reviewed on 22 Jun 2025

Pelican Grand Beach Resort - A Noble House Resort
Reviewed on 1 Jul 2025

EAST Miami Residences
Reviewed on 23 May 2025
Summerland Key Essential Information
Language | English |
---|---|
Currency | U.S dollars |
Closest Airport | Key West Intl. Airport (EYW) |
Max Temp Winter | 24ºC |
Max Temp Summer | 29ºC |
Top Sights | Bahia Honda State Park, Florida Keys Beaches and Calusa Beach |
Our guide on 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.
Our pick of the best Summerland Key Hotel Deals

Reviewed on 22 Jun 2025

Reviewed on 29 Jun 2025

Reviewed on 12 Jun 2025
Frequently asked questions
Unmissable things to do in Summerland Key

Full Day Charter Snorkeling Sandbar and Eco Safari Adventure
- Neighbourhoods in Summerland Key
- Nearby Cities
- Best holiday destinations by month
- Expedia Latest Trends
Expedia Latest Trends
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.