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
Price found within the past 48 hours. Click for updated prices.
The Link Hotel South Beach
South Beach
CA $1,101
per person
Oct 18 - Oct 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9.6/10 Exceptional! (56 reviews)
Things to know: it’s managed by nearby restaurant so it’s important that you check in during certain hours so they can greet you! Loved the location and property
Reviewed on Jul 25, 2026
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
CA $16,040
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
8/10 Very good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016
Where to stay in Summerland Key
Find the best Summerland Key areas and neighborhoods for the activities you enjoy most. Learn more about 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.
Sugarloaf Shores
While Sugarloaf Shores isn't home to many top sights, Florida Keys Beaches and Upper Sugarloaf Sound are some notable places to visit nearby.
Cudjoe Gardens
When in Cudjoe Gardens, you can plan a visit to Upper Sugarloaf Key and Florida Keys Beaches, some noteworthy sights in the nearby area.
Breezeswept Beach Estates
While Breezeswept Beach Estates isn't home to many top sights, Cook Island and Venture Out Keys are some notable places to visit nearby.
Ready to book your vacation to Summerland Key?
Summerland Key Hotel Deals
Parmer's Resort
565 Barry Avenue Summerland Key FL
Fully refundableReserve now, pay when you stay
CA $140
CA $203 total
Aug 26 - Aug 27
includes taxes & fees
9/10 Wonderful! (1,007 reviews)
"We stayed at Parmer’s Resort for just one night and overall had a great experience. The room was clean and comfortable, and the staff was very helpful and friendly. They gave us excellent recommendations for places to visit in the area. Based on their recommendation, we decided to visit Kiki’s Sandbar, ..."
Reviewed on Aug 23, 2026
Sugarloaf Key Hotel at KOA Resort
251 Co Rd 939 Summerland Key FL
9.8/10 Exceptional! (624 reviews)
"The Property was really nice But no pets on the beach that was A down"
Reviewed on Aug 24, 2026
Sugarloaf Key RV Resort & Cottages
311 Johnson Rd Summerland Key FL
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stay near popular Summerland Key attractions
Sugarloaf Beach
8.4/10 (38 reviews)
Why not spend a lazy afternoon at Sugarloaf Beach during your trip to Summerland Key?
Upper Sugarloaf Key
8.6/10 (54 reviews)
Commune with nature and explore the great outdoors at Upper Sugarloaf 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.
Upper Sugarloaf Sound
9.2/10 (17 reviews)
Commune with nature and explore the great outdoors at Upper Sugarloaf Sound during your travels in Summerland Key.
Venture Key
Commune with nature and explore the great outdoors at Venture 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.
Boondocks Grille & Draft House
Boondocks Grille & Draft House is just one of the places to see in Summerland Key, so why not enjoy the other things to explore during your travels?
What to do in Summerland Key
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
CA $78
per adult
88% of travellers recommend
Key West Haunted Tour : Ghosts & Gravestones
CA $55
per adult
88% of travellers recommend
Frequently asked questions
How much does a Summerland Key vacation package cost?
Offering great value package deals from CA $1,101 on Expedia, you'll be pleasantly surprised at how much a vacation to Summerland Key costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Summerland Key?
If you're looking to book a cheap Summerland Key vacation package, consider travelling in September, October and November. You'll typically find better rates on hotels and airfares during these months — ideal for a budget-friendly break.
How many days is enough for Summerland Key?
We'd suggest booking a Summerland Key vacation for a minimum of 4 days. This gives you plenty of time to tick off top attractions including Blue Hole and Cook Island, and also explore neighbourhoods like Eden Pines and Cutthroat Harbour Estates. You could even squeeze in a day trip (or two) from Summerland Key.
How to find the best Summerland Key package deals?
Use Expedia's filter tool to find some terrific Summerland Key package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or search for Summerland Key package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a Summerland Key vacation as a package?
You can enjoy significant savings on your Summerland Key retreat by booking a tailored vacation package. Check the "Package" heading, then enter your travel dates and destination to browse the best flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Summerland Key?
If you're considering an impromptu Summerland Key getaway, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can score awesome deals on your flights and hotels by booking well in advance.
How to plan a trip to Summerland Key?
- Pick your dates: The things you plan to do in Summerland Key and your preferred season can help you decide when to get away.
- Calculate your budget: Ensure you have enough money to cover everything from dining out and transportation to flights and activities. Your accommodations will likely be the largest expense during your trip to Summerland Key.
- Decide how long to go for: Now that you know more about Summerland Key, you can work out the perfect length of your vacation. Create a draft plan and allocate enough time to get through everything on your must-do list.
- Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to choose a Summerland Key vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
