Summerland Key Vacations from $450
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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
Price found within the past 48 hours. Click for updated prices.
Casablanca Miami Beach
North Beach
Price was $5,979, price is now $2,577 per person
$2,577
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Miami (MIA)
5.8/10 (324 reviews)
Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great.
It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it.
Reviewed on Feb 22, 2026
Andaz Miami Beach Resort & Spa
Mid Beach
Save 100% on your flight
Price was $1,242, price is now $588 per person
$588
per person
Aug 6 - Aug 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
9/10 Wonderful! (284 reviews)
Property was amazing! Favorite part was the fact that there is a pool for just adults and one for those traveling with children. Cannot wait to go back!
Reviewed on May 25, 2026
The Crosby Miami Worldcenter
Downtown Miami
Save 100% on your flight
Price was $934, price is now $487 per person
$487
per person
Aug 6 - Aug 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
8.4/10 Very Good! (179 reviews)
Stay was great but NO ONSITE PARKING!
Reviewed on May 24, 2026
Don't see what you're looking for?
See all available trips from Columbus to Summerland Key
View all tripsWhere 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.
Discover the most popular places to visit in Summerland Key
Sugarloaf Beach
Why not spend a lazy afternoon at Sugarloaf Beach during your trip to Summerland Key?
Upper Sugarloaf Key
4/5(21 reviews)
Commune with nature and explore the great outdoors at Upper Sugarloaf Key during your travels in Summerland Key.
Upper Sugarloaf Sound
Commune with nature and explore the great outdoors at Upper Sugarloaf Sound during your travels in Summerland Key.
What to do in Summerland Key
Key West Dolphin & Snorkeling Tour - Small Group
$135
per adult
100% of travellers recommend
Summerland Key Hotel Deals
Parmer's Resort
565 Barry Avenue Summerland Key FL
Fully refundableReserve now, pay when you stay
$228 nightly
The price is $257 total per night from Jun 3 to Jun 4
$257 total
Jun 3 - Jun 4
Total with taxes and fees
9/10 Wonderful! (1,003 reviews)
"Dock only had 1 power outlet that worked. 3 others were rusted shut and broken. We had 12-15 gallon of fuel stolen from our boat when docked over night. Other than that a great place for home base to fish out of. Staff was great. Very limited breakfast. Ice was available daily. I would definitely ..."
Reviewed on May 31, 2026
Sugarloaf Key Hotel at KOA Resort
251 Co Rd 939 Summerland Key FL
Sugarloaf Key RV Resort & Cottages
311 Johnson Rd Summerland Key FL
9.8/10 Exceptional! (7 reviews)
"I prefer Communication via email or text. This was the plus for me with the resort. It was very easy to check in after hours and the reach the resort. Welcome package with all you need to get to the cottage. Beautiful, clean and just ready to start your vacation. This place is 25 min from Key West! ..."
Reviewed on May 26, 2026
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.
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.