Summerland Key Vacations from $564
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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 $5,507, price is now $2,165 per person
$2,165
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
5.8/10 (322 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
President Hotel
South Beach
Price was $1,368, price is now $697 per person
$697
per person
Jun 19 - Jun 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
8.4/10 Very Good! (2,145 reviews)
A clean simple place to stay in a great location. I couldn’t get the water warm during the first shower use, but the staff was very good about sending up maintenance right away. They just told me that it needed to run for 10 minutes first. They give you ample towels for the pool and the beach. The buffet breakfast was a great addition. However, it is a basic hotel, nothing fancy. I didn’t like their shampoo and I didn’t find the beds to be very comfortable. Fine for an affordable quick getaway. They also give you two free water bottles a day, which is nice.
Reviewed on Apr 9, 2026
Cavalier Hotel South Beach
South Beach
Save 100% on your flight
Price was $1,211, price is now $649 per person
$649
per person
May 22 - May 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
8.6/10 Excellent! (1,000 reviews)
Its my fourth time there and i loved it
Reviewed on Apr 6, 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
Sugarloaf Key Hotel at KOA Resort
251 Co Rd 939 Summerland Key FL
9.8/10 Exceptional! (546 reviews)
Fantastic place! We stayed in the hotel part of the resort - our apartment was big (even though it was the standard size) and it was spotless. The kitchen had all the plates, cups, and utensils etc you could need, and there was a washer and dryer with detergent. We loved the many USB ports all over ...
Reviewed on Apr 8, 2026
Parmer's Resort
565 Barry Avenue Summerland Key FL
Fully refundableReserve now, pay when you stay
$217 nightly
The price is $244 total per night from Apr 27 to Apr 28
$244 total
Apr 27 - Apr 28
Total with taxes and fees
9/10 Wonderful! (1,010 reviews)
The accommodations that were offered to us were off property, faced a dirty lot with trash receptacles and smelled like mold and mildew! As soon as we saw our accommodations we asked for compensation, in which they blamed Expedia. Expedia told us that it was up to Parker’s to provide a refund. Upon ...
Reviewed on Apr 9, 2026
Looe Key Reef Resort
27340 Overseas Highway Summerland Key FL
Fully refundableReserve now, pay when you stay
$229 nightly
The price is $257 total per night from May 4 to May 5
$257 total
May 4 - May 5
Total with taxes and fees
7.6/10 Good! (1,005 reviews)
Yes very nice
Reviewed on Apr 6, 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.
