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.
Brickell Bay 3505
Brickell
Price was CA $2,261, price is now CA $955 per person
CA $955
per person
Jul 10 - Jul 13
found 9 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
9/10 Wonderful! (2 reviews)
The room was clean, there was a problem at the check out time as all the guest have the same check out and all the elevators collapse, it took us more than an hour to get down.
The parking is really a problem as we had to go up almost 20 floors.
Location is pretty good.
Reviewed on Apr 14, 2026
Miami Downtown Condos
Downtown Miami
Price was CA $6,653, price is now CA $2,932 per person
CA $2,932
per person
Jun 23 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.2/10 Very Good! (151 reviews)
The room was overall good order and clean. 5 Star is reserved for properties that go above and beyond with details and exceed expectations. This property was great with regards to cleanliness, but not 5 star. Minor details, small spots here and there and other fine details that can be overlooked but keeps it from a 5 star rating
Reviewed on May 1, 2026
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.
Summerland Key Hotel Deals
Parmer's Resort
565 Barry Avenue Summerland Key FL
Fully refundableReserve now, pay when you stay
The price is CA $207 per night from May 28 to May 29
CA $207
CA $277 total
May 28 - May 29
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
Our room had insects.
Reviewed on May 6, 2026
Sugarloaf Key Hotel at KOA Resort
251 Co Rd 939 Summerland Key FL
9.8/10 Exceptional! (566 reviews)
The staff and the property were excellent. They really work hard to keep things clean and they’re very friendly. The property features are excellent for the most part. The only disappointment was the beach. It was small and the water was very dirty. Not something I’d swim in but none of the beaches ...
Reviewed on May 5, 2026
Sugar Loaf Lodge
17001 Overseas Hwy Summerland Key FL
The price is CA $230 per night from May 13 to May 14
CA $230
CA $259 total
May 13 - May 14
includes taxes & fees
8.2/10 Very Good! (1,003 reviews)
Nice clean and well maintained property
Reviewed on May 4, 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.
What to do in Summerland Key
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
CA $77
per adult
88% of travellers recommend
Key West Haunted Tour : Ghosts & Gravestones
CA $61
per adult
88% of travellers recommend
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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.
