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 $2,157, price is now CA $882 per person
CA $882
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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 $4,029, price is now CA $1,787 per person
CA $1,787
per person
Jul 10 - Jul 17
found 13 hours ago
Roundtrip flight included
Montreal (YMQ) 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
Casablanca Miami Beach
North Beach
Price was CA $7,644, price is now CA $3,454 per person
CA $3,454
per person
Jul 12 - Jul 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
5.8/10 (323 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
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 $218 per night from May 27 to May 28
CA $218
CA $290 total
May 27 - May 28
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
“Cute Costal Cottages”. We stayed in the “Snapper”. Beds very comfortable, staff very attentive and friendly. We had private outdoor seating facing water. We enjoyed the hammocks in the shade. They serve lemonade and cookies in the afternoon. Breakfast was a great plus. There was a daily charter ...
Reviewed on May 1, 2026
Sugarloaf Key Hotel at KOA Resort
251 Co Rd 939 Summerland Key FL
9.8/10 Exceptional! (564 reviews)
Great place to enjoy
Reviewed on Apr 29, 2026
Sugar Loaf Lodge
17001 Overseas Hwy Summerland Key FL
Fully refundableReserve now, pay when you stay
The price is CA $230 per night from May 13 to May 14
CA $230
CA $258 total
May 13 - May 14
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
Stay was alright. A little dated and a few electrical wires on show. Needs a bit of an upgrade but it was alright for an overnight stay.
Reviewed on Apr 27, 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
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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.
