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 W - Bayshore Unit 1003
East Fort Lauderdale
Price was CA $3,415, price is now CA $1,284 per person
CA $1,284
per person
Jul 7 - Jul 12
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
6/10 (2 reviews)
I thoroughly enjoyed my stay at this hotel. The host was incredibly friendly and attentive, and the communication was prompt and efficient. The hotel itself was beautiful, and the staff was incredibly kind and helpful.
Reviewed on May 20, 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 Upper Sugarloaf 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 $186 per night from May 21 to May 22
CA $186
CA $254 total
May 21 - May 22
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
"Staff was helpful and friendly. The only complaint I have is not enough soap/shampoo for more than 1 night. Other than that, excellent place to stay...nothing fancy but clean, comfortable and close to Key West and other points of interest. I would definitely stay here again."
Reviewed on May 19, 2026
Sugarloaf Key Hotel at KOA Resort
251 Co Rd 939 Summerland Key FL
9.8/10 Exceptional! (573 reviews)
"Spotless, beautiful, accomodations. Easy in/easy out parking.The digital cable and semi-useful stove top could be improved. The pool was beautiful but the music blasting that started early a.m. limited our time at the pool. Cannot relax with constant blasting music. Staff was excellent."
Reviewed on May 19, 2026
Sugar Loaf Lodge
17001 Overseas Hwy Summerland Key FL
Fully refundableReserve now, pay when you stay
The price is CA $232 per night from May 21 to May 22
CA $232
CA $261 total
May 21 - May 22
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"Free parking. The hotel is very dated, but we had a great time."
Reviewed on May 19, 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 $76
per adult
88% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
CA $38
per adult
88% of travellers recommend
Key West Haunted Tour : Ghosts & Gravestones
CA $55
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.
