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.
Carillon Miami Wellness Resort
North Beach
Price was CA $2,081, price is now CA $1,210 per person
CA $1,210
per person
May 24 - May 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.8/10 Excellent! (787 reviews)
The staff were so so nice! The hotel was so clean and so green and so cool and I loved every minute of it
Reviewed on Feb 5, 2026
Creekside Inn
Price was CA $3,199, price is now CA $1,403 per person
CA $1,403
per person
Jun 1 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
7.8/10 Good! (1,027 reviews)
Good location. Beds were uncomfortable and pillows were very hard. The worse part was, you could hear right thru the walls. I could hear the people in the neighboring room. Had a hard time sleeping due to the noise. I would not stay here again.
Reviewed on Mar 22, 2026
Casablanca Miami Beach
North Beach
Price was CA $7,959, price is now CA $3,611 per person
CA $3,611
per person
May 13 - May 18
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Miami (MIA)
5.8/10 (321 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
1 Hotel South Beach
South Beach
Price was CA $6,278, price is now CA $3,606 per person
CA $3,606
per person
May 28 - Jun 3
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
9.4/10 Exceptional! (1,464 reviews)
This hotel is so beautiful and the staff is so kind and accommodating. The pool and beach areas are stunning, the food is delicious, the rooms are spacious, the beds are so comfortable, and the location is perfect. It’s the best hotel experience I’ve ever had, and I can’t wait to go back again!
Reviewed on Mar 7, 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
Sugarloaf Key Hotel at KOA Resort
251 Co Rd 939 Summerland Key FL
9.8/10 Exceptional! (516 reviews)
Our stay at this property was amazing! Staff is kind and courteous and tend to our needs. Room was clean and had all we need it to make light breakfast and lunch and dinner if need it.
Reviewed on Mar 22, 2026
Parmer's Resort
565 Barry Avenue Summerland Key FL
Fully refundableReserve now, pay when you stay
The price is CA $246 per night from Mar 29 to Mar 30
CA $246
CA $321 total
Mar 29 - Mar 30
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
The perfect amount of extra touches makes this property the best place to stay in the lower keys.
Reviewed on Mar 18, 2026
Looe Key Reef Resort
27340 Overseas Highway Summerland Key FL
Fully refundableReserve now, pay when you stay
The price is CA $291 per night from Apr 9 to Apr 10
CA $291
CA $327 total
Apr 9 - Apr 10
includes taxes & fees
7.6/10 Good! (1,006 reviews)
No ice machine
Reviewed on Mar 22, 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 $79
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.
