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.
Park Central South Beach
South Beach
Price was CA $1,175, price is now CA $565 per person
CA $565
per person
Oct 31 - Nov 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.2/10 Very Good! (946 reviews)
Perfect location, great restaurants and bars nearby, and good service!
Reviewed on Aug. 29, 2025
Pelican Grand Beach Resort - A Noble House Resort
East Fort Lauderdale
Price was CA $2,461, price is now CA $1,220 per person
CA $1,220
per person
Oct 15 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.8/10 Excellent! (1,211 reviews)
Room and property were good . Rocks in lazy river . Not enough tubes . Poor bar service. .
Very expensive for parking .
Could not understand girl at check in I have no idea what she was saying .
Door in room was hard to close , toilet paper dispenser was falling off wall . Mattress was mushy .views were outstanding . Location very good .
Reviewed on Aug. 29, 2025
1 Hotel South Beach
South Beach
Price was CA $4,047, price is now CA $2,201 per person
CA $2,201
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9.4/10 Exceptional! (1,278 reviews)
Without a doubt, best property I’ve ever experienced..
Reviewed on Aug. 30, 2025
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 $147 per night from Sep 8 to Sep 9
CA $147
CA $210 total
Sep 8 - Sep 9
includes taxes & fees
Looe Key Reef Resort
27340 Overseas Highway, Summerland Key, FL
Fully refundableReserve now, pay when you stay
The price is CA $139 per night from Sep 1 to Sep 2
CA $139
CA $157 total
Sep 1 - Sep 2
includes taxes & fees
Sugar Loaf Lodge
17001 Overseas Hwy, Summerland Key, FL
Fully refundableReserve now, pay when you stay
The price is CA $136 per night from Sep 1 to Sep 2
CA $136
CA $153 total
Sep 1 - Sep 2
includes taxes & fees
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
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
CA $38
per adult
78% of travellers recommend
Key West & Parasailing Adventure from Miami
CA $171
per traveller
78% 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.