Longboat Key Vacation Packages
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Your Longboat Key Vacation
With a reputation for its laid-back lifestyle and spectacular views, Longboat Key is an ideal getaway destination. Lock in one of our Longboat Key vacation packages and experience all that this fascinating city has to offer. IMG Academy, Coquina Beach and Cortez Beach are just a few of the attractions worth checking out during your trip to Longboat Key. Expedia will help you escape your daily routine. Tailor your vacation to Longboat Key to suit your travel style, whatever that may be.
Top Longboat Key Vacation Deals
Price found within the past 48 hours. Click for updated prices.
ChartHouse Clearwater Beach Marina Hotel
Price was CA $1,247, price is now CA $860 per person
CA $860
per person
Sep 21 - Sep 25
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (1,149 reviews)
The hotel has only been around one year and everything was exceptional
Reviewed on Jun 27, 2026
Cedar Cove Resort and Cottages
Price was CA $1,949, price is now CA $1,435 per person
CA $1,435
per person
Sep 6 - Sep 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9.2/10 Wonderful! (532 reviews)
We stayed for three nights in the Violet room and it was delightful. This place isn’t “fancy” in the modern materialistic sense, but the staff were wonderful, its clean and well maintained for being right on the beach, super quiet, convenient to everything, and best of all, the beachfront is unmatched in its beauty and accessibility.
We visited Bean Point and Coquina Beach, and found that the beachfront right out our door at Cedar Cove is as good as it gets! Highly recommend :)
Reviewed on Jun 26, 2026
La Tortuga Historic Downtown Pass A Grille
Pass-a-Grille
Price was CA $2,873, price is now CA $2,140 per person
CA $2,140
per person
Aug 14 - Aug 21
found 2 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Tampa (TPA)
8.8/10 Excellent! (33 reviews)
This place is one of the cleanest hotels I’ve ever been to which is important to me. Great location on the island, I wish there was just better food around there.
Reviewed on May 23, 2026
Longboat Key Hotel Deals
The St. Regis Longboat Key Resort
1601 Gulf Of Mexico Drive Longboat Key FL
Fully refundableReserve now, pay when you stay
The price is CA $1,333 per night from Jul 6 to Jul 7
CA $1,333
CA $1,610 total
Jul 6 - Jul 7
includes taxes & fees
9.8/10 Exceptional! (80 reviews)
"This hotel was one of the best kept, best employees and services of any national or international hotels we have stayed in over the past 10 years. Everything was FIRST CLASS."
Reviewed on Jun 18, 2026
Zota Beach Resort
4711 Gulf of Mexico Dr Longboat Key FL
Fully refundableReserve now, pay when you stay
The price is CA $339 per night from Jun 30 to Jul 1
CA $339
CA $448 total
Jun 30 - Jul 1
includes taxes & fees
9/10 Wonderful! (1,010 reviews)
"Service was great I love the option for valet really quick to get your car."
Reviewed on Jun 26, 2026
The Resort at Longboat Key Club
220 Sands Point Road Longboat Key FL
Fully refundableReserve now, pay when you stay
The price is CA $677 per night from Jul 25 to Jul 26
CA $677
CA $845 total
Jul 25 - Jul 26
includes taxes & fees
9/10 Wonderful! (722 reviews)
"My stay was amazing Every staff member I crossed paths with was very polite and helpful"
Reviewed on Jun 25, 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.
Stay near popular Longboat Key attractions
What to do in Longboat Key
Mangrove Tunnel & Manatee Kayak Eco-Tour
CA $82
per adult
94% of travellers recommend
Sarasota Guided Mangrove Tunnel Kayak Tour
CA $82
per adult
96% of travellers recommend
Bradenton: Anna Maria Island Guided Kayaking Manatee Tour
CA $76
per adult
100% 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.
