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.
Ocean Club Treasure Island Hotel
Sunshine Beach
Price was CA $2,240, price is now CA $1,208 per person
CA $1,208
per person
Jan 21 - Jan 28
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (1,282 reviews)
Nice property, clean pool. Units were not sound roof at all, you could hear every little noise from each room and other units, but it did not ruin our time there.
Reviewed on Nov 10, 2026
Westwinds Waterfront Resort
Save 100% on your flight
Price was CA $2,019, price is now CA $1,249 per person
CA $1,249
per person
Feb 1 - Feb 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9/10 Wonderful! (742 reviews)
It was a great location for the beach, dinner, and awesome spot to just hang out on the property! Beautiful beautiful place!!
Reviewed on Nov 9, 2026
La Tortuga Historic Downtown Pass A Grille
Pass-a-Grille
Price was CA $3,558, price is now CA $2,268 per person
CA $2,268
per person
Jan 23 - Jan 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
8.8/10 Excellent! (37 reviews)
Great location on 8th Ave. We loved being so close to the historic section.
Reviewed on Nov 8, 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 $1,114 per night from Nov 18 to Nov 19
CA $1,114
CA $1,363 total
Nov 18 - Nov 19
includes taxes & fees
Zota Beach Resort
4711 Gulf of Mexico Dr Longboat Key FL
Fully refundableReserve now, pay when you stay
The price is CA $295 per night from Nov 18 to Nov 19
CA $295
CA $397 total
Nov 18 - Nov 19
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
"Todo súper bueno y tranq un lugar q trasmite paz"
Reviewed on Nov 10, 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 $651 per night from Nov 12 to Nov 13
CA $651
CA $816 total
Nov 12 - Nov 13
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.
Stay near popular Longboat Key attractions
What to do in Longboat Key
Mangrove Tunnel & Manatee Kayak Eco-Tour
CA $83
per adult
96% of travellers recommend
Anna Maria Island & Bradenton Beach Parasailing Tour
CA $154
per adult
100% of travellers recommend
Frequently asked questions
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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.
