
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.





Legacy Hotel at IMG Academy
per person
Sep 25 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Sarasota (SRQ)
9/10 Wonderful! (859 reviews)
It is difficult to get the bill at the end of your stay emailed to you, but the stay and property was really nice. The young waitress was absolutely amazing with impeccable customer service. Loved the atmosphere and the beds are really spacious and not like other hotels that claim they gave you a queen and it looks like a double. I just wished room service gave the room a proper cleaning while we were there at least once or twice for the 8 nights we stayed and not just straightening up the room.
Reviewed on Aug. 5, 2025
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 $963 per night from Aug 25 to Aug 26
CA $963
CA $1,173 total
Aug 25 - Aug 26
includes taxes & fees
9.6/10 Exceptional! (35 reviews)
"Amazing"
Reviewed on Jul. 22, 2025

Zota Beach Resort
4711 Gulf of Mexico Dr, Longboat Key, FL
Fully refundableReserve now, pay when you stay
The price is CA $343 per night from Sep 1 to Sep 2
CA $343
CA $450 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Beautiful hotel very good services bed comfort"
Reviewed on Aug. 3, 2025

The Resort at Longboat Key Club
220 Sands Point Road, Longboat Key, FL
Fully refundableReserve now, pay when you stay
The price is CA $552 per night from Sep 1 to Sep 2
CA $552
CA $686 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (661 reviews)
Great exclusive place
"At $500 / night the place had better be 5* and more !! Service was great !!"
Reviewed on Aug. 2, 2025
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 Longboat Key

Siesta Key, FL - Clear Kayak LED Night Glass Bottom Tour
CA $89
per adult

Anna Maria Island and Bradenton: Sunset Kayak Dolphin Tour
CA $82
per adult
90% 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.