
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.


The Avalon Club
Save 100% on your flight
per person
Jun. 12 - Jun. 16
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (393 reviews)
I will definitely try to stay here while in the area. Perfect location and the property is amazing
Reviewed on Mar. 21, 2025

Plaza Beach Hotel Beachfront Resort
Save 100% on your flight
per person
May 8 - May 15
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
8.8/10 Excellent! (1,000 reviews)
This was a last minute find for and day stay for our family vacation, everyone was so friendly!
Reviewed on Jan. 19, 2025

Wyndham Grand Clearwater Beach
Save 100% on your flight
per person
Jun. 2 - Jun. 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (2,050 reviews)
Elevator wait time and small area around the pool were the only negatives.. very clean and nice staff. I liked the water fill up by the ice machines. Great location and access to beach!
Reviewed on Mar. 28, 2025

Legacy Vacation Resorts - Indian Shores
Save 100% on your flight
per person
Jun. 20 - Jun. 27
found 2 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Tampa (TPA)
9.2/10 Wonderful! (880 reviews)
Property very clean, employees are very professional, plenty of space in my room. You can hang by pool or just chill out on back deck. Firepit at nite was nice also. One thing they need to add is a shower bar(something to hold on while showering)…other then that i would book at legacy again.
Reviewed on Mar. 9, 2025
Longboat Key Hotel Deals

The St. Regis Longboat Key Resort
1601 Gulf Of Mexico Drive, Longboat Key, FL
The price is CA $1,559 per night from Apr. 22 to Apr. 23
CA $1,559
CA $1,850 total
includes taxes & fees
Apr 22 - Apr 23
9.8/10 Exceptional! (16 reviews)
"Need a better system for assigning chairs around adult pool...also beach lounger experience needs to be upgraded to be more luxurious probably sun beds with shade...also first day adult pool too warm waterfall was offsecond day waterfall on but was ice cold soadult pool was a bit cool must do better ..."
Reviewed on Mar. 23, 2025

Zota Beach Resort
4711 Gulf of Mexico Dr, Longboat Key, FL
Fully refundableReserve now, pay when you stay
The price is CA $471 per night from Apr. 27 to Apr. 28
CA $471
CA $597 total
includes taxes & fees
Apr 27 - Apr 28
8.8/10 Excellent! (1,003 reviews)
"We stayed an extra day in Sarasota, and decided to stay here. So glad we did. The beach and pool were amazing. The staff is great, and the room was perfect as well. My only regret was not staying here from the very beginning"
Reviewed on Mar. 27, 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 $771 per night from Apr. 28 to Apr. 29
CA $771
CA $936 total
includes taxes & fees
Apr 28 - Apr 29
8.8/10 Excellent! (639 reviews)
"Absolutely beautiful clean rooms and great service staff. Dean is the man to talk to. He went above and beyond to make sure we were taken care of."
Reviewed on Mar. 27, 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.
Frequently asked questions
What to do in Longboat Key

Fly Above Water, eFoil Adventure in Sarasota
CA $359
per adult

Sunset Boat Tour Around Anna Maria Island
CA $573
per traveller
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