Legacy Trail Vacation Packages
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Save up to CA $1,096 when you book a flight and hotel together*
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Top Legacy Trail Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Ocean Club Treasure Island Hotel
Save 100% on your flight
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9.6/10 Exceptional! (518 reviews)
Do not hesitate to book! Excellent location and hotel. They thought of everything and provide laundry detergent, dryer sheets, dish soap, and toiletries. Beach is excellent and pool, while small, was perfect.
Reviewed on Jul. 15, 2025
The Avalon Club
Save 100% on your flight
per person
Sep 27 - Oct 3
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Tampa (TPA)
9.4/10 Exceptional! (430 reviews)
Beautiful property I would highly recommend this place to anyone looking for clean,friendly,convenience with a beautiful view.
Reviewed on Jul. 10, 2025
Twin Palms at Siesta
Save 100% on your flight
per person
Sep 24 - Sep 30
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Sarasota (SRQ)
9.6/10 Exceptional! (545 reviews)
Property was very nice, room was beautifully decorated and very clean and comfortable. Nice kitchenette. The pool and pool area very nice. The location is great. Close to the beach and some restaurants and bars. Each room was provided a wagon, cooler, chairs and umbrella to use for the beach which was so nice. I would definitely stay there again!
Reviewed on Jun. 29, 2025
Legacy Trail Hotel Deals
Kompose Boutique Hotel
965 University Pkwy, Sarasota, FL
Fully refundableReserve now, pay when you stay
The price is CA $90 per night from Aug 3 to Aug 4
CA $90
CA $118 total
Aug 3 - Aug 4
includes taxes & fees
9/10 Wonderful! (4,136 reviews)
"It was good"
Reviewed on Jul. 14, 2025
Tropical Beach Resorts
6717 Sara Sea Circle, Siesta Key, FL
Fully refundableReserve now, pay when you stay
The price is CA $220 per night from Aug 3 to Aug 4
CA $220
CA $279 total
Aug 3 - Aug 4
includes taxes & fees
9.2/10 Wonderful! (4,766 reviews)
"Great location. Close to private beach and walking distance to awesome restaurants and nightlife. Very friendly staff."
Reviewed on Jul. 13, 2025
Compass Hotel by Margaritaville Anna Maria Sound
12324 Manatee Avenue West, Bradenton, FL
Fully refundableReserve now, pay when you stay
The price is CA $232 per night from Aug 17 to Aug 18
CA $232
CA $295 total
Aug 17 - Aug 18
includes taxes & fees
9.4/10 Exceptional! (1,571 reviews)
"Beautiful resort, amazing view friendly staff"
Reviewed on Jul. 15, 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.
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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.