Legacy Trail Vacation Packages
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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
Sunshine Beach
CA $2,850
per person
Dec 29 - Jan 4
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (1,252 reviews)
This is one of the most fantastic hotels I have ever visited. Firstly the staff deserve a hundred stars for their amazing service. The lady manager was amazing so friendly support and professional. The apartment was fabulous so spotless modern with first class amenities. The view from the balcony was stunning. The bed was extremely comfortable. The cleaning service that I received half way through my 2 week vacation was amazing. This is my only choice for Treasure Island stay. Thank you to the team
Reviewed on Oct 14, 2026
Cedar Cove Resort and Cottages
CA $4,675
per person
Dec 29 - Jan 4
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.2/10 Wonderful! (604 reviews)
Property was great. Loved the location. On the quieter side but close to everything
Reviewed on Oct 13, 2026
Ready to book your vacation to Legacy Trail?
Legacy Trail Hotel Deals
Hyatt Regency Orlando International Airport
9300 Jeff Fuqua Boulevard Orlando FL
Fully refundableReserve now, pay when you stay
CA $311
CA $350 total
Nov 2 - Nov 3
includes taxes & fees
9.4/10 Exceptional! (4,542 reviews)
"The hotel was clean, ready. Staff was helpful and accommodating."
Reviewed on Oct 14, 2026
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
8800 Vistana Centre Dr Orlando FL
CA $195
CA $219 total
Nov 5 - Nov 6
includes taxes & fees
Marriott's Grande Vista
5925 Avenida Vista Orlando FL
Fully refundableReserve now, pay when you stay
CA $137
CA $154 total
Nov 11 - Nov 12
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.
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- Visit Siesta Key Village
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- St. Armands Circle
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- Ca’ d’Zan
- Caspersen Beach
- Nokomis Beach
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- Siesta Key Beach
- Van Wezel Performing Arts Hall
- Sunshine Skyway Bridge
- Visit Gulf Gate Estates
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- Sarasota Opera House
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- All inclusive Vacation Packages Siesta Key
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
