Legacy Trail Vacation Packages & Trips 2026 from CA $870

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Top Legacy Trail Vacation Deals

Price found within the past 48 hours. Click for updated prices.

Saddlebrook Resort

Wesley Chapel South

Save 100% on your flight

CA $870

per person

Dec 5 - Dec 12

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

8/10 Very good! (170 reviews)

The Fold Hotels Indian Shores

Save 100% on your flight

CA $1,446

per person

Dec 23 - Dec 30

found 1 day ago

Roundtrip flight included

Ottawa (YOW) to Tampa (TPA)

9.2/10 Wonderful! (1,018 reviews)

Such a nice place! Walking distance to the beach. The staff are very friendly and responsive. Our room was very clean and modern. Great stay!!

Reviewed on Sep 10, 2026

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

CA $1,551

per person

Nov 10 - Nov 17

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Tampa (TPA)

9.6/10 Exceptional! (1,252 reviews)

The room was great! Very spacious and great view of the ocean. We will be back!

Reviewed on Oct 4, 2026

Cedar Cove Resort and Cottages

Save 100% on your flight

CA $2,638

per person

Nov 10 - Nov 17

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Tampa (TPA)

9.2/10 Wonderful! (603 reviews)

Seaside at Anna Maria Island Inn

Save 100% on your flight

CA $4,657

per person

Dec 21 - Dec 28

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

9.4/10 Exceptional! (132 reviews)

I would like to see microwave in rooms.

Reviewed on Oct 4, 2026

Ready to book your vacation to Legacy Trail?

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Legacy Trail Hotel Deals

Hyatt Regency Orlando International Airport

9300 Jeff Fuqua Boulevard Orlando FL

Fully refundableReserve now, pay when you stay

CA $314

CA $353 total

Nov 2 - Nov 3

includes taxes & fees

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

8800 Vistana Centre Dr Orlando FL

Fully refundableReserve now, pay when you stay

CA $195

CA $219 total

Oct 25 - Oct 26

includes taxes & fees

9.2/10 Wonderful! (6,939 reviews)

"."

Reviewed on Oct 4, 2026

Fontainebleau Miami Beach

4441 Collins Avenue Miami Beach FL

Fully refundableReserve now, pay when you stay

CA $352

CA $497 total

Oct 5 - Oct 6

includes taxes & fees

See all 259,677 properties in Florida

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.