Legacy Trail Vacation Packages & Trips 2026 from CA $992

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Top Legacy Trail Vacation Deals

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

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Downtown Tampa

CA $992

per person

Dec 23 - Dec 30

found 1 day ago

Roundtrip flight included

Ottawa (YOW) to Tampa (TPA)

8.6/10 Excellent! (938 reviews)

Valet staff was awesome!

Reviewed on Oct 3, 2026

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 14 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Tampa (TPA)

9.6/10 Exceptional! (1,236 reviews)

Room, pool and bar were amazing. My only complaint was beach too far to walk for afew of the others. Had to buy beach chairs as there were none at beach unless you paid a third party.

Reviewed on Oct 3, 2026

Cedar Cove Resort and Cottages

Save 100% on your flight

CA $2,028

per person

Dec 5 - Dec 12

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Tampa (TPA)

9.2/10 Wonderful! (603 reviews)

Inn on the Beach - 18+ only

Pass-a-Grille

Save 100% on your flight

CA $1,549

per person

Dec 21 - Dec 28

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

9.8/10 Exceptional! (453 reviews)

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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

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.