Legacy Trail Vacation Packages & Trips 2026 from CA $1,188

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Top Legacy Trail Vacation Deals

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

CW Hotel

CA $1,188

per person

Oct 24 - Oct 31

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

9.6/10 Exceptional! (48 reviews)

Everyone was friendly. Great views from our room. Amazing location, walkable to pier/beach. Parking was $40 I think, reasonable for the area. Resort fee of $40, had access to pool we didn’t use. Didn’t really get any value out of resort fee. $300 security deposit seems a bit high but was removed from credit card in a couple days. Just one elevator for 8 floors so sometimes a wait/full. Would stay there again.

Reviewed on Aug 18, 2026

Ocean Club Treasure Island Hotel

Sunshine Beach

CA $1,242

per person

Nov 1 - Nov 8

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Tampa (TPA)

9.6/10 Exceptional! (1,128 reviews)

The Avalon Club

CA $2,001

per person

Oct 24 - Oct 31

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

9.4/10 Exceptional! (581 reviews)

Very clean building and rooms. Didn’t like the expensive resort and parking fees.

Reviewed on Aug 18, 2026

Cedar Cove Resort and Cottages

CA $2,107

per person

Oct 20 - Oct 27

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Tampa (TPA)

9.2/10 Wonderful! (568 reviews)

The Westin Sarasota

Central Sarasota

CA $1,285

per person

Oct 20 - Oct 25

found 1 day ago

Roundtrip flight included

Hamilton (YHM) to Tampa (TPA)

9/10 Wonderful! (1,151 reviews)

Great location. Very walkable to marina and downtown. Awesome view from rooftop bar. Nice pool and pool deck on rooftop as well. Great staff. 2nd stay here.

Reviewed on Aug 18, 2026

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Legacy Trail Hotel Deals

Rosen Inn Lake Buena Vista

8442 Palm Parkway Orlando FL

Fully refundableReserve now, pay when you stay

CA $86

CA $97 total

Sep 7 - Sep 8

includes taxes & fees

DoubleTree by Hilton at the Entrance to Universal Orlando

5780 Major Blvd Orlando FL

Fully refundable

CA $109

CA $122 total

Sep 1 - Sep 2

includes taxes & fees

8.6/10 Excellent! (6,993 reviews)

"Clean room, helpfull staff"

Reviewed on Aug 19, 2026

Fontainebleau Miami Beach

4441 Collins Avenue Miami Beach FL

Fully refundableReserve now, pay when you stay

CA $289

CA $422 total

Aug 23 - Aug 24

includes taxes & fees

8.4/10 Very good! (8,815 reviews)

"We had the best anniversary day ever by booking in fountain blue. The stuff was so friendly and they take care of us."

Reviewed on Aug 19, 2026

See all 258,181 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.