Legacy Trail Vacation Packages 2026 from $547

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The Latest Legacy Trail vacation packages

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

The Fold Hotels Indian Shores

$547

per person

Dec 24 - Dec 27

found 1 day ago

Roundtrip flight included

Philadelphia (PHL) to Tampa (TPA)

9.2/10 Wonderful! (1,018 reviews)

Will be back!

Reviewed on Oct 8, 2026

Stylish Treasure Island Escape

Sunshine Beach

Save 100% on your flight

$4,976

per person

Dec 22 - Dec 28

found 1 day ago

Roundtrip flight included

Philadelphia (PHL) to Tampa (TPA)

No reviews

voco Sarasota by IHG

Central Sarasota

Save 100% on your flight

$633

per person

Dec 10 - Dec 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (1,002 reviews)

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$722

per person

Dec 10 - Dec 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,252 reviews)

Great place to stay! I have stayed here multiple times!

Reviewed on Oct 9, 2026

The Hotel Zamora

Save 100% on your flight

$792

per person

Nov 12 - Nov 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.8/10 Excellent! (423 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

$219 nightly

$246 total

Nov 2 - Nov 3

Total with taxes and fees

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

8800 Vistana Centre Dr Orlando FL

Fully refundableReserve now, pay when you stay

$137 nightly

$154 total

Oct 29 - Oct 30

Total with taxes and fees

DoubleTree by Hilton at the Entrance to Universal Orlando

5780 Major Blvd Orlando FL

Fully refundable

$101 nightly

$114 total

Oct 19 - Oct 20

Total with taxes and fees

See all 254,864 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.