Legacy Trail Vacation Packages 2026 from $890

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The Latest Legacy Trail vacation packages

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

The Avalon Club

Save 100% on your flight

$890

per person

Dec 12 - Dec 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (608 reviews)

Great place to stay with the family. Rooms were clean and spacious. Parking was easy. Walkable to many stores and restaurants. Very close to the beach, and the hotel has everything needed for your beach day: towels, chairs, umbrellas, floaties, and sand toys.

Reviewed on Oct 7, 2026

Stylish Treasure Island Escape

Sunshine Beach

Save 100% on your flight

$4,956

per person

Dec 22 - Dec 28

found 1 day ago

Roundtrip flight included

Philadelphia (PHL) to Tampa (TPA)

No reviews

Cedar Cove Resort and Cottages

Save 100% on your flight

$1,172

per person

Dec 22 - Dec 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (604 reviews)

So clean and anything at all that we needed the staff was more than willing to do great experience

Reviewed on Oct 4, 2026

BeachTrail Lodging

Save 100% on your flight

$1,221

per person

Dec 25 - Dec 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.8/10 Exceptional! (101 reviews)

The cottage was well stocked with a snack basket and a super dog basket. The kitchen was stocked with all needed essentials and the parking also worked out well.

Reviewed on Apr 14, 2026

The Hotel Zamora

Save 100% on your flight

$981

per person

Dec 12 - Dec 19

found 16 hours ago

Roundtrip non-stop 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

Nov 1 - Nov 2

Total with taxes and fees

DoubleTree by Hilton at the Entrance to Universal Orlando

5780 Major Blvd Orlando FL

Fully refundable

$93 nightly

$104 total

Oct 27 - Oct 28

Total with taxes and fees

8.6/10 Excellent! (7,079 reviews)

"Room was very clean. Front desk staff were great! Will definitely return!"

Reviewed on Oct 10, 2026

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.