Legacy Trail Vacation Packages 2026 from $531

The Latest Legacy Trail vacation packages

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

Hibiscus Suites - Gateway to Siesta Key

Save 100% on your flight

$531

per person

Oct 1 - Oct 5

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

8.6/10 Excellent! (2,412 reviews)

Very comfortable and clean

Reviewed on Aug 25, 2026

Cedar Cove Resort and Cottages

Save 100% on your flight

$1,490

per person

Oct 5 - Oct 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (579 reviews)

Todo fue maravilloso

Reviewed on Aug 25, 2026

The Avalon Club

Save 100% on your flight

$1,007

per person

Nov 4 - Nov 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (581 reviews)

4 or 5th time staying here . This place is by far the best place in Clearwater to stay . You don’t need to move your car once you check in . Everything right near you and the place is always clean !!

Reviewed on Aug 24, 2026

Wyndham Grand Clearwater Beach

Save 100% on your flight

$952

per person

Oct 6 - Oct 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (3,754 reviews)

Stylish Treasure Island Escape

Sunshine Beach

Save 100% on your flight

$5,613

per person

Nov 1 - Nov 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

No reviews

Don't see what you're looking for?

See all available trips from Columbus to Legacy Trail

View all trips

Legacy Trail Hotel Deals

Rosen Inn Lake Buena Vista

8442 Palm Parkway Orlando FL

Fully refundableReserve now, pay when you stay

Get rates

DoubleTree by Hilton at the Entrance to Universal Orlando

5780 Major Blvd Orlando FL

Fully refundableReserve now, pay when you stay

8.6/10 Excellent! (7,038 reviews)

"Outdated but convenient for what we needed"

Reviewed on Aug 25, 2026

Get rates

Fontainebleau Miami Beach

4441 Collins Avenue Miami Beach FL

Fully refundableReserve now, pay when you stay

8.4/10 Very Good! (8,809 reviews)

"We had an excellent stay at the Fontainebleau Miami Beach! The hotel itself is beautiful, clean, and very well maintained. From the moment we arrived, the staff, beach service, and security throughout the resort were all excellent. Our room was extremely clean and comfortable, and the housekeeping ..."

Reviewed on Aug 25, 2026

Get rates

See all 258,263 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.