Legacy Trail Vacation Packages 2026 from $657

Plan, book, travel with confidence
Better together
Save up to $2,000 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

The Latest Legacy Trail vacation packages

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

ChartHouse Clearwater Beach Marina Hotel

Save 100% on your flight

$657

per person

Sep 15 - Sep 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,341 reviews)

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$851

per person

Sep 19 - Sep 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,128 reviews)

The hotel has been renovated. We had a great stay

Reviewed on Aug 16, 2026

CW Hotel

Save 100% on your flight

$827

per person

Sep 19 - Sep 26

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (48 reviews)

Cedar Cove Resort and Cottages

Save 100% on your flight

$1,432

per person

Oct 5 - Oct 12

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (568 reviews)

Staff was extremely friendly and helpful will definitely be returning

Reviewed on Aug 15, 2026

The Westin Sarasota

Central Sarasota

Save 100% on your flight

$824

per person

Oct 23 - Oct 28

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (1,151 reviews)

Everything about this property was just wonderful. The convenience of where it's located to the breakfast that was served. We'll go again hands down!

Reviewed on Aug 16, 2026

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

$63 nightly

$70 total

Aug 20 - Aug 21

Total with taxes and fees

DoubleTree by Hilton at the Entrance to Universal Orlando

5780 Major Blvd Orlando FL

Fully refundable

$78 nightly

$88 total

Sep 1 - Sep 2

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

$123 nightly

$139 total

Sep 7 - Sep 8

Total with taxes and fees

See all 257,414 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.