Legacy Trail Vacation Packages 2026 from $818

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The Latest Legacy Trail vacation packages

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

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$818

per person

Dec 2 - Dec 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,236 reviews)

Okay hotel but nowhere near the price premium that was paid, not sure how this hotel has such high reviews this was our most expensive reservation and left the most to be desired. Not a bad spot, but definitely not outstanding.

Reviewed on Oct 1, 2026

CW Resort

Save 100% on your flight

$870

per person

Dec 5 - Dec 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (188 reviews)

Dilan was an amazing help on our first night throughly explaining all questions asked. We went on the dolphin jet ski adventure through the resort. It was super fun and we definitely saw some dolphins. Stephanie was our leader and she was very personable and nice as well as dilan. Drinks and food are great as well. Our room was super clean and had amazing views of the ocean.

Reviewed on Oct 1, 2026

Stylish Treasure Island Escape

Sunshine Beach

Save 100% on your flight

$4,987

per person

Dec 22 - Dec 28

found 14 hours ago

Roundtrip flight included

Philadelphia (PHL) to Tampa (TPA)

No reviews

The Avalon Club

Save 100% on your flight

$1,093

per person

Dec 5 - Dec 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (605 reviews)

The place was so clean and put together. I would recommend this place to anyone.

Reviewed on Oct 1, 2026

Cedar Cove Resort and Cottages

$1,828

per person

Dec 26 - Dec 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (603 reviews)

Best place to stay on island!

Reviewed on Oct 1, 2026

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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

Oct 5 - Oct 6

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 25 - Oct 26

Total with taxes and fees

9.2/10 Wonderful! (6,902 reviews)

"Super clean, helpful and friendly staff"

Reviewed on Oct 1, 2026

Fontainebleau Miami Beach

4441 Collins Avenue Miami Beach FL

Fully refundableReserve now, pay when you stay

$378 nightly

$431 total

Oct 3 - Oct 4

Total with taxes and fees

See all 259,677 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.