
Legacy Trail Vacations from $690
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The Latest Legacy Trail vacation packages
Price found within the past 48 hours. Click for updated prices.


The Residences at Siesta Key Beach by Hyatt Vacation Club
South Village
Save 100% on your flight
Price was $3,567, price is now $2,192 per person
$2,192
per person
Jun 25 - Jul 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.8/10 Exceptional! (347 reviews)
Great location,big and well maintained living space
There was a love bag infested balcony and staff was not caring about our experience
Reviewed on May 21, 2026

The Avalon Club
Save 100% on your flight
Price was $1,267, price is now $833 per person
$833
per person
Aug 14 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (538 reviews)
Was able to cook and wash easily. Cleaning staff available
Reviewed on May 24, 2026

Landing Bradenton Near G.T. Bray Park
Save 100% on your flight
Price was $1,462, price is now $978 per person
$978
per person
Jun 25 - Jul 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (4 reviews)
Place was lovely
Exceeded expectations
Reviewed on Dec 22, 2025

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View all tripsLegacy Trail Hotel Deals

Kompose Boutique Hotel
965 University Pkwy Sarasota FL
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $113 total per night from Jun 23 to Jun 24
$113 total
Jun 23 - Jun 24
Total with taxes and fees
9.2/10 Wonderful! (5,409 reviews)
"Beautiful!"
Reviewed on May 24, 2026

Compass Hotel by Margaritaville Anna Maria Sound
12324 Manatee Avenue West Bradenton FL
Fully refundableReserve now, pay when you stay
$203 nightly
The price is $229 total per night from Jun 1 to Jun 2
$229 total
Jun 1 - Jun 2
Total with taxes and fees
9.4/10 Exceptional! (2,182 reviews)
"The property was very nice and the hotel was perfect. Very close to everything."
Reviewed on May 24, 2026

Golden Host Resort - Sarasota
4675 N Tamiami Trl Sarasota FL
Fully refundable
$73 nightly
The price is $83 total per night from Jun 14 to Jun 15
$83 total
Jun 14 - Jun 15
Total with taxes and fees
8.6/10 Excellent! (2,513 reviews)
"Really decent motel."
Reviewed on May 24, 2026
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.
Find the Best Legacy Trail Vacation Packages
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.



















