
Legacy Trail Vacations from $375
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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 $2,898, price is now $1,607 per person
$1,607
per person
Feb 5 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
9.6/10 Exceptional! (294 reviews)
The unit was gorgeous and so was the property. Everything exceeded our expectations.
Reviewed on Dec 26, 2025
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Kompose Boutique Hotel
965 University Pkwy Sarasota FL
Fully refundableReserve now, pay when you stay
$138 nightly
The price is $156 total per night from Jan 5 to Jan 6
$156 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
9/10 Wonderful! (4,809 reviews)
Great staff. Clean rooms and hotel. Good Breakfast. Good amenities. The weird part was the bathrooms but it was managable
Reviewed on Dec 27, 2025

Tropical Beach Resorts
6717 Sara Sea Circle Siesta Key FL
Fully refundableReserve now, pay when you stay
$164 nightly
The price is $185 total per night from Jan 4 to Jan 5
$185 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9.2/10 Wonderful! (5,166 reviews)
Have been staying here for years. Never had a bad experience. Staff is wonderful.
Reviewed on Dec 24, 2025

Compass Hotel by Margaritaville Anna Maria Sound
12324 Manatee Avenue West Bradenton FL
Fully refundableReserve now, pay when you stay
$228 nightly
The price is $258 total per night from Jan 5 to Jan 6
$258 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
9.4/10 Exceptional! (1,892 reviews)
The stay was excellent! We’re looking forward to our next stay.
Reviewed on Dec 27, 2025
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.



















