Legacy Trail Vacations from $399
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The Latest Legacy Trail vacation packages
Price found within the past 48 hours. Click for updated prices.
The Avalon Club
Save 100% on your flight
Price was $2,050, price is now $1,154 per person
$1,154
per person
Jan 20 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
18.8/10 Exceptional! (481 reviews)
Excellent staff. Very clean, spacious, great location
Reviewed on Nov 17, 2025
DoubleTree by Hilton Tampa Rocky Point Waterfront
Rocky Point
Save 100% on your flight
Price was $1,531, price is now $891 per person
$891
per person
Jan 4 - Jan 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
16.4/10 Exceptional! (1,006 reviews)
Room was clean and very quiet, with very comfortable beds and very fast internet connection. Convenient location for our agenda in Tampa.
Reviewed on Nov 17, 2025
Longboat Bay Club
Save 100% on your flight
Price was $1,353, price is now $801 per person
$801
per person
Jan 19 - Jan 23
found 15 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
20/10 Exceptional! (1 review)
Great property with beach access across the street! 2 br unit was huge as were the balconies. Our unit 105 was quite dated but still nice.
Reviewed on May 19, 2025
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Kompose Boutique Hotel
965 University Pkwy Sarasota FL
Fully refundableReserve now, pay when you stay
$74 nightly
The price is $84 total per night from Dec 2 to Dec 3
$84 total
Dec 2 - Dec 3
Total with taxes and fees
9/10 Wonderful! (4,639 reviews)
Staff was excellent. Breakfast was great. Facilities were clean and well maintained.
Reviewed on Nov 17, 2025
Tropical Beach Resorts
6717 Sara Sea Circle Siesta Key FL
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $172 total per night from Nov 20 to Nov 21
$172 total
Nov 20 - Nov 21
Total with taxes and fees
9.2/10 Wonderful! (5,093 reviews)
Spotless room, excellent staff, perfect location.
Reviewed on Nov 15, 2025
Carlisle Inn
3727 Bahia Vista Sarasota FL
Fully refundableReserve now, pay when you stay
$125 nightly
The price is $142 total per night from Nov 23 to Nov 24
$142 total
Nov 23 - Nov 24
Total with taxes and fees
9.8/10 Exceptional! (2,091 reviews)
Everything was great
Reviewed on Nov 15, 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.
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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.