
Legacy Trail Vacations from $312
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The Latest Legacy Trail vacation packages
Price found within the past 48 hours. Click for updated prices.




Wyndham Grand Clearwater Beach
Save 100% on your flight
per person
Oct 21 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (2,436 reviews)
Food was very good. Location perfect. Did not like: 1) pool size too small for large number of guests, 2) parking expensive, 3) pool guard not very professional as he woke up my wife and ordered her to show him the hotel bracelet.
Reviewed on Aug 5, 2025

The Avalon Club
Save 100% on your flight
per person
Oct 21 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (435 reviews)
The property was really nice! I stood in a 2 bedroom and the ocean view was spectacular. There was always someone available if I needed anything and it was a jump, skip and hop away from the beach. Everything is within walking distance of the property. Gas station was right around the corner and a cute park across the street if you have little kiddies. I would stay in this property again and very soon :)
Reviewed on Jul 31, 2025
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Kompose Boutique Hotel
965 University Pkwy, Sarasota, FL
Fully refundableReserve now, pay when you stay
$82 nightly
The price is $92 total per night from Aug 10 to Aug 11
$92 total
Aug 10 - Aug 11
Total includes taxes and fees
9/10 Wonderful! (4,217 reviews)
"Clean, cute, would have preferred private bathroom/shower"
Reviewed on Aug 4, 2025

Tropical Beach Resorts
6717 Sara Sea Circle, Siesta Key, FL
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $180 total per night from Sep 1 to Sep 2
$180 total
Sep 1 - Sep 2
Total includes taxes and fees
9.2/10 Wonderful! (4,825 reviews)
"The hotel is an good location close to restaurants and bars.the beach is an waliking distance. What we don't like.. we found a roach on our room.."
Reviewed on Aug 3, 2025

Compass Hotel by Margaritaville Anna Maria Sound
12324 Manatee Avenue West, Bradenton, FL
Fully refundableReserve now, pay when you stay
$182 nightly
The price is $206 total per night from Aug 12 to Aug 13
$206 total
Aug 12 - Aug 13
Total includes taxes and fees
9.4/10 Exceptional! (1,624 reviews)
"Was looking for the beach area although was very small and washed away sand. We just went to Annamarie’s island for the beach. Their pool and breakfast buffet are very good!!"
Reviewed on Aug 4, 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.