Legacy Trail Vacation Packages
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Top Legacy Trail vacation package deals
Price found within the past 48 hours. Click for updated prices.
3.5-star property
The Residences at Siesta Key Beach by Hyatt Vacation Club
South Village
9.6/10 Exceptional! (294 reviews)
Apr 20 - Apr 23
3 night stay
Boston (BOS) to Sarasota (SRQ)
Delta • Non-stop • Coach
Sarasota (SRQ) to Boston (BOS)
Spirit Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,533, price is now $923 per person
$923
per person
found 1 day ago
We had a fantastic vacation at the Hyatt. The rooms are immaculate and have everything you need for your vacation. Beach staff was wonderful with daily umbrella service and the continental breakfast was very convenient. We look forward to returning!
Reviewed on May 10, 2025
4.0-star property
Ocean Club Treasure Island Hotel
Sunshine Beach
9.6/10 Exceptional! (712 reviews)
Mar 21 - Mar 28
7 night stay
Boston (BOS) to Tampa (TPA)
JetBlue Airways • Coach
Tampa (TPA) to Boston (BOS)
Southwest Airlines • Coach
Save 100% on your flight
Price was $3,163, price is now $2,030 per person
$2,030
per person
found 1 day ago
Great spot, had a great time
Reviewed on Dec 4, 2025
2.5-star property
Pelican Pointe Clearwater Beach Hotel
9/10 Wonderful! (1,003 reviews)
Apr 8 - Apr 15
7 night stay
Boston (BOS) to Tampa (TPA)
Delta • Non-stop • Coach
Tampa (TPA) to Boston (BOS)
Spirit Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,311, price is now $857 per person
$857
per person
found 1 day ago
Every thing of the above was good
Reviewed on Nov 26, 2025
2.0-star property
ChartHouse Clearwater Beach Marina Hotel
9.6/10 Exceptional! (531 reviews)
Mar 12 - Mar 17
5 night stay
Boston (BOS) to Tampa (TPA)
Southwest Airlines • Non-stop • Coach
Tampa (TPA) to Boston (BOS)
Spirit Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,645, price is now $1,106 per person
$1,106
per person
found 1 day ago
Todo perfecto y el trato increible
Reviewed on Oct 24, 2025
Top rated hotels for your Legacy Trail vacation package
Golden Host Resort - Sarasota
4675 N Tamiami Trl Sarasota FL
Free Cancellation
11.04 mi from city center
$88 nightly
The price is $99 total per night
$99 total
Feb 11 - Feb 12
Total with taxes and fees
Golden Host Resort - Sarasota features an outdoor pool, free WiFi in public areas, and coffee in a common area. Free parking is included with your stay. The 24-hour front desk has multilingual staff ready to help secure valuables, and answer any questions about the area. Additional amenities include a library, express check-out, and free newspapers.
Pool
Parking included
Kompose Boutique Hotel
965 University Pkwy Sarasota FL
Free Cancellation
Reserve now, pay when you stay
11.51 mi from city center
$113 nightly
The price is $128 total per night
$128 total
Feb 8 - Feb 9
Total with taxes and fees
At Kompose Boutique Hotel, guests enjoy an outdoor pool, a 24-hour gym, and free WiFi in public areas. Self parking is offered for USD 5.35 per night. The front desk has multilingual staff standing by 24 hours a day to assist with securing valuables and luggage storage. Additional amenities include a hot tub, a 24-hour business center, and a microwave in a common area.
Pool
Hot Tub
Tropical Beach Resorts
6717 Sara Sea Circle Siesta Key FL
Free Cancellation
Reserve now, pay when you stay
3.88 mi from city center
$222 nightly
The price is $251 total per night
$251 total
Feb 8 - Feb 9
Total with taxes and fees
At Tropical Beach Resorts, guests have access to an outdoor pool, free WiFi in public areas, and coffee in a common area. If you drive, put free parking to good use. A multilingual staff is on hand to assist with luggage storage, concierge services, and securing valuables. Other amenities at this beach aparthotel include a library, free newspapers, and laundry facilities.
Pool
Kitchen
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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