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
Delray House With Hot tub & Game Room
Palm River-Clair Mel
2/10 (2 reviews)
Feb 7 - Feb 14
7 night stay
Boston (BOS) to Sarasota (SRQ)
Southwest Airlines • Non-stop • Coach
Sarasota (SRQ) to Boston (BOS)
JetBlue Airways • Non-stop • Coach
Save 100% on your flight
Price was $1,343, price is now $603 per person
$603
per person
found 9 hours ago
3.0-star property
The Suites at Fishermen’s Village- 2 Bedroom Suites
Punta Gorda Isles
9.8/10 Exceptional! (1,027 reviews)
Feb 3 - Feb 11
8 night stay
Boston (BOS) to Punta Gorda Airport (PGD)
Southwest Airlines • Non-stop • Coach
Punta Gorda Airport (PGD) to Boston (BOS)
JetBlue Airways • Non-stop • Coach
Price was $2,015, price is now $1,063 per person
$1,063
per person
found 1 day ago
My college friends and I loved this hotel! We are now adults and appreciated the absolute cleanliness and friendliness of the staff.
I will be referring this hotel to all my friends for future visits to this area!
Reviewed on Mar 30, 2025
3.5-star property
The Residences at Siesta Key Beach by Hyatt Vacation Club
South Village
9.6/10 Exceptional! (294 reviews)
Mar 2 - Mar 6
4 night stay
Boston (BOS) to Sarasota (SRQ)
United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,487, price is now $1,417 per person
$1,417
per person
found 9 hours 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
Wyvern Hotel, an Ascend Collection Hotel
Downtown Punta Gorda
9/10 Wonderful! (1,003 reviews)
Feb 3 - Feb 11
8 night stay
Boston (BOS) to Punta Gorda Airport (PGD)
Southwest Airlines • Non-stop • Coach
Punta Gorda Airport (PGD) to Boston (BOS)
JetBlue Airways • Non-stop • Coach
Save 100% on your flight
Price was $1,467, price is now $871 per person
$871
per person
found 1 day ago
Clean, spacious, quiet room.
Reviewed on Nov 19, 2025
Top rated hotels for your Legacy Trail vacation package
Kompose Boutique Hotel
965 University Pkwy Sarasota FL
Free Cancellation
Reserve now, pay when you stay
11.51 mi from city center
$79 nightly
The price is $90 total per night
$90 total
Dec 18 - Dec 19
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
3.9 mi from city center
$147 nightly
The price is $166 total per night
$166 total
Dec 18 - Dec 19
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 tours or tickets, securing valuables, and luggage storage. Other amenities at this beach aparthotel include a library, free newspapers, and laundry facilities.
Pool
Kitchen
Compass Hotel by Margaritaville Anna Maria Sound
12324 Manatee Avenue West Bradenton FL
Free Cancellation
Reserve now, pay when you stay
22.58 mi from city center
$178 nightly
The price is $201 total per night
$201 total
Dec 23 - Dec 24
Total with taxes and fees
At Compass Hotel by Margaritaville Anna Maria Sound, guests enjoy features like an outdoor pool, a 24-hour gym, and free WiFi in public areas. There's free parking if you drive. The 24-hour front desk has multilingual staff ready to assist with securing valuables, concierge services, and luggage storage. Additional amenities include conference space, coffee/tea in a common area, and a microwave in a common area.
Pool
Breakfast included
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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