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.
Ocean Club Treasure Island Hotel
4.0-star property

Ocean Club Treasure Island Hotel

Sunshine Beach
9.6/10 Exceptional! (635 reviews)

Nov 12 - Nov 15

3 night stay

Boston (BOS) to Tampa (TPA)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $675, price is now $415 per person
$415
per person
found 1 day ago
This was our second time staying at this property. We stayed for eight nights this time. The rooms are lovely but our stay was not nearly as enjoyable as the first time a year ago. There were a lot of children there during our stay. It was practically impossible to use the pool because the kids took over with their inflatables and games. We will likely look elsewhere next time due to the volume of children.

Reviewed on Apr 29, 2025

Mar Bay Motel &Suites
2.0-star property

Mar Bay Motel &Suites

8.6/10 Excellent! (59 reviews)

Nov 9 - Nov 16

7 night stay

Boston (BOS) to Tampa (TPA)

Delta • Coach

Tampa (TPA) to Boston (BOS)

Southwest Airlines • Coach
Save 100% on your flight
Price was $937, price is now $494 per person
$494
per person
found 1 day ago
The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5-star property

The Residences at Siesta Key Beach by Hyatt Vacation Club

South Village
9.6/10 Exceptional! (290 reviews)

Nov 21 - Nov 25

4 night stay

Boston (BOS) to Sarasota (SRQ)

JetBlue Airways • Coach

Sarasota (SRQ) to Boston (BOS)

Delta • Coach
Save 100% on your flight
Price was $2,313, price is now $1,350 per person
$1,350
per person
found 18 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

The Avalon Club
4.0-star property

The Avalon Club

9.4/10 Exceptional! (456 reviews)

Dec 25 - Dec 28

3 night stay

Boston (BOS) to Tampa (TPA)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,733, price is now $1,633 per person
$1,633
per person
found 1 day ago
You can walk to different restaurants. The only bad thing is that the bed in the master bedroom was not in good condition and the metal base was broken. I had to move to another room within the same unit.

Reviewed on Aug 17, 2025

Pelican Post at Anna Maria Island Inn
3.0-star property

Pelican Post at Anna Maria Island Inn

9.2/10 Wonderful! (301 reviews)

Nov 16 - Nov 23

7 night stay

Boston (BOS) to Sarasota (SRQ)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,405, price is now $886 per person
$886
per person
found 1 day ago
Property was great, room was big, king size bed was extremely comfortable with large pillows. We appreciated the large tv! Only downside was no ice machine or restroom to use prior to check in.

Reviewed on Aug 27, 2024

Top rated hotels for your Legacy Trail vacation package

Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
965 University Pkwy, Sarasota, FL
Free Cancellation
Reserve now, pay when you stay
11.51 mi from city center
$57 nightly
The price is $64 total per night
$64 total
Oct 7 - Oct 8
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 luggage storage and securing valuables. Additional amenities include a hot tub, a 24-hour business center, and a microwave in a common area.
Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
6717 Sara Sea Circle, Siesta Key, FL
Free Cancellation
Reserve now, pay when you stay
3.9 mi from city center
$147 nightly
The price is $166 total per night
$166 total
Oct 7 - Oct 8
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, securing valuables, and concierge services. Other amenities at this beach aparthotel include a library, free newspapers, and laundry facilities.
Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

4 out of 5
12324 Manatee Avenue West, Bradenton, FL
Free Cancellation
Reserve now, pay when you stay
22.58 mi from city center
$203 nightly
The price is $229 total per night
$229 total
Oct 7 - Oct 8
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 luggage storage, securing valuables, and concierge services. Additional amenities include conference space, coffee/tea in a common area, and a microwave in a common area.
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