
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.

4.0-star property
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
9.2/10 Wonderful! (1,562 reviews)
Dec 19 - Dec 24
5 night stay
Boston (BOS) to Punta Gorda Airport (PGD)
Southwest Airlines • Non-stop • Coach
Punta Gorda Airport (PGD) to Boston (BOS)
Breeze Airways • Non-stop • Coach
Save 100% on your flight
Price was $858, price is now $493 per person
$493
per person
found 1 day ago
I have a very high stress life. My stay there was great. The staff were excellent, the pool was fantastic and their music at the pool was amazing. The food was excellent. I found the resort to be very calming and quiet. I cannot think of one bad thing to say. I took my 22 yr old daughter with me and we just chilled at the pool, ate ourselves to death. And did a lot of walking around there.
Reviewed on Oct 9, 2025

4.0-star property
DoubleTree by Hilton Tampa Rocky Point Waterfront
Rocky Point
8.2/10 Very Good! (1,019 reviews)
Dec 9 - Dec 16
7 night stay
Boston (BOS) to Sarasota (SRQ)
Spirit Airlines • Roundtrip • Coach
Price was $1,290, price is now $630 per person
$630
per person
found 1 day ago
The air in my room is not working properly. It is staying cool enough but only with the fan staying on continuously.
The restaurant only had a few items on the menu because something was still broken and will be for about another month according to a restaurant staff member.
My bathroom faucet is loose and wobbly.
First and last time here
Guy working the front desk this evening had horrible body odor.
Don’t like to complain, but not a good look for a Hilton hotel
Reviewed on Jan 3, 2025

4.0-star property
The Avalon Club
9.4/10 Exceptional! (466 reviews)
Jan 17 - Jan 24
7 night stay
Boston (BOS) to Tampa (TPA)
JetBlue Airways • Non-stop roundtrip • Coach
Price was $2,667, price is now $1,357 per person
$1,357
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


3.5-star property
Hilton St. Petersburg Carillon Park
9.2/10 Wonderful! (1,013 reviews)
Jan 9 - Jan 13
4 night stay
Boston (BOS) to Tampa (TPA)
Frontier Airlines • Coach
Tampa (TPA) to Boston (BOS)
JetBlue Airways • Coach
Price was $847, price is now $506 per person
$506
per person
found 1 day ago
Pool was very relaxing
Reviewed on Sep 1, 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
$71 nightly
The price is $81 total per night
$81 total
Oct 30 - Oct 31
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.
Pool
Hot Tub

Tropical Beach Resorts
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 29 - Oct 30
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.
Pool
Kitchen

Spark by Hilton Sarasota Siesta Key Gateway
6600 S Tamiami Trl, Sarasota, FL
Free Cancellation
Reserve now, pay when you stay
3.57 mi from city center
$106 nightly
The price is $120 total per night
$120 total
Nov 3 - Nov 4
Total with taxes and fees
Guests staying at Spark by Hilton Sarasota Siesta Key Gateway enjoy an outdoor pool, free WiFi in public areas, and a hot tub. You can take advantage of free parking, along with a free beach shuttle. The 24-hour front desk has multilingual staff ready to assist with securing valuables and luggage storage. Additional amenities include coffee/tea in a common area, express check-out, and free newspapers.
Pool
Hot Tub
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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