Legacy Trail Vacation Packages
Book a Stay + Flight or Car to save on your trip
Top Legacy Trail vacation package deals
Price found within the past 48 hours. Click for updated prices.
3.5-star property
voco Sarasota by IHG
Central Sarasota
9.2/10 Wonderful! (1,017 reviews)
Oct 9 - Oct 12
3 night stay
New York (JFK) to Tampa (TPA)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $445, price is now $264 per person
$264
per person
found 1 day ago
Hotel was great. They are close to restaurants and have a shuttle that will take you places like St Armand’s Circle. They also have beach towels, chairs and umbrellas that you can use at the beach. We would stay at hotel again for sure.
Reviewed on Jun 30, 2024
4.0-star property
Ocean Club Treasure Island Hotel
9.6/10 Exceptional! (618 reviews)
Oct 16 - Oct 20
4 night stay
Detroit (DTW) to Tampa (TPA)
Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,005, price is now $577 per person
$577
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
4.0-star property
The Westin Sarasota
Central Sarasota
9/10 Wonderful! (1,069 reviews)
Oct 12 - Oct 17
5 night stay
Detroit (DTW) to Tampa (TPA)
Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $812, price is now $492 per person
$492
per person
found 1 day ago
$50 per valet without other option is too high
Reviewed on Sep 8, 2025
2.0-star property
Captiva Beach Resort
9/10 Wonderful! (1,127 reviews)
Oct 12 - Oct 17
5 night stay
Detroit (DTW) to Sarasota (SRQ)
Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $824, price is now $502 per person
$502
per person
found 1 day ago
Loved the location and the quietness.
Reviewed on Feb 9, 2023
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
The price is $81 total per night
$81 total
per night
Sep 10 - Sep 11
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
3.9 mi from city center
The price is $180 total per night
$180 total
per night
Sep 10 - Sep 11
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, tours or tickets, and securing valuables. 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
The price is $195 total per night
$195 total
per night
Sep 21 - Sep 22
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.
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.
