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
Ocean Club Treasure Island Hotel
Sunshine Beach
9.6/10 Exceptional! (1,282 reviews)
Jan 13 - Jan 19
6 night stay
Boston (BOS) to Tampa (TPA)
JetBlue Airways • Roundtrip • Coach
Price was $1,395, price is now $846 per person
$846
per person
found 1 day ago
We only book for 1 night which was a bad mistake but you live and learn, next time longer. This is a great hotel and the staff were great and it had everything close. Love the bed it was very comfortable, every room was clean and spacious with the convenience of a washer and dryer. It was right at the beach with easy access as well as the pool. Lots of parking outside and in the garage, nice.
Reviewed on Oct 26, 2026
4.0-star property
CW Resort
9.4/10 Exceptional! (255 reviews)
Jan 13 - Jan 19
6 night stay
Boston (BOS) to Tampa (TPA)
JetBlue Airways • Roundtrip • Coach
Price was $1,861, price is now $1,174 per person
$1,174
per person
found 1 day ago
Great location for walking to Pier 60 and the beach. Very clean room and property. Enjoyed our spacious 2-bedroom suite. Beautiful pool and deck area overlooking the water. We didn't use the restaurant or bar, but it was a nice area, food looked great. Staff was friendly, especially the valet staff for the parking garage/accessing the car. Would definitely stay again : )
Reviewed on Oct 26, 2026
4.0-star property
The Avalon Club
9.4/10 Exceptional! (608 reviews)
Jan 13 - Jan 19
6 night stay
Boston (BOS) to Tampa (TPA)
JetBlue Airways • Roundtrip • Coach
Price was $1,676, price is now $1,066 per person
$1,066
per person
found 1 day ago
Much more spacious than we expected. Very clean, entire staff were very friendly and knowledgeable. A nice scent was all over the hotel, a nice touch. Definitely would recommend this hotel.
Reviewed on Oct 23, 2026
4.0-star property
La Tortuga Historic Downtown Pass A Grille
Pass-a-Grille
8.8/10 Excellent! (36 reviews)
Jan 13 - Jan 19
6 night stay
Boston (BOS) to Tampa (TPA)
JetBlue Airways • Roundtrip • Coach
Price was $1,607, price is now $1,043 per person
$1,043
per person
found 1 day ago
Such a beautiful place!!! My only recommendation is they need to lock the gates at the pool! We left at 3:30 am and there were 3 people swimming in the pool… they took off running away when they saw us, so definitely not guests!!!
The property is so beautiful and well cared for that I’d hate to see someone destroy something!
Reviewed on Oct 18, 2026
Top rated hotels for your Legacy Trail vacation package
Hyatt Regency Orlando International Airport
9300 Jeff Fuqua Boulevard Orlando FL
Free Cancellation
Reserve now, pay when you stay
47.57 mi from city center
$220 nightly
The price is $248 total per night
$248 total
Nov 25 - Nov 26
Total with taxes and fees
At Hyatt Regency Orlando International Airport, guests enjoy features like an outdoor pool, a 24-hour gym, and free WiFi in public areas. Parking is available for USD 19 per night (USD 25 per night for valet parking), and there's also limo/town car service. Multilingual staff at the 24-hour front desk can assist with dry cleaning/laundry, luggage storage, and concierge services. Additional amenities include conference space, a 24-hour business center, and a computer station.
Pool
Free WiFi
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
8800 Vistana Centre Dr Orlando FL
Free Cancellation
Reserve now, pay when you stay
40.7 mi from city center
$111 nightly
The price is $125 total per night
$125 total
Nov 16 - Nov 17
Total with taxes and fees
Guests of Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando enjoy 6 outdoor pools, a children's pool, and a gym. Self parking is offered for USD 42.60 per night. The 24-hour front desk has multilingual staff ready to assist with luggage storage, concierge services, and securing valuables. Other amenities at this family-friendly aparthotel include 8 hot tubs, a sauna, and outdoor tennis courts.
Pool
Hot Tub
Marriott's Grande Vista
5925 Avenida Vista Orlando FL
Free Cancellation
Reserve now, pay when you stay
42.98 mi from city center
$96 nightly
The price is $108 total per night
$108 total
Nov 19 - Nov 20
Total with taxes and fees
Marriott's Grande Vista features a golf course, a full-service spa, and 4 outdoor pools. Self parking is offered for USD 31.95 per night. Front-desk staff can answer questions 24/7, and assist with tours or tickets, dry cleaning/laundry, and luggage storage. Other amenities at this spa aparthotel include a children's pool, a 24-hour gym, and 4 hot tubs.
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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