
Legacy Trail Vacation Packages
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4.0-star property
Ocean Club Treasure Island Hotel
9.4/10 Exceptional! (386 reviews)
Jul 24 - Jul 30
6 night stay
Boston (BOS) to Tampa (TPA)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 20 hours 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 Avalon Club
9.6/10 Exceptional! (393 reviews)
Jul 9 - Jul 13
4 night stay
Boston (BOS) to Tampa (TPA)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
This hotel is very clean. It comes with everything that you can possibly need just like home. Staff is friendly, welcoming and very helpful. I will definitely stay here again.
Reviewed on Jun 7, 2024

3.5-star property
The Residences at Siesta Key Beach by Hyatt Vacation Club
9.8/10 Exceptional! (237 reviews)
Jun 20 - Jun 27
7 night stay
Boston (BOS) to Sarasota (SRQ)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
The property was a perfect beach-side location. Loved everything about the outdoor facilities. We had some less than impressive interactions with the front desk, valet, and morning breakfast staff. They all seemed under trained and uninformed. Had to call for valet almost every time we arrived or needed our car. I asked for help of all persons for what I thought were simple requests for their respective positions and was met with confusion and lack of knowledge. This is from billing, to requesting a life jacket, to simply asking for a clean bowl at breakfast. The 3 bedroom we had was an incredible HUGE layout and bedrooms and kitchen were unbelievably wonderful. However, the living room sofa and chair along with outdoor cushions had met their lifetime. All needed to be replaced and were stained, flat, and uncomfortable. I think with a few new pieces of furniture and better staff training this place would be 5/5 because it was overall awesome!
Reviewed on Apr 22, 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
The price is $100 per night
$100
includes taxes & fees
$88 per night
May 13 - May 14
At Kompose Boutique Hotel, guests enjoy an outdoor pool, a 24-hour gym, and free WiFi in public areas. Free parking is available if you drive. 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

Golden Host Resort - Sarasota
4675 N Tamiami Trl, Sarasota, FL
Free Cancellation
11.04 mi from city center
The price is $90 per night
$90
includes taxes & fees
$79 per night
May 14 - May 15
Golden Host Resort - Sarasota features an outdoor pool, free WiFi in public areas, and coffee in a common area. Free parking is included with your stay. The 24-hour front desk has multilingual staff ready to help secure valuables, and answer any questions about the area. Additional amenities include a library, express check-out, and free newspapers.
Pool
Parking included

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 $214 per night
$214
includes taxes & fees
$189 per night
May 18 - May 19
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 securing valuables, concierge services, and luggage storage. Other amenities at this beach aparthotel include a library, free newspapers, and laundry facilities.
Pool
Kitchen
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.