Legacy Trail Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Legacy Trail Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Saddlebrook Resort
Wesley Chapel South
Price was $847, price is now $389 per person
$389
per person
Mar 5 - Mar 9
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Book a stay at this spa resort in Wesley Chapel. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the clean rooms in our reviews. Popular attractions Saddlebrook Golf Course and KRATE Shopping Center are located nearby.
SkyBeach Resort
Greater Pinellas Point
Save 100% on your flight
Price was $1,456, price is now $867 per person
$867
per person
Jan 31 - Feb 7
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Book a stay at this beach hotel in St. Petersburg. Enjoy 2 outdoor pools, a private beach, and a marina. Popular attractions Salvador Dali Museum and Fort De Soto Park are located nearby.
Sleeps 6 Hot Tub Fenced Yard Cozy Chic
Town 'n' Country
Save 100% on your flight
Price was $1,074, price is now $673 per person
$673
per person
Feb 20 - Feb 24
found 20 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
Book a stay at this spa villa in Tampa. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Raymond James Stadium and George M. Steinbrenner Field are located nearby.
Island Grand at TradeWinds
Save 100% on your flight
Price was $1,522, price is now $956 per person
$956
per person
Jan 31 - Feb 7
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
Book a stay at this beach resort in St. Pete Beach. Enjoy free WiFi, 5 outdoor pools, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions John's Pass Village & Boardwalk and Splash Island Water Park are located nearby.
FUSION Resort Waterfront Suites
Save 100% on your flight
Price was $1,963, price is now $1,244 per person
$1,244
per person
Feb 12 - Feb 18
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Tampa (TPA)
Stay at this aparthotel in Treasure Island. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the pool and the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.
The Avalon Club
Save 100% on your flight
Price was $3,386, price is now $2,147 per person
$2,147
per person
Mar 15 - Mar 20
found 1 day ago
Roundtrip non-stop flight included
Oklahoma City (OKC) to Tampa (TPA)
Book a stay at this beach aparthotel in Clearwater Beach. Enjoy a beach locale, a fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Clearwater Beach and Sand Key Park are located nearby.
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Kompose Boutique Hotel
965 University Pkwy Sarasota FL
18.54 km from city center
Book a stay at this business-friendly hotel in Sarasota. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast ...
Tropical Beach Resorts
6717 Sara Sea Circle Siesta Key FL
6.28 km from city center
Book a stay at this beach aparthotel in Siesta Key. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the pool and the helpful staff in ...
Compass Hotel by Margaritaville Anna Maria Sound
12324 Manatee Avenue West Bradenton FL
36.37 km from city center
Stay at this hotel in Bradenton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
Carlisle Inn
3727 Bahia Vista Sarasota FL
10.49 km from city center
Stay at this hotel in Sarasota. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
Hibiscus Suites - Gateway to Siesta Key
1735 Stickney Point Rd Sarasota FL
6.08 km from city center
Book a stay at this business-friendly aparthotel in Sarasota. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and ...
Golden Host Resort - Sarasota
4675 N Tamiami Trl Sarasota FL
17.78 km from city center
Book a stay at this business-friendly hotel in Sarasota. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the pool and the helpful ...
Hyatt Place Sarasota/Bradenton Airport
950 University Parkway Sarasota FL
18.49 km from city center
Book a stay at this business-friendly hotel in Sarasota. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Lido Beach Resort
700 Benjamin Franklin Dr Sarasota FL
13.41 km from city center
Book a stay at this beach resort in Sarasota. Enjoy free WiFi, 2 outdoor pools, and a private beach. Our guests praise the helpful staff in our reviews. Popular ...
Siesta Key Palms Resort
1800 Stickney Point Rd Sarasota FL
6.02 km from city center
Stay at this hotel in Sarasota. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular ...
DoubleTree by Hilton Sarasota Bradenton Airport
8009 15th Street E Sarasota FL
19.95 km from city center
Book a stay at this business-friendly hotel in Sarasota. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Pelican Post at Anna Maria Island Inn
202 1st St N Bradenton Beach FL
34.28 km from city center
Stay at this apartment in Bradenton Beach. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the pool and the helpful staff in our reviews. ...
Art Ovation Hotel, Autograph Collection
1255 North Palm Avenue Sarasota FL
13.75 km from city center
Book a stay at this business-friendly hotel in Sarasota. Enjoy free WiFi, 2 bars/lounges, and a rooftop terrace. Our guests praise the helpful staff and the ...
SeaSpray Resort
574 Canal Rd Siesta Key FL
9.42 km from city center
Stay at this aparthotel in Siesta Key. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Siesta Key Beach and Lido Beach are located ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Mon, Feb 2 - Mon, Feb 9
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$117 Roundtrip, found 3 days ago
$117
Roundtrip
found 3 days ago
Mon, Feb 2 - Mon, Feb 9
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$127 Roundtrip, found 3 days ago
$127
Roundtrip
found 3 days ago
Mon, Feb 2 - Mon, Feb 9
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$142 Roundtrip, found 3 days ago
$142
Roundtrip
found 3 days ago
Mon, Feb 2 - Mon, Feb 9
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$151 Roundtrip, found 3 days ago
$151
Roundtrip
found 3 days ago
Mon, Mar 2 - Thu, Mar 19
ORD
O'Hare Intl.
SRQ
Sarasota-Bradenton Intl.
$262 Roundtrip, found 2 days ago
$262
Roundtrip
found 2 days ago