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.
La Quinta Inn & Suites by Wyndham Tampa Brandon West
Price was $435, price is now $326 per person
$326
per person
Feb 23 - Feb 27
found 24 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
Book a stay at this business-friendly hotel in Tampa. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Seminole Hard Rock Casino Tampa and Florida State Fairgrounds are located nearby.
Saddlebrook Resort
Wesley Chapel South
Save 100% on your flight
Price was $778, price is now $360 per person
$360
per person
Feb 23 - Feb 27
found 24 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.
Hotel Tampa Riverwalk
Downtown Tampa
Save 100% on your flight
Price was $1,148, price is now $818 per person
$818
per person
Feb 23 - Feb 27
found 24 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
Book a stay at this business-friendly hotel in Tampa. Enjoy 2 bars/lounges, breakfast (surcharge), and a fitness center. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Tampa Riverwalk and Port of Tampa are located nearby.
The Westshore Grand, A Tribute Portfolio Hotel, Tampa
Beach Park
Save 100% on your flight
Price was $940, price is now $678 per person
$678
per person
Feb 23 - Feb 27
found 24 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
Book a stay at this business-friendly hotel in Tampa. Enjoy free parking, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Raymond James Stadium and Tampa Riverwalk are located nearby.
Landing Apartments near Sun City Center and Riverview
Save 100% on your flight
Price was $980, price is now $726 per person
$726
per person
Feb 23 - Feb 27
found 24 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
Stay at this aparthotel in Wimauma. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Lake Wimauma and Sandpiper Golf Club are located nearby.
Mint House Tampa Downtown
Downtown Tampa
Save 100% on your flight
Price was $900, price is now $704 per person
$704
per person
Feb 23 - Feb 27
found 24 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
Stay at this hotel in Tampa. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Port of Tampa and Tampa Riverwalk 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 ...
Captiva Beach Resort
6772 Sara Sea Circle Siesta Key FL
6.22 km from city center
Book a stay at this beach condo in Siesta Key. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the clean rooms in ...
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 ...
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 ...
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 ...
The St. Regis Longboat Key Resort
1601 Gulf Of Mexico Drive Longboat Key FL
19.33 km from city center
Book a stay at this luxury hotel in Longboat Key. Enjoy a full-service spa, 3 restaurants, and a private beach. Popular attractions Lido Beach and St. Armands ...
Spark by Hilton Sarasota Siesta Key Gateway
6600 S Tamiami Trl Sarasota FL
5.75 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 pool and the helpful staff ...
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 ...
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 - Fri, Feb 6
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$117 Roundtrip, found 2 days ago
$117
Roundtrip
found 2 days ago
Mon, Feb 2 - Mon, Feb 9
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$151 Roundtrip, found 2 days ago
$151
Roundtrip
found 2 days ago
Mon, Feb 2 - Mon, Feb 9
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$159 Roundtrip, found 2 days ago
$159
Roundtrip
found 2 days ago
Mon, Feb 2 - Mon, Feb 9
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$178 Roundtrip, found 2 days ago
$178
Roundtrip
found 2 days ago
Thu, Mar 5 - Mon, Mar 9
LGA
LaGuardia
SRQ
Sarasota-Bradenton Intl.
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago