Legacy Trail Vacation Packages for 2025
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.
Hibiscus Suites - Gateway to Siesta Key
Save 100% on your flight
Price was $672, price is now $455 per person
$455
per person
Dec 5 - Dec 10
found 2 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this business-friendly aparthotel in Sarasota. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
DoubleTree by Hilton Tampa Rocky Point Waterfront
Rocky Point
Save 100% on your flight
Price was $958, price is now $589 per person
$589
per person
Dec 5 - Dec 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
Stay at this 4-star business-friendly hotel in Tampa. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Raymond James Stadium and George M. Steinbrenner Field are located nearby.
Ramada by Wyndham Tampa Westshore Airport South
Westshore
Save 100% on your flight
Price was $735, price is now $457 per person
$457
per person
Dec 5 - Dec 11
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 Raymond James Stadium and Tampa Riverwalk are located nearby.
The Westin Sarasota
Central Sarasota
Save 100% on your flight
Price was $1,179, price is now $761 per person
$761
per person
Dec 5 - Dec 11
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Stay at this 4-star spa hotel in Sarasota. Enjoy a full-service spa, 2 restaurants, and a rooftop terrace. Our guests praise the breakfast and the pool in our reviews. Popular attractions Lido Beach and Siesta Key Beach are located nearby.
Landing Apartments near North Fort Myers
Hancock
Save 100% on your flight
Price was $941, price is now $613 per person
$613
per person
Dec 2 - Dec 10
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Punta Gorda Airport (PGD)
Stay at this 4-star aparthotel in North Fort Myers. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Pine Island Shopping Center and Fort Myers Shopping Center are located nearby.
Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG
Save 100% on your flight
Price was $691, price is now $484 per person
$484
per person
Dec 5 - Dec 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
Book a stay at this business-friendly hotel in Oldsmar. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Oldsmar Flea Market and Tampa Bay Downs are located nearby.
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Kompose Boutique Hotel
965 University Pkwy, Sarasota, FL
18.54 km from city center
Stay at this 3-star 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
Stay at this 3.5-star beach aparthotel in Siesta Key. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the pool and the helpful staff ...
Spark by Hilton Sarasota Siesta Key Gateway
6600 S Tamiami Trl, Sarasota, FL
5.75 km from city center
Stay at this 3-star business-friendly hotel in Sarasota. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
Tropical Breeze Resort
140 Columbus Blvd., Siesta Key, FL
10.42 km from city center
Stay at this 3-star beach hotel in Siesta Key. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in ...
The Westin Sarasota
100 Marina View Drive, Sarasota, FL
13.87 km from city center
Stay at this 4-star spa hotel in Sarasota. Enjoy a full-service spa, 2 restaurants, and a rooftop terrace. Our guests praise the breakfast and the pool in our ...
Carlisle Inn
3727 Bahia Vista, Sarasota, FL
10.49 km from city center
Stay at this 3.5-star hotel in Sarasota. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular ...
Compass Hotel by Margaritaville Anna Maria Sound
12324 Manatee Avenue West, Bradenton, FL
36.37 km from city center
Stay at this 4-star hotel in Bradenton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular ...
DoubleTree by Hilton Sarasota Bradenton Airport
8009 15th Street E, Sarasota, FL
19.95 km from city center
Stay at this 4-star business-friendly hotel in Sarasota. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Hyatt Place Sarasota/Bradenton Airport
950 University Parkway, Sarasota, FL
18.49 km from city center
Stay at this 3-star business-friendly hotel in Sarasota. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Anna Maria Beach Resort
6306 Gulf Dr, Holmes Beach, FL
39.63 km from city center
Stay at this 3.5-star beach hotel in Holmes Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our ...
The St. Regis Longboat Key Resort
1601 Gulf Of Mexico Drive, Longboat Key, FL
19.33 km from city center
Stay at this 5-star luxury hotel in Longboat Key. Enjoy a full-service spa, 3 restaurants, and a private beach. Popular attractions Lido Beach and St. Armands ...
Comfort Suites Sarasota - Siesta Key
5690 Honore Ave, Sarasota, FL
4.6 km from city center
Stay at this 3-star business-friendly hotel in Sarasota. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Siesta Key Palms Resort
1800 Stickney Point Rd, Sarasota, FL
6.02 km from city center
Stay at this 3.5-star hotel in Sarasota. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
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.
Sat, Nov 15 - Tue, Nov 18
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$137 Roundtrip, found 23 hours ago
$137
Roundtrip
found 23 hours ago
Wed, Nov 12 - Thu, Nov 13
JFK
John F. Kennedy Intl.
SRQ
Sarasota-Bradenton Intl.
$159 Roundtrip, found 2 days ago
$159
Roundtrip
found 2 days ago
Wed, Nov 12 - Thu, Nov 13
EWR
Newark Liberty Intl. Airport
SRQ
Sarasota-Bradenton Intl.
$167 Roundtrip, found 2 days ago
$167
Roundtrip
found 2 days ago
Wed, Jan 7 - Sun, Jan 11
JFK
John F. Kennedy Intl.
SRQ
Sarasota-Bradenton Intl.
$177 Roundtrip, found 2 days ago
$177
Roundtrip
found 2 days ago