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.
Ramada by Wyndham Tampa Westshore Airport South
Westshore
Save 100% on your flight
Price was $735, price is now $460 per person
$460
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.
Family Home Tampa
Forest Hills
Save 100% on your flight
Price was $1,625, price is now $973 per person
$973
per person
Dec 3 - Dec 10
found 7 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
Stay at this guesthouse in Tampa. Enjoy free WiFi, free parking, and a garden. Popular attractions Busch Gardens Tampa Bay and Raymond James Stadium are located nearby.
DoubleTree by Hilton Tampa Rocky Point Waterfront
Rocky Point
Save 100% on your flight
Price was $966, price is now $593 per person
$593
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.
Cedar Cove Resort and Cottages
Save 100% on your flight
Price was $2,147, price is now $1,340 per person
$1,340
per person
Dec 3 - Dec 10
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Sarasota (SRQ)
Stay at this 3-star beach resort in Holmes Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Coquina Beach and Bean Point Beach 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 1 day 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 1 day 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.
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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 ...
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 ...
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 ...
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 ...
Extended Stay America Premier Suites - Bradenton
4550 53rd Ave E, Bradenton, FL
24.01 km from city center
Stay at this hotel in Bradenton. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mall at University Town Center and Rosedale Golf and ...
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 ...
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 1 day ago
$137
Roundtrip
found 1 day ago
Wed, Nov 12 - Thu, Nov 13
JFK
John F. Kennedy Intl.
SRQ
Sarasota-Bradenton Intl.
$159 Roundtrip, found 3 days ago
$159
Roundtrip
found 3 days ago
Wed, Nov 12 - Thu, Nov 13
EWR
Newark Liberty Intl. Airport
SRQ
Sarasota-Bradenton Intl.
$167 Roundtrip, found 3 days ago
$167
Roundtrip
found 3 days ago
Wed, Jan 7 - Sun, Jan 11
JFK
John F. Kennedy Intl.
SRQ
Sarasota-Bradenton Intl.
$177 Roundtrip, found 3 days ago
$177
Roundtrip
found 3 days ago