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.
voco Sarasota by IHG
Central Sarasota
Save 100% on your flight
Price was $848, price is now $561 per person
$561
per person
May 6 - May 11
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Book a stay at this business-friendly hotel in Sarasota. Enjoy breakfast (surcharge), 24-hour room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions St. Armands Circle and Lido Beach are located nearby.
Ocean Club Treasure Island Hotel
Sunshine Beach
Save 100% on your flight
Price was $1,931, price is now $1,142 per person
$1,142
per person
May 16 - May 23
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Book a stay at this beach hotel in Treasure Island. Enjoy free WiFi, free parking, and a beach locale. 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.
FUSION Resort Waterfront Suites
Save 100% on your flight
Price was $1,692, price is now $1,105 per person
$1,105
per person
Jun 8 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) 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 Westin Sarasota
Central Sarasota
Save 100% on your flight
Price was $1,110, price is now $740 per person
$740
per person
May 6 - May 11
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Book a stay at this 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 St. Armands Circle and Lido Beach are located nearby.
Cedar Cove Resort and Cottages
Save 100% on your flight
Price was $2,703, price is now $1,804 per person
$1,804
per person
Jun 12 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Sarasota (SRQ)
Book a stay at this beach resort in Holmes Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Bradenton Beach and Coquina Beach are located nearby.
Plaza Beach Hotel Beachfront Resort
Save 100% on your flight
Price was $1,501, price is now $1,028 per person
$1,028
per person
Jun 8 - Jun 14
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Tampa (TPA)
Book a stay at this beach hotel in St. Pete Beach. Enjoy free WiFi, a private beach, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions John's Pass Village & Boardwalk and Fort De Soto Park are located nearby.
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View all tripsTop Hotel Deals
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 ...
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 ...
Compass Hotel by Margaritaville Anna Maria Sound
12324 Manatee Avenue West Bradenton FL
36.31 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 ...
Tropical Beach Resorts
6717 Sara Sea Circle Siesta Key FL
6.25 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 ...
Azul Resort Siesta Key
1105 Point of Rocks Rd Siesta Key FL
6.13 km from city center
Book a stay at this beach hotel in Siesta Key. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Siesta Key Beach and Lido Beach are located ...
Tropical Breeze Resort
140 Columbus Blvd. Siesta Key FL
10.42 km from city center
Book a stay at this 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 ...
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 ...
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 ...
Zota Beach Resort
4711 Gulf of Mexico Dr Longboat Key FL
25.52 km from city center
Book a stay at this beach resort in Longboat Key. Enjoy free WiFi, a private beach, and breakfast (surcharge). Our guests praise the pool and the helpful staff ...
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 ...
Siesta Key Beach Resort and Suites
5311 Ocean Blvd Siesta Key FL
10.16 km from city center
Stay at this resort in Siesta Key. Enjoy free WiFi, free bicycles on site, and parking (surcharge). Our guests praise the pool and the helpful staff in our reviews. ...
The St. Regis Longboat Key Resort
1601 Gulf Of Mexico Drive Longboat Key FL
19.29 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 St. Armands Circle and Lido ...
Palmetto Marriott Resort & Spa
600 US HIGHWAY 41 Palmetto FL
32.98 km from city center
Book a stay at this luxury hotel in Palmetto. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Popular attractions Palmetto Historical Park and Manatee ...
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.
Thu, Apr 16 - Sat, Apr 18
ATL
Hartsfield-Jackson Atlanta Intl.
SRQ
Sarasota-Bradenton Intl.
$190 Roundtrip, found 1 day ago
$190
Roundtrip
found 1 day ago
Tue, Apr 28 - Tue, May 5
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$227 Roundtrip, found 5 hours ago
$227
Roundtrip
found 5 hours ago
Tue, Apr 28 - Tue, May 5
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$237 Roundtrip, found 5 hours ago
$237
Roundtrip
found 5 hours ago
Tue, Apr 28 - Tue, May 5
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$237 Roundtrip, found 5 hours ago
$237
Roundtrip
found 5 hours ago
Tue, Apr 28 - Tue, May 5
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$237 Roundtrip, found 5 hours ago
$237
Roundtrip
found 5 hours ago