Legacy Trail Vacation Packages for 2026

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Top Hotel Deals

Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
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

Tropical Beach Resorts

3.5 out of 5
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

Compass Hotel by Margaritaville Anna Maria Sound

4 out of 5
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

Carlisle Inn

3.5 out of 5
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

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
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

Captiva Beach Resort

3 out of 5
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

Hyatt Place Sarasota/Bradenton Airport

3 out of 5
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

Golden Host Resort - Sarasota

3 out of 5
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

Lido Beach Resort

4 out of 5
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

Siesta Key Palms Resort

3.5 out of 5
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

The St. Regis Longboat Key Resort

5 out of 5
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

Spark by Hilton Sarasota Siesta Key Gateway

3 out of 5
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

Art Ovation Hotel, Autograph Collection

4 out of 5
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 ...
Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn

3 out of 5
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. ...
DoubleTree by Hilton Sarasota Bradenton Airport

DoubleTree by Hilton Sarasota Bradenton Airport

4 out of 5
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 ...
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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.

Delta
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
Select Delta flight, departing Mon, Feb 2 from Logan Intl. to Sarasota-Bradenton Intl., returning Fri, Feb 6, priced at $117 found 2 days ago
Southwest Airlines
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
Select Southwest Airlines flight, departing Mon, Feb 2 from Logan Intl. to Sarasota-Bradenton Intl., returning Mon, Feb 9, priced at $151 found 2 days ago
American Airlines
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
Select American Airlines flight, departing Mon, Feb 2 from Logan Intl. to Sarasota-Bradenton Intl., returning Mon, Feb 9, priced at $159 found 2 days ago
JetBlue Airways
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
Select JetBlue Airways flight, departing Mon, Feb 2 from Logan Intl. to Sarasota-Bradenton Intl., returning Mon, Feb 9, priced at $178 found 2 days ago
United
Thu, Mar 5 - Mon, Mar 9
LGA
LaGuardia
SRQ
Sarasota-Bradenton Intl.
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Select United flight, departing Thu, Mar 5 from LaGuardia to Sarasota-Bradenton Intl., returning Mon, Mar 9, priced at $217 found 1 day ago