Legacy Trail Vacation Packages for 2026

Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*

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Legacy Trail Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $632, price is now $383 per person
$383
per person
Jan 16 - Jan 20
found 2 hours ago
Roundtrip flight included
Cleveland (CLE) to Tampa (TPA)
Stay at this hotel in Safety Harbor. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Philippe Park and Chi Chi Rodriguez Golf Club are located nearby.

Sleeps 6 Hot Tub Fenced Yard Cozy Chic

Sleeps 6 Hot Tub Fenced Yard Cozy Chic

3 out of 5
Town 'n' Country
Save 100% on your flight
Price was $891, price is now $532 per person
$532
per person
Jan 16 - Jan 20
found 2 hours ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
Book a stay at this spa villa in Tampa. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Raymond James Stadium and George M. Steinbrenner Field are located nearby.

Bali Hai Beachfront Resort and Spa

Bali Hai Beachfront Resort and Spa

3.5 out of 5
Save 100% on your flight
Price was $1,898, price is now $1,247 per person
$1,247
per person
Jan 16 - Jan 20
found 2 hours ago
Roundtrip flight included
Cleveland (CLE) to Sarasota (SRQ)
Book a stay at this beach resort in Holmes Beach. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Bean Point Beach and Coquina Beach are located nearby.

Hilton Garden Inn Sarasota - Bradenton Airport

Hilton Garden Inn Sarasota - Bradenton Airport

3 out of 5
Save 100% on your flight
Price was $1,964, price is now $1,328 per person
$1,328
per person
Feb 21 - Feb 28
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
Book a stay at this business-friendly hotel in Sarasota. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Lido Beach and St. Armands Circle are located nearby.

Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $1,696, price is now $1,152 per person
$1,152
per person
Feb 21 - Feb 28
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tampa (TPA)
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 and the pool in our reviews. Popular attractions Lido Beach and St. Armands Circle are located nearby.

Weathered The Storm

Weathered The Storm

3 out of 5
Price was $842, price is now $587 per person
$587
per person
Feb 21 - Feb 28
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Sarasota (SRQ)
Book a stay at this beach houseboat in Bradenton. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Coquina Beach and Bean Point Beach are located nearby.

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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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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. ...
The Ritz-Carlton, Sarasota

The Ritz-Carlton, Sarasota

5 out of 5
1111 Ritz Carlton Dr Sarasota FL
14.02 km from city center
Book a stay at this luxury hotel in Sarasota. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
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See all available properties in Legacy Trail
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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.

Frontier Airlines
Sun, Feb 22 - Fri, Mar 6
PHL
Philadelphia Intl.
SRQ
Sarasota-Bradenton Intl.
$149 Roundtrip, found 1 day ago
$149
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Feb 22 from Philadelphia Intl. to Sarasota-Bradenton Intl., returning Fri, Mar 6, priced at $149 found 1 day ago
Delta
Fri, Jan 9 - Sat, Jan 24
EWR
Newark Liberty Intl. Airport
SRQ
Sarasota-Bradenton Intl.
$157 Roundtrip, found 2 days ago
$157
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Jan 9 from Newark Liberty Intl. Airport to Sarasota-Bradenton Intl., returning Sat, Jan 24, priced at $157 found 2 days ago
United
Tue, Jan 6 - Tue, Jan 27
EWR
Newark Liberty Intl. Airport
SRQ
Sarasota-Bradenton Intl.
$167 Roundtrip, found 9 hours ago
$167
Roundtrip
found 9 hours ago
Select United flight, departing Tue, Jan 6 from Newark Liberty Intl. Airport to Sarasota-Bradenton Intl., returning Tue, Jan 27, priced at $167 found 9 hours ago
American Airlines
Tue, Jan 6 - Tue, Jan 27
EWR
Newark Liberty Intl. Airport
SRQ
Sarasota-Bradenton Intl.
$188 Roundtrip, found 9 hours ago
$188
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Tue, Jan 6 from Newark Liberty Intl. Airport to Sarasota-Bradenton Intl., returning Tue, Jan 27, priced at $188 found 9 hours ago
JetBlue Airways
Mon, Mar 16 - Fri, Mar 20
JFK
John F. Kennedy Intl.
SRQ
Sarasota-Bradenton Intl.
$197 Roundtrip, found 5 days ago
$197
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Mon, Mar 16 from John F. Kennedy Intl. to Sarasota-Bradenton Intl., returning Fri, Mar 20, priced at $197 found 5 days ago