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.
The Barrymore Hotel Tampa Riverwalk

The Barrymore Hotel Tampa Riverwalk

3 out of 5
Downtown Tampa
Save 100% on your flight
Price was $893, price is now $596 per person
$596
per person
Aug 1 - Aug 8
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Tampa (TPA)
Book a stay at this business-friendly hotel in Tampa. Enjoy free WiFi, breakfast (surcharge), and a free area shuttle. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Tampa Riverwalk and Port of Tampa are located nearby.

The BC Resort on the Water

The BC Resort on the Water

4 out of 5
Save 100% on your flight
Price was $959, price is now $626 per person
$626
per person
Aug 1 - Aug 8
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Tampa (TPA)
Book a stay at this business-friendly aparthotel in St. Petersburg. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions John's Pass Village & Boardwalk and St. Petersburg - Clearwater Beaches are located nearby.

SkyBeach Resort

SkyBeach Resort

4 out of 5
Greater Pinellas Point
Save 100% on your flight
Price was $1,024, price is now $686 per person
$686
per person
Aug 1 - Aug 8
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Tampa (TPA)
Book a stay at this beach hotel in St. Petersburg. Enjoy 2 outdoor pools, 2 restaurants, and a private beach. Popular attractions Pass-a-Grille Beach and Salvador Dali Museum are located nearby.

Landing Apartments near Sun City Center and Riverview

Landing Apartments near Sun City Center and Riverview

4 out of 5
Save 100% on your flight
Price was $1,284, price is now $893 per person
$893
per person
Aug 1 - Aug 8
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Tampa (TPA)
Book a stay at this business-friendly aparthotel in Wimauma. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Lake Wimauma and Sandpiper Golf Club are located nearby.

The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 out of 5
South Village
Save 100% on your flight
Price was $2,547, price is now $1,794 per person
$1,794
per person
Jun 20 - Jun 24
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
Book a stay at this beach hotel in Siesta Key. Enjoy free breakfast, free WiFi, and free valet parking. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,021, price is now $735 per person
$735
per person
Jun 20 - Jun 24
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Tampa (TPA)
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.

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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 ...
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 ...
Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

4 out of 5
12324 Manatee Avenue West Bradenton FL
36.31 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

Tropical Beach Resorts

3.5 out of 5
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 ...
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 ...
Siesta Key Beach Resort and Suites

Siesta Key Beach Resort and Suites

2.5 out of 5
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. ...
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 ...
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 ...
Zota Beach Resort

Zota Beach Resort

4 out of 5
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 ...
The Westin Sarasota

The Westin Sarasota

4 out of 5
100 Marina View Drive Sarasota FL
13.87 km from city center
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 ...
Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
5450 Bollettieri Blvd. Bradenton FL
27.34 km from city center
Book a stay at this golf hotel in Bradenton. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
Tortuga Inn Beach Resort

Tortuga Inn Beach Resort

2.5 out of 5
1325 Gulf Drive North Bradenton Beach FL
35.13 km from city center
Book a stay at this beach hotel in Bradenton Beach. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms ...
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 ...
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 ...
The St. Regis Longboat Key Resort

The St. Regis Longboat Key Resort

5 out of 5
1601 Gulf Of Mexico Drive Longboat Key FL
19.29 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 Lido Beach and Longboat Key ...
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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
Wed, Jun 17 - Sun, Jun 21
ATL
Hartsfield-Jackson Atlanta Intl.
SRQ
Sarasota-Bradenton Intl.
$220 Roundtrip, found 2 days ago
$220
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Jun 17 from Hartsfield-Jackson Atlanta Intl. to Sarasota-Bradenton Intl., returning Sun, Jun 21, priced at $220 found 2 days ago
Delta
Wed, Dec 23 - Sat, Dec 26
ATL
Hartsfield-Jackson Atlanta Intl.
SRQ
Sarasota-Bradenton Intl.
$239 Roundtrip, found 1 day ago
$239
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Dec 23 from Hartsfield-Jackson Atlanta Intl. to Sarasota-Bradenton Intl., returning Sat, Dec 26, priced at $239 found 1 day ago
Southwest Airlines
Thu, Jun 18 - Mon, Jun 22
ATL
Hartsfield-Jackson Atlanta Intl.
SRQ
Sarasota-Bradenton Intl.
$259 Roundtrip, found 2 days ago
$259
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, Jun 18 from Hartsfield-Jackson Atlanta Intl. to Sarasota-Bradenton Intl., returning Mon, Jun 22, priced at $259 found 2 days ago
United
Sat, Jun 6 - Sun, Jun 14
EWR
Newark Liberty Intl. Airport
SRQ
Sarasota-Bradenton Intl.
$309 Roundtrip, found 6 days ago
$309
Roundtrip
found 6 days ago
Select United flight, departing Sat, Jun 6 from Newark Liberty Intl. Airport to Sarasota-Bradenton Intl., returning Sun, Jun 14, priced at $309 found 6 days ago
American Airlines
Wed, Jul 8 - Sat, Jul 18
ORD
O'Hare Intl.
SRQ
Sarasota-Bradenton Intl.
$351 Roundtrip, found 3 days ago
$351
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Jul 8 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Sat, Jul 18, priced at $351 found 3 days ago