Legacy Trail Vacation Packages for 2025

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Legacy Trail Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Innisbrook Resort

Innisbrook Resort

3.5 out of 5
Save 100% on your flight
per person
Jul 15 - Jul 19
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Tampa (TPA)
Book a stay at this spa resort in Palm Harbor. Enjoy free WiFi, 6 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Innisbrook Golf Club and Leepa-Rattner Museum of Art are located nearby.

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
per person
Jul 15 - Jul 19
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Tampa (TPA)
Stay at this 4-star beach aparthotel in Clearwater Beach. Enjoy a beach locale, a fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Clearwater Beach and Pier 60 Park are located nearby.

Courtyard by Marriott Clearwater Beach

Courtyard by Marriott Clearwater Beach

3 out of 5
Save 100% on your flight
per person
Jul 15 - Jul 19
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Tampa (TPA)
Stay at this 3-star business-friendly hotel in Clearwater Beach. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Pier 60 Park and Clearwater Beach are located nearby.

The Hotel Zamora

The Hotel Zamora

4 out of 5
Save 100% on your flight
per person
Jul 15 - Jul 19
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Tampa (TPA)
Stay at this 4-star beach hotel in St. Pete Beach. Enjoy a marina, 3 bars/lounges, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions John's Pass Village & Boardwalk and Fort De Soto Park are located nearby.

Pelican Pointe Clearwater Beach Hotel

Pelican Pointe Clearwater Beach Hotel

2.5 out of 5
Save 100% on your flight
per person
Jul 15 - Jul 19
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Tampa (TPA)
Stay at this hotel in Clearwater Beach. Enjoy free WiFi, a beach locale, and laundry facilities. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Beach Walk and Pier 60 Park are located nearby.

Edge Hotel Clearwater Beach

Edge Hotel Clearwater Beach

3.5 out of 5
Save 100% on your flight
per person
Jul 15 - Jul 19
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Tampa (TPA)
Stay at this 3.5-star business-friendly hotel in Clearwater Beach. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the pool and the bar in our reviews. Popular attractions Beach Walk and Pier 60 Park 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
Stay at this 3-star business-friendly hotel in Sarasota. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the pool ...
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 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 ...
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
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 ...
Golden Host Resort - Sarasota

Golden Host Resort - Sarasota

3 out of 5
4675 N Tamiami Trl, Sarasota, FL
17.78 km from city center
Stay at this 3-star business-friendly hotel in Sarasota. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the pool and the bar in our ...
Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
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 ...
Embassy Suites by Hilton Sarasota, FL

Embassy Suites by Hilton Sarasota, FL

3.5 out of 5
202 North Tamiami Trail, Sarasota, FL
14.01 km from city center
Stay at this 3.5-star business-friendly hotel in Sarasota. Enjoy free breakfast, free WiFi, and room service. Our guests praise the breakfast and the pool in ...
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 motel 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 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 ...
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 ...
Anna Maria Beach Resort

Anna Maria Beach Resort

3.5 out of 5
6306 Gulf Dr, Holmes Beach, FL
39.63 km from city center
Stay at this 3.5-star beach aparthotel in Holmes Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in ...
Palmetto Marriott Resort & Spa

Palmetto Marriott Resort & Spa

4.5 out of 5
600 US HIGHWAY 41, Palmetto, FL
32.98 km from city center
Stay at this 4.5-star luxury hotel in Palmetto. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Popular attractions Manatee County Agricultural Museum ...
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 3-star apartment in Bradenton Beach. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the pool and the helpful staff in ...
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
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 ...
Siesta Key Palms Resort

Siesta Key Palms Resort

3 out of 5
1800 Stickney Point Rd, Sarasota, FL
6.02 km from city center
Stay at this 3-star hotel in Sarasota. Enjoy 2 outdoor pools, free bicycles on site, and a garden. Our guests praise the pool and the helpful staff in our reviews. ...
Zota Beach Resort

Zota Beach Resort

4 out of 5
4711 Gulf of Mexico Dr, Longboat Key, FL
25.52 km from city center
Stay at this 4-star beach resort in Longboat Key. Enjoy free WiFi, a private beach, and breakfast (surcharge). Our guests praise the pool and the helpful staff ...
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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.