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Book Exclusive Legacy Trail Vacation Packages
Legacy Trail flight + hotel packages
Price found within the past 48 hours. Click for updated prices.
![Bay Palms Waterfront Resort - Hotel and Marina](https://images.trvl-media.com/lodging/2000000/1620000/1618600/1618599/2f3a988e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Bay Palms Waterfront Resort - Hotel and Marina
Belle Vista
Save 100% on your flight
per person
Jul. 17 - Jul. 22
found 19 hours ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
Stay at this 3-star family-friendly hotel in St. Pete Beach. Enjoy free WiFi, a marina, and room service. 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.
![The Avalon Club](https://images.trvl-media.com/lodging/68000000/67580000/67572800/67572769/7ffbf6d0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
The Avalon Club
Save 100% on your flight
per person
Aug. 2 - Aug. 9
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) 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 pool and the helpful staff in our reviews. Popular attractions Clearwater Beach and Pier 60 Park are located nearby.
![Plaza Beach Hotel Beachfront Resort](https://images.trvl-media.com/lodging/1000000/900000/894000/893981/057d756a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Plaza Beach Hotel Beachfront Resort
Save 100% on your flight
per person
Jul. 17 - Jul. 22
found 19 hours ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
Stay at this 3-star beach hotel in St. Pete Beach. Enjoy free WiFi, a private beach, and room service. Our guests praise the pool and the bar in our reviews. Popular attractions John's Pass Village & Boardwalk and Fort De Soto Park are located nearby.
![Bayview Plaza Waterfront Resort](https://images.trvl-media.com/lodging/1000000/910000/904800/904795/137059ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Bayview Plaza Waterfront Resort
Belle Vista
Save 100% on your flight
per person
Jul. 17 - Jul. 22
found 19 hours ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
Stay at this 3-star family-friendly hotel in St. Pete Beach. Enjoy free WiFi, a marina, 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.
![Cedar Cove Resort and Cottages](https://images.trvl-media.com/lodging/9000000/8100000/8099700/8099611/7751c173_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Cedar Cove Resort and Cottages
Save 100% on your flight
per person
Jul. 23 - Jul. 27
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Sarasota (SRQ)
Stay at this 3-star beach hotel in Holmes Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Cortez Beach and Coquina Beach are located nearby.
Top Legacy Trail hotels deals
![Kompose Boutique Hotel](https://images.trvl-media.com/lodging/39000000/38220000/38215400/38215316/c2a1ef6e_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Kompose Boutique Hotel
965 University Pkwy, Sarasota, FL
Free cancellation
Reserve now, pay when you stay
The price is CA $107 per night
CA $107
per night
Jun. 23 - Jun. 24
Stay at this 3-star business-friendly hotel in Sarasota. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions St. Armands Circle and Lido Beach are located nearby.
Pool
Hot tub
![Hyatt Regency Sarasota](https://images.trvl-media.com/lodging/1000000/30000/27300/27206/bd597624_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Hyatt Regency Sarasota
1000 Blvd Of The Arts, Sarasota, FL
Free cancellation
The price is CA $197 per night
CA $197
per night
Jun. 30 - Jul. 1
Book a stay at this eco-certified hotel in Sarasota. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions St. Armands Circle and Lido Beach are located nearby.
Pool
Hot tub
![The Westin Sarasota](https://images.trvl-media.com/lodging/17000000/16820000/16819000/16818933/03c1f9e9_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
The Westin Sarasota
100 Marina View Drive, Sarasota, FL
Free cancellation
Reserve now, pay when you stay
The price is CA $287 per night
CA $287
per night
Jun. 23 - Jun. 24
Stay at this 4-star spa hotel in Sarasota. Enjoy a full-service spa, 2 restaurants, and a rooftop terrace. Our guests praise the pool and the restaurant in our reviews. Popular attractions St. Armands Circle and Lido Beach are located nearby.
Pool
Spa
![Perfectly Located Home with Pool and Spa](https://images.trvl-media.com/lodging/86000000/85480000/85471300/85471275/81aec2a5_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Perfectly Located Home with Pool and Spa
Stay at this vacation home in Bradenton Beach. Enjoy private pools, a water park, and patios. Popular attractions Cortez Beach and Coquina Beach are located nearby.
Pool
Hot tub
![Sandcastle Resort at Lido Beach](https://images.trvl-media.com/lodging/1000000/30000/21000/20959/d734514b_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Sandcastle Resort at Lido Beach
1540 Ben Franklin Dr, Sarasota, FL
Free cancellation
Reserve now, pay when you stay
The price is CA $246 per night
CA $246
per night
Jun. 17 - Jun. 18
Book a stay at this beach hotel in Sarasota. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the restaurant in our reviews. Popular attractions Lido Beach and St. Armands Circle are located nearby.
On private beach
Pool
![Carlisle Inn](https://images.trvl-media.com/lodging/20000000/19770000/19761100/19761082/6d3b7469_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Carlisle Inn
3727 Bahia Vista, Sarasota, FL
Free cancellation
Reserve now, pay when you stay
The price is CA $187 per night
CA $187
per night
Jun. 17 - Jun. 18
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 attractions Lido Beach and St. Armands Circle are located nearby.
Pool
Breakfast included
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.
Popular places to visit
Siesta Key Beach
4.5/5(75 reviews)
Nothing says vacation like spending a lazy day at Siesta Key Beach, a popular beach in Siesta Key. Amble around this relaxing area's seaside or experience its live music.
Lido Beach
4.5/5(46 reviews)
Nothing says vacation like spending a lazy day at Lido Beach, a popular beach in Sarasota. Wander the picturesque gardens or discover the area's beautiful sunsets.
St. Armands Circle
4.5/5(49 reviews)
Enjoy the beautiful sunsets and explore St. Armands Circle, a well-known green space in Sarasota. Wander the beautiful beaches and seaside in the area.
Photos of local treasures
Browse Legacy Trail vacation photos for more inspiration
![Legacy Trail](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/496000/496378-legacy-trail.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)