Legacy Trail Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
Top Legacy Trail Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel
Wesley Chapel South
Save 100% on your flight
per person
Jul. 25 - Jul. 30
found 22 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
6.8/10 (1,004 reviews)
Beautiful grounds. Rooms were clean and spacious. Would stay here again
Reviewed on May 29, 2024
Plaza Beach Hotel Beachfront Resort
Save 100% on your flight
per person
Jul. 21 - Jul. 27
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Tampa (TPA)
8.8/10 Excellent! (1,000 reviews)
Lively motel with great location and access to the beach. Friendly staff. Kitchenette is great convenience. Would stay again.
Reviewed on Jun. 2, 2024
Where to stay in Legacy Trail
Find the best Legacy Trail areas and neighborhoods for the activities you enjoy most. Learn more about Legacy Trail
Downtown Sarasota
If you're spending some time in Downtown Sarasota, Sarasota Opera House and Payne Park are top sights worth seeing.
Legacy Trail Hotel Deals
Kompose Boutique Hotel
965 University Pkwy, Sarasota, FL
Fully refundableReserve now, pay when you stay
The price is CA $118 per night from Jun. 10 to Jun. 11
CA $118
CA $152 total
includes taxes & fees
Jun 10 - Jun 11
8.8/10 Excellent! (3,444 reviews)
"It is a beautiful eco friendly hotel, quite comfortable."
Reviewed on Jun. 2, 2024
Hyatt Regency Sarasota
1000 Blvd Of The Arts, Sarasota, FL
Fully refundable
The price is CA $217 per night from Jun. 9 to Jun. 10
CA $217
CA $292 total
includes taxes & fees
Jun 9 - Jun 10
8/10 Very Good! (1,010 reviews)
"Bathroom is really small with a sulfer smell when you flush."
Reviewed on Jun. 2, 2024
The Westin Sarasota
100 Marina View Drive, Sarasota, FL
Fully refundableReserve now, pay when you stay
The price is CA $285 per night from Jun. 9 to Jun. 10
CA $285
CA $352 total
includes taxes & fees
Jun 9 - Jun 10
8.6/10 Excellent! (1,016 reviews)
"Nice location and staff. Will stay again."
Reviewed on Jun. 3, 2024
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.
Discover the most popular places to visit in Legacy Trail
Siesta Key Beach
4.5/5(75 reviews)
The soft, white sand on Siesta Key’s award-winning family-friendly beach is perfect for relaxing under a sun umbrella and taking part in a game of volleyball.
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)
Consider this area as a circular outdoor mall. Like any mall, you can shop, dine, browse or just people-watch. Unlike most malls, this one never closes to walkers.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.