Legacy Trail Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to CA $1,096 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Top Legacy Trail Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hampton Inn Tampa Downtown Channel District
Downtown Tampa
per person
Nov 8 - Nov 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Sarasota (SRQ)
9.4/10 Exceptional! (1,756 reviews)
Food — I haven’t tried the food yet but so far, Hampton never failed me with their food options especially for breakfast. Also, the hotel is clean.
Reviewed on Aug. 18, 2025
Legacy Trail Hotel Deals
Kompose Boutique Hotel
965 University Pkwy, Sarasota, FL
Fully refundableReserve now, pay when you stay
The price is CA $74 per night from Aug 19 to Aug 20
CA $74
CA $100 total
Aug 19 - Aug 20
includes taxes & fees
9/10 Wonderful! (4,245 reviews)
"Excellent customer service"
Reviewed on Aug. 16, 2025
Tropical Beach Resorts
6717 Sara Sea Circle, Siesta Key, FL
Fully refundableReserve now, pay when you stay
The price is CA $193 per night from Sep 1 to Sep 2
CA $193
CA $249 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (4,876 reviews)
"Exelent"
Reviewed on Aug. 17, 2025
Compass Hotel by Margaritaville Anna Maria Sound
12324 Manatee Avenue West, Bradenton, FL
Fully refundableReserve now, pay when you stay
The price is CA $231 per night from Aug 28 to Aug 29
CA $231
CA $295 total
Aug 28 - Aug 29
includes taxes & fees
9.4/10 Exceptional! (1,657 reviews)
"Great place"
Reviewed on Aug. 16, 2025
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.
Other vacations you might like
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
Expedia's Latest Trends
Hotels
- Hotels in Kissimmee
- Brickell hotels
- Hotels near Port of Miami
- Hotels in Clearwater
- Hotels in Miami Beach
- Hotels in Clearwater Beach
- Hotels near Port Everglades
- Downtown Miami hotels
- Oceanfront Hotels in Hollywood
- Hotels near Walt Disney World® Resort
- Hotels in Dunedin
- Hotels in St. Pete Beach
- Port Canaveral hotels
- Hotels in Lauderdale-by-the-Sea
- South Beach hotels
- Hotels in Hollywood
Cars
Cruises
Activities
Vacation Rentals
General
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.