
Legacy Trail Vacations from $685
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Legacy Trail vacation packages
Price found within the past 48 hours. Click for updated prices.


Cedar Cove Resort and Cottages
Save 100% on your flight
Price was $1,690, price is now $888 per person
$888
per person
Aug 15 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (510 reviews)
Property was great! I would definitely recommend people to stay here great place parking is a bit of an issue if you have more than one car coming in but that comes with the island pretty typical but overall great
Reviewed on May 17, 2026

Ocean Club Treasure Island Hotel
Sunshine Beach
Price was $1,970, price is now $1,266 per person
$1,266
per person
Jun 27 - Jul 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (950 reviews)
Great location. Super clean and entire property is well maintained. Large 2 bedroom suite with well equipped kitchen, and large laundry machines. Bar onsite was nice as well. We loved our stay!
Reviewed on May 21, 2026

The Residences at Siesta Key Beach by Hyatt Vacation Club
South Village
Save 100% on your flight
Price was $2,070, price is now $1,382 per person
$1,382
per person
Aug 13 - Aug 16
found 13 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.8/10 Exceptional! (347 reviews)
Great location,big and well maintained living space
There was a love bag infested balcony and staff was not caring about our experience
Reviewed on May 21, 2026

Captiva Beach Resort
South Village
Save 100% on your flight
Price was $1,290, price is now $863 per person
$863
per person
Aug 15 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,255 reviews)
Great spot, short walk to the beach. Perfect for a couples weekend getaway.
Reviewed on May 23, 2026
Don't see what you're looking for?
See all available trips from Columbus to Legacy Trail
View all tripsLegacy Trail Hotel Deals

Kompose Boutique Hotel
965 University Pkwy Sarasota FL
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $114 total per night from May 25 to May 26
$114 total
May 25 - May 26
Total with taxes and fees
9.2/10 Wonderful! (5,405 reviews)
"Beautiful hotel! Clean and friendly staff"
Reviewed on May 24, 2026

Compass Hotel by Margaritaville Anna Maria Sound
12324 Manatee Avenue West Bradenton FL
Fully refundableReserve now, pay when you stay
$203 nightly
The price is $229 total per night from Jun 1 to Jun 2
$229 total
Jun 1 - Jun 2
Total with taxes and fees
9.4/10 Exceptional! (2,178 reviews)
"Everything was great, I'll come back to have a fun time!"
Reviewed on May 23, 2026

Golden Host Resort - Sarasota
4675 N Tamiami Trl Sarasota FL
Fully refundable
$75 nightly
The price is $85 total per night from May 31 to Jun 1
$85 total
May 31 - Jun 1
Total with taxes and fees
8.6/10 Excellent! (2,510 reviews)
"kind staff,nice pool and long chair, nice hanging area around the pool,great bar and drinks. Bad side, entry door verry dirty, bugs in my bed,on the floor, damp floor and dammaged floor. Not worth the price i paid."
Reviewed on May 23, 2026
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.
Find the Best Legacy Trail Vacation Packages
More vacations you might like
Explore a world of travel with Expedia
- Hotels near Palmer Ranch
- Hotels near Sarasota Square
- Hotels near Stoneybrook Golf & Country Club
- Hotels near Gulf Gate Golf Club
- Hotels near Vamo
- Beach Hotels in Vamo
- Historic Hotels in Vamo
- Hotels with a Pool in Vamo
- 4 Star Hotels in Vamo
- Family Hotels in Vamo
- Hotels near Gulf Gate Estates
- Cheap Hotels in Gulf Gate Estates
- Hotels with Restaurants in Gulf Gate Estates
- Beach Hotels in Gulf Gate Estates
- Historic Hotels in Gulf Gate Estates
- Hotel Wedding Venues Hotels in Gulf Gate Estates
- Business Hotels in Gulf Gate Estates
- Hotels with Free Breakfast in Gulf Gate Estates
- Hotels with Balconies in Gulf Gate Estates
- Adults Only Resorts & in Gulf Gate Estates
- 3 Star Hotels in Gulf Gate Estates
- Hotels near Coral Cove
- Hotels near Serenoa Golf Club
- Hotels near Bee Ridge
- Hotels near Jim Neville Marine Preserve
- Cheap Hotels in Bee Ridge
- Pet-Friendly Hotels in Bee Ridge
- Beach Hotels in Bee Ridge
- Resorts & Hotels with Spas in Bee Ridge
- 3 Star Hotels in Bee Ridge
- Extended Stay Hotels in Bee Ridge
- 5 Star Hotels in Bee Ridge
- Hotels with Free Parking in Bee Ridge
- Historic Hotels in Bee Ridge
- Hotels near Gulf Gate Mall
- Siesta Key Hotels
- Sarasota Hotels
- Hotels near Turtle Beach
- Hotels near Historic Spanish Point
- Hotels near The Oaks Club
- Hotels near South Gate Ridge
- 5 Star Hotels in South Gate Ridge
- Cheap Hotels in Osprey
- Osprey Hotels
- Houseboats in Osprey
- Resorts in Osprey
- Beach Hotels in Osprey
- Motels in Osprey
- Vacation Homes in Osprey
- Boutique Hotels in Osprey
- B&B in Osprey
- Hilton Hotels in Osprey
- Luxury Hotels in Osprey
- 5 Star Hotels in Osprey
- Villas in Osprey
- Hotels with Bars in Osprey
- 3 Star Hotels in Osprey
- Guest Houses in Osprey
- Cabin Rentals in Osprey
- Romantic Hotels in Osprey
- 4 Star Hotels in Osprey
- Resorts & Hotels with Spas in Osprey
- Hyatt Hotels in Osprey
- Golf Hotels in Osprey
- Hotels with Room Service in Osprey
- Hotel Wedding Venues Hotels in Osprey
- Sarasota Square
- Stoneybrook Golf & Country Club
- Pelican Plaza
- Gulf Gate Golf Club
- Visit Vamo
- Visit Gulf Gate Estates
- Jim Neville Marine Preserve
- Turtle Beach
- Historic Spanish Point
- Nancy's Consignments
- Visit Bee Ridge
- Osprey Vacations
- Siesta Key Marina
- Visit South Gate Ridge
- Evie's Golf Center
- Point of Rocks
- Crescent Beach
- Visit Osprey
- Car rentals near Gulf Gate Estates
- Car rentals near Bee Ridge
- Dollar Rent A Car Rental Cars in Bee Ridge
- Enterprise Rental Cars in Bee Ridge
- U-Save Rental Cars in Bee Ridge
- Car rentals near Historic Spanish Point
- Car rentals near Turtle Beach
- Car rentals near Osprey Village
- Car rentals near Osprey
- Enterprise Rental Cars in Osprey
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.



















