Title: Legacy Trail Vacation Packages 2026 from $435 | Expedia.com

[Legacy Trail Travel Guide](https://expedia.com/Legacy-Trail.dx553248621532652531)[Hotels in Legacy Trail](https://expedia.com/Legacy-Trail-Hotels.d553248621532652531.Travel-Guide-Hotels)[Vacation Rentals in Legacy Trail](https://expedia.com/Legacy-Trail-Vacation-Rentals.d553248621532652531.Travel-Guide-VacationRentals)[Flights to Legacy Trail](https://expedia.com/Cheap-Flights-To-Legacy-Trail.d553248621532652531.Travel-Guide-Flights)[Car Rentals in Legacy Trail](https://expedia.com/Car-Rentals-In-Legacy-Trail.d553248621532652531.Car-Rental-Guide)

![](https://images.trvl-media.com/place/553248635975846806/d70ae022-0498-403c-94d8-dc8f29b7750f.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Legacy Trail Vacations from $435

## Book a Hotel + Flight or Car together to unlock savings

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## The Latest Legacy Trail vacation packages

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

![Mar Bay Motel &Suites](https://images.trvl-media.com/lodging/24000000/23610000/23608800/23608750/3f239251_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Mar Bay Motel &Suites

Save 100% on your flight

$435

per person

Apr 30 - May 4

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

8.6/10 Excellent! (68 reviews)

Great location, very quiet and the staff is professional and courteous!

Reviewed on Mar 22, 2026

![voco Sarasota by IHG](https://images.trvl-media.com/lodging/2000000/1580000/1577400/1577382/6f2696b7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### voco Sarasota by IHG

Central Sarasota

Save 100% on your flight

$722

per person

May 23 - May 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (1,012 reviews)

We enjoyed our stay at vocoSarasota.. The best part was the amazing and very accommodating staff especially the Shuttle drivers Rich, Barry and Cody. they were terrific. Rooms were very nice. I just wished they had better outdoor accomodations especially the pool area.The daily breakfast was good even when the chef had to be the Manager on duty. Just a few hiccups with that. overall it was a delightful stay and the location was perfect!!!!

Reviewed on Mar 17, 2026

![The Westin Sarasota](https://images.trvl-media.com/lodging/17000000/16820000/16819000/16818933/2384a13f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Westin Sarasota

Central Sarasota

Save 100% on your flight

$1,010

per person

May 1 - May 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (1,193 reviews)

The hotel is beautiful, the rooms are clean, and the staff are very friendly. I love the rooftop.

Reviewed on Mar 19, 2026

![Ocean Club Treasure Island Hotel](https://images.trvl-media.com/lodging/97000000/96160000/96150700/96150639/a3e54a35_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Ocean Club Treasure Island Hotel

Sunshine Beach

$776

per person

Jun 4 - Jun 8

found 17 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (846 reviews)

The rooms were nice. I saw several people with pets, one of those people told me how nice the hotel staff was to his dog. The staff were always polite and friendly. We would definitely stay there again.

Reviewed on Mar 17, 2026

![Kompose Boutique Hotel](https://images.trvl-media.com/lodging/39000000/38220000/38215400/38215316/3006ffef_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Kompose Boutique Hotel

Save 100% on your flight

$574

per person

May 25 - May 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (5,126 reviews)

My flight was cancelled by the airline. My reservation has passed the cancellation period, but the hotel staff cancelled my reservation with a full refund. Very nice and very friendly. Will definitely try to stay here again next time.

Reviewed on Mar 21, 2026

Don't see what you're looking for?

See all available trips from Columbus to Legacy Trail

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-22/2026-04-29/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PGD&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## Legacy Trail Hotel Deals

![Kompose Boutique Hotel](https://images.trvl-media.com/lodging/39000000/38220000/38215400/38215316/3006ffef_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Kompose Boutique Hotel

965 University Pkwy Sarasota FL

Fully refundableReserve now, pay when you stay

$152 nightly

$172 total

Apr 20 - Apr 21

Total with taxes and fees

9.2/10 Wonderful! (5,161 reviews)

My flight was cancelled by the airline. My reservation has passed the cancellation period, but the hotel staff cancelled my reservation with a full refund. Very nice and very friendly. Will definitely try to stay here again next time.

Reviewed on Mar 21, 2026

[](https://expedia.com/Hotel-Search?startDate=4%2F20%2F2026&endDate=4%2F21%2F2026&selected=38215316&PinnedHotelID=38215316&HadPinnedHotel=true&regionId=553248621532652531)

![Golden Host Resort - Sarasota](https://images.trvl-media.com/lodging/1000000/30000/21400/21331/6dc32504_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Golden Host Resort - Sarasota

4675 N Tamiami Trl Sarasota FL

Fully refundable

$84 nightly

$95 total

Apr 19 - Apr 20

Total with taxes and fees

8.4/10 Very Good! (2,362 reviews)

Nice !!!!

Reviewed on Mar 21, 2026

[](https://expedia.com/Hotel-Search?startDate=4%2F19%2F2026&endDate=4%2F20%2F2026&selected=21331&PinnedHotelID=21331&HadPinnedHotel=true&regionId=553248621532652531)

![Compass Hotel by Margaritaville Anna Maria Sound](https://images.trvl-media.com/lodging/42000000/41970000/41961400/41961327/e1f2d8a8_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Compass Hotel by Margaritaville Anna Maria Sound

12324 Manatee Avenue West Bradenton FL

Fully refundableReserve now, pay when you stay

$245 nightly

$277 total

Apr 12 - Apr 13

Total with taxes and fees

9.4/10 Exceptional! (2,014 reviews)

The hotel was so clean, updated, the pool area and the restaurant are great. We really enjoyed the breakfast and the staff were so friendly.

Reviewed on Mar 21, 2026

[](https://expedia.com/Hotel-Search?startDate=4%2F12%2F2026&endDate=4%2F13%2F2026&selected=41961327&PinnedHotelID=41961327&HadPinnedHotel=true&regionId=553248621532652531)

[See all 17,621 properties in Legacy Trail](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F23%2F2026&endDate=3%2F24%2F2026&regionId=553248621532652531)

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

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- [4 Star Hotels in Osprey ](https://www.expedia.com/4Star-Osprey-Hotels.s40-0-d55888.Travel-Guide-Filter-Hotels)
- [Resorts & Hotels with Spas in Osprey ](https://www.expedia.com/Osprey-Hotels-Spa-Hotel.0-0-d55888-tSpaHotel.Travel-Guide-Filter-Hotels)
- [Hyatt Hotels in Osprey ](https://www.expedia.com/Osprey-Hotels-Hyatt-Hotels.0-0-d55888--bHyattHotels.Travel-Guide-Filter-Hotels)
- [Golf Hotels in Osprey ](https://www.expedia.com/Osprey-Hotels-Golf-Hotel.0-0-d55888-tGolfHotel.Travel-Guide-Filter-Hotels)
- [Hotels with Room Service in Osprey ](https://www.expedia.com/Osprey-Hotels-Hotels-With-Room-Service.0-0-d55888-tHotelswithRoomService.Travel-Guide-Filter-Hotels)
- [Hotel Wedding Venues Hotels in Osprey ](https://www.expedia.com/Osprey-Hotels-Wedding-Hotels.0-0-d55888-tWeddingHotels.Travel-Guide-Filter-Hotels)

- [Flights to Sarasota ](https://www.expedia.com/Cheap-Flights-To-Sarasota.d602719.Travel-Guide-Flights)
- [Flights to Osprey ](https://www.expedia.com/Cheap-Flights-To-Osprey.d55888.Travel-Guide-Flights)
- [Flights from Osprey ](https://www.expedia.com/lp/flights/55888/flights-from-osprey)

- [Sarasota Square ](https://www.expedia.com/Sarasota-Square-Vamo.d553248621563219817.Vacation-Attraction)
- [Stoneybrook Golf & Country Club ](https://www.expedia.com/Stoneybrook-Golf-Country-Club-Palmer-Ranch.d6068717.Vacation-Attraction)
- [Pelican Plaza ](https://www.expedia.com/Pelican-Plaza-Vamo.d6296232.Vacation-Attraction)
- [Gulf Gate Golf Club ](https://www.expedia.com/Gulf-Gate-Golf-Club-Gulf-Gate-Estates.d6295672.Vacation-Attraction)
- [Visit Vamo ](https://www.expedia.com/Sarasota-Vamo.dx553248623282278448)
- [Visit Gulf Gate Estates ](https://www.expedia.com/Sarasota-Gulf-Gate-Estates.dx553248623282278406)
- [Jim Neville Marine Preserve ](https://www.expedia.com/Jim-Neville-Marine-Preserve-Siesta-Key.d6295999.Vacation-Attraction)
- [Turtle Beach ](https://www.expedia.com/Turtle-Beach-Florida.d6296228.Vacation-Attraction)
- [Historic Spanish Point ](https://www.expedia.com/Historic-Spanish-Point-Osprey.d6295820.Vacation-Attraction)
- [Nancy's Consignments ](https://www.expedia.com/Nancys-Consignments-Osprey.d553248621532652544.Vacation-Attraction)
- [Visit Bee Ridge ](https://www.expedia.com/Sarasota-Bee-Ridge.dx6293915)
- [Osprey Vacations ](https://www.expedia.com/Osprey.d55888.Destination-Travel-Guides)
- [Siesta Key Marina ](https://www.expedia.com/Siesta-Key-Marina-Siesta-Key.d6295966.Vacation-Attraction)
- [Visit South Gate Ridge ](https://www.expedia.com/Sarasota-South-Gate-Ridge.dx553248623282278427)
- [Evie's Golf Center ](https://www.expedia.com/Evies-Golf-Center-Sarasota.d6295670.Vacation-Attraction)
- [Point of Rocks ](https://www.expedia.com/Point-Of-Rocks-Siesta-Key.d6295822.Vacation-Attraction)
- [Crescent Beach ](https://www.expedia.com/Crescent-Beach-Siesta-Key.d553248621532652551.Vacation-Attraction)
- [Visit Osprey ](https://www.expedia.com/Osprey.dx55888)

- [Car rentals near Gulf Gate Estates ](https://www.expedia.com/Car-Rentals-In-Gulf-Gate-Estates.d553248623282278406.Car-Rental-Guide)
- [Car rentals near Bee Ridge ](https://www.expedia.com/Car-Rentals-In-Bee-Ridge.d6293915.Car-Rental-Guide)
- [Dollar Rent A Car Rental Cars in Bee Ridge ](https://www.expedia.com/Dollar-Rent-A-Car-Car-Rentals-In-Bee-Ridge.d6293915-c43.Car-Rental-Guide-Suppliers)
- [Enterprise Rental Cars in Bee Ridge ](https://www.expedia.com/Enterprise-Car-Rentals-In-Bee-Ridge.d6293915-c15.Car-Rental-Guide-Suppliers)
- [U-Save Rental Cars in Bee Ridge ](https://www.expedia.com/U-Save-Car-Rentals-In-Bee-Ridge.d6293915-c34.Car-Rental-Guide-Suppliers)
- [Car rentals near Historic Spanish Point ](https://www.expedia.com/Car-Rentals-In-Historic-Spanish-Point.d6295820.Car-Rental-Guide)
- [Car rentals near Turtle Beach ](https://www.expedia.com/Car-Rentals-In-Turtle-Beach.d6296228.Car-Rental-Guide)
- [Car rentals near Osprey Village ](https://www.expedia.com/Car-Rentals-In-Osprey-Village.d553248635976482375.Car-Rental-Guide)
- [Car rentals near Osprey ](https://www.expedia.com/Car-Rentals-In-Osprey.d55888.Car-Rental-Guide)
- [Enterprise Rental Cars in Osprey ](https://www.expedia.com/Enterprise-Car-Rentals-In-Osprey.d55888-c15.Car-Rental-Guide-Suppliers)

- [Osprey Vacation Rentals ](https://www.expedia.com/Osprey-Vacation-Rentals.d55888.Travel-Guide-VacationRentals)

- [Things to do in Osprey ](https://www.expedia.com/Things-To-Do-In-Osprey.d55888.Travel-Guide-Activities)

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

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