Legacy Trail Vacation Packages 2025/2026 from $399

Legacy Trail flight + hotel vacation packages

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

Sleeps 6 Hot Tub Fenced Yard Cozy Chic

Town 'n' Country

Save 100% on your flight

$399

per person

Jan 31 - Feb 3

found 4 hours ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

A full-service spa, free self parking, and laundry facilities are featured at this villa. Barbecue grills and a virtual front desk are also provided.

Kompose Boutique Hotel

Save 100% on your flight

$522

per person

Feb 6 - Feb 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.

The Avalon Club

Save 100% on your flight

$1,154

per person

Jan 20 - Jan 27

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

This aparthotel features a bar/lounge, a poolside bar, and an outdoor pool. Business travelers can take advantage of the business center. There's a gym on site, and a 24-hour front desk and a coffee shop are also provided.

Compass Hotel by Margaritaville Anna Maria Sound

Save 100% on your flight

$678

per person

Feb 4 - Feb 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

This hotel features an outdoor pool, a 24-hour gym, and a restaurant. Relax with a drink at the bar/lounge and enjoy free perks like buffet breakfast and free self parking. Free WiFi in public areas, a snack bar/deli, and a communal living room are also on offer.

BlockHaven near Legoland & Disney

Save 100% on your flight

$470

per person

Feb 1 - Feb 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This vacation home features a garden, laundry facilities, and free self parking. A picnic area and barbecue grills are also provided.

Top Legacy Trail hotels deals

Kompose Boutique Hotel

965 University Pkwy Sarasota FL

Free Cancellation

Reserve now, pay when you stay

$75 nightly

$85 total

Nov 30 - Dec 1

Total with taxes and fees

Pool

Hot Tub

Tropical Beach Resorts

6717 Sara Sea Circle Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$138 nightly

$156 total

Nov 20 - Nov 21

Total with taxes and fees

An outdoor pool, free self parking, and laundry facilities are featured at this aparthotel. WiFi in public areas is free. A garden, a library, and a picnic area are also on offer.

Pool

Kitchen

Carlisle Inn

3727 Bahia Vista Sarasota FL

Free Cancellation

Reserve now, pay when you stay

$125 nightly

$142 total

Nov 23 - Nov 24

Total with taxes and fees

This hotel features an outdoor pool, a 24-hour gym, and a restaurant. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A 24-hour business center, a coffee shop, and a terrace are also on offer.

Pool

Breakfast included

Golden Host Resort - Sarasota

4675 N Tamiami Trl Sarasota FL

Free Cancellation

$90 nightly

$101 total

Nov 23 - Nov 24

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Free self parking, a terrace, and a garden are also offered.

Pool

Parking included

Compass Hotel by Margaritaville Anna Maria Sound

12324 Manatee Avenue West Bradenton FL

Free Cancellation

Reserve now, pay when you stay

$159 nightly

$179 total

Nov 30 - Dec 1

Total with taxes and fees

Pool

Breakfast included

Spark by Hilton Sarasota Siesta Key Gateway

6600 S Tamiami Trl Sarasota FL

Free Cancellation

Reserve now, pay when you stay

$111 nightly

$126 total

Nov 25 - Nov 26

Total with taxes and fees

This hotel features an outdoor pool, a hot tub, and a restaurant. Business travelers can take advantage of the free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy free perks like continental breakfast and free self parking.

Pool

Hot Tub

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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.

Frequently asked questions

How much are vacation packages to Legacy Trail?

Let Travelocity take the worry out of arranging your visit to Legacy Trail. Check out our fabulous $399 package deal and save both time and money. With your hotel and flights locked in, you can channel your energy into planning the fun parts of your escape — like getting to those must-do attractions!

Where can I get the best vacation package deals for Legacy Trail?

Travelocity can help you find a Legacy Trail package deal. With more than 400 airlines and 1,000,000 properties around the world, there's no doubt you'll be able to put together the perfect itinerary.

Why should I book my Legacy Trail vacation package with Travelocity?

Whether you're searching for the ultimate unplugged getaway or you crave the hustle and bustle of the big city, booking everything with Travelocity saves you time, money and hassle. No need to search through hundreds of different websites to find the best deal — our Price Match Guarantee ensures you'll always score the lowest possible price, and our team of customer service experts are available round-the-clock.