Legacy Trail Vacation Packages 2025/2026 from $332

Legacy Trail flight + hotel vacation packages

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

Hilton Garden Inn Sarasota - Bradenton Airport

Save 100% on your flight

$332

per person

Jan 30 - Feb 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and perks like free self parking.

Cedar Cove Resort and Cottages

$870

per person

Jan 23 - Jan 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

This resort doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a snack bar/deli are also on offer.

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

$888

per person

Feb 1 - Feb 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Punta Gorda Airport (PGD)

A full-service spa, 7 restaurants, and 2 outdoor pools are all featured at this resort. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls and an off-leash area. Relax with a drink at one of the 2 poolside bars and enjoy the 2 hot tubs and 24-hour gym.

The Residences at Siesta Key Beach by Hyatt Vacation Club

South Village

$1,525

per person

Feb 10 - Feb 15

just found

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

A private beach and an outdoor pool are featured at this smoke-free aparthotel. Relax with free beach cabanas, sun loungers, and beach umbrellas. Enjoy the gym and free perks like continental breakfast and valet parking.

Compass Hotel by Margaritaville Anna Maria Sound

$801

per person

Feb 1 - Feb 8

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.

Top Legacy Trail hotels deals

Kompose Boutique Hotel

965 University Pkwy Sarasota FL

Free Cancellation

Reserve now, pay when you stay

$71 nightly

$81 total

Dec 2 - Dec 3

Total with taxes and fees

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.

Pool

Hot Tub

Tropical Beach Resorts

6717 Sara Sea Circle Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$152 nightly

$172 total

Nov 23 - Nov 24

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.

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

$157 nightly

$177 total

Nov 30 - Dec 1

Total with taxes and fees

Spark by Hilton Sarasota Siesta Key Gateway

6600 S Tamiami Trl Sarasota FL

Free Cancellation

Reserve now, pay when you stay

$119 nightly

$135 total

Nov 29 - Nov 30

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.

Don't see what you're looking for?

See all available properties in Legacy Trail

View all properties

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 $332 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.