Legacy Trail Vacation Packages 2025/2026 from $500

Legacy Trail flight + hotel vacation packages

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

Legacy Hotel at IMG Academy

Save 100% on your flight

per person

Sep 18 - Sep 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free self parking and free WiFi. You'll appreciate the area shuttle, valet parking, and coffee shop/cafe.

Clearwater Suites

Save 100% on your flight

per person

Oct 20 - Oct 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

An outdoor pool, self parking, and laundry facilities are featured at this hotel. Staff at the 24-hour front desk can provide around-the-clock assistance.

Hibiscus Suites - Gateway to Siesta Key

Save 100% on your flight

per person

Oct 25 - Nov 1

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

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

Wyndham Grand Clearwater Beach

Save 100% on your flight

per person

Oct 20 - Oct 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

A full-service spa, 3 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center, express check-out, and valet parking. Enjoy the 24-hour gym and unwind at the bar/lounge and poolside bar.

Ocean Club Treasure Island Hotel

Save 100% on your flight

per person

Oct 16 - Oct 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This hotel features an outdoor pool and a hot tub. Relax with a drink at the poolside bar and enjoy perks like free self parking and free WiFi. A garden, luggage storage, and concierge services 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

$76 nightly

$85 total

Aug 17 - Aug 18

Total includes 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. Enjoy the hot tub and perks like free self parking.

Pool

Hot Tub

Tropical Beach Resorts

6717 Sara Sea Circle, Siesta Key, FL

Free Cancellation

Reserve now, pay when you stay

$159 nightly

$180 total

Sep 1 - Sep 2

Total includes taxes and fees

This aparthotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Spend a day at the beach surfing, or relax with sun loungers and beach umbrellas. There's an outdoor pool on site, and laundry facilities and concierge services are also offered.

Pool

Kitchen

Compass Hotel by Margaritaville Anna Maria Sound

12324 Manatee Avenue West, Bradenton, FL

Free Cancellation

Reserve now, pay when you stay

$182 nightly

$206 total

Aug 21 - Aug 22

Total includes taxes and fees

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.

Pool

Breakfast included

The Westin Sarasota

100 Marina View Drive, Sarasota, FL

Free Cancellation

Reserve now, pay when you stay

$201 nightly

$227 total

Aug 17 - Aug 18

Total includes taxes and fees

A full-service spa, 2 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Enjoy the 24-hour gym and perks like a free beach shuttle. You'll appreciate the a rooftop terrace, bar/lounge, and laundry facilities.

Pool

Spa

Embassy Suites by Hilton Sarasota, FL

202 North Tamiami Trail, Sarasota, FL

Free Cancellation

Reserve now, pay when you stay

$168 nightly

$190 total

Aug 21 - Aug 22

Total includes taxes and fees

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

Pool

Breakfast included

Golden Host Resort - Sarasota

4675 N Tamiami Trl, Sarasota, FL

Free Cancellation

$79 nightly

$90 total

Aug 17 - Aug 18

Total includes 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

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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 $500 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.