Legacy Trail Vacation Packages 2026 from $463

Legacy Trail flight + hotel vacation packages

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

Mar Bay Motel &Suites

Save 100% on your flight

$463

per person

Mar 8 - Mar 13

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. A garden, a library, and a picnic area are also on offer.

voco Sarasota by IHG

Central Sarasota

Save 100% on your flight

$743

per person

Mar 7 - Mar 12

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

This hotel features an outdoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 3 conference rooms, express check-out, and laundry service. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.

FUSION Resort Waterfront Suites

Save 100% on your flight

$1,067

per person

Mar 25 - Mar 30

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

This aparthotel features an outdoor pool and a rooftop terrace. Enjoy the hot tub and perks like free self parking and free WiFi. A 24-hour business center, luggage storage, and concierge services are also on offer.

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$1,548

per person

Apr 4 - Apr 11

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.

Plaza Beach Hotel Beachfront Resort

Save 100% on your flight

$1,416

per person

Mar 25 - Mar 30

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

A private beach and an outdoor pool are featured at this hotel. Relax with beach cabanas and sun loungers, and cool off with a drink at the beachside bar. There's fun for all ages with mini golf and a playground, and barbecue grills are available on site.

Top Legacy Trail hotels deals

Kompose Boutique Hotel

965 University Pkwy Sarasota FL

Free Cancellation

Reserve now, pay when you stay

$100 nightly

$113 total

Jan 21 - Jan 22

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

$189 nightly

$214 total

Jan 21 - Jan 22

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

Golden Host Resort - Sarasota

4675 N Tamiami Trl Sarasota FL

Free Cancellation

$84 nightly

$95 total

Jan 21 - Jan 22

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

$193 nightly

$218 total

Jan 27 - Jan 28

Total with 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

Lido Beach Resort

700 Benjamin Franklin Dr Sarasota FL

Free Cancellation

Reserve now, pay when you stay

$329 nightly

$372 total

Jan 25 - Jan 26

Total with taxes and fees

This smoke-free resort features a private beach, 2 outdoor pools, and a restaurant. Spend a day at the beach surfing, or relax with beach cabanas and sun loungers. Enjoy the gym and perks like free WiFi.

On private beach

Pool

Carlisle Inn

3727 Bahia Vista Sarasota FL

Free Cancellation

Reserve now, pay when you stay

$219 nightly

$247 total

Jan 21 - Jan 22

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

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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 $463 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.