Legacy Trail Vacation Packages 2026 from $521

Legacy Trail flight + hotel vacation packages

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

The Westin Sarasota

Central Sarasota

Save 100% on your flight

$521

per person

Sep 6 - Sep 12

found 1 day ago

Roundtrip non-stop flight included

Hartford (BDL) to Tampa (TPA)

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.

Mar Bay Motel &Suites

Save 100% on your flight

$527

per person

Jul 20 - Jul 25

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.

CW Hotel

$846

per person

Jul 19 - Jul 24

found 1 hour ago

Roundtrip non-stop flight included

Hartford (BDL) to Tampa (TPA)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the gym and perks like free WiFi. You'll appreciate the hot tub, poolside bar, and concierge services.

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$1,372

per person

Sep 5 - Sep 12

found 15 hours ago

Roundtrip flight included

Hartford (BDL) to Tampa (TPA)

This hotel features an outdoor pool and a gym. Enjoy the hot tub and perks like free self parking and free WiFi. A poolside bar, a 24-hour front desk, and a garden are also provided.

The Avalon Club

Save 100% on your flight

$1,147

per person

Aug 16 - Aug 22

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This aparthotel features a bar/lounge, a poolside bar, and an outdoor pool. There's a gym on site, and a 24-hour front desk and a coffee shop are also provided.

Top Legacy Trail hotels deals

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

8800 Vistana Centre Dr Orlando FL

Free Cancellation

Reserve now, pay when you stay

$135 nightly

$152 total

Jul 14 - Jul 15

Total with taxes and fees

This smoke-free aparthotel features 3 restaurants, 6 outdoor pools, and 10 outdoor tennis courts. There's fun for all ages with a free kid's club and mini golf, and barbecue grills are available on site. Enjoy the 8 hot tubs and perks like free WiFi.

Pool

Hot Tub

Loews Miami Beach Hotel – South Beach

1601 Collins Ave Miami Beach FL

$248 nightly

$283 total

Jun 16 - Jun 17

Total with taxes and fees

A full-service spa, 4 restaurants, and 2 hot tubs are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, express check-out, and valet parking. You'll appreciate the outdoor pool, bar/lounge, and limo/town car service.

Pool

Hot Tub

Fontainebleau Miami Beach

4441 Collins Avenue Miami Beach FL

Free Cancellation

Reserve now, pay when you stay

$354 nightly

$404 total

Jun 16 - Jun 17

Total with taxes and fees

This luxury hotel features a full-service spa, a nightclub, and 9 restaurants. Families will appreciate the children's pool, onsite laundry facilities, and babysitting. Enjoy the 3 outdoor pools and perks like free WiFi.

Pool

Hot Tub

DoubleTree by Hilton at the Entrance to Universal Orlando

5780 Major Blvd Orlando FL

Free Cancellation

$89 nightly

$101 total

Jul 12 - Jul 13

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an outdoor pool, and a 24-hour gym. There's fun for all ages with a children's pool and an arcade/game room, and families will appreciate the onsite laundry facilities. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.

Pool

Hot Tub

The Grove Resort & Water Park Orlando

14501 Grove Resort Avenue Winter Garden FL

Free Cancellation

Reserve now, pay when you stay

$248 nightly

$279 total

Jun 16 - Jun 17

Total with taxes and fees

Free water park access, 3 restaurants, and 6 outdoor pools are all featured at this resort. Bring the family and enjoy the lazy river, children's club, and mini golf. Enjoy the 2 hot tubs and perks like free WiFi.

Pool

Hot Tub

Hilton Daytona Beach Oceanfront Resort

100 N Atlantic Ave Daytona Beach FL

Free Cancellation

Reserve now, pay when you stay

$118 nightly

$133 total

Jul 5 - Jul 6

Total with taxes and fees

4 restaurants, 2 outdoor pools, and 2 hot tubs are among this hotel's featured amenities. Traveling on business? Take advantage of the 24-hour business center, express check-in, and valet parking. Enjoy the 24-hour gym and visit the 2 beach bars and poolside bar for drinks.

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 $521 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.