Legacy Trail Vacation Packages 2026 from $436

Legacy Trail flight + hotel vacation packages

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

ChartHouse Clearwater Beach Marina Hotel

Save 100% on your flight

$436

per person

Sep 25 - Sep 28

found 16 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free WiFi. A rooftop terrace is on site, and self parking and a 24-hour front desk are also offered.

Cedar Cove Resort and Cottages

Save 100% on your flight

$791

per person

Sep 11 - Sep 15

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Tampa (TPA)

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.

CW Hotel

Save 100% on your flight

$970

per person

Aug 25 - Aug 30

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) 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

$908

per person

Sep 16 - Sep 21

found 1 day ago

Roundtrip flight included

New York (JFK) 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.

East Gulf Dockside Beach Homes

Save 100% on your flight

$792

per person

Oct 8 - Oct 14

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) to Tampa (TPA)

This apartment features 6 beach bars, laundry facilities, and a virtual front desk. Take advantage of the free self parking.

Top Legacy Trail hotels deals

Hyatt Regency Orlando International Airport

9300 Jeff Fuqua Boulevard Orlando FL

Free Cancellation

Reserve now, pay when you stay

$179 nightly

$201 total

Jul 20 - Jul 21

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an outdoor pool, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a bar/lounge on site, and laundry facilities and concierge services are also provided.

Pool

Free WiFi

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

8800 Vistana Centre Dr Orlando FL

Free Cancellation

Reserve now, pay when you stay

$137 nightly

$154 total

Aug 9 - Aug 10

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

Fontainebleau Miami Beach

4441 Collins Avenue Miami Beach FL

Free Cancellation

Reserve now, pay when you stay

$388 nightly

$442 total

Jul 19 - Jul 20

Total with taxes and fees

This luxury hotel features a full-service spa, a nightclub, and 9 restaurants. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Relax with a drink at one of the 2 poolside bars and enjoy the 4 outdoor pools and gym.

Pool

Hot Tub

Loews Miami Beach Hotel – South Beach

1601 Collins Ave Miami Beach FL

Free Cancellation

Reserve now, pay when you stay

$248 nightly

$283 total

Jul 19 - Jul 20

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

The Island Resort at Fort Walton Beach

Miracle Strip Parkway Southeast, 1500 Fort Walton Beach FL

Free Cancellation

Reserve now, pay when you stay

$196 nightly

$221 total

Aug 17 - Aug 18

Total with taxes and fees

This resort features 3 restaurants, 2 outdoor pools, and a hot tub. There's fun for all ages with a children's club and a children's pool, and families will appreciate the onsite laundry facilities. Relax with a drink at one of the 3 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

$228 nightly

$257 total

Jul 19 - Jul 20

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

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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 $436 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.