Legacy Trail Vacation Packages 2026 from $534

Legacy Trail flight + hotel vacation packages

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

CW Resort

$534

per person

Jan 16 - Jan 19

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Hibiscus Suites - Gateway to Siesta Key

$750

per person

Jan 8 - Jan 15

found 1 day ago

Roundtrip 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.

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$1,110

per person

Feb 5 - Feb 9

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Crystal Palms Beach Resort

Sunshine Beach

$795

per person

Jan 28 - Feb 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This aparthotel features an outdoor pool and a hot tub. Dry cleaning, laundry facilities, and barbecue grills are also on offer.

Sailport Waterfront Suites

Rocky Point

$813

per person

Feb 3 - Feb 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This aparthotel features a restaurant, an outdoor pool, and a bar/lounge. Business travelers can take advantage of the 24-hour business center. You'll appreciate the gym, poolside bar, and snack bar/deli.

Top Legacy Trail hotels deals

Hyatt Regency Orlando International Airport

9300 Jeff Fuqua Boulevard Orlando FL

Free Cancellation

Reserve now, pay when you stay

$215 nightly

$242 total

Nov 23 - Nov 24

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

$111 nightly

$125 total

Dec 15 - Dec 16

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

Marriott's Grande Vista

5925 Avenida Vista Orlando FL

Free Cancellation

Reserve now, pay when you stay

$96 nightly

$108 total

Dec 10 - Dec 11

Total with taxes and fees

This smoke-free aparthotel features a golf course, a full-service spa, and 3 restaurants. There's fun for all ages with mini golf and a children's pool, and barbecue grills are available on site. Enjoy the 4 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

$93 nightly

$104 total

Nov 23 - Nov 24

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

Fontainebleau Miami Beach

4441 Collins Avenue Miami Beach FL

Free Cancellation

Reserve now, pay when you stay

$368 nightly

$420 total

Nov 19 - Nov 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

Westgate Lakes Resort & Spa Universal Studios Area

9500 Turkey Lake Rd Orlando FL

$116 nightly

$131 total

Nov 16 - Nov 17

Total with taxes and fees

This smoke-free hotel features a full-service spa, a water park, and a marina. There's fun for all ages with mini golf and a children's pool, and barbecue grills are available on site. Enjoy the 7 outdoor pools and get free valet parking.

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 $534 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.