Legacy Trail Vacation Packages 2026 from $715

Legacy Trail flight + hotel vacation packages

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

Saddlebrook Resort

Wesley Chapel South

Save 100% on your flight

$715

per person

Aug 16 - Aug 23

found 1 day ago

Roundtrip flight included

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

A golf course, 3 restaurants, and 2 outdoor pools are all featured at this smoke-free resort. Family-friendly amenities include a children's pool and kid-friendly dining, along with hiking/biking trails. Enjoy the 15 outdoor tennis courts and perks like free WiFi.

CW Hotel

Save 100% on your flight

$836

per person

Jul 21 - Jul 25

found 16 hours ago

Roundtrip flight included

Dallas (DFW) to Tampa (TPA)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the hot tub and perks like free WiFi. There's a poolside bar on site, and a 24-hour front desk and concierge services are also provided.

The Residences at Siesta Key Beach by Hyatt Vacation Club

South Village

Save 100% on your flight

$1,414

per person

Aug 25 - Aug 29

found 1 day ago

Roundtrip non-stop flight included

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

A private beach and an outdoor pool are featured at this smoke-free hotel. Relax with free beach cabanas, sun loungers, and beach umbrellas. Enjoy the gym and free perks like continental breakfast and valet parking.

Cedar Cove Resort and Cottages

Save 100% on your flight

$794

per person

Aug 7 - Aug 11

found 16 hours ago

Roundtrip flight included

Dallas (DFW) 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.

Landing St. Petersburg Near South Branch Potomac River

Save 100% on your flight

$913

per person

Aug 8 - Aug 15

found 4 hours ago

Roundtrip flight included

New York (NYC) to Tampa (TPA)

This aparthotel features an outdoor pool and a gym. Enjoy the a rooftop terrace and perks like free self parking and free WiFi. Dry cleaning, barbecue grills, and a virtual front desk 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

$90 nightly

$101 total

Jun 3 - Jun 4

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

Compass Hotel by Margaritaville Anna Maria Sound

12324 Manatee Avenue West Bradenton FL

Free Cancellation

Reserve now, pay when you stay

$177 nightly

$200 total

Jun 9 - Jun 10

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

Golden Host Resort - Sarasota

4675 N Tamiami Trl Sarasota FL

Free Cancellation

$75 nightly

$85 total

Jun 7 - Jun 8

Total with taxes and fees

This hotel features 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

Tropical Beach Resorts

6717 Sara Sea Circle Siesta Key FL

$209 nightly

$236 total

Jun 8 - Jun 9

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

Spark by Hilton Sarasota Siesta Key Gateway

6600 S Tamiami Trl Sarasota FL

Free Cancellation

Reserve now, pay when you stay

$130 nightly

$147 total

Jun 4 - Jun 5

Total with taxes and fees

This hotel features a bar/lounge, a poolside bar, and an outdoor pool. Business travelers can take advantage of the free WiFi in public areas. Enjoy the hot tub and free perks like continental breakfast and free self parking.

Pool

Hot Tub

Siesta Key Beach Resort and Suites

5311 Ocean Blvd Siesta Key FL

$241 nightly

$273 total

Jun 3 - Jun 4

Total with taxes and fees

This resort features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the hot tub and perks like free WiFi. Self parking, a terrace, and a garden are also offered.

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 $715 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.