Legacy Trail Vacation Packages 2025/2026 from $418

Legacy Trail flight + hotel vacation packages

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

The Suites at Fishermen’s Village- 2 Bedroom Suites

Punta Gorda Isles

Save 100% on your flight

per person

Jul 26 - Jul 31

found 4 hours ago

Roundtrip flight included

Chicago (CHI) to Punta Gorda Airport (PGD)

A marina, 4 restaurants, and an outdoor pool are all featured at this smoke-free condo resort. Relax with a drink at one of the 4 bars/lounges and enjoy free perks like free self parking and WiFi in public areas. A coffee shop, a snack bar/deli, and a picnic area are also on offer.

Coral Reef Beach Resort

Save 100% on your flight

per person

Sep 10 - Sep 15

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Tampa (TPA)

This apartment features 2 outdoor pools and 3 hot tubs. Business travelers can take advantage of the free WiFi in public areas. Free self parking, laundry facilities, and a virtual front desk are also on offer.

The Avalon Club

Save 100% on your flight

per person

Aug 16 - Aug 23

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Tampa (TPA)

This aparthotel features a bar/lounge, a poolside bar, and an outdoor pool. Business travelers can take advantage of the business center. There's a gym on site, and a 24-hour front desk and a coffee shop are also provided.

Barsala At The Wayland Condos

Save 100% on your flight

per person

Aug 28 - Sep 1

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Tampa (TPA)

This aparthotel features an outdoor pool and a gym. WiFi in public areas is free. Barbecue grills and a virtual front desk are also provided.

Sunseeker Resort Charlotte Harbor

Save 100% on your flight

per person

Aug 26 - Aug 29

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Punta Gorda Airport (PGD)

A full-service spa, 7 restaurants, and 2 outdoor pools are all featured at this luxury resort. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls and an off-leash area. Relax with a drink at one of the 2 poolside bars and enjoy the 2 hot tubs and 24-hour gym.

Top Legacy Trail hotels deals

Kompose Boutique Hotel

965 University Pkwy, Sarasota, FL

Free Cancellation

Reserve now, pay when you stay

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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. Enjoy the hot tub and perks like free self parking.

Pool

Hot Tub

Compass Hotel by Margaritaville Anna Maria Sound

12324 Manatee Avenue West, Bradenton, FL

Free Cancellation

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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

Spark by Hilton Sarasota Siesta Key Gateway

6600 S Tamiami Trl, Sarasota, FL

Free Cancellation

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

Pool

Hot Tub

Tropical Beach Resorts

6717 Sara Sea Circle, Siesta Key, FL

Free Cancellation

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This aparthotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Spend a day at the beach surfing, or relax with sun loungers and beach umbrellas. There's an outdoor pool on site, and laundry facilities and concierge services are also offered.

Pool

Kitchen

Golden Host Resort - Sarasota

4675 N Tamiami Trl, Sarasota, FL

Free Cancellation

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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

Embassy Suites by Hilton Sarasota, FL

202 North Tamiami Trail, Sarasota, FL

Free Cancellation

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This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the 24-hour gym and free on-the-go breakfast.

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 $418 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.