Legacy Trail Vacation Packages 2025/2026 from $500

Legacy Trail flight + hotel vacation packages

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

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Save 100% on your flight

$500

per person

Dec 7 - Dec 12

found 18 hours ago

Roundtrip flight included

Cleveland (CLE) to Punta Gorda Airport (PGD)

A full-service spa, 7 restaurants, and 2 outdoor pools are all featured at this 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.

Sleeps 6 Hot Tub Fenced Yard Cozy Chic

Town 'n' Country

Save 100% on your flight

$523

per person

Nov 6 - Nov 10

found 18 hours ago

Roundtrip flight included

Minneapolis (MSP) to Sarasota (SRQ)

A full-service spa, free self parking, and laundry facilities are featured at this villa. Barbecue grills and a virtual front desk are also provided.

Anna Maria Beach Resort

Save 100% on your flight

$1,277

per person

Nov 6 - Nov 10

found 22 hours ago

Roundtrip non-stop flight included

Cleveland (CLE) to Sarasota (SRQ)

This hotel features an outdoor pool and a hot tub. Guests will appreciate free perks like free self parking and WiFi in public areas. A garden and a picnic area are also provided.

The Residences at Siesta Key Beach by Hyatt Vacation Club

South Village

Save 100% on your flight

$2,487

per person

Nov 22 - Nov 29

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Sarasota (SRQ)

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

The Avalon Club

Save 100% on your flight

$705

per person

Dec 5 - Dec 8

found 1 day ago

Roundtrip flight included

Cleveland (CLE) 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.

Top Legacy Trail hotels deals

Kompose Boutique Hotel

965 University Pkwy, Sarasota, FL

Free Cancellation

Reserve now, pay when you stay

$69 nightly

$78 total

Oct 6 - Oct 7

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

Tropical Beach Resorts

6717 Sara Sea Circle, Siesta Key, FL

Free Cancellation

Reserve now, pay when you stay

$147 nightly

$166 total

Oct 6 - Oct 7

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

Compass Hotel by Margaritaville Anna Maria Sound

12324 Manatee Avenue West, Bradenton, FL

Free Cancellation

Reserve now, pay when you stay

$203 nightly

$229 total

Oct 12 - Oct 13

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

Carlisle Inn

3727 Bahia Vista, Sarasota, FL

Free Cancellation

Reserve now, pay when you stay

$152 nightly

$172 total

Oct 12 - Oct 13

Total with taxes and fees

This hotel features an outdoor pool, a 24-hour gym, and a restaurant. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A 24-hour business center, a coffee shop, and a terrace are also on offer.

Pool

Breakfast included

The Westin Sarasota

100 Marina View Drive, Sarasota, FL

Free Cancellation

Reserve now, pay when you stay

$200 nightly

$226 total

Oct 6 - Oct 7

Total with taxes and fees

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.

Pool

Spa

Tropical Breeze Resort

140 Columbus Blvd., Siesta Key, FL

Free Cancellation

Reserve now, pay when you stay

$223 nightly

$252 total

Oct 6 - Oct 7

Total with taxes and fees

This hotel's 2 outdoor pools and hot tub are among the featured amenities. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a garden, and luggage storage are also on offer.

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 $500 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.