Legacy Trail Vacation Packages 2026 from $421

Legacy Trail flight + hotel vacation packages

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

voco Sarasota by IHG

Central Sarasota

$421

per person

May 1 - May 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This hotel features an outdoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 3 conference rooms, express check-out, and laundry service. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.

Mar Bay Motel &Suites

Save 100% on your flight

$513

per person

Apr 30 - May 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. A garden, a library, and a picnic area are also on offer.

Captiva Beach Resort

South Village

Save 100% on your flight

$802

per person

Apr 16 - Apr 21

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Sarasota (SRQ)

A private beach and an outdoor pool are featured at this smoke-free condo. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area, laundry facilities, and barbecue grills are also on offer.

Cedar Cove Resort and Cottages

Save 100% on your flight

$791

per person

May 1 - May 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

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.

Hotel Tampa Riverwalk

Downtown Tampa

Save 100% on your flight

$942

per person

Apr 29 - May 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

This hotel features 2 bars/lounges, a poolside bar, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Enjoy the outdoor pool and conveniences like a 24-hour front desk and wedding services.

Top Legacy Trail hotels deals

Kompose Boutique Hotel

965 University Pkwy Sarasota FL

Free Cancellation

Reserve now, pay when you stay

$144 nightly

$163 total

Mar 19 - Mar 20

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.

Golden Host Resort - Sarasota

4675 N Tamiami Trl Sarasota FL

Free Cancellation

$96 nightly

$108 total

Mar 1 - Mar 2

Total with taxes and fees

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.

Tropical Beach Resorts

6717 Sara Sea Circle Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$309 nightly

$349 total

Mar 3 - Mar 4

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.

Compass Hotel by Margaritaville Anna Maria Sound

12324 Manatee Avenue West Bradenton FL

Free Cancellation

Reserve now, pay when you stay

$294 nightly

$332 total

Mar 1 - Mar 2

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.

Lido Beach Resort

700 Benjamin Franklin Dr Sarasota FL

Free Cancellation

Reserve now, pay when you stay

$619 nightly

$699 total

Mar 4 - Mar 5

Total with taxes and fees

This smoke-free resort features a private beach, 2 outdoor pools, and a restaurant. Spend a day at the beach surfing, or relax with beach cabanas and sun loungers. Enjoy the gym and perks like free WiFi.

Spark by Hilton Sarasota Siesta Key Gateway

6600 S Tamiami Trl Sarasota FL

Free Cancellation

Reserve now, pay when you stay

$220 nightly

$249 total

Mar 1 - Mar 2

Total with taxes and fees

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.

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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 $421 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.