Legacy Trail Vacation Packages 2026 from $703

Legacy Trail flight + hotel vacation packages

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

Captiva Beach Resort

South Village

Save 100% on your flight

$703

per person

Apr 15 - Apr 20

found 17 hours 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

$2,348

per person

Mar 14 - Mar 21

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.

The Residences at Siesta Key Beach by Hyatt Vacation Club

South Village

Save 100% on your flight

$1,842

per person

Feb 25 - Mar 2

found 1 day ago

Roundtrip non-stop flight included

Minneapolis (MSP) 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.

Hibiscus Suites - Gateway to Siesta Key

Save 100% on your flight

$733

per person

Apr 15 - Apr 22

found 1 day ago

Roundtrip non-stop 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.

Plaza Beach Hotel Beachfront Resort

Save 100% on your flight

$1,450

per person

Apr 5 - Apr 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

A private beach and an outdoor pool are featured at this hotel. Relax with beach cabanas and sun loungers, and cool off with a drink at the beachside bar. There's fun for all ages with mini golf and a playground, and barbecue grills are available on site.

Top Legacy Trail hotels deals

Kompose Boutique Hotel

965 University Pkwy Sarasota FL

Free Cancellation

Reserve now, pay when you stay

$149 nightly

$168 total

Jan 28 - Jan 29

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

$190 nightly

$214 total

Jan 29 - Jan 30

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

Golden Host Resort - Sarasota

4675 N Tamiami Trl Sarasota FL

Free Cancellation

$77 nightly

$87 total

Jan 27 - Jan 28

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.

Pool

Parking included

Lido Beach Resort

700 Benjamin Franklin Dr Sarasota FL

Free Cancellation

Reserve now, pay when you stay

$419 nightly

$473 total

Feb 1 - Feb 2

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.

On private beach

Pool

Compass Hotel by Margaritaville Anna Maria Sound

12324 Manatee Avenue West Bradenton FL

Free Cancellation

Reserve now, pay when you stay

$195 nightly

$220 total

Jan 26 - Jan 27

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

Pelican Post at Anna Maria Island Inn

202 1st St N Bradenton Beach FL

$213 nightly

$241 total

Jan 26 - Jan 27

Total with taxes and fees

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

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 $703 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.