Legacy Trail Beach Vacations

Book a Beach Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to $1,045 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Top Beach vacation packages in Legacy Trail

Price found within the past 48 hours. Click for updated prices.
Sunseeker Resort Charlotte Harbor
Ocean Club Treasure Island Hotel
Wyndham Grand Clearwater Beach
The Westin Sarasota
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5* Beach vacations in Legacy Trail

Price found within the past 48 hours. Click for updated prices.
Indian Rocks Escape
The Ritz-Carlton, Sarasota
The Gemma by Brightwild
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3 Night Beach vacations in Legacy Trail

Price found within the past 48 hours. Click for updated prices.
Hotel Alba, Tapestry Collection by Hilton
The Avalon Club
Ocean Club Treasure Island Hotel
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See all available trips from Columbus to Legacy Trail
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4 Night Beach vacations in Legacy Trail

Price found within the past 48 hours. Click for updated prices.
Sunseeker Resort Charlotte Harbor
The Residences at Siesta Key Beach by Hyatt Vacation Club
Ocean Club Treasure Island Hotel
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See all available trips from Columbus to Legacy Trail
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Find your perfect Legacy Trail beach vacation

How do I book the best Legacy Trail beach vacation packages?

Life’s a beach when you dive into our brilliant Legacy Trail beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.

How can I find cheap beach vacations in Legacy Trail?

A rental steps from the shore creates an amazingly affordable Legacy Trail beach vacation. Seaside sojourns during low season start from $443. Prices and availability are subject to change. Additional terms may apply.

How can I book the best family beach vacations in Legacy Trail?

With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.

How do I find a Legacy Trail beachfront vacation?

Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.

Can I book a package including a Legacy Trail vacation beach house rental?

Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.

Can I find Legacy Trail beach vacation deals?

Sort your search results by deals to delight in amazing Legacy Trail beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.

Can I book a Legacy Trail beach trip with free cancellation and/or flexible dates?

Just like the Legacy Trail tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.

Why should I book my Legacy Trail beach vacation with Expedia?

Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in Legacy Trail. (OK, maybe not that last part.)

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.