A sunny street lined with historic buildings, a 'ONE WAY' sign, and a flagpole with flags.

Key West Beach Vacations

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Top Beach vacation packages in Key West

Price found within the past 48 hours. Click for updated prices.
  • Aug 27 - Aug 31

    The Perry Hotel & Marina Key West + Flight

    Stock Island
    4 nights
    4.0 star property
    9.4/10 - Exceptional (1,290 reviews)
    "This place is AMAZING, everything was perfect. Cleanness, staff, location, outstanding!!"
    Reviewed July 16, 2026
    Roundtrip Boston (BOS) - Key West (EYW)
    BOS - EYW1 stop EYW - BOS1 stop
    $907
    $699
    per traveler
    found 2 days ago
    The Perry Hotel & Marina Key West

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Top Beach Key West Hotels

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.

Find your perfect Key West beach vacation

How do I book the best Key West beach vacation packages?

Life’s a beach when you dive into our brilliant Key West 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 Key West?

A rental steps from the shore creates an amazingly affordable Key West beach vacation. Seaside sojourns during low season start from $699. Prices and availability are subject to change. Additional terms may apply.

How can I book the best family beach vacations in Key West?

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 Key West 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 Key West 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 Key West beach vacation deals?

Sort your search results by deals to delight in amazing Key West 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 Key West beach trip with free cancellation and/or flexible dates?

Just like the Key West 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 Key West 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 Key West. (OK, maybe not that last part.)