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A tropical island with clear blue waters, palm trees, and a thatched-roof hut.

Cudjoe Key Beach Vacations

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Top Beach vacation packages in Cudjoe Key

Price found within the past 48 hours. Click for updated prices.
  • Exterior
    Oct 10 - Oct 13

    Atlantic View Luxury Villa with Pool + Flight

    Summerland Key
    3 nights
    3.5 star property
    7.4/10 - Good (3 reviews)
    "Everything the description states is inaccurate. The Host was not available at any time, it plain as day states to contact host for gate code and I notified 24hrs before, I called at 1pm the next day, no response, I called at 3pm and texted that i would arrive at house by 5pm like check in states with no response, I stopped for lunch and my new arrival was at 6pm, which is the time I arrived at the house, I called several times to host for gate code, and no success again, It was frustrating I..."
    Reviewed June 8, 2026
    Roundtrip • New York (NYC) - Miami (MIA)
    JFK - EYW • 1 stop EYW - EWR • 1 stop
    $1,487
    $1,392
    per traveler
    found 21 hours ago
    Atlantic View Luxury Villa with Pool

What to do in Cudjoe Key

Marathon Backcountry Permit

Marathon Backcountry Fishing Charter

$667
per traveler
60% of travelers recommend
Marathon Backcountry Fishing Charter
See all activities in Cudjoe Key

Top Beach Cudjoe Key Hotels

Coffee/tea maker, fridge, microwave, oven

Charming cottages, dockage, pool, just minutes to Key West

Charming cottages, dockage, pool, just minutes to Key West
0.4 mi from Cudjoe Key
8.6 out of 10, Excellent, (130 reviews)
"Great location. Nothing fancy, but a good value. Dock and waterfront access. The pool was lovely, but not heated. Very quiet other than road noise. This unit #6 was the only one without a screened in porch. That would have been a nice addition. Overall a good value. "
Charming cottages, dockage, pool, just minutes to Key West
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.
See all properties in Cudjoe Key

Find your perfect Cudjoe Key beach vacation

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

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

A rental steps from the shore creates an amazingly affordable Cudjoe Key beach vacation. Seaside sojourns during low season start from $1,392. Prices and availability are subject to change. Additional terms may apply.

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

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 Cudjoe Key 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 Cudjoe Key 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 Cudjoe Key beach vacation deals?

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

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