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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.
  • Premium Room, 1 King Bed, Lanai, Lagoon View (Kitchenette) | View from room
    Oct 1 - Oct 4

    Kingsail Resort + Flight

    Marathon
    3 nights
    2.0 star property
    8.6/10 - Excellent (1,101 reviews)
    "Nice placeto stay. I had goo time"
    Reviewed July 26, 2026
    Roundtrip • Philadelphia (PHL) - Miami (MIA)
    PHL - MIA • Nonstop MIA - PHL • Nonstop
    $316
    $237
    per traveler
    found 15 hours ago
    Kingsail Resort
  • 3 outdoor pools, cabanas (surcharge), pool umbrellas
    Aug 29 - Sep 4

    Villas At Hawks Cay Resort + Flight

    Marathon
    6 nights
    4.0 star property
    8.0/10 - Very Good (225 reviews)
    "Due to maintenance issues, we had to be moved three times; the rooms were full of dampness and had bathroom leaks—I’m going to post videos of the place as proof. They told me they wouldn't charge us for everything we’d been through, yet after we left, they charged my card anyway. Now I have to file a dispute; unfortunately, it was a very bad stay."
    Reviewed July 28, 2026
    Roundtrip • New York (NYC) - Miami (MIA)
    LGA - MIA • Nonstop MIA - JFK • Nonstop
    Save 100% on your flight
    $2,885
    $1,892
    per traveler
    found 1 day ago
    Villas At Hawks Cay Resort
  • On the beach, sun loungers, beach umbrellas, beach towels
    Oct 1 - Oct 4

    Isla Bella Beach Resort & Spa + Flight

    Marathon
    3 nights
    5.0 star property
    9.2/10 - Wonderful (1,199 reviews)
    "Location was great! Snorkel/ water sports right on the property!"
    Reviewed July 28, 2026
    Roundtrip • Philadelphia (PHL) - Miami (MIA)
    PHL - MIA • Nonstop MIA - PHL • Nonstop
    Save 100% on your flight
    $714
    $507
    per traveler
    found 17 hours ago
    Isla Bella Beach Resort & Spa
  • 3 outdoor pools, cabanas (surcharge), pool umbrellas
    Oct 1 - Oct 4

    Hawks Cay Resort + Flight

    Marathon
    3 nights
    4.0 star property
    8.2/10 - Very Good (1,017 reviews)
    "Room we booked was not available. Took THREE hours (7pm) to get a room but with parking lot view when we booked a water view. Self parking situation is awful. Not enough spots. Management was condescending and took forever to come out and resolve issue the room issue. Front desk staff were non caring, emotionless people. Grounds were nice. Stayed here four years ago and had an issue with room as well but not this bad! Will never stay here again. Management refunded us 50% of the room cost..."
    Reviewed July 27, 2026
    Roundtrip • Philadelphia (PHL) - Miami (MIA)
    PHL - MIA • Nonstop MIA - PHL • Nonstop
    Save 100% on your flight
    $948
    $687
    per traveler
    found 17 hours ago
    Hawks Cay Resort
  • 3 outdoor pools, sun loungers
    Oct 1 - Oct 4

    Tranquility Bay Beachfront Hotel and Resort + Flight

    Marathon
    3 nights
    4.0 star property
    8.8/10 - Excellent (1,000 reviews)
    "Only downside is that the bar closes at 9pm. Everything else is great."
    Reviewed July 27, 2026
    Roundtrip • Philadelphia (PHL) - Miami (MIA)
    PHL - MIA • Nonstop MIA - PHL • Nonstop
    Save 100% on your flight
    $607
    $452
    per traveler
    found 17 hours ago
    Tranquility Bay Beachfront Hotel and Resort

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 $237. 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.)