Cudjoe Key Beach Vacations

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

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 . 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.)

Top Beach Cudjoe Key Hotels

ISLAND PARADISE

ISLAND PARADISE

Cudjoe Key
  • 46 min drive from Smathers Beach
Book a stay at this family-friendly resort in Summerland Key. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Florida Keys Beaches and ...
Perfect place to stay
"The home had everything you could need or want in a vacation home. Venture out is a large park with lots of amenities but surprisingly quiet. It’s in a great location to visit Key West or Marathon. I will definitely consider a stay here when I return to the Keys."

Reviewed on Dec 29, 2024

ISLAND PARADISE
RV resort site/rvsite/spot/lot Cudjoe Florida mm23 Key West MONTHLY DISCOUNT

RV resort site/rvsite/spot/lot Cudjoe Florida mm23 Key West MONTHLY DISCOUNT

Cudjoe Key
  • 47 min drive from Smathers Beach
Book a stay at this family-friendly resort in Summerland Key. Enjoy a garden, tennis courts, and a pool table. Popular attractions Florida Keys Beaches and Venture ...
10/10 Exceptional! (2 reviews)
Great location
"We stayed for a week and then my mother in law stayed for 3 weeks. Loved the convenience of the location."

Reviewed on Mar 23, 2025

RV resort site/rvsite/spot/lot Cudjoe Florida mm23 Key West MONTHLY DISCOUNT
Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes

Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes

Cudjoe Key
  • 45 min drive from Smathers Beach
Make the most of this fantastic location, as you'll be near the beach with a holiday stay at this vacation home. An outdoor pool and beach towels are just a ...
9.6/10 Exceptional! (230 reviews)

Travelers like: on the beach, beach towels, outdoor pool

Beautiful place!
"The house is absolutely beautiful! You cannot beat the location. We met the owner while we were at the gated community and he was very accommodating. You can kayak right out back, there are great views from the pool which was kept nice and cool during the summer. We highly recommend this place. Just ..."

Reviewed on Aug 21, 2025

Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes
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.

More vacations you might like

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