Cudjoe Key Rentals

Compare 6 vacation rentals.
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Make Cudjoe Key your next getaway

If the sun, sand, and water of the Florida Keys is calling your name, consider spending your next vacation on Cudjoe Key, FL, where you'll find all the water sports the Keys are known for in a spot that's a bit less traveled, giving you a chance to wrap yourself in Florida's beautiful natural surroundings and reconnect with your family, friends and yourself. What better way to revel in the soothing benefits of the Keys than to stay in one of our cozy vacation rentals?

Explore Cudjoe Key house rentals, and more


House rentals

View 6 House rentals

Popular amenities for Cudjoe Key vacation rentals

Dog-friendly Hot tub Internet
Dock Holiday
2 Bedroom | 2 Bath | Sleeps 4

Dock Holiday - Cudjoe Key, FL

$336 avg / night
Hawkins Lookout
3 Bedroom | 2.5 Bath | Sleeps 6

Hawkins Lookout - Cudjoe Key, FL

$355 avg / night
Parrotfish Point
3 Bedroom | 2 Bath | Sleeps 6

Parrotfish Point - Cudjoe Key, FL

$417 avg / night
The Mermaid Manor
4 Bedroom | 4 Bath | Sleeps 10

The Mermaid Manor - Cudjoe Key, FL

$634 avg / night
Key Lime Time
2 Bedroom | 2 Bath | Sleeps 6

Key Lime Time - Cudjoe Key, FL

$412 avg / night

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Recent Cudjoe Key guest reviews

This house has everything you would need from pots, pans, spices, kitchen equipment, outside chairs, snorkeling gear and even water shoes. Very nice rental
Kristin F. | May 2024
We were looking for a property outside of key west where it’s wasn’t as busy and we found it. We enjoyed the amenities of the VO resort as well as a fishing charter at the same location. After a busy day are key west we were able to come back to dock holiday and relax. And enjoyed seeing the manatees that would show up in the channel on occasion.
Ron G. | Mar 2024
This home was fantastic! Aside from the trouble we had with getting a response from the management company on a couple of issues upon arrival(the owner quickly took care of the issues after a couple of weeks waiting for Vacasa), our stay was great! The house was clean and decorated beautifully. Location was fantastic, right on the water with beautiful sunsets every night. Close to some of the best restaurants in the keys! The small plunge pool was refreshing on those hot days. It was nice to be able to park under the house in the shade as well. Very peaceful setting.
Cindi T. | Mar 2024
Cudjoe Key vacation rental FAQ

Yes, 11 of our Cudjoe Key homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 25 of our Cudjoe Key vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >

Some of the most popular amenities in our Cudjoe Key vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Cudjoe Key team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Cudjoe Key, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning

Where is Cudjoe Key, FL?

This small key is located between Sugarloaf Key and Big Pine Key in the lower reaches of Florida's famous island chain. To get here, simply follow US Highway 1 from Miami for 140 miles, or make the 20-mile drive from diverse and exciting Key West if you're coming the other way.

This island is also home to the Cudjoe Key Air Force Station, where you will see the notorious Fat Albert. A long white blimp, Fat Albert is used by the US Federal government to patrol boat traffic and aircraft using radar devices.

Things to Do on Cudjoe Key, FL

Get out on the water with a charter excursion or rent a boat and captain your own ship. Drop your line starboard and catch a tarpon or shark, or get beneath the surface of the sparkling waters and do some snorkeling or diving. Paddle your way through the channels in a kayak, or rent a bike and peddle peacefully through a tropical paradise.

Looking for relaxation? Indulge yourself at Angelic Moon Holistic Day Spa. The only green-focused day spa in the Keys, Angelic Moon uses natural, organic, fair-trade ingredients in all their treatments, with an eye on a whole-person approach to bringing you to a state of blissful relaxation and rejuvenation. 

Take an easy, breezy day trip to Summerland Key, four miles away, for an eco tour or to check out the reefs. No matter how you fill your days on Cudjoe Key, you'll be happy to return to your own private vacation rental to savor a freshly cooked meal and enjoy the comforts of home.