Cudjoe Key Rentals

Compare 7 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 7 House rentals

Cudjoe Key vacation rentals for every getaway

Dog-friendly Hot tub Internet
Parrotfish Point
3 Bedroom | 2 Bath | Sleeps 6

Parrotfish Point - Cudjoe Key, FL

$345 avg / night
The Blue Marlin
2 Bedroom | 2.5 Bath | Sleeps 6

The Blue Marlin - Cudjoe Key, FL

$138 avg / night
Hawkins Lookout
3 Bedroom | 2.5 Bath | Sleeps 6

Hawkins Lookout - Cudjoe Key, FL

$250 avg / night
Dock Holiday
2 Bedroom | 2 Bath | Sleeps 4

Dock Holiday - Cudjoe Key, FL

$249 avg / night
Key Lime Time
2 Bedroom | 2 Bath | Sleeps 6

Key Lime Time - Cudjoe Key, FL

$305 avg / night

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Recent Cudjoe Key vacation rental reviews

Dock Holiday offered a fantastic location with quick access out of the canal at Venture Out into Kemo Channel. Stayed for a week and the home was just perfect for our fishing/ lobstering adventures.
Dom V. | Aug 2023
Nice two bedroom layout, great kitchen, good airconditioning.
Maurice J. | Aug 2023
The house was terrific. Amongst many guests we had my 3 siblings and their spouses. The room layout was perfect for 4 couples. Neighbors were great. Highly recommended.
Randy B. | May 2023
Cudjoe Key vacation rental FAQ

Yes, 9 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. 21 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.