Cudjoe Key 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?

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Popular amenities for Cudjoe Key vacation rentals

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Dog-friendly Internet Pool

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Recent Cudjoe Key guest reviews

From the moment we arrived, this home felt like exactly what we’d been searching for. We’ve stayed at other monthly rentals and been let down by sparse kitchens and under-equipped spaces, but not here. The kitchen had everything we needed, the spaces were comfortable and functional, and the home truly felt like a home - because for Pete, the owner, it is one. Pete was an absolute pleasure to work with. When I had a small health emergency during our stay, he was incredibly gracious and accommodating, extending our time without hesitation. That kind of generosity says everything. You can tell this isn’t just an investment property to him - it’s a place he genuinely loves and cares for. The thoughtful upgrades and attention to detail throughout the home reflect that, and it shows in every corner. My husband fell in love with the dock and the warmth of the neighborhood - the kind of place where neighbors actually wave and stop to chat. Our dog had the time of her life swimming and watching fish from the dock, which honestly became one of our favorite daily rituals too. We even made friends with the sea turtles that would drift by throughout the day. We brought our boat and were thrilled to find a ramp just across the bay. Sunset cruises quickly became our evening tradition, though competing with the view from the porch was nearly impossible. Those sunsets were something else. As a remote worker, I genuinely appreciated having a solid desk area, but I’d often migrate to the porch, which stayed comfortable and breezy throughout the day. Productive and peaceful - a rare combo! The location is ideal. Quiet enough to truly decompress, but about 25 minutes to Key West and close to some great restaurants and bars when you want a night out. It’s the perfect home base for exploring the Keys without feeling like you’re in the middle of everything. We will absolutely be back. Highest recommendation.
Becca . | Jun 2026
Cudjoe Key vacation rental FAQ

Yes. 18 of our Cudjoe Key vacation rentals have internet access, so you can stay connected throughout your trip.

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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 the 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.

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No problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for Cudjoe Key, log in to Trip Manager to explore the options available for your specific trip.

Book confidently. Stay comfortably.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
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Seamless check-in
Vacasa Guest Value Prop Icons 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.