Cudjoe Key holiday homes

We found 760 holiday rentals — enter your dates for availability

Select from 205 homes, 40 cottages and other holiday rentals in Cudjoe Key to find one that's perfect for your trip. Whether you’re staying in a holiday home with your children or with friends, you'll have the best amenities for spending time at your home away from home, which might include parking and a hot tub. At the end of the day, you're sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Take in the tropical beauty of Cudjoe Key

The ocean views and other outdoor surroundings create an inviting atmosphere in Cudjoe Key. Well known for its cycling, seafood restaurants and boating, this welcoming city won't disappoint. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Cudjoe Key

Are you hoping to discover things to do while you're in town? Travellers enjoy fun activities like cycling, boating and fishing. Venture out of your holiday home and experience everything that makes Cudjoe Key a fun spot to go on holiday. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Key West Golf Club (16.7 mi / 26.9 km)
  • Blue Hole (8 mi / 12.9 km)

Exploring the natural landscape of Cudjoe Key

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Cudjoe Key is a great spot to appreciate mother nature. These are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Upper Sugarloaf Key (2 mi / 3.3 km)
  • Florida Keys Beaches (5.4 mi / 8.8 km)
  • Sugarloaf Beach (5.8 mi / 9.3 km)
  • Saddlebunch Keys (8.3 mi / 13.3 km)
  • Cook Island (8.4 mi / 13.5 km)
  • Looe Key National Marine Sanctuary (10.3 mi / 16.6 km)

How to get to and around Cudjoe Key

The nearest airport is in Key West, FL (EYW-Key West Intl.), located 18.1 mi (29.1 km) from the city centre. If you can't find a flight that's convenient for your trip, you could book a flight to Marathon, FL (MTH-Florida Keys Marathon), which is 28.3 mi (45.5 km) away.

Frequently asked questions

What is the best area to stay in Cudjoe Key when booking a holiday home?
If you’re planning a getaway in Cudjoe Key, Cutthroat Harbour Estates is among the most sought-after destinations to stay. No matter your travel style, Bookabach is sure to have a property here that’s right for you.
What is the most popular type of holiday home accommodation in Cudjoe Key?
Houses are the most popular kind of holiday home in Cudjoe Key, according to our data. Even if you have something else in mind, Bookabach has properties in loads of shapes and sizes. Browse our many options to find your perfect match.
How much does it cost to rent a holiday home in Cudjoe Key?
Different things determine what you’ll pay for your holiday home in Cudjoe Key, such as the time of year, property type and length of stay. Still, all of our holiday homes have something in common — unbeatable value. Just enter your travel dates to find your ideal match.
How much does it cost to rent a beach house in Cudjoe Key?
Prices for beach houses in Cudjoe Key differ depending on the type and size of the property and when you plan to travel. Just enter your travel dates into Bookabach and the number of guests to view your home options and prices. From there you can use our filter tool to refine your search results by amenities, ratings, nearby activities and more.
Are there pet-friendly holiday homes in Cudjoe Key?
Pack a suitcase for your puppy dog because Cudjoe Key has 60 holiday homes that put out the welcome mat to pets. Let your four-legged buddy join in with the family fun at one of our pet-friendly holiday homes on Bookabach. Simply enter your travel dates then check our “Pets allowed” filter box.
Can I rent a house with a pool in Cudjoe Key?
Mark the “pool” box in our filter tool and select from 23 houses with private pools in Cudjoe Key on Bookabach. Ball games, gentle soak or noodle joust? How you spend your leisure time is up to you when your Bookabach holiday property boasts a swimming pool.
What are popular home amenities in Cudjoe Key?
Some of the most popular home amenities people look for in Cudjoe Key are a nearby waterfront, a firepit and a garden. Whether you’re on the road with friends, family or even pets, Bookabach holiday properties provide the best amenities for starting a new adventure with the people that matter most.
Are there large group holiday homes in Cudjoe Key?
With six holiday homes that can sleep 10 guests or more in Cudjoe Key, you don’t have to leave anyone off your invite list. From family get-togethers to special events like anniversary parties and weddings, Bookabach can help you find a large group home to match the occasion.
Are there holiday homes in Cudjoe Key that welcome kids?
Cudjoe Key has 60 family-friendly holiday homes to choose from. And tracking down a stay that welcomes little ones is simple with our “Properties good for families” filter. On top of having the whole place to yourselves, you’ll enjoy access to perks and amenities such as extra bedrooms, yards and private pools.
What are the top attractions for families in Cudjoe Key?
Keeping the kiddos entertained during your Cudjoe Key holiday is simple with these cool family-friendly attractions:

  • Florida Keys Beaches
  • Sugarloaf Beach
  • National Key Deer Refuge Visitor Centre

Can I find two-bedroom holiday homes in Cudjoe Key?
Choose from 17 two-bedroom homes in Cudjoe Key. Put the kids in the second room or maybe fill it with a couple of your nearest and dearest friends. There’s a comfy spot for whoever’s fortunate enough to be coming along for the ride.
Are there holiday homes with WiFi in Cudjoe Key?
You can choose from 24 holiday homes with WiFi in Cudjoe Key. If you want to disconnect from the world while on holiday, but still want to be connected to the web, these properties have just what you need. Narrow your search by applying the WiFi filter on Bookabach.
How can I find holiday homes with air conditioning in Cudjoe Key?
Cudjoe Key has 58 holiday homes where you can unwind in air-conditioned comfort. To find a stay on Bookabach that comes with this amenity, enter your desired travel dates and use the filter tool to select the “air conditioning” box.
How old do you have to be to rent a holiday home in Cudjoe Key?
It’s a good idea to check with the Cudjoe Key holiday property you’d like on Bookabach as the minimum age differs. However, generally it’s 16, 18 or 21.
How long can I rent a holiday home in Cudjoe Key for?
It’s up to the Cudjoe Key property. To view all available options offering extended stays, simply enter your travel dates and guest number into Bookabach. Look forward to having the entire place to yourself, as well as comforts such as air conditioning, a fully-equipped kitchen and an outdoor space where the kids can run around and play. Keep your eyes open for long-term stays that offer discounted weekly or monthly prices.

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