Discover a selection of 500 vacation rentals in Cudjoe Key, FL that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $125 per night, and houses and cottages are popular options for a stay in Cudjoe Key. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Cudjoe Key
Destination guide

Your key to a perfect beach vacation

Almost at the end of scenic Highway 1 that meanders through the paradise that is the Florida Keys, you'll find tranquil Cudjoe Key. Less well known than neighboring Sugarloaf Key and Big Pine Key, the island is home to beautiful stretches of pristine sands along shallow blue waters. Just 19 miles from hopping Key West, you'll have the best of both worlds _ world-class nightlife when you venture out and perfect serenity when you come home. The warm sea air and soothing surf make a Cudjoe Key vacation rental the picture-perfect beach vacation you've been dreaming of.

Things to do

Blimps, bands, and blue holes

There's no shortage of quirky sights near Cudjoe Key. Looe Key National Marine Preserve, popular for diving and snorkeling, hosts a one-of-a-kind underwater music festival each year. Cudjoe Key is also home to Fat Albert, the landmark grounded white blimp that patrols boat traffic and broadcasts U.S. TV to Cuba. The Blue Hole, the only freshwater lake in the Keys, lets you get up close and personal with turtles, alligators, and exotic birds. In half an hour you can be at the Southernmost Point in the U.S. and enjoying the sunset festival at Key West's Mallory Square.


Beach, beach, and more beach

The beach is the heart of Cudjoe Key life, and it's easy to see why. The sands are the perfect spot to work on your tan or catch the breathtaking sunset (the clothing-optional set should check out Geiger Key Abandoned Beach). The water is equally enticing, whether you're in it or on it. Rent a boat, kayak, or canoe and explore the wildlife of the surrounding channels. Charter fishing trips will help you catch your dinner, while snorkeling and diving trips are on hand if you just want to play. For an adrenaline rush and killer views, you can't top skydiving.

Natural features

See you later, alligator

Palm trees and blue skies will greet you at every turn when you book a Cudjoe Key vacation rental. If you can tear yourself away from the perfect beaches, there's plenty of other nature to explore. You'll find exotic plant and animal species that you won't see anywhere else in the U.S., including the namesake deer at the Key Deer Refuge (also home to turtles, gators, and colorful birds). The Florida Keys are also the only place in the country you can find the American crocodile. Coconuts and key limes are everywhere, making for some killer pie options.

How to get there

How to get to and around Cudjoe Key

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

What are the top vacation rentals in or near Cudjoe Key?

Whatever your vacation needs, you'll find a rental property in or around Cudjoe Key that fits you like a glove. Here are some of our favorites:

  • Make use of handy amenities like water sports equipment and cookware, dishware and utensils at "Sombrero Beach Home On Canal With Private Dock And Heated Pool". Located around 25 miles from Cudjoe Key, this unique option has 3 bedrooms and good guest reviews.
  • Alternatively, make yourself comfy at "Key West Oasis, Seperate Cottage". Located around 20 miles from the heart of Cudjoe Key, it has 2 bedrooms and features a living room and a microwave oven.

For even more great options, use the search bar at the top of the page to find the perfect Cudjoe Key vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Cudjoe Key?

Get away from the treadmill of daily life at one of our weekend getaways in or near Cudjoe Key. Whether you want to catch up with friends or spend valued time with the fam, there'll be something to suit your needs. Here are some of our most popular options:

  • "Kayak Boot Key Harbor, 75ft Canal Home" is perfect for a few days of fun and relaxation. It features a host of amenities, such as beach towels and internet services, and is located 25 miles to the east of Cudjoe Key.
  • Alternatively, create memories with your favorite people at "Wow Private Pool, Ocean Front", which is around 30 miles to the east of Cudjoe Key. Take advantage of air conditioning, WiFi and more here.

Can I find studio apartments for rent in and around Cudjoe Key?

Yes, you can! If you're tracking down a simple but stylish stay, you can't go past a studio apartment. These compact properties exude charm and are often located in the middle of town. Check out the following options in or near Cudjoe Key:

  • Get away on your own or take a few pals to "Waterfront Luxury Living Inside And Out". You'll have lots of amenities at your fingertips, including a nearby marina and air conditioning.
  • Another fantastic property is "Condo In Old Town Key West's Truman Annex". Don't be fooled by its modest size — this comfortable apartment is filled with convenient amenities like an ocean view, coffee and tea making facilities and much more.

Can I find short term rentals in or near Cudjoe Key?

Whether you're seeking a studio apartment for you and a friend or a house big enough for the whole family, there's no shortage of short-term rentals in and around Cudjoe Key. These retreats make a comfortable base for a quick visit:

  • For a memorable vacation, it's hard to go past "Coconut Sunsets And Open Water Views". It's near the center of Cudjoe Key, in addition to lots of things to put on your itinerary.
  • Alternatively, book a few nights at "Cloud 9 ~ It's Heaven On Earth In This 3b". This conveniently located property will feel like your home away from home.

What are the best romantic weekend getaways in or near Cudjoe Key?

Forget flowers and chocolates. Sometimes all you need is to escape for a weekend, just you and your sweetie. At Vrbo, we've got romantic getaways in and around Cudjoe Key that would make Cupid envious. Here are some we think you'll adore:

  • Put on some mellow music and slow dance the nights away at "Sombrero Beach Home On Canal With Private Dock And Heated Pool". Around 25 miles from Cudjoe Key, this property has everything you need for a romantic getaway, including a restaurant dining guide and air conditioning.
  • "Key West Oasis, Seperate Cottage" is another top option that's sure to impress. It's around 20 miles from Cudjoe Key and comes with beauty services and outdoor furniture.

Are there mansions for rent in or near Cudjoe Key?

Nothing says "best vacation evvv-er" like staying in a mansion. Spoil the family with a truly unforgettable escape at one of these mansions for rent in or near Cudjoe Key:

  • Charm, character and style — "Noona's Mansion @ The Annex Grand Home And Pool + Last Key Services" has it all with some to spare. Approximately 20 miles southwest of Cudjoe Key and offering a swimming pool and beauty services, this showstopper is tough to beat.
  • With a swimming pool, golf and a wealth of other top-rated amenities, "Captiva" ~ , Azul Historic Mansion Suite With Community Pool" will get your team's tick of approval. This plush retreat is around 20 miles to the southwest of Cudjoe Key.

What are the best large group vacation rentals in or near Cudjoe Key?

Check out these large group vacation rentals in or near Cudjoe Key and forget about leaving anyone off your guest list:

  • Offering comfort, space and privacy, you'll get everyone's nod of approval at "New Photos: Drive To Your Getaway". Up to 12 people can be accommodated at this escape which has 5 bedrooms, a swimming pool and a water view. It's around 20 miles to the southwest of Cudjoe Key.
  • Nothing's more important than spending time with the people you love, and "Spectacular Waterfront Estate" makes it easy to do that. Located around 25 miles to the east of Cudjoe Key, as many as 14 people can stay in this vacation rental which has 6 bedrooms. A swimming pool and a kitchen are among the many amenities you'll have at hand.

What are the best houses for rent with a pool in or near Cudjoe Key?

A pool is often a must-have amenity for any unforgettable vacation. Enjoy splashing around or simply unwinding by the water at one of these rejuvenating retreats in or near Cudjoe Key:

  • Toss your swimsuit in your suitcase and stay at "Casa Capri Beautiful Tropical Style House With 3 King Suites Pool 2 Mi To Beach". Other amenities here include childrens activities and a kitchen.
  • "Casa Cay West Beautiful Tropical House 3 Bedrooms 2 King Suites Pool 2 Mi Beach" is another top option. After you've enjoyed a dip with the kiddos, take advantage of other conveniences like free toiletries and a porch.

What are the best large family vacation rentals in or near Cudjoe Key?

Whether your ideal escape is up in the mountains or down by the sea, you'll enjoy it even more if you share it with loved ones. Look up these large family vacation rentals in or near Cudjoe Key and bring the whole gang:

  • Sleeping up to 7 guests in 3 bedrooms, "Cloud 9 ~ It's Heaven On Earth In This 3b" is the ideal place to vacation with the family. This escape is 20 miles to the southwest of Cudjoe Key and has creature comforts that include a balcony and a kitchen.
  • "Casa Cove Beautiful Tropical Decorated 3 King Suites Pool 2 Mi Beach" is another top pick for families. It's about 17 miles to the southwest of Cudjoe Key, has 3 bedrooms and accommodates up to 8 people. Useful amenities here include a dining table and childrens activities.

If you'd love to sightsee, there are loads of family-friendly attractions close by to stick on your itinerary. Dolphin Research Center, The Turtle Hospital and Great White Heron National Wildlife Refuge are good places to start.

Can I find family cabin rentals in or near Cudjoe Key?

Get away from the hustle and bustle and treat the people you love to a vacation of a different sort. Stay in one of these family cabins in or near Cudjoe Key and get the camping experience — but with all the comforts of home!

  • "Cabin - Sand Is The New Snow - New 4bedroom W" - Around 25 miles east of the center of Cudjoe Key, this family-friendly escape comes with a balcony and a porch.
  • "Cabin - Orange Blossom Suite | 1 Bedroom 1 Bath In Steps Off Duval" - Another awesome choice, this rental comes with cable/satellite TV services, a dishwasher and more. You'll find it around 20 miles to the southwest of Cudjoe Key.

For more options, use the search bar at the top of the page and adjust the filters to find the Cudjoe Key vacation rental that's perfect for your needs.