Discover a selection of 372 vacation rentals in Cudjoe Key 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 kitchens. Prices start at $110 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.
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.


Don't forget to pack the sunscreen

A Cudjoe Key vacation rental means endless summer. Seasons aren't measured by temperature, but rather precipitation. You have your choice of hot and dry (November to April) or hot and wet (June to October). The dry season sees sunny skies and warm breezes, but year round you'll have daytime temperatures ranging from the 70s to the 90s. Water temps are pleasantly in the 80s. You might want a light sweater in January or February, when the mercury can dip into the 60s overnight, but you can leave all thoughts of snow behind.

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

Traveling 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 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.

How many vacation rentals are available around Cudjoe Key?

Our 2020 property listings offer a large selection of 372 vacation rentals around Cudjoe Key. From 309 house rentals to 29 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What is the best area to stay when traveling to Cudjoe Key?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Cudjoe Key:

  • Cutthroat Harbor Estates: 128 vacation rentals
  • Cudjoe Gardens: 43 vacation rentals
  • Old Town: 1,071 vacation rentals
  • Historic Seaport: 794 vacation rentals
  • Uptown/Upper Duval: 267 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular point of interests near where I can stay when traveling to Cudjoe Key?

Vrbo offers a large selection of vacation rentals near lovely places in Cudjoe Key. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Bahia Honda State Park and Beach: 1,373 vacation rentals
  • Southernmost Point: 1,489 vacation rentals
  • South Beach: 1,490 vacation rentals
  • Fort Zachary Taylor Historic State Park: 1,489 vacation rentals
  • Mallory Square: 1,490 vacation rentals

But there are many other points of interest around Cudjoe Key listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Cudjoe Key?

Yes, of course. Vrbo has 309 Houses in Cudjoe Key. Our other popular types of vacation rentals in Cudjoe Key include:

  • Cottages: 29 rentals available
  • Bungalows: 29 rentals available
  • Cabins: 29 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Condos/Apartments and more.

Can I find a vacation rental with pool in Cudjoe Key?

Yes, you can select your preferred vacation rental with pool among our 223 vacation rentals with pool available in Cudjoe Key. Please use our search bar to access the selection of vacation rentals available.

    Explore destinations around Cudjoe Key

    Cutthroat Harbor Estates
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