Cudjoe Key vacation rentals

We found 773 vacation rentals — enter your dates for availability

Select from 205 homes, 40 cottages, and other vacation rentals in Cudjoe Key to find one that's perfect for your trip. Whether you’re staying in a vacation home with friends, family, or even just your pets, you'll have the best amenities for spending time at your home away from home, including parking and a TV. Whatever you're looking for, you'll find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Cudjoe Key

Showing deals for:Sep 12 - Sep 19
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Find out more about Cudjoe Key

Find out more about Cudjoe Key

Why visit Cudjoe Key

  1. Scenic Outdoor Adventures: Cudjoe Key is perfect for outdoor enthusiasts, with beautiful beaches and stunning natural landscapes to explore.
  2. Charming Vacation Rentals: Enjoy a variety of comfortable accommodations, from cozy cottages to modern condos, ideal for families and friends.
  3. Access to Cudjoe Bay: Experience the tropical vibes and friendly locals while kayaking or lounging by the bay.
  4. Family-Friendly Activities: Engage in budget-friendly excursions that cater to all ages, ensuring fun for everyone.
  5. Relaxing Atmosphere: Unwind in the tranquil environment of the Florida Keys, making it a perfect getaway.

Popular types of accommodation around Cudjoe Key

Discover the charm of Cudjoe Key with our diverse selection of vacation rentals. From houses to cozy cottages and modern condos, we have the perfect getaway for every traveler. Whether you're seeking relaxation or adventure, our Cudjoe Key vacation rentals provide the ideal base to explore the beauty of the Florida Keys. Let us help you find the perfect accommodation for your unforgettable trip!

  • Houses: The top choice for visitors to Cudjoe Key, offering spacious accommodations ideal for families and groups.
  • Condos: A popular option for those seeking modern amenities and often stunning views, perfect for couples or small families.
  • Cottages: These quaint and cozy retreats provide a charming atmosphere for a peaceful getaway.
  • Apartments: A practical choice for travelers wanting convenience and comfort, often located near local attractions.
  • Villas: Luxurious and spacious, these upscale rentals are perfect for a lavish stay in paradise.**

Top attractions near Cudjoe Key

Cudjoe Key is an ideal destination for outdoor and family vacations, offering beautiful beaches and island experiences. Visitors can explore attractions like Cudjoe Gardens and enjoy beach access, making it perfect for those seeking relaxation and adventure. The area also features charming vacation rental homes, providing a comfortable stay while you discover the natural beauty of the Florida Keys. Whether you're traveling with family or friends, Cudjoe Key has something for everyone.

  1. Florida Keys Beaches: Located 5 miles from Cudjoe Key, this beach offers a quintessential tropical vibe with soft sands and clear waters, perfect for sunbathing and relaxation.
  2. Upper Sugarloaf Key: Just 2 miles away, this charming neighborhood boasts a lively atmosphere with local shops and eateries, providing an authentic taste of island life.
  3. Upper Sugarloaf Sound: Situated 4 miles from Cudjoe Key, this picturesque island features stunning outdoor spaces, ideal for kayaking and enjoying the natural beauty of the Florida Keys.

What do I need to keep in mind when booking a vacation around Cudjoe Key

If you’re planning a trip with a group, family, pets, or looking for extended stays, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Cudjoe Key with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Cudjoe Key with young kids: Traveling with young kids can be a bit tricky. It's important to prioritize their comfort and safety, along with finding age-appropriate amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Cudjoe Key: For many families, a vacation wouldn’t be the same without their furry companions. If you relate to that, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and cozy beds, ensuring that every member of the family feels at home.
  • Planning for a long term stay visiting Cudjoe Key: If you're in search of vacation rentals at discounted rates for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can quickly discover and save on monthly rental options. Additionally, think about including features like parking, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay in and around Cudjoe Key

Cudjoe Key offers a perfect escape for outdoor enthusiasts and families alike. Explore the stunning Cudjoe Bay, where tropical vibes meet friendly locals. Enjoy budget-friendly excursions and relax in the beautiful Florida Keys getaway atmosphere. Whether you're seeking adventure or a tranquil beach day, Cudjoe Key and its charming surroundings provide an unforgettable vacation experience that caters to all tastes.

  • Cutthroat Harbor Estates: Nestled around Cudjoe Key, Cutthroat Harbor Estates is a charming neighborhood that invites travelers seeking a blend of outdoor activities and family-friendly experiences. This area is perfect for those who enjoy spending time by the beach, with easy access to sandy shores and recreational areas. Visitors can explore local shopping spots, including malls and boutiques, making it a convenient hub for both relaxation and entertainment. The picturesque beachfront and nearby islands provide a stunning backdrop for family outings, ensuring that Cutthroat Harbor Estates is a delightful destination for all ages.
  • Cudjoe Gardens: Just a stone's throw from Cudjoe Key, Cudjoe Gardens is a delightful neighborhood known for its vibrant outdoor scene and family-oriented experiences. With easy access to beautiful beaches and lush islands, this area is ideal for sunbathing and water activities. Cudjoe Gardens also features shopping areas and recreational facilities, allowing travelers to enjoy a mix of leisure and adventure. The neighborhood's inviting atmosphere and close-knit community feel make it a great place to unwind and explore the natural beauty of the Florida Keys.
  • Lower Keys: Located a mere 3 miles from Cudjoe Key, the Lower Keys is a breathtaking island destination that offers a perfect escape for outdoor enthusiasts and beach lovers. With its stunning beaches and family-friendly activities, visitors can indulge in a variety of recreational pursuits, from snorkeling to kayaking. The area boasts a range of shopping options, including charming local stores and malls. The Lower Keys' unique blend of natural beauty and vibrant community makes it an essential stop on your Florida vacation, promising unforgettable experiences and scenic vistas.

Best time to go to Cudjoe Key, Summerland Key

If you're planning a trip to Cudjoe Key, Summerland Key, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from July to September, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January71.1°F (21.7°C)No Rain (Dry)Mostly SunnyAverageAverage
February72.1°F (22.3°C)No Rain (Dry)Mostly SunnyAverageAverage
March73.2°F (22.9°C)No Rain (Dry)Mostly SunnyAverageSlightly High
April76.8°F (24.9°C)No Rain (Dry)Mostly SunnyAverageSlightly High
May79.3°F (26.3°C)Light RainMostly SunnyAverageAverage
June82.6°F (28.1°C)Light RainMostly SunnyAverageAverage
July84.0°F (28.9°C)Light RainMostly SunnyHighAverage
August84.4°F (29.1°C)Light RainMostly SunnyHighSlightly Low
September83.7°F (28.7°C)Light RainMostly SunnyHighSlightly Low
October80.8°F (27.1°C)Light RainMostly SunnyLowSlightly Low
November76.6°F (24.8°C)Light RainMostly SunnyLowAverage
December73.8°F (23.2°C)No Rain (Dry)Mostly SunnyLowSlightly High

Booking with Vrbo is a breeze

Are you eager to save on your upcoming journey? Being flexible with your travel dates can lead to better pricing, as rates often fluctuate. Additionally, consider booking a longer stay to enjoy substantial savings. To discover a Vrbo property that aligns with your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to support you in finding the perfect getaway!

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on your entire reservation. Being the planner truly has its rewards! When you join our travel rewards program, One Key, you'll gain access to exclusive member discounts and start accumulating OneKeyCash™ on eligible bookings. Sign up today and begin enjoying your savings!

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board offers a user-friendly platform where you can effortlessly create new trips, resume planning from where you last stopped, or organize your travel arrangements. You can easily access your saved or booked properties, which are neatly categorized as Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

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.

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.

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 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.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Cudjoe Key?
Cottages are the most popular style of vacation rental in Cudjoe Key, according to our data. Even if you’ve got something different in mind, Vrbo has properties in all shapes and sizes. Browse our many options to find your perfect Cudjoe Key pad.
How much does it cost to rent a vacation rental in Cudjoe Key?
The average price for a vacation rental in Cudjoe Key is based on a number of factors, such as season, property type and length of stay. Whether you’d like a sprawling villa with space for extended family or a cozy condo ideal for just you and the kids, just add your travel dates to view stays with amazing value.
How much does it cost to rent a beach house in Cudjoe Key?
When you travel and the size and style of the property will influence how much you’ll pay for your beachside stay. Enter your Cudjoe Key travel dates to view your available options on Vrbo. Looking for a backyard so the kids can run around, or a pool to keep them busy? Use our filters to select the amenities and features you want in your beach house.
Are there pet-friendly vacation rentals in Cudjoe Key?
Yes. You can choose from 222 stays that allow pets in Cudjoe Key on Vrbo. Our furry companions deserve a getaway too, so simply use our search function for pet-friendly vacation rentals to book a property where your pooch can share in the good times.
Can I rent a house with a pool in Cudjoe Key?
Grab your swimsuit and inflatable swan, because there are 178 houses with a private pool in Cudjoe Key. Book a stay at one of these popular vacation homes and you’ll enjoy pool days every day. Simply enter your travel dates into Vrbo, then use the “pool” filter to find the perfect place to make a splash!
What are popular rental amenities in Cudjoe Key?
Some of the most popular rental amenities people search for in Cudjoe Key are a beach view, a fireplace and a nearby waterfront. Whether you’re traveling with your besties, family or even pets, Vrbo vacation properties have the best amenities for starting a new adventure with the people you love.
Are there large group vacation rentals in Cudjoe Key?
You can choose from 15 vacation properties in Cudjoe Key that can accommodate 10 or more people. Whether you’re planning a vacation with extended family or an event like a birthday party, there’s plenty of space to get your group together under the same roof.
Are there vacation rentals in Cudjoe Key that welcome kids?
Gather your entire family for an adventure in Cudjoe Key at one of our 218 family-friendly vacation properties. These stays offer amenities that are just perfect for trips with the kids, such as laundry facilities, multiple bedrooms and swimming pools. Just check the “Properties good for families” filter box and pick out your favorite.
Are there one-bedroom vacation rentals in Cudjoe Key?
Yes, you can take your pick from 18 one-bedroom rentals in Cudjoe Key. Whether you’re on the lookout for a secluded cottage or a cabin, our one-bedroom rentals are great if you don’t need a lot of space. One of the best things about having your own pad? You won’t ever have to share your getaway with strangers.
Can I find two-bedroom vacation rentals in Cudjoe Key?
Cudjoe Key has 127 two-bedroom properties for you to pick from. Go for a vacation home with all the space and comfort you’re looking for at a price that’s hard to resist on Vrbo.
Are there vacation rentals with WiFi in Cudjoe Key?
You can choose from 90 vacation rentals with WiFi in Cudjoe Key. If you want to disconnect from daily life on your vacation, 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 Vrbo.
How can I find vacation rentals with air conditioning in Cudjoe Key?
Cudjoe Key has 216 vacation rentals where you can wind down in air-conditioned comfort. To find a stay on Vrbo that comes with this perk, choose your travel dates and use the handy filter tool to select the “air conditioning” box.
How old do you have to be to rent a vacation rental in Cudjoe Key?
We recommend checking with the Cudjoe Key vacation rental you’d like on Vrbo as the age limit differs. However, typically it’s 16, 18 or 21.
How long can I rent a vacation rental in Cudjoe Key for?
It’s really down to the Cudjoe Key property. To see all available options offering extended stays, simply enter your travel dates and guest number into the Vrbo search page. You can look forward to having the property to yourself, along with home comforts like a fully-equipped kitchen and an outdoor space where the little ones can play. Keep an eye out for long-term stays that offer discounted weekly or monthly prices.
Does Vrbo offer discounts for vacation homes in Cudjoe Key?
Whether you’re after one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you’re sure to score some great deals and discounts on Vrbo. From weekend trips to extended getaways, we’ve got you covered for your next Cudjoe Key escape.

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