Cudjoe Key vacation rentals

We found 777 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:Nov 14 - Nov 21
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Find out more about Cudjoe Key

Find out more about Cudjoe Key

Why visit Cudjoe Key

  1. Outdoor adventures: Cudjoe Key is perfect for families and friends seeking activities like kayaking, fishing, and snorkeling in stunning marine parks.
  2. Beautiful beaches: Relax on picturesque beaches that offer a serene environment for sunbathing and beachcombing.
  3. Cultural excursions: Venture to nearby Key West for vibrant culture, dining, and historic sites.
  4. Unique accommodations: Choose from a variety of vacation rentals, including cozy cottages and spacious homes, tailored to your needs.
  5. Friendly atmosphere: Experience the welcoming charm of Cudjoe Key, perfect for creating unforgettable memories.

Popular types of accommodation around Cudjoe Key

Discover the charm of Cudjoe Key with a variety of vacation rentals to suit your needs. Whether you prefer a spacious private vacation home, a cozy cottage, or a modern condo, there's something for everyone. Explore our selection of accommodations in Cudjoe Key and find the perfect spot for your getaway in the Florida Keys. Let us help you create unforgettable memories with transparent pricing and reassurance every step of the way.

  • Houses: The top choice for visitors in Cudjoe Key, these homes offer spacious living and a home-like atmosphere for families or groups.
  • Condos: A popular option for those seeking a blend of comfort and amenities, condos provide a convenient stay close to local attractions.
  • Cottages: Charming and often set in picturesque locations, cottages are perfect for a quaint getaway.
  • Apartments: Ideal for couples or solo travellers, apartments offer a practical and comfortable living space.
  • Villas: Luxurious and spacious, villas are the ultimate choice for a lavish vacation experience.**

Top attractions around Cudjoe Key

Cudjoe Key is perfect for outdoor and beach-loving families seeking adventure. With its stunning islands and beautiful beaches, this destination offers a variety of attractions, including marine parks that cater to those looking to explore the natural beauty of the area. Whether you're travelling with family or friends, Cudjoe Key promises a memorable vacation experience filled with outdoor activities and relaxation by the sea.

  1. Florida Keys Beaches: This stunning beach, located 8.0km from Cudjoe Key, offers a quintessential tropical experience with soft sands and clear waters, perfect for sunbathing and swimming.
  2. Upper Sugarloaf Key: Just 3.2km away, this charming neighbourhood boasts a vibrant local atmosphere, with quaint shops and friendly locals, ideal for exploring the unique island culture.
  3. Upper Sugarloaf Sound: Located 6.4km from Cudjoe Key, this picturesque island features outdoor activities and serene beach vibes, perfect for kayaking and relaxing by the water.

Things to do recommended for groups

Groups visiting Cudjoe Key can enjoy a round of golf at the Key West Golf Club, explore the vibrant Big Pine Key Flea Market, and experience the cultural charm of the Tennessee Williams Fine Art Center, all within easy reach for a memorable local adventure.

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

If you're planning a trip with friends, family, pets, or considering an extended stay, be sure to apply the appropriate filters to align with your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Cudjoe Key with a group: Think about how many bedrooms you require, as well as features like a full kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Cudjoe Key with young kids: Traveling with young children can present its challenges. It's important to prioritize their comfort and safety, along with ensuring access to suitable 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 trip just wouldn’t feel complete without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Cudjoe Key: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay around Cudjoe Key

Cudjoe Key, a charming village in the Florida Keys, offers a delightful blend of outdoor adventures and beach relaxation. Explore the scenic Cudjoe Bay or venture to the nearby Key West for vibrant culture and activities. The friendly atmosphere, coupled with family-friendly options, makes it an ideal destination for memorable excursions. Don't miss the historic Cudjoe Key Air Force Station and the stunning landscapes of Monroe County, ensuring a vacation filled with tropical vibes and unforgettable experiences.

  • Cutthroat Harbor Estates: Nestled around Cudjoe Key, Cutthroat Harbor Estates is a delightful neighbourhood that offers a perfect blend of outdoor adventures and family-friendly experiences. This community is ideal for those looking to embrace the sunshine and explore the beautiful beaches and islands nearby. Visitors can enjoy various recreational activities, from swimming and sunbathing to fishing. The area features a shopping mall centre and local shopping areas for those wishing to indulge in some retail therapy. Whether you’re looking for a relaxing day at the beach or an active outing with family, Cutthroat Harbor Estates has something for everyone.
  • Cudjoe Gardens: Cudjoe Gardens is another charming neighbourhood located close to Cudjoe Key, renowned for its vibrant outdoor and beach experiences. This area is perfect for families seeking fun and relaxation. Visitors can explore the local recreational areas and enjoy the scenic beauty of nearby beaches and islands. With access to shopping areas and a shopping mall centre, you can easily find everything from souvenirs to local delicacies. Cudjoe Gardens offers a welcoming atmosphere that encourages exploration and enjoyment of the natural surroundings.
  • Lower Keys: Situated three miles from Cudjoe Key, the Lower Keys are a stunning island destination known for their idyllic landscapes and outdoor activities. This area is a haven for beach lovers and families alike, providing ample opportunities for recreation and relaxation. Visitors can explore the local shopping areas and shopping mall centre, while the nearby beaches and islands offer breathtaking views and exciting activities. The Lower Keys are a must-visit for anyone looking to experience the charm and natural beauty of Florida's coastline.

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 simple

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can help, as prices tend to vary. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, be sure to use our filters to sort by price, location, and type of vacation rental. We're here to support you in finding the best options for your travel needs.

Vrbo Trips: Planning made easy

Vrbo's Trip Board is designed to help you plan your travels seamlessly. It provides a dedicated space to create new trips, manage your plans, and review or organize your bookings. Your saved or booked properties are conveniently categorized into Potential, Upcoming, or Current Trips for easy access. To explore your Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

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 biking, seafood restaurants and boating, this welcoming city won't disappoint. A vacation rental can help make your stay complete. Many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Cudjoe Key

Do you want to find things to do during your stay? Travelers enjoy fun activities like biking, boating and fishing. Venture out of your vacation home and experience everything that makes Cudjoe Key a fun place to get away. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • 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 an outdoor enthusiast or just want to take in the scenery, Cudjoe Key is a great place to get out in nature. Here are some of the area’s most enchanting natural features, all within 30 miles (48.2 km) of the city center:

  • Upper Sugarloaf Key (2 mi / 3.3 km)
  • Venture Out Keys (2.6 mi / 4.2 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)
  • 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 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 best area to stay in Cudjoe Key when booking a vacation rental?
If you're planning a getaway in Cudjoe Key, Cutthroat Harbor Estates is among the most sought-after destinations to stay. No matter your travel style, Vrbo is sure to have a property here that's right for you.
What is the most popular type of vacation rental accommodation in Cudjoe Key?
Houses are the most popular kind of vacation rental in Cudjoe Key, according to our data. Even if you have something else in mind, Vrbo 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 vacation rental in Cudjoe Key?
Different things determine what you'll pay for your vacation rental in Cudjoe Key, such as the time of year, property type and length of stay. Still, all of our vacation 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 Vrbo and the number of guests to view your rental 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 vacation rentals in Cudjoe Key?
Pack a suitcase for your puppy dog because Cudjoe Key has 60 vacation rentals 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 vacation rentals on Vrbo. 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 Vrbo. Ball games, gentle soak or noodle joust? How you spend your leisure time is up to you when your Vrbo vacation property boasts a swimming pool.
What are popular rental amenities in Cudjoe Key?
Some of the most popular rental 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, Vrbo vacation properties provide the best amenities for starting a new adventure with the people that matter most.
Are there large group vacation rentals in Cudjoe Key?
With six vacation rentals 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, Vrbo can help you find a large group rental to match the occasion.
Are there vacation rentals in Cudjoe Key that welcome kids?
Cudjoe Key has 60 family-friendly vacation rentals 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 vacation is simple with these cool family-friendly attractions:

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

Can I find two-bedroom vacation rentals in Cudjoe Key?
Choose from 17 two-bedroom rentals 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 vacation rentals with WiFi in Cudjoe Key?
You can choose from 24 vacation rentals with WiFi in Cudjoe Key. If you want to disconnect from the world while on 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 58 vacation rentals where you can unwind in air-conditioned comfort. To find a stay on Vrbo 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 vacation rental in Cudjoe Key?
It's a good idea to check with the Cudjoe Key vacation property you'd like on Vrbo as the minimum age differs. However, generally it's 16, 18 or 21.
How long can I rent a vacation rental 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 Vrbo. 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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