Cudjoe Key holiday lettings

We found 765 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.

Holiday rentals with weekly discounts - Cudjoe Key

Showing deals for:10 Oct - 17 Oct
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Why visit Cudjoe Key

  • Stunning Natural Beauty: Cudjoe Key showcases picturesque islands and sandy beaches, perfect for outdoor enthusiasts and families.
  • Proximity to Key West: Just a short drive away, Key West offers vibrant culture and nightlife, enhancing your holiday experience.
  • Relaxing Beach Activities: Enjoy sun-soaked adventures or serene days lounging by the beach, ideal for unwinding.
  • Variety of Accommodations: Choose from private vacation homes, charming cottages, and modern condos tailored to your needs.
  • Friendly Local Atmosphere: Experience the warmth of welcoming locals and budget-friendly options throughout the area.

Popular types of accommodation around Cudjoe Key

If you’re pondering the ideal accommodation for your getaway in Cudjoe Key, worry not – we’ve got you sorted. The most sought-after options include houses, charming cottages, and modern condos. Whether you're after cottage rentals in Cudjoe Key or simply exploring nightly prices and additional amenities, we provide the information you need to make an informed choice. Experience transparency and reassurance while discovering your perfect holiday retreat!

  • Houses: The top choice for holidaymakers in Cudjoe Key, offering spacious and comfortable residences perfect for families or groups.
  • Condos: A popular option, these self-contained units provide a blend of convenience and luxury, ideal for couples or small families.
  • Cottages: Quaint and charming, cottages offer a cosy retreat for those seeking a peaceful getaway.
  • Apartments: Versatile and often centrally located, apartments are great for visitors wanting easy access to local attractions.
  • Villas: Luxurious and spacious, villas are perfect for travellers looking for an upscale experience with private amenities.**

Top attractions near Cudjoe Key

Cudjoe Key offers a splendid destination for outdoor and beach-loving families. With its picturesque islands, sandy beaches, and visitor centres, there are plenty of attractions to explore. Whether you're seeking adventure or a relaxing getaway, Cudjoe Key provides a delightful experience for travellers looking to immerse themselves in Florida's natural beauty and charm.

  • Florida Keys Beaches: Located 3.1km from Cudjoe Key, this beach offers a quintessential beach experience with soft sands and crystal-clear waters, perfect for sunbathing and relaxing.
  • Upper Sugarloaf Key: Just 1.2km away, this charming neighbourhood exudes a lively city vibe, where you can explore local shops and enjoy the unique atmosphere.
  • Upper Sugarloaf Sound: Situated 2.5km from Cudjoe Key, this beautiful island is ideal for outdoor enthusiasts, offering stunning beach views and a tranquil environment for kayaking and wildlife spotting.

Things to do recommended for couples

Seeking a romantic escape in Cudjoe Key? Enjoy a sunset kayak tour through mangroves, indulge in a candlelit dinner at a waterfront restaurant, or relax on a secluded beach. Don't miss the chance to explore the vibrant underwater world while snorkelling together in the clear waters.

Things to do recommended for families

Your family will love exploring the vibrant marine life while snorkelling at Looe Key Reef, or enjoying a picnic at the tranquil Cudjoe Key Park. Don't miss the chance to visit the nearby Bahia Honda State Park for its beautiful beaches and nature trails.

Things to do recommended for groups

Enjoy a round of golf at Key West Golf Club, 10.6km away, or explore the vibrant Big Pine Key Flea Market, just 5.6km from Cudjoe Key. For a touch of culture, visit the Tennessee Williams Fine Art Center, also 10.6km distant, perfect for entertainment and romance.

Booking with Vrbo is a breeze

Are you hoping to save on your next getaway? Being flexible with your travel dates can be advantageous, as prices often fluctuate. Additionally, you may enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that aligns with your budget, simply utilise our filters to sort by price, location, and type of holiday rental.

Where to stay in and around Cudjoe Key

Cudjoe Key offers a delightful escape for those seeking sun-soaked adventures and serene beaches. Nestled in the stunning Florida Keys, this charming village is perfect for family holidays and outdoor exploration. Nearby, you'll find the vibrant atmosphere of Key West and the tranquil beauty of Summerland Key, each boasting friendly locals and budget-friendly options. Whether you're after tropical excursions or simply relaxing by the beach, Cudjoe Key is an ideal choice for your next getaway.

  • Summerland Key: Summerland Key is a beautiful island city located merely 1.9km from Cudjoe Key. Known for its stunning natural surroundings, it offers a fantastic outdoor experience perfect for families. Visitors can enjoy a variety of activities such as beach outings, shopping at local centres, and exploring recreational areas. The area's highlights include pristine beaches and family-friendly spots, making it an ideal destination for relaxation and fun. The local charm and scenic views also provide a picturesque backdrop for memorable family moments.
  • Cutthroat Harbor Estates: Nestled around Cudjoe Key, Cutthroat Harbor Estates is a charming neighbourhood that invites outdoor enthusiasts and families alike. The area boasts beautiful beaches and lush islands, providing ample opportunities for adventure and relaxation. Visitors can explore nearby shopping areas and recreational spaces, ensuring a well-rounded travel experience. This friendly community is perfect for those seeking a laid-back atmosphere while enjoying the natural beauty of the Florida Keys.
  • Cudjoe Gardens: Cudjoe Gardens, situated in close proximity to Cudjoe Key, is another delightful neighbourhood for tourists looking for outdoor adventures and family activities. The area features inviting beaches and local islands, perfect for sunbathing and swimming. With numerous shopping venues and recreational facilities nearby, there’s something for everyone in this lively community. Cudjoe Gardens offers a chance to experience the charm of local living while enjoying the stunning coastal scenery.

Best time to go to Cudjoe 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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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

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

If you're travelling with a group, as a family, bringing your pets along, or seeking longer stays, it's important to filter according to your priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Cudjoe Key with a group: Think about how many bedrooms you'll require, along with amenities like a fully-equipped kitchen or outdoor space 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 be quite demanding. It’s important to prioritise their comfort and safety, along with suitable amenities for their age, 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, a family holiday isn't truly enjoyable without their furry companion. If that resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Cudjoe Key: If you're searching for holiday rentals that offer discounts for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include preferences such as a parking space, a well-equipped kitchen, or a private pool in your search as well.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board provides a convenient platform for you to plan new adventures, manage your existing arrangements, or review your bookings. Your saved or reserved properties are now neatly categorized into Potential, Upcoming, or Current Trips. To delve into Trip Boards, please visit: https://www.vrbo.com/en-gb/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 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)
  • Venture Out Keys (2.6 mi / 4.2 km)
  • Upper Sugarloaf Sound (3.3 mi / 5.3 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)

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 rental?
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, Vrbo is sure to have a property here that's right for you.
What is the most popular type of holiday rental accommodation in Cudjoe Key?
Houses are the most popular kind of holiday 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 holiday rental in Cudjoe Key?
Different things determine what you'll pay for your holiday rental 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 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 holiday rentals in Cudjoe Key?
Pack a suitcase for your puppy dog because Cudjoe Key has 60 holiday 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 holiday 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 holiday 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 holiday properties provide the best amenities for starting a new adventure with the people that matter most.
Are there large group holiday rentals in Cudjoe Key?
With six holiday 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 holiday rentals in Cudjoe Key that welcome kids?
Cudjoe Key has 60 family-friendly holiday 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 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 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 holiday rentals with WiFi in Cudjoe Key?
You can choose from 24 holiday rentals 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 Vrbo.
How can I find holiday rentals with air conditioning in Cudjoe Key?
Cudjoe Key has 58 holiday 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 holiday rental in Cudjoe Key?
It's a good idea to check with the Cudjoe Key holiday 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 holiday 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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