Cudjoe Key holiday lettings

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Holiday rentals with weekly discounts – Cudjoe Key

Showing deals for:25 Sept - 2 Oct

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Why visit Cudjoe Key

  • Stunning Beaches: Relax on beautiful sun-kissed shores, ideal for sunbathing and swimming.
  • Outdoor Adventures: Engage in water sports like kayaking and fishing in the serene waters of the Florida Keys.
  • Family-Friendly Atmosphere: Enjoy a welcoming environment perfect for family vacations and excursions.
  • Charming Accommodations: Choose from cosy cottages and modern condos that provide a relaxing retreat.
  • Natural Beauty: Explore the local marine park and uncover the island's picturesque scenery.

Popular types of accommodation around Cudjoe Key

Embark on an unforgettable getaway in Cudjoe Key, Florida, where stunning natural beauty meets laid-back charm. Enjoy a selection of houses, cosy cottages, and modern condos that cater to your every need. Explore the serene waters of the Florida Keys, indulge in fishing, kayaking, or simply relax on the picturesque shores. With its unique attractions and welcoming atmosphere, Cudjoe Key is the perfect destination for your next vacation rental adventure.

  • Houses: These spacious and well-appointed homes are the top choice for visitors seeking comfort and privacy during their stay in Cudjoe Key.
  • Condos: Ideal for those who prefer a blend of convenience and amenities, condos offer a stylish base for exploring the local area.
  • Cottages: Quaint and charming, cottages provide a cosy retreat with a touch of traditional Florida charm.
  • Apartments: Perfect for shorter stays, apartments offer a practical and central option for holidaymakers.
  • Villas: Luxurious and spacious, villas are perfect for families or groups looking for a lavish getaway in Cudjoe Key.**

Top attractions near Cudjoe Key

Cudjoe Key, Florida, is an idyllic destination perfect for outdoor and family vacations, offering stunning beaches and picturesque scenery. Visitors can explore the local marine park, relax on sun-kissed shores, and take part in various water activities. With its charming vacation rental getaways, Cudjoe Key provides a serene escape for those seeking a blend of adventure and relaxation in a beautiful island setting.

  • Florida Keys Beaches: Experience the quintessential beach vibes with soft sands and crystal-clear waters. Ideal for sunbathing, swimming, or simply enjoying the tropical atmosphere, this beach is a perfect spot to unwind.
  • Cook Island: A hidden gem offering stunning outdoor experiences. With its pristine beaches, Cook Island is perfect for exploring nature, sunbathing, and enjoying water sports in a serene setting.
  • Coupon Bight Aquatic Preserve: A tranquil sanctuary, this preserve offers romantic and family-friendly experiences. Its secluded waters are perfect for relaxing, kayaking, or observing diverse marine life in a tropical paradise.

Things to do recommended for couples

Experience romance in Cudjoe Key by sharing a sunset kayak tour through tranquil waters, or enjoy a candlelit dinner at a waterfront restaurant. Don't forget to explore the stunning natural beauty of the nearby Dry Tortugas National Park for an unforgettable day together.

Things to do recommended for families

Families visiting Cudjoe Key can explore the beautiful waters with a kayaking adventure in the Florida Keys, enjoy wildlife encounters at the Dolphin Research Center in nearby Grassy Key, or relax on the sandy beaches, perfect for building sandcastles and enjoying a day in the sun.

Things to do recommended for groups

Explore the stunning waters of the Florida Keys with a group kayak tour through the mangroves, or enjoy a thrilling day of fishing and diving. Don’t miss the chance to witness the breathtaking sunset at Big Pine Key, perfect for a shared experience.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

When travelling with a group, family, or pets, or if you're seeking longer stays, it's important to apply the appropriate filters to meet your needs. Here are some helpful booking tips for using Vrbo.

  • Traveling to Cudjoe Key with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Cudjoe Key with young kids: Travelling with young children can present its challenges. It's important to prioritise their comfort and safety, as well as seek out facilities suitable for their age, like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that cater to families.
  • Taking your pets with you to Cudjoe Key: For many, a family holiday isn't truly fulfilled without their furry companion by their side. If that resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Cudjoe Key: If you’re in search of holiday lets with special offers for stays of a month or more, you’ve come to the right place. By utilising the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features such as a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Cudjoe Key

Cudjoe Key, Florida, offers a delightful blend of outdoor adventures and family-friendly experiences. Visitors can explore the tranquil beaches, indulge in water sports, or simply relax in the warm sun while enjoying the friendly atmosphere. The village is perfect for excursions, where you can uncover the natural beauty of the island and savour local cuisine. Whether you're seeking relaxation or adventure, Cudjoe Key promises a memorable vacation for all travellers.

  • Summerland Key: Nestled in the Florida Keys, Summerland Key is an idyllic island community that offers a perfect blend of outdoor adventures and family-friendly experiences. With its stunning beaches and lush landscapes, it's a haven for nature enthusiasts. Visitors can explore local recreational areas, enjoy shopping at nearby centres, or simply soak up the sun on the family beaches. The proximity to Cudjoe Key makes it easy to enjoy the best of both worlds: tranquillity and accessibility to the vibrant island atmosphere.
  • Cutthroat Harbor Estates: This charming neighbourhood, located near Cudjoe Key, is an excellent destination for those seeking a beach-centric vacation. Cutthroat Harbor Estates is known for its outdoor activities and family-oriented environment, making it ideal for a relaxing getaway. With convenient access to shopping malls and resorts, you'll find everything you need for a comfortable stay. The area's stunning beaches and inviting family beaches are perfect for swimming, sunbathing, and creating lasting memories.
  • Cudjoe Gardens: Cudjoe Gardens is a welcoming neighbourhood that combines a city-themed atmosphere with family and business-friendly amenities. This area is particularly suited for visitors looking for a blend of leisure and practicality, featuring various shopping centres and recreational spaces. With its proximity to beautiful beaches and islands, Cudjoe Gardens offers a fantastic opportunity to explore the natural beauty of the Keys while enjoying the conveniences of urban living. It's an excellent choice for families and business travellers alike.

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.

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 cut costs on your upcoming journey? Being flexible with your travel dates can be advantageous, as prices often fluctuate. Additionally, opting for a longer stay can lead to substantial savings. To discover a Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly platform for planning your journeys, allowing you to start new trips, resume previous ones, or keep track of your arrangements. You can easily find your saved or booked properties sorted into categories such as Potential, Upcoming, or Current Trips. To begin exploring 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:

  • Florida Keys Beaches (5.4 mi / 8.8 km)
  • Upper Sugarloaf Key (2 mi / 3.3 km)
  • Sugarloaf Beach (5.8 mi / 9.3 km)
  • Cook Island (8.4 mi / 13.5 km)
  • Looe Key National Marine Sanctuary (10.3 mi / 16.6 km)
  • Shark Key (10.4 mi / 16.7 km)

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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