Cudjoe Head holiday lettings

We found 35 holiday rentals — enter your dates for availability

Discover a selection of holiday rentals in Cudjoe Head that are perfect for your trip. Whether you’re staying in a holiday home with your children or with friends, you'll have the amenities that you expect and more, which might include a pool and a washer and dryer. Whatever you're looking for, you're sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.
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Find out more about Cudjoe Head

Find out more about Cudjoe Head

Why visit Cudjoe Head

  • Stunning scenery: Cudjoe Head offers breathtaking views that make it a perfect spot for relaxation and photography.
  • Outdoor adventures: Engage in various outdoor activities, ideal for beach lovers and adventure seekers alike.
  • Cultural festivals: Experience vibrant local culture during the annual Cudjoe Head Festival, showcasing music and traditions.
  • Diverse accommodation options: Choose from charming villas, stylish apartments, and private holiday homes for your stay.
  • Serene atmosphere: Enjoy the peacefulness of this small village, perfect for a tranquil getaway.

Popular types of accommodation in Cudjoe Head

Planning a getaway to Cudjoe Head? The excitement of selecting the perfect accommodation awaits! From charming villas and stylish apartments to houses, you'll find a range of fantastic options to suit your needs. Whether you're searching for the best hotels in Cudjoe Head or unique private stays, our platform offers transparency and savings to ensure you have a delightful experience. Explore the top Cudjoe Head hotels and make your holiday truly memorable.

  • Villas: The top choice for visitors to Cudjoe Head, villas offer luxurious spaces with stunning views, perfect for a lavish getaway.
  • Apartments: Ideal for those seeking convenience and comfort, apartments provide a homely atmosphere with essential amenities for a pleasant stay.
  • Houses: A popular option for families and groups, these homes offer privacy and a unique local experience during your holiday.**

Top attractions near Cudjoe Head

Cudjoe Head, located in Saint Peter Parish, Montserrat, is an ideal destination for those seeking outdoor adventures and stunning scenery, particularly for beach enthusiasts. Visitors can enjoy the local sights, participate in the annual Cudjoe Head Festival, and explore the surrounding areas. Whether you're travelling solo, with family, or friends, Cudjoe Head offers a delightful blend of relaxation and excitement for an unforgettable holiday experience.

  • Little Bay: just 1.6km from Cudjoe Head, Little Bay boasts golden sands and crystal-clear waters, perfect for sunbathing and swimming. The relaxed beach vibes make it an ideal spot for unwinding and enjoying the stunning Caribbean views.
  • Woodlands Beach: Located 1.2km away, Woodlands Beach offers a serene atmosphere with soft sands and gentle waves. It's a great location for a peaceful day by the sea, with opportunities for picnicking and enjoying the natural surroundings.
  • Rendezvous Beach: Also 1.2km from Cudjoe Head, Rendezvous Beach features a tranquil setting with picturesque scenery. The inviting waters and soft sands make it a perfect place for a relaxing day of leisure and exploration.

Things to do recommended for couples

For a romantic getaway in Cudjoe Head, enjoy a sunset picnic on the beach, explore the lush hiking trails of Montserrat, or indulge in a candlelit dinner at a local restaurant. Don't miss the breathtaking views from the top of the volcano for a memorable experience together.

Things to do recommended for families

Families will delight in exploring the lush hiking trails of the Montserrat Volcano Observatory, or enjoy the stunning beaches at Little Bay. The local culture can be experienced through traditional music and dance events, creating cherished memories for all.

Things to do recommended for groups

Embark on an adventurous group hike along the Blackwood Allen Trail, Duberry-Cassava Trail, or Rendezvous Circle Trail, all located a mere 1.9km from Cudjoe Head. Each trail offers stunning scenery and a chance to connect with nature, perfect for outdoor enthusiasts seeking memorable experiences.

What do I need to keep in mind when booking a vacation in 'Cudjoe Head

If you're travelling with a group, family, or pets, or if you're seeking longer stays, it's important to prioritise your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Cudjoe Head with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Cudjoe Head with young kids: Travelling with young children can present its challenges. It's important to prioritise their comfort and safety, along with ensuring that suitable amenities, like a private swimming pool, are available. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Cudjoe Head: For many, a family holiday wouldn’t be the same without their furry companion by their side. If you can relate, take a look at Vrbo properties that are pet-friendly. Most of these accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Cudjoe Head: If you're seeking holiday rentals with special offers 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 accommodations. You might also want to include options like a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay near Cudjoe Head

Cudjoe Head, nestled in Saint Peter Parish, Montserrat, offers an enchanting blend of outdoor adventures and breathtaking scenery. As you explore this charming small village, be sure to discover the vibrant Montserrat festivals that celebrate local culture. With its stunning views and romantic spots, Cudjoe Head is perfect for those seeking both relaxation and adventure in this picturesque Caribbean paradise.

  • St. John's: St. John's, located a mere 497m from Cudjoe Head, is the vibrant capital of Montserrat, offering a delightful blend of outdoor adventure and striking scenery. Visitors are drawn to its lush landscapes and breathtaking lookouts, making it an ideal spot for nature lovers. Popular activities include exploring local educational venues and enjoying the pristine beaches nearby. The proximity to the famous Soufrière Hills volcano adds an element of adventure, allowing tourists to experience the island's geological wonders while soaking up the sun on the beach.
  • St. Peter's: Just 621m from Cudjoe Head, St. Peter's is known for its romantic atmosphere and outdoor activities. This charming city boasts stunning lookouts and serene beaches, perfect for couples and adventurers alike. The area's natural beauty encourages exploration, whether through leisurely strolls along the coastline or more exhilarating hikes. Visitors can marvel at the captivating views of the nearby volcano, making St. Peter's a lovely destination for those seeking both relaxation and adventure.
  • Davy Hill: Located 559m from Cudjoe Head, Davy Hill is a gem for outdoor enthusiasts eager to explore Montserrat's natural landscapes. The area is well-known for its hiking trails and easy access to scenic routes that lead to picturesque lookouts and stunning beaches. With the Soufrière Hills volcano nearby, Davy Hill offers unique opportunities for adventure and exploration, making it an excellent base for those looking to immerse themselves in the island's breathtaking scenery.

Best time to go to Cudjoe Head

If you're planning a trip to Cudjoe Head, it's a good idea to check both the weather and property rates. The warmest month is September. Peak season runs from January to March, while off-peak times, like May to June and September tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January78.1°F (25.6°C)No Rain (Dry)Mostly SunnyHighAverage
February77.7°F (25.4°C)No Rain (Dry)Mostly SunnyHighSlightly Low
March77.7°F (25.4°C)No Rain (Dry)Mostly SunnyHighSlightly High
April78.6°F (25.9°C)No Rain (Dry)Mostly SunnyAverageSlightly High
May80.2°F (26.8°C)Light RainMostly SunnyLowAverage
June81.3°F (27.4°C)No Rain (Dry)Mostly SunnyLowSlightly High
July81.7°F (27.6°C)Light RainMostly SunnyAverageAverage
August82.2°F (27.9°C)Light RainMostly SunnyAverageAverage
September82.6°F (28.1°C)Light RainMostly SunnyLowSlightly Low
October82.0°F (27.8°C)Light RainMostly SunnyAverageAverage
November80.8°F (27.1°C)Light RainMostly SunnyAverageSlightly Low
December79.3°F (26.3°C)Light RainMostly SunnyAverageAverage

Booking with Vrbo is a breeze

Looking to make the most of your next holiday? Consider being flexible with your travel dates, as this can help you secure better prices. Moreover, extending your stay can often result in significant savings. To discover the ideal Vrbo property that suits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's clever Trip Board feature offers you a dedicated space to plan new adventures, pick up right where you left off, or review and arrange your travel plans. You can easily locate the properties you've previously saved or booked under Potential, Upcoming, or Current Trips. To make the most of Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Book a holiday rental for your Cudjoe Head getaway

Learn about the unique charm of Cudjoe Head with a stay in a holiday home rental. This city has something for everyone. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Exploring the natural features in Cudjoe Head

Whether you're an adventurous traveller or just want to appreciate the scenery, Cudjoe Head is a great place to spend some time outside. These are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Woodlands Beach (1.8 mi / 2.9 km)
  • Montserrat Volcano Observatory (2.3 mi / 3.8 km)
  • Lime Kiln Beach (2.8 mi / 4.6 km)
  • Foxes Bay Beach (4.5 mi / 7.3 km)
  • Little Bay (1.3 mi / 2.2 km)
  • Rendezvous Beach (1.8 mi / 3 km)

Travelling to and around Cudjoe Head

The nearest airport is in Plymouth (MNI-Gerald's Field), located 1 mi (1.7 km) from the city centre.

Frequently asked questions

What is the best area to stay in Cudjoe Head when booking a holiday rental?
When considering a holiday rental in Cudjoe Head, Saint Peter Parish, Montserrat, a popular area to stay is near the picturesque Little Bay. This neighbourhood offers a delightful blend of stunning coastal views and easy access to the beach, making it an excellent choice for those looking to relax by the sea. Here, you can enjoy vibrant sunsets and the soothing sounds of the waves, creating a tranquil atmosphere for your getaway.

In terms of attractions, the nearby Montserrat Volcano Observatory is an absolute must-visit. It provides fascinating insights into the island's volcanic activity, and the views from the observatory are simply breathtaking. Another point of interest is the beautiful, unspoilt beaches, such as Woodlands Beach, which is great for sunbathing or a leisurely swim in the crystal-clear waters.
How much does it cost to rent a holiday home in Cudjoe Head?
Prices for holiday rentals in Cudjoe Head vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Cudjoe Head to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Cudjoe Head holiday house rentals?
You can find great discounts on house rentals in Cudjoe Head on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Cudjoe Head?
For renting a beach house in Cudjoe Head, Saint Peter Parish, Montserrat, travellers should consider the picturesque coastline along the Caribbean Sea. The area near Cudjoe Head itself is known for its serene beaches and stunning views, making it an excellent choice for those seeking a tranquil escape. Many properties in this vicinity often feature amenities such as private balconies, outdoor dining areas, and expansive gardens, allowing guests to fully immerse themselves in the natural beauty of the surroundings.

Additionally, the nearby Little Bay area offers a selection of holiday rentals that are just a short walk from the beach. Here, visitors can find charming cottages and villas equipped with modern conveniences such as air conditioning, Wi-Fi, and fully stocked kitchens, great for families or groups looking for a self-catering experience. The local beach is ideal for swimming and sunbathing, and some properties may even offer direct beach access.
What is the most popular type of holiday rental accomodation in Cudjoe Head?
In Cudjoe Head, villas are particularly popular, with several available throughout the area. These properties typically offer spacious living areas, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups seeking a comfortable stay. Many villas also feature private outdoor spaces such as gardens or patios, great for enjoying the warm Montserrat climate.

Holiday houses are another common option, also available in several numbers. These homes provide a similar feel to villas, often boasting unique designs and additional amenities like BBQ facilities and laundry services, suiting guests looking for a home away from home.
Are there any family house rentals in Cudjoe Head?
In Cudjoe Head, Saint Peter Parish, there are several family-friendly holiday rentals available, making it an excellent choice for those travelling with children. This coastal area offers a relaxed atmosphere and easy access to stunning beaches and local attractions. Many of the properties feature spacious living areas, fully equipped kitchens, and outdoor spaces great for family gatherings or barbecues.
Can I rent a holiday home with a pool or hot tub in Cudjoe Head?
In Cudjoe Head, Montserrat, there are several holiday homes available for rent that feature pools and potentially hot tubs. This picturesque area offers a serene setting for travellers, with easy access to the island's beautiful beaches and lush landscapes. Many of the rentals come equipped with amenities such as private pools, outdoor seating areas, and fully equipped kitchens, providing a comfortable and enjoyable stay.
Can I find long-stay holiday rentals in Cudjoe Head?
A long-stay holiday rental in Cudjoe Head is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there any remote work holiday rentals in Cudjoe Head?
In Cudjoe Head, Saint Peter Parish, Montserrat, there are several remote work holiday rentals available, making it an appealing destination for those looking to blend work and leisure. Many of these properties come equipped with essential amenities such as Wi-Fi, dedicated desks, and comfortable desk chairs, ensuring a productive environment for remote workers. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Cudjoe Head holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Cudjoe Head with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Cudjoe Head?
In Cudjoe Head, popular rental amenities primarily include essential kitchen facilities, making it convenient for guests to prepare their own meals. Most holiday rentals are equipped with a microwave, an oven, and cookware, dishware, and utensils. This allows travellers to enjoy a home-cooked meal after a day of exploring the beautiful landscapes of Montserrat.
How early should I book a Cudjoe Head holiday rental?
Book your Cudjoe Head holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Cudjoe Head home rental booking on Vrbo?
To find Cudjoe Head holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Cudjoe Head holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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