May Pen holiday lettings

We found 114 holiday rentals — enter your dates for availability
Discover a selection of 7 homes and other holiday rentals in May Pen that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll have the amenities that you expect and more, such as parking and air conditioning. At the end of the day, you're sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why visit May Pen

  • Urban Parks: Enjoy a relaxing day at Longville Park, perfect for leisurely strolls and picnics amidst nature.
  • Cultural Heritage: Visit the historic May Pen Cemetery, a site rich in local history and significance.
  • Community Vibrance: Experience the lively atmosphere in Yard Newport News, where local traditions and community life thrive.
  • Motorsport Adventures: Head to Bushy Park for exciting motorsport activities that cater to thrill-seekers.
  • Authentic Local Markets: Explore bustling local markets to immerse yourself in authentic Jamaican culture and cuisine.

Popular types of accommodation in May Pen

Welcome to May Pen, Clarendon, Jamaica, a vibrant city rich in culture and history. Here, you can explore local attractions such as the May Pen Cemetery, known for its historical significance, and the bustling local markets where you can experience authentic Jamaican life. For your stay, consider the popular options of apartments, villas, or houses, ensuring a comfortable and memorable visit. Enjoy the charm of May Pen while finding the perfect rental house for your getaway.

  • Apartments: The top choice for travellers in May Pen, offering convenient amenities and a home-like atmosphere.
  • Villas: A luxurious option for those seeking spacious accommodations and private retreats.
  • Houses: Ideal for families or groups, these homes provide comfort and seclusion.
  • Condos: A popular selection, featuring modern facilities and proximity to local attractions.
  • Cabins: A charming choice for nature lovers looking for a rustic escape.**

Top attractions near May Pen

May Pen, Clarendon, Jamaica, offers a rich blend of wellness and cultural experiences. Visitors can explore urban parks perfect for relaxation and outdoor activities, alongside historic churches that reflect the area's heritage. The city serves as a family-friendly destination, providing engaging attractions and landmarks that cater to those seeking a vibrant cultural atmosphere. Whether you're enjoying leisurely strolls or immersing yourself in local traditions, May Pen promises a delightful escape.

  • Cecil Charlton Park: This urban park offers a serene escape with lush green spaces, perfect for family outings and outdoor activities. Enjoy leisurely strolls or picnics in a vibrant environment.
  • St Catherine District Prison: A notable landmark, this site provides a unique glimpse into Jamaica's history. Its friendly atmosphere makes it suitable for family excursions, offering insights into local heritage.
  • Marshall's Pen Great House: A historic house that embodies Jamaican culture, showcasing traditional architecture and rich history, ideal for those seeking to immerse themselves in the local heritage.

Things to do recommended for couples

Experience the charm of May Pen with a romantic riverside picnic along the Rio Minho, or explore the stunning landscapes of the surrounding hills. Enjoy a candlelit dinner at a local restaurant, savouring authentic Jamaican cuisine while soaking in the vibrant atmosphere.

Things to do recommended for families

Families visiting May Pen can explore the vibrant local markets, enjoy a day at the nearby May Pen Park, or take a short trip to the stunning beaches of Hellshire. Don't miss the chance to taste authentic Jamaican cuisine at local eateries for a true cultural experience.

Things to do recommended for groups

Explore the vibrant local culture with a visit to the May Pen Market, where you can sample authentic Jamaican cuisine. Alternatively, take a guided tour of the historic landmarks in Clarendon, or enjoy a day at the nearby Seven Rivers, perfect for relaxation and group activities.

*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 in May Pen

When travelling with a group, family, pets, or planning an extended stay, it's important to apply the appropriate filters based on your priorities. Here are some helpful booking tips for Vrbo to assist you.

  • Traveling to May Pen with a group: Think about how many bedrooms you require, as well as features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to May Pen with young kids: Travelling with young children can present its challenges. It's essential to prioritise their comfort and safety, along with providing suitable amenities, like a private swimming pool. Additionally, it's wise to take into account how close you are to family-friendly attractions.
  • Taking your pets with you to May Pen: For many, a family holiday isn't truly complete without their furry companion. If this resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations supply feeding bowls and beds, ensuring that everyone feels comfortably at home.
  • Planning for a long term stay visiting May Pen: If you're in search of holiday rentals with great offers for stays of a month or more, you've come to the perfect spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don’t forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near May Pen

May Pen, Clarendon, Jamaica, offers a vibrant cultural experience and a wealth of outdoor activities. Explore the scenic Longville Park, perfect for leisurely strolls or picnics. Discover the local charm in Yard Newport News, where vibrant community life thrives. For a touch of adventure, head to Bushy Park, known for its thrilling motorsport activities. With its blend of wellness and culture, May Pen is an ideal destination for those seeking an authentic Jamaican experience.

  • Thompson Town: Nestled approximately 19km from May Pen, Thompson Town is an inviting city that beckons adventure seekers and romantics alike. Its stunning natural landscapes make it a fantastic destination for outdoor enthusiasts. Visitors can explore a variety of activities, including a thrilling zipline ropes course and serene recreational areas. Notable attractions include a picturesque waterfall and a nearby beach, perfect for relaxation. The modern civic government building adds a touch of contemporary charm to this historic locale, making it an ideal spot for a day trip full of excitement and exploration.
  • Sandy Bay: Located a mere 10km from May Pen, Sandy Bay offers a delightful blend of business and culture. This vibrant city is renowned for its beautiful beach, which is perfect for sunbathing or a leisurely stroll. Visitors will appreciate the local monument that reflects the area’s rich heritage, alongside a modern civic government building that signifies its growth. Sandy Bay is an excellent choice for those looking to immerse themselves in local culture while enjoying a relaxing beach experience.
  • Gravel Hill District: Just 11km from May Pen, Gravel Hill District is a serene destination ideal for wellness and cultural experiences. Visitors can indulge in rejuvenating spa treatments and body therapies that promise relaxation and renewal. The area boasts a charming beach and a range of historic sites, allowing travellers to delve into the local history while enjoying the soothing coastal atmosphere. Gravel Hill District is perfect for those seeking a tranquil escape infused with cultural richness.

Best time to go to May Pen

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

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January74.7°F (23.7°C)No Rain (Dry)Mostly SunnyAverageAverage
February74.8°F (23.8°C)No Rain (Dry)Mostly SunnyAverageSlightly High
March75.7°F (24.3°C)No Rain (Dry)Mostly SunnyAverageSlightly High
April77.9°F (25.5°C)Light RainMostly SunnyAverageAverage
May79.3°F (26.3°C)Light RainMostly SunnySlightly HighSlightly High
June80.6°F (27.0°C)Light RainMostly SunnySlightly HighAverage
July81.5°F (27.5°C)Light RainMostly SunnySlightly HighAverage
August81.1°F (27.3°C)Light RainMostly SunnySlightly LowAverage
September80.2°F (26.8°C)Light RainMostly SunnyAverageSlightly Low
October78.3°F (25.7°C)Light RainMostly SunnySlightly LowSlightly Low
November76.6°F (24.8°C)Light RainMostly SunnySlightly LowSlightly Low
December75.4°F (24.1°C)No Rain (Dry)Mostly SunnyAverageAverage

Booking with Vrbo is a breeze

Are you keen to make the most of your budget on your next getaway? Being flexible with your travel dates can be beneficial, as prices often fluctuate. Additionally, opting for a longer stay can lead to substantial savings. To discover a Vrbo property that aligns with your budget, feel free to utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board provides an excellent platform for you to plan new trips, revisit your arrangements, or manage your bookings efficiently. Your saved or booked properties are conveniently organised into categories: Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Find the perfect holiday rental for your May Pen getaway

Learn about the unique charm of May Pen with a stay in a holiday home rental. This city has something for everyone. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around May Pen

Are you hoping to find attractions to visit in the city? Venture out of your cosy holiday rental and check out everything that makes May Pen a fun place to get away to. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Milk River Bath (10.4 mi / 16.8 km)
  • Wynter's Park & Farm (14.7 mi / 23.6 km)

Transport options to and around May Pen

Fly into Kingston (KIN-Norman Manley Intl.), the closest airport, located 31.6 mi (50.9 km) from the city centre.

Frequently asked questions

What is the best area to stay in May Pen when booking a holiday rental?
When considering a holiday rental in May Pen, Clarendon, Jamaica, a popular area to stay is the town centre. This vibrant locale offers a convenient base with a variety of properties, ranging from cosy guesthouses to more spacious rentals. The town centre is particularly appealing due to its accessibility to local shops, markets, and eateries, allowing visitors to immerse themselves in the local culture.

In addition to its practical amenities, the area is close to top attractions. The nearby May Pen Cemetery, one of the largest in Jamaica, is a site of historical significance, while the stunning Clarendon Parish Church offers a glimpse into the island's architectural heritage.
How much does it cost to rent a holiday home in May Pen?
Prices for holiday rentals in May Pen 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 May Pen 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 May Pen holiday house rentals?
You can find great discounts on house rentals in May Pen 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.
What is the most popular type of holiday rental accomodation in May Pen?
In May Pen, holiday houses are the most popular type of holiday rental, with around 21 available throughout the area. These houses provide ample space and often come equipped with multiple bedrooms, fully equipped kitchens, and outdoor areas for relaxing and enjoying the warm Jamaican climate. Additionally, there are several apartments and villas scattered around, offering alternative options for those seeking a more compact or luxurious stay.
Are there any family house rentals in May Pen?
In May Pen, Clarendon, there are several family-friendly house rentals available, providing comfortable accommodations for visitors. These properties often come with spacious living areas, full kitchens for preparing meals, and outdoor spaces where children can play freely. Many homes are equipped with modern amenities such as Wi-Fi and air conditioning, ensuring a pleasant stay for families.

The locale is conveniently situated near attractions such as the historic town centre and local markets, where families can experience firsthand the vibrant culture of Jamaica. Additionally, the nearby scenic areas offer opportunities for outdoor activities and exploration.
Can I rent a holiday home with a pool or hot tub in May Pen?
In May Pen, Jamaica, there are several holiday homes available for rent that feature pools and hot tubs. This charming town offers a variety of options for travellers looking to enjoy a relaxing getaway with the added luxury of private swimming facilities. Many properties come equipped with essential amenities such as air conditioning, spacious living areas, and fully equipped kitchens, making them ideal for families or groups.

The rentals are often set in tranquil surroundings, providing a peaceful atmosphere to unwind and enjoy the Jamaican sunshine. Some homes may also feature outdoor entertainment areas, superb for barbecues or lounging by the poolside.
Can I find long-stay holiday rentals in May Pen?
A long-stay holiday rental in May Pen 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 May Pen?
In May Pen, Clarendon, there are approximately 21 remote work-friendly holiday rentals available. These accommodations are well-suited for those looking to combine work and leisure, offering essential amenities such as reliable Wi-Fi and dedicated desk spaces in various properties. Many rentals also provide comfortable living areas that allow for a productive work environment while ensuring a pleasant stay.

The area is rich in local culture and history, making it a great backdrop for remote working. Travellers can expect to find properties that feature a range of conveniences, including air conditioning and kitchen facilities, enabling them to prepare meals and enjoy a homely atmosphere during their stay. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any May Pen holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in May Pen 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 May Pen?
In May Pen, popular rental amenities include fully equipped kitchens, which allow guests to prepare their own meals during their stay. Many properties also feature onsite parking, providing convenience for those travelling with their own vehicles. Additionally, rentals often come with porches or lanais, great for enjoying the warm Jamaican weather. Air conditioning is a common amenity, ensuring comfort during the hotter months. Many accommodations also include blenders, making it easy for guests to whip up refreshing smoothies or cocktails.
When is the best time to visit May Pen for a holiday rental?
May is the most popular time to visit May Pen, Clarendon, Jamaica, as it marks the beginning of the peak season, which runs from May to July. This vibrant period attracts holidaymakers eager to enjoy the island's stunning beaches, rich culture, and welcoming atmosphere. The warm climate, with temperatures typically ranging from 25 to 30 degrees Celsius, creates ideal conditions for outdoor activities like exploring local markets and soaking up the sun.

During these months, the area buzzes with activity, offering numerous opportunities for sightseeing and immersion in Jamaican culture. Visitors can partake in local festivals and events, adding an authentic flavour to their experience.

If you're looking for a more budget-friendly option, consider visiting in November, when the tourist crowds have thinned. This quieter month allows you to enjoy the beauty of May Pen at a more leisurely pace while still experiencing the warm, pleasant weather typical of the region.

Ultimately, the best time to book a holiday rental in May Pen will depend on whether you prefer the lively option of peak season or the tranquil charm of the off-peak months.
How early should I book a May Pen holiday rental?
Book your May Pen 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.
What are the top attractions in May Pen?
In May Pen, Clarendon, visitors can explore a range of attractions that showcase the local culture and natural beauty. The town is known for the historic May Pen Cemetery, which features unique tombs and memorials, reflecting the area's heritage. Nearby, the Clarendon Parish Church offers a glimpse into the architectural styles of the region and is often a focal point for local events.

Nature enthusiasts can venture to the nearby Milk River, renowned for its therapeutic mineral waters, where visitors can relax in its warm, healing springs. Additionally, the lush landscapes surrounding May Pen provide opportunities for outdoor activities such as hiking and exploring the rich flora and fauna of the area.

The bustling town centre features local markets where visitors can sample Jamaican cuisine and shop for handmade crafts, offering a taste of the vibrant culture that characterises Clarendon.
Can I change or cancel my May Pen home rental booking on Vrbo?
To find May Pen 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 cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the May Pen 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.