Holiday houses in May Pen

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Top-rated holiday rentals in May Pen

Guests agree: these stays are highly rated for location, cleanliness and more.

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Superhost
A single-story home with a welcoming front porch is showcased. Light yellow and creamy white exterior walls are complemented by a manicured lawn and garden. A small outdoor table and chairs are set on the porch, with a pathway of stones leading to the entrance.
Home in Old Harbour
4.83 out of 5 average rating, 23 reviews

Cool Cozy Cottage II. 2 bedroom oasis Free parking

This beautiful 2 bedroom 1 bathroom home is located in the peaceful community of Aviary Old Harbour. Relax in comfort in Queen size bed in the main room with ac comfort. The second room is equipped with two twin beds. 24hrs camera that monitors the entrance. The location gives easy access to the Highway leading to Kingston, Ocho Rios and Montego Bay and also to Mandeville. Enjoy modern amenities with access to wifi and our outdoor verandah. Checkin with through the use of our key box system.

Guest favourite
A spacious kitchen area features light blue walls and marble flooring. A large island with two stools is positioned centrally, complemented by modern cabinetry. A six-burner gas stove with an oven is situated against the wall, with ample natural light filtering through the windows.
Home in May Pen
4.87 out of 5 average rating, 30 reviews

The Rose Garden (2 A/Cs + 2 baths)

Duplex in peaceful location near Glenmuir Rd. This listing is unit #2 with over 40 amenities, including private entrance, A/C, WiFi, 3 Smart TVs, Hot water, 2 bedrooms (1 en-suite), 2 bathrooms, living/dining areas, equipped kitchen, front & back porch and other amenities designed for your comfort. Only 3 min. from Highway 2000, Guests are centrally located with access to north, east and west coasts and minutes away from grocery store, entertainment, malls & restaurants in May Pen

Top Guest favourite
A well-appointed bedroom features a spacious bed with a cozy blanket and decorative pillows. The green curtains frame the window, while a sleek dresser is positioned against the wall. An air conditioning unit is mounted above, providing comfort during warm days. Inset is an image of the pool area.
Home in Old Harbour
4.92 out of 5 average rating, 48 reviews

Chillax Manor Your Private Oasis for Relaxation

Get this entire space with Pool access! Nestled in a gated community, Chillax Manor is perfect for your next getaway. The Manor offers you a luxury hotel feel. It is the getaway that your family will enjoy while being centrally located place to everything. You deserve to chill in this impeccable two-bedroom, one-bathroom peaceful spot with a pergola. Chillax Manor is also equipped with the necessary toiletries and a few complimentary beverages/snacks.

Top Guest favourite
The exterior of the vacation home showcases a two-story design with a distinct color palette and arched windows. A paved driveway leads to a spacious garage, framed by decorative columns. The sky above is partly cloudy, enhancing the inviting presence of the property.
Home in Clarendon
5 out of 5 average rating, 35 reviews

Step into TRENZ …Airbnb

Step into Trenz Airbnb. A luxurious vacation home conveniently and centrally located in the gated community of Paisley Place. Trenz offers 3 modern bedrooms, each outfitted with its own en-suite bathroom, air conditioning, and hot water to sleep 6 persons comfortably. You’ll be 5 minutes away from : *May Pen Town Centre * The major highways * Millennium Mall. * Knutsford Express You’ll be 15-20 minutes away from: * Fyah Side *Murrays Fish & Jerk

Top Guest favourite
A decorative entrance sign displaying 'Colbeck Manor' is mounted on a beige wall. Surrounding greenery features well-maintained flowering plants, adding a touch of color against the background of a clear blue sky.
Home in Old Harbour
5 out of 5 average rating, 19 reviews

Colbeck364 Comfort Stay

Colbeck364 Comfort Stay – Relax in Style! Welcome to Colbeck364 Comfort Stay, a fully air-conditioned retreat in Colbeck Manor, Old Harbour, St. Catherine. Enjoy a community pool, gym, high-speed Wi-Fi, and Smart TV. The home features a fully equipped kitchen, stylish interiors, and a secure gated community. Just minutes from Old Harbour town, shopping, and major highways. Book now for a relaxing and comfortable stay!

Guest favourite
A modern kitchen is presented with dark cabinetry and a granite countertop. Kitchen appliances, including a microwave, stove, and double-door refrigerator, provide functionality. A dining table set for two is featured, with a glass and decorative elements, enhancing the space's practical appeal.
Apartment in May Pen
4.89 out of 5 average rating, 45 reviews

Home

Kick back and relax in this calm, stylish space. Home is centrally located in a gated secure premises in May Pen, Clarendon. It is 2 mins from the nearest hospital. Doctors offices, restaurants, shopping, spas, salons, etc. Attractions in Clarendon includes, the Milk River Mineral bath, Farquahar beach, salt River mineral spring and other hidden gems. Home is also 2 mins away from the high way 2000.

Guest favourite
A modern living area features a plush blue sectional sofa adorned with decorative throw pillows. A white marble coffee table sits atop a patterned area rug. In the background, a dining space is visible, furnished with dark chairs and a softly lit kitchen.
Home in Old Harbour
4.89 out of 5 average rating, 27 reviews

K&W comfort suite Fully air condition, gated.

Relax by yourself or with the whole family at this newly built, fully air condition, clean, modern, comfortable well secured home. Gated community with 24 security service. Less than 2 minutes away from Norman Manley highway and 5 minutes from old Harbour town, 20 minutes from vibrant Kingston city, and 15 minutes from Clarendon. New Harbour 2 community entrance.

Guest favourite
A modern living space is presented, featuring a comfortable sectional sofa and an ottoman. An entertainment unit displays a large screen showcasing the Netflix logo. The kitchen area is visible, with bar stools arranged at a sleek counter, and natural light filters through the window.
Home in Old Harbour
4.95 out of 5 average rating, 38 reviews

Central & Stylish 2BR, Comfy, Low Cost & Games

Bring the family to this cozy 2BR stay close to town! Relax in a stylish space with a full kitchen, comfy living room, and PS4 entertainment for kids (and adults!). Everything you need, shops, dining, and attractions, is just minutes away. With easy access and a welcoming atmosphere, this is the perfect family base for both fun and relaxation.

Guest favourite
The front view of the home is framed by blooming flowering trees, with a gated entrance leading to a spacious driveway. The light-colored house features arched windows, a peaked roof, and is welcomed by clear blue skies.
Home in Old Harbour
4.88 out of 5 average rating, 59 reviews

HVille159

This is a quiet, peaceful gated community with 24 hours security. This two bedroom home is relaxing and comfortable with luxury at its core. Located close to the north-south and east-west highways, HVille159 offers easy commute to and from Kingston or other parishes.

Superhost
A well-lit bedroom features a spacious bed with decorative pillows and a patterned blanket. Natural light enters through two windows, framed by light curtains. A wooden dresser is positioned against one wall, and a ceiling fan adds a functional touch to the room.
Home in Four Paths
4.77 out of 5 average rating, 13 reviews

2 Bed 1 bath Home Away From Home

Amenities Included- ✅Heated water ✅Multiple Car parking spaces ✅24 Hour security systems available for the safety of our guests. ✅Air conditioning In all bedrooms ✅Porch For seating And more. Washer and dryer Oven and Stove Coffee Machine Microwave

Superhost
A neutral-toned bedroom features a spacious bed with a tufted headboard, flanked by nightstands. Light curtains frame the window, and a cozy seating area with a two-tone sofa is positioned nearby. A textured area rug adds warmth to the tile flooring.
Apartment in Four Paths
4.84 out of 5 average rating, 31 reviews

Home Away From Home 4

Our Home Away From Home can be your next destination for a getaway of any type. Whether it's for a long or short stay we welcome you. Our peaceful 1-bedroom apartment fully renovated and equipped with everything for your comfort.

Superhost
A modern two-story building is depicted with a bright white exterior and a distinctive blue roof. A private pool is situated in the front, while a spacious terrace overlooks the area. Surrounding greenery complements the residence within a gated community.
Apartment in Paisley
4.83 out of 5 average rating, 6 reviews

Queen bed suite with full kitchen

Kick back and relax in this calm, stylish space in Jamaica. 1 bed suite located in gated community has on site pool, smart locks full kitchen, newly built

Popular amenities for May Pen holiday rentals

When is the best time to visit May Pen?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$154 NZD$154 NZD$170 NZD$170 NZD$170 NZD$205 NZD$210 NZD$218 NZD$173 NZD$147 NZD$147 NZD$147 NZD
Avg. temp27°C27°C27°C28°C29°C29°C30°C30°C29°C29°C28°C27°C

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in May Pen?

    Yes! Work meets play with ease at over 10 vacation rentals in May Pen featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do apartment rentals in May Pen have a kitchen?

    Absolutely! We offer over 10 apartment rentals with a kitchen in May Pen. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in apartment rentals in May Pen?

    Experience the best of May Pen with our apartment rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • What are the most popular amenities for House Rentals in May Pen?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with a kitchen, over 10 homes with wifi, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there family-friendly vacation rentals in May Pen?

    May Pen has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do apartment rentals in May Pen have wifi?

    Absolutely! We offer over 10 apartment rentals with wifi in May Pen. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in May Pen have free parking?

    Absolutely! We offer over 10 apartment rentals with free parking in May Pen. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in May Pen have air conditioning?

    Absolutely! We offer over 10 apartment rentals with air conditioning in May Pen. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in May Pen

  • Total holiday rentals

    Explore 30 holiday rentals in May Pen

  • Nightly prices starting at

    May Pen holiday rentals start at $69 NZD per night before taxes and fees

  • Verified guest reviews

    Over 150 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of May Pen holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across May Pen rentals

  • 4.9 Average rating

    May Pen stays are highly rated by guests—averaging 4.9 out of 5!

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