
House holiday rentals in May Pen
Find and book unique houses on Airbnb
Quick stats about house rentals in May Pen

Total holiday rentals
Explore 10 holiday rentals in May Pen

Nightly prices starting at
May Pen holiday rentals start at $56 AUD per night before taxes and fees

Verified guest reviews
Over 70 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Wi-Fi availability
10 of May Pen holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across May Pen rentals

4.8 Average rating
May Pen stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated house rentals in May Pen
Guests agree: These houses are highly rated for location, cleanliness and more.

Sleep Easy, Relax in Comfort
Welcome to my home! A new two bedroom house located near the border of St. Catherine and Kingston, in a quiet and relaxing country style gated community. This location provides 12 minutes access to Kingston, 8 minutes to Portmore, 10 minutes to Spanish Town, and in about 3 minutes you’ll be able to access the highway leading to Ocho Rios. This means you could be climbing Dunn's River Falls in 45 minutes. The space is fully equipped to make your stay as comfortable as possible. Come and enjoy!

🏝🏝HIDDEN GEMS 💎 💎 🏝🏝 Vacation Home 🏡🏞
This carefully designed house is ideal for persons looking for a cool refreshing modern and comfortable vacation stay . It is perfectly located in quiet and secure gated community Phoenix park village ,in the well developed sunshine city of portmore st catharine . It is most suitable for you because of its convenient access to all it has to offer around it ,its famous helshure beach, movie theater ,shopping malls ,clubs ,restaurants etc . it is the place for families ,couples, or just friends

Kgap Ranch,3 bedrooms with private pool and gym
KGAP Ranch, a perfect family getaway. Enjoy the experience that this 3 bedroom,3.5 bathroom oasis has to offer. Located in a quiet,safe & centrally located neighborhood. Less than 3 minutes access to high way 2000, 30 minutes from Kingston where major attractions like Usain Bolt tracks & records,Club Meca, Macau Gaming lounge & Bar.We are one hour away from excursions in Ocho Rios.KGAP Ranch is equipped with coded doors & security gates. Our host is responsive and reachable 24 hours.

Camerons Cove-378 Home in Whim Estates Old Harbour
A cozy and well-appointed space designed for comfort and relaxation in a gated and secured community. Located in a convenient and desirable area, you’ll love the warm and welcoming atmosphere, perfect for families, couples, or solo travelers. What makes it so special is the thoughtful amenities, stylish decor, and personalized touches that make you feel right at home. Whether you’re looking for a peaceful retreat or easy access to local attractions, we offer you an unforgettable stay.

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

Elegant 2BR, Pool, Gym & Games Room - Book Now
Make lasting memories with your loved ones at this family-friendly 2-bedroom retreat! The home is fully furnished with modern comforts and features a vibrant games room for endless fun, plus access to a pool and gym for all ages to enjoy. With plenty of room for everyone, the home combines relaxation, entertainment, and convenience. Located just minutes from town, you’ll have quick access to restaurants, shops, and local attractions, making it easy to plan family outings.

The Oasis @ Caymanas Country Club btw Portmore/Kgn
The property is located in the quiet and peaceful Caymanas Country Club gated community with 24x7 security. The community is centrally located and is 15 minutes away from Kingston, 5 minutes away from Portmore and 45 minutes drive to Ocho Rios via the nearby entrance of the North-South Highway. Some of the amenities in the community includes jogging trail, adult and kids size swimming pool, basketball and tennis court. I welcome you to be part of The Oasis family.

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.

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!

The Geenie Gates - Fully Air Conditioned
Welcome to The Geenie Gate! Step into a world where comfort and luxury feel like pure magic. Here, high-tech convenience meets high-end style in an oasis designed just for you. Imagine jewel-toned lighting, smart features that respond to your touch and voice, and spaces crafted for ultimate relaxation. Let the outside world fade away—your hidden retreat awaits. Ready to experience the magic? Just make a wish.”

Luxury Oasis of New Harbour Village III
Royal Oasis is a peaceful, centrally-located, and gated place with 24-hour security. It is five (5) minutes from Old Harbour Town, two (2) minutes from the highway, and thirty (30) minutes from Kingston. It has three (3) Air conditioners, one in each bedroom and another in the living room. This property is also 5 minutes from the beach and 15 minutes from Salt River.

Evertonbnb 592 - With Private Heated Jacuzzi Pool
Luxury home with Private Heated Jacuzzi Pool, Gazbo and Lounge, Outside dining and Barbecue pit. Lots of room for fun. Quiet Gated Community with 24 Hour security. 2 minutes off the Old Harbour Highway Exit. 5 Minutes to the Town Centre. 30 Minutes via the highway to Pricesmart Shopping.
Popular amenities for May Pen house rentals
House rentals with a pool

Oak Château: Rest, Renew, Restore.

Beautiful 7-min city escape with view & pool

Chillax Island Stay – Private Pool & Gazebo

Charming Oasis Getaway

Comfort Cottage: Private Oasis w/Pool & Security

Poolhouse@Countryclub | Private Pool | Gated

Serene Vistas, Caymanas Country Club

Colbeck Villa
Weekly house rentals

Beautiful Battersea Lodge

Avi's Luxury Haven: Modern, Cozy and Quiet Getaway

K&W comfort suite Fully air condition, gated.

CW Palace. Wifi and Fully Air Conditioning

The Cherryhill of Old Harbor

Cool Cozy Cottage II. 2 bedroom oasis Free parking

Jems of the Estates

Rest with no Stress In A gated community
Private house rentals

Beautiful Luxury 3BR in Gated Kingston's Haven.

JSuites: Apartment in Old Harbour

Cozy Groundfloor 2BR Getaway in Old Harbour.

Caribbean Dream II

Gated Retreat with Resort Pool, Caymanas Estate

Simm's Estate lux with Jacuzzi

Le Mar Manor Exquisite Comfort

Cozy and spacious home.
Destinations to explore
- Kingston Holiday rentals
- Montego Bay Holiday rentals
- Ocho Rios Holiday rentals
- Negril Holiday rentals
- Portmore Holiday rentals
- Mandeville Holiday rentals
- Treasure Beach Holiday rentals
- Guardalavaca Holiday rentals
- Old Harbour Holiday rentals
- Holguín Holiday rentals
- Port Antonio Holiday rentals
- Discovery Bay Holiday rentals
- Ocho Rios Bay Beach
- Bob Marley Museum
- Phoenix Park Village
- Hellshire Beach
- Hope Botanical Gardens
- Emancipation Park
- Sabina Park
- YS Falls
- Reggae Beach
- Fort Clarence Beach
- Floyd's Pelican Bar
- Green Grotto Caves
- Lovers Leap
- University of the West Indies
- Strawberry Hill
- Turtle River Park
- Devon House
- Rafjam Bed & Breakfast
- Somerset Falls
- Dolphin Cove Ocho Rios
- Bob Marley's Mausoleum
- Independence Park
- Martha Brae Rafting Village
- Whispering Seas





