
Vacation rentals in May Pen
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Top-rated vacation rentals in May Pen
Guests agree: these stays are highly rated for location, cleanliness, and more.

Modern Home (Gated Community) Old Harbour NHV3
New modern Gated Comm. 1 King, 1 Queen bed, 2 baths located in NHV3, Old Harbour with GAZEBO and BAR. This amazing home also decked with LED Lighing, 1 Kitch and laundry. It's fully A/C in Living n Bed Rm. Grilled with 24/7 security, Smart lock, Free NetFlix, also CCTV Cameras for your safety, a fire place. All furnitures are brand new to suit your needs. This is situated closed to Restaurant, Jerk Centre, KFC, Juici Beef, High 2000, 30mins portmore, spanish Town 1 hour to Ocho Rios. +Car Rental

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.

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.

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!

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.

Luxe Oasis@Colbeck Gated. Private. Chef. Pool. Gym
Welcome to Luxe Oasis— your private, secure escape in the heart of Old Harbour. Whether you're traveling for rest, romance, or remote work, our modern, gated property offers the perfect blend of comfort and convenience—with home-cooked meal options available upon request! ⏳ Our calendar fills fast—especially on weekends and holidays! Book now and experience laid-back luxury at The Manor ✨

Colbeck Villa
Relax with the whole family at this peaceful place to stay. The Colbeck Villa located in a gated community with pool gym. The home is a beautiful 2 bedroom 1 bathroom house with all modern amenities. The home is fully Air Condition with ceiling fans. Clean and spacious bedrooms living room and kitchen. Comfortable beds, sofa and chairs. You will enjoy you stay at the Colbeck Villa.

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

Trenz De Luxe
Live the lifestyle you deserve! Trenz De Luxe is an exquisite property nestled in a prestigious gated community, just outside May Pen town centre. The home offers the perfect blend of luxury, convenience, and style.

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 vacation rentals
Other great vacation rentals in May Pen

Cozy Groundfloor 2BR Getaway in Old Harbour.

Full town/house - 2 bedrooms (queen & single)

The Geenie Gates - Fully Air Conditioned

May pen Studio Apartment unit

The Oasis at Whim

Solace King Suite # 1 New Luxury 1 Bed 1 Bath Apt.

Livingwell Homes Jamaica

The Peterkin’s Comfy Complete Home
When is the best time to visit May Pen?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec | 
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$18,616 GYD | G$18,616 GYD | G$20,499 GYD | G$20,499 GYD | G$20,499 GYD | G$24,682 GYD | G$16,734 GYD | G$16,734 GYD | G$17,780 GYD | G$17,780 GYD | G$17,780 GYD | G$17,780 GYD | 
| Avg. temp | 27°C | 27°C | 27°C | 28°C | 29°C | 29°C | 30°C | 30°C | 29°C | 29°C | 28°C | 27°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 house rentals in May Pen?
Experience the best of May Pen with our house rentals, starting at about $40 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 Apartment Rentals in May Pen?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with wifi, over 10 homes with air conditioning, 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 house rentals in May Pen have wifi?
Absolutely! We offer over 10 house rentals with wifi in May Pen. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in May Pen have free parking?
Absolutely! We offer over 10 house 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 vacation rentals in May Pen

Total vacation rentals
Explore 30 vacation rentals in May Pen

Nightly prices starting at
May Pen vacation rentals start at G$8,367 GYD per night before taxes and fees

Verified guest reviews
Over 150 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of May Pen vacation rentals include wi-fi access

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

4.9 Average rating
May Pen stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
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