Book Holiday Homes in May Pen

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Featured Holiday Homes in May Pen

Cozy retreat pool access super close to the Town. Entire home available to you!

Cozy retreat pool access super close to the Town. Entire home available to you!

Old Harbour
Stay at this vacation home in Old Harbour. Enjoy free WiFi, a garden, and patios.
Cozy retreat pool access super close to the Town. Entire home available to you!
Beautiful 3 bedroom Townhouse- 1.2km Town Center

Beautiful 3 bedroom Townhouse- 1.2km Town Center

Mandeville
Stay at this vacation home in Mandeville. Popular attractions Mandeville Parish Church and Mega Mart are located nearby.
Beautiful 3 bedroom Townhouse- 1.2km Town Center
Charming 2-bed House in Portmore Gated Community

Charming 2-bed House in Portmore Gated Community

3 out of 5
Portmore
Stay at this 3-star residence in Portmore. Enjoy free WiFi, free parking, and a garden. Popular attractions Sovereign Village Mall and Iron Bridge are located ...
Charming 2-bed House in Portmore Gated Community
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Mckay's Home Away from Home

Mckay's Home Away from Home

Hatfield
The price is NZ$242 per night from 7 Jan to 8 Jan
NZ$242
includes taxes & fees
7 Jan - 8 Jan 2025
Stay at this vacation home in Mandeville. Enjoy free WiFi, a garden, and cable/satellite TV service. Popular attractions Manchester Parish Court and Cecil Charlton ...
Mckay's Home Away from Home
Peterkin's Retreat Vacation Home

Peterkin's Retreat Vacation Home

Manchester
The price is NZ$605 per night from 24 Dec to 25 Dec
NZ$605
includes taxes & fees
24 Dec - 25 Dec
Stay at this vacation home in Mandeville. Enjoy a fitness center, patios, and cable/satellite TV service. Popular attractions Mega Mart and Marshall’s Pen are ...
Peterkin's Retreat Vacation Home
Beautiful spacious Town house.

Beautiful spacious Town house.

Spanish Town
Stay at this vacation home in Spanish Town. Enjoy free WiFi, cable/satellite TV service, and a spa tub. Popular attractions Courthouse Ruins and St Catherine ...
Beautiful spacious Town house.
Relax and enjoy in this beautiful home in a quiet neighbourhood.

Relax and enjoy in this beautiful home in a quiet neighbourhood.

Mineral Hieghts
The price is NZ$247 per night from 24 Dec to 25 Dec
NZ$247
includes taxes & fees
24 Dec - 25 Dec
Stay at this vacation home in May Pen. Enjoy free WiFi, a garden, and cable/satellite TV service.
Relax and enjoy in this beautiful home in a quiet neighbourhood.
A luxury everyone can afford.

A luxury everyone can afford.

Four Paths
Stay at this vacation home in Clarendon. Enjoy air conditioning.
A luxury everyone can afford.
Beautiful Top Apartment in St. Elizabeth, Jamaica with an amazing Mountain View!

Beautiful Top Apartment in St. Elizabeth, Jamaica with an amazing Mountain View!

Junction
Stay at this vacation home in Spur Tree. Enjoy free WiFi, balconies, and an in-room coffeemaker.
Beautiful Top Apartment in St. Elizabeth, Jamaica with an amazing Mountain View!
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

May Pen Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our May Pen vacation homes are the perfect way for you to wing it.

Holiday houses in May Pen let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of May Pen in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local May Pen adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in May Pen with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of May Pen vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

May Pen Holiday Homes essential information

Accommodation
159 Holiday Homes
Lowest Price
NZ$92
Highest Price
NZ$605
Popular accommodation
Cozy retreat pool access super close to the Town. Entire home available to you!, Beautiful 3 bedroom Townhouse- 1.2km Town Center, Charming 2-bed House in Portmore Gated Community, Mckay's Home Away from Home, Peterkin's Retreat Vacation Home, Beautiful spacious Town house. , Relax and enjoy in this beautiful home in a quiet neighbourhood., A luxury everyone can afford., Beautiful Top Apartment in St. Elizabeth, Jamaica with an amazing Mountain View!

Top trending hotels in May Pen

Relax N SunShine

Relax N SunShine

May Pen
The price is NZ$92 per night from 24 Dec to 25 Dec
NZ$92
includes taxes & fees
24 Dec - 25 Dec
Stay at this B&B in May Pen. Enjoy free WiFi, a garden, and patios.
Relax N SunShine
Relax and enjoy in this beautiful home in a quiet neighbourhood.

Relax and enjoy in this beautiful home in a quiet neighbourhood.

Mineral Hieghts
The price is NZ$247 per night from 24 Dec to 25 Dec
NZ$247
includes taxes & fees
24 Dec - 25 Dec
Stay at this vacation home in May Pen. Enjoy free WiFi, a garden, and cable/satellite TV service.
Relax and enjoy in this beautiful home in a quiet neighbourhood.
Joyful Ambiance Retreat

Joyful Ambiance Retreat

May Pen
Stay at this villa in May Pen. Enjoy free WiFi, a fitness center, and a garden.
Joyful Ambiance Retreat
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Diamonds

Diamonds

3 out of 5
23 Montgomery Boulevard, Palmetto Meadows, May Pen, Clarendon
Stay at this 3-star guesthouse in May Pen. Enjoy free WiFi, free parking, and laundry facilities.
Diamonds
Don't see what you're looking for?
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.