May Pen Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for May Pen vacation rentals

A covered balcony with white balustrades, a stone floor, and a view of greenery.

1. Sandy Bay Paradise Retreat - 7 Bedrooms

Sandy Bay Paradise Retreat - 7 Bedrooms
3.0 star property
Sandy Bay
The price is ￥69,441
￥84,568 total
includes taxes & fees
Nov 24 - Nov 25
Sandy Bay Paradise Retreat - 7 Bedrooms
A modern living room with a leather sofa, a coffee table, and a dining area with a table and chairs.

2. Cozy Relaxing Home in Old Harbour

Cozy Relaxing Home in Old Harbour
2.0 star property
Old Harbour
The price is ￥26,603
￥2,146,023 total
includes taxes & fees
Nov 6 - Nov 7
Cozy Relaxing Home in Old Harbour
A modern living room with a white sofa, a glass coffee table, and a staircase leading to an upper level.

3. Tuscany Sun Villa at Legacy Townhouse

Tuscany Sun Villa at Legacy Townhouse
2.0 star property
Thompson Town
The price is ￥118,763
￥136,735 total
includes taxes & fees
Nov 6 - Nov 7
Tuscany Sun Villa at Legacy Townhouse
A pool area with a gazebo, lounge chairs, and a view of the surrounding landscape.

4. Mountain Top Villa

Mountain Top Villa
3.5 star property
Mandeville
8.4 out of 10, Very good, (27 reviews)
"Hotal it self was beautiful , lay out great , room was a bit small but manageable. Overall a great stay I would highly recommend"
United Kingdom
Robert
The price is ￥9,287
￥14,797 total
includes taxes & fees
Nov 6 - Nov 7
Mountain Top Villa
A modern kitchen with a built-in oven, a refrigerator, and a dining area with a table set for four.

5. Phoenix Park Villas Portmore

Phoenix Park Villas Portmore
4.0 star property
Portmore
9.2 out of 10, Wonderful, (7 reviews)
"I will definitely recommend that you stay here is so peaceful security are strictly on point with everything and the comfort of the home is great will be staying back for sure ."
United States
Kimoya
The price is ￥28,503
￥54,492 total
includes taxes & fees
Nov 6 - Nov 7
Phoenix Park Villas Portmore
A kitchen with a central island, bar stools, wooden cabinets, a window with a view, and a microwave.

6. Coke's Guest House

Coke's Guest House
2.0 star property
Mandeville
The price is ￥13,539
￥15,728 total
includes taxes & fees
Nov 6 - Nov 7
Coke's Guest House
A balcony with a view of a pool and a building in the background.

7. Caldo Tours

Caldo Tours
2.5 star property
Ewarton
10.0 out of 10, Exceptional, (3 reviews)
"Very inviting and the owner's are wonderful people that keeps you comfortable and satisfied "
United States
Stephen
The price is ￥18,527
￥20,538 total
includes taxes & fees
Nov 6 - Nov 7
Caldo Tours
A neatly made bed with white linens and a beige throw blanket, flanked by two bedside tables with lamps, in a room with a blue headboard.

8. 1BR Villas Phoenix Park Village ll

1BR Villas Phoenix Park Village ll
2.0 star property
Portmore
The price is ￥14,252
￥28,424 total
includes taxes & fees
Nov 6 - Nov 7
1BR Villas Phoenix Park Village ll
A swimming pool with blue chairs and a covered area, surrounded by a brick walkway.

9. Harbour Oasis Retreat - Charming 2 Bedroom House

Harbour Oasis Retreat - Charming 2 Bedroom House
3.5 star property
Old Harbour
The price is ￥17,433
￥32,452 total
includes taxes & fees
Dec 2 - Dec 3
Harbour Oasis Retreat - Charming 2 Bedroom House
A hallway with a tiled floor and a door leading to a balcony.

10. Immaculate 2-bed Apartment in Spanish Town

Immaculate 2-bed Apartment in Spanish Town
3.0 star property
Spanish Town
The price is ￥10,708
￥12,474 total
includes taxes & fees
Nov 7 - Nov 8
Immaculate 2-bed Apartment in Spanish Town
A building with a balcony and a staircase.

11. Lovely 1-bed Cottage in St Catherine

Lovely 1-bed Cottage in St Catherine
3.0 star property
Ewarton
10.0 out of 10, Exceptional, (1 review)
"I enjoyed my stay at the cottage, hosts were very helpful and my stay was very quiet and peaceful. Will definitely stay here again in the future."
United States
DESMOND
The price is ￥2,792
￥4,596 total
includes taxes & fees
Dec 2 - Dec 3
Lovely 1-bed Cottage in St Catherine
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.
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Top May Pen Hotel Reviews

A modern building with a pool, large windows, and trees.
The Garden Hotel Mandeville

The Garden Hotel Mandeville

The Garden Hotel Mandeville
Mandeville

10/10 Excellent

Excellent service, food is great. Nice relaxing environment
United States
Melissa
Reviewed November 2, 2026
The Garden Hotel Mandeville

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