Family-friendly holiday houses in May Pen

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in May Pen

Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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Superhost

Apartment in Bog Walk

4.68 out of 5 average rating, 37 reviews

Far-I Guesthouse

If you are interested in having an authentic Jamaican experience, we would love to welcome you to a modern studio apartment situated in a rural but upcoming community. The area is peaceful, with many orange and banana farms which adds to the rural feel and a sense of tranquility. The property itself is littered with fruit trees and flowers and we recently added a small swimming pool. It is also 7 minutes drive from the cooling Rio Cobre River, which is ideal for a refreshing swim on a warm day.

19 – 26 May

$554 AUD total

Guest favourite

Home in Saint Catherine Parish

4.94 out of 5 average rating, 50 reviews

Caymanas Estates Villa!

A lovely two bedroom home, in a beautifully landscaped gated community with air conditioning, water heater, pools, tennis court, gazebos and quiet environs. Oasis Villa is ideal for a couple or a family to take their vacation. It is also located "smack" in the middle of the major cities of Portmore, Kingston and Spanish Town and therefore, the usual comforts are close by; KFC, Tastees, Burger King, Hellshire Beach for seafood meals, restaurants, plazas, supermarkets, banks and a whole lot more.

25 Mar – 1 Apr

$1,181 AUD total

Home in Hellshire

5.0 out of 5 average rating, 3 reviews

Sunset Oasis: 3BR Portmore Gem

Discover your private slice of paradise , nestled in the heart of Portmore. This charming retreat offers a serene escape with its cozy, modern interiors. Each bedroom is designed for comfort, ensuring a restful night's sleep. The living area, complete with WiFi and smart TV, and over head projector, opens up to a lush outdoor space, ideal for evening barbecues or morning coffee. Located just minutes from stunning beaches and local eateries, our home promises an unforgettable Jamaican getaway.

11 – 18 Sept

$1,999 AUD total

Guest favourite

Home in Saint Catherine Parish

4.88 out of 5 average rating, 113 reviews

The Caymanas Villa

My place is a modern country side home that is close to golf resorts, polo clubs, beaches, the city center, with mountain side views. My place is good for couples, solo adventurers, business travelers, and families. This is a secure facility that is centrally located in Jamaica with within 1km from both north-south and east-west high way 2hrs drive to Montego bay and 20 min to Kingston. This facility has recreational spaces, such as jogging trail, swing pool, basket ball and tennis court.

26 Oct – 2 Nov

$1,196 AUD total

Guest favourite

Home in Portmore

4.91 out of 5 average rating, 92 reviews

The Oasis I, Portmore Country Club

The Oasis is a modernly decorated home located in Portmore Country Club, a quiet, peaceful and family orientated gated community with 24/7 security. The house is centrally located in Jamaica within 5km from both north-south and east-west high way with travel time of 2hrs drive to Montego Bay, 40 min to Ocho Rios and 20 min to Kingston. The Oasis provides a relaxed, cozy and comfortable environment with air conditioned rooms that are suited for couples, families and business travelers.

4 – 11 Sept

$1,112 AUD total

Superhost

Home in Mandeville

4.81 out of 5 average rating, 32 reviews

Cozy Dwelling - Secured Complex

Enjoy cool cool Mandeville in a way you never thought possible. Our property is located in the upscale ,highly sought after community of Ingleside. You can expect to enjoy utmost privacy and security at this location . Enjoy expansive indoor and outdoor spaces caressed by the cool, natural Mandeville breeze,while still having easy access to businesses, restaurants, pubs, sports, gym, and nightlife. Emergency services (Hospitals, Police, Fire Services) are less than 10 minutes drive away.

1 – 8 May

$1,008 AUD total

Superhost

Townhouse in Portmore

4.48 out of 5 average rating, 27 reviews

ROWESVALE

Rowesvale is a comfortable and peaceful family dwelling with air-conditioned rooms located in Greater Portmore. It is suitable for families, business professionals and vacationers. It is centrally located, 40 minutes from Norman Manley International Airport and 3 minutes from newly exquisitely designed shopping malls. Its central location puts you 1 hour from Ocho Rios, 15 mins from Helshire Beach, 10 mins from Forth Clarence Beach and only 34 mins from the famous Bob Marley museum.

5 – 12 Apr

$585 AUD total

Guest favourite

Home in Spanish Town

4.7 out of 5 average rating, 111 reviews

Comfort Cottage | private pool | 24hr security

Our place is close to major thoroughfares, town centre, hospital and transportation. Restaurants, supermarkets and shopping are just minutes away. The community has a kids park, adults park with jogging trail, club house, playfield, tennis court, and basketball court. The home is fully furnished and air-conditioned for your comfort. Our place is good for couples, solo adventurers, business travelers, and families (with kids).

14 – 21 Apr

$1,107 AUD total

Guest favourite

Guesthouse in Summerfield

4.89 out of 5 average rating, 18 reviews

HershyB's Farm & Guest House

My place is close to family-friendly activities and public transport. You’ll love my place because of the cosiness, the location, and the views. You can go hiking through the farm and enjoy the organic beauty of Jamaica. My place is good for couples, solo adventurers, business travellers and families. The apartment is not wheelchair accessible, you will need to climb steps to access the apartment.

1 – 8 Oct

$496 AUD total

Guest favourite

Condo in Twickenham Park

4.9 out of 5 average rating, 52 reviews

Your Cozy Comfy & Safe 2 Bedroom Apartment

Entire 2 bedroom cozy apartment for a maximum of four guests, centrally located in Twickenham Park, St. Catherine in a safe gated community with 24-hour security. The apt is fully equipped and features Air Conditioning, Hot Water, WIFI & Kitchen Amenities. Enjoy a relaxing & quiet stay away from the bustle of the city, but get to Kingston or Portmore in a flash. All backgrounds are welcome.

20 – 27 Mar

$581 AUD total

Home in Saint Catherine Parish

4.76 out of 5 average rating, 38 reviews

Morgan's Retreat at Caymanas Estate near Kingston

Step into a world where comfort, luxury, and a warm embrace await you. We're delighted to invite you to Morgan's Retreat, a haven that beckons you to experience the genuine essence of a home away from home. Nestled within the oasis of Caymanas Estate, this is not just a place to stay – it's a sanctuary that will envelop you in a sense of belonging and familiarity.

5 – 12 June

$1,067 AUD total

Guest favourite

Home in St. Catherine,Jamaica

5.0 out of 5 average rating, 26 reviews

S-Cape to paradise

Beautiful & comfortable 2 bedroom 2 bathroom house located in a quiet, gated residential area. Family room, dining, kitchen a/c, wash room swimming pools, tennis & basket ball court, jogging trail and 3mins away from the golf club 24 hrs Security.

27 June – 4 July

$1,310 AUD total