Family-friendly holiday rentals in Hellshire

An outdoor seating area features dark wicker furniture with bright turquoise cushions, providing a comfortable space for relaxation. The view includes a landscaped yard with palm trees and a swimming pool, outlined by a wooden pergola and surrounded by vibrant greenery.

4.86 out of 5 average rating, 230 reviews

🏝🏝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

4.96 out of 5 average rating, 141 reviews

Farm stay in Eleven Mile

Rasta family fruit farm hilltop cabin kingston

If you want real roots Jamaica Our place on di hill aint no faker If you like fresh cool breeze And every kinda fruit pon di trees. Butterflies, birds and plants Sweet Reggae to dance Riddims and a whole heap of flavour, Rasta ital behaviour Hilltop views. Outstanding reviews. A community of family and friends. A memory for life it all depends … if you decide to book now! Authentic cabin/outside cool shower/inside toilet/nature everywhere/ double bed/hammock 20mins airport and kingston

4.96 out of 5 average rating, 264 reviews

Cabin in Liguanea

City Nirvana |Perf Location | Unwind & Enjoy

You're invited to enjoy our safe urban retreat- hidden in plain sight- a wooden cabin, located next to City Cabin in the vibrant Liguanea area. Reconnect with nature, enjoy amazing mountain views, stroll through our verdant garden and listen to birds at day and creatures at night. The perfect base for exploring the Bob Marley Museum, Devon House, restaurants, coffee shops, stores, supermarkets some within walking distance, others a short ride away. Welcome, be our guest, we'd love to host you!

A spacious backyard is showcased with a large pool surrounded by a tiled deck. A cedar wood gazebo is visible, featuring seating and umbrellas for shade. Lounge chairs are positioned beside the pool, inviting relaxation. The house is seen in the background with a door leading to a utility area.

4.95 out of 5 average rating, 87 reviews

Chillax Island Stay – Private Pool & Gazebo

🌴 Welcome to Chillax Island Stay, your fully solar-powered, comfortable getaway. Experience our modern solar and battery backup system, which ensures uninterrupted essential amenities even during power outages. Whether you’re visiting family, working remotely, or seeking a relaxing escape, you’ll appreciate a clean, secure environment where everything functions smoothly. Unwind in our spacious backyard, complete with a private pool, beautiful gazebo, and plenty of space to relax and chill.

4.88 out of 5 average rating, 154 reviews

The living room features a colorful three-piece suite arranged around a glass coffee table, with a natural sheepskin rug beneath. Large windows are adorned with roman blinds, allowing natural light to fill the space. A ceiling fan enhances the comfort of the area.

Bungalow in Portmore

Luxury 2 bedroom beach villa in gated community

53 Bay Front is a stunningly furnished 2 bed 2 bath villa beside Forum beach. The secure gated community features 24/7/365 manned entrance gates & is centrally located in Port Henderson, Portmore. The villa has high-speed wireless internet, cable and Smart TVs. Air-conditioning in both bedrooms, a fully-equipped kitchen, spacious living room, breakfast bar, open plan dining area and a utility room with washer & dryer. You will also enjoy the outside areas: back patio, front garden & lawn.

4.71 out of 5 average rating, 152 reviews

A vibrant living area features a coral-colored sofa adorned with decorative pillows. Two turquoise ottomans are placed on a patterned area rug. Bright blue and pink curtains frame a window, allowing natural light to fill the space. A small table with lamps adds functional elegance.

Home in Hellshire

TaylorMade 2 bdrm - Near the beach

Sandhill Vista is a calm relaxing community nestled at the foot hills of the Hellshire; overlooking the Caribbean sea. The house is ideal for families, couples seeking serenity. Relaxed ocean front environment for re-cupping from a great day of adventure. All bedrooms are fitted with cable TV for your comfort. We guarantee Fresh linens and towels, a fully equip Kitchen, Hot water, in-suite laundry. Lockbox access and 24/7 Support are designed to make your stay as smooth as possible.

5 out of 5 average rating, 7 reviews

Tropical Solitude

Enjoy a stylish experience at our sunshine city abode- centrally-located, clean, modern, smart, sophisticated, 24/7 security (gated and outdoor camera), that offers indoor and outdoor relaxation. Close proximity to restaurants, supermarkets, entertainment (movie theater, parties, family parks), beaches, business, shopping malls, private & public hospitals. Motor vehicle rental, chauffer, tour guide, airport transportation, personal chef, gym instructor available upon request.

4.9 out of 5 average rating, 167 reviews

★ Suite Comfort ★ Classic and Modern City Haven ☀

Welcome to Phoenix Park Village.This house is located in the beautiful city of Portmore. Whether you are here on business or pleasure, you will find that this home will suit all your needs. This flat is tastefully decorated and equipped with modern furniture and appliances, Free Wifi, Smart TVs with fire stick for home entertainment streaming, Internal Washer, hot water pipes, AC Units and Ceiling Fans. Nothing but elegance and comfort for the ultimate JAMAICAN VACATION!

A modern dining area is showcased with a round white table surrounded by four sleek gray chairs. Fresh yellow flowers are placed in the center. Natural light floods the space through a decorative window, highlighting the adjacent kitchen and laundry appliances.

4.85 out of 5 average rating, 140 reviews

GATED COMMUNITY!! 2BR/1BA Home Portmore/Jamaica!

Relax with your family, This place can host up to 6 people, this house have air conditioning in "ALL" rooms. This house also includes a washer & dryer, high-speed internet WIFI, along with smart 4K TV’s. Rest assured with 24 hour security on premises in this gated community. Don’t want to cook? this house is 8 minutes away from popular restaurants and 20 to 35 minutes from Kingston and Norman Manley International Airport Depending on traffic. Why wait Book now!!!!

A bright, open living area features a gray sofa and a blue armchair, inviting relaxation. A coffee table holds decorative items, and a potted plant adds a touch of greenery. The kitchen is visible in the background, equipped with modern appliances and bar seating.

4.85 out of 5 average rating, 101 reviews

Luxurious,Cozy 2BR/1BA Home in gated community.

Make the most of this beautiful, modern, stylish, charming 2bedroom, 1bath house at Phonexi park village. We are located in a secure and quiet community with 24hrs security. This home is great for families,friends and couples who are looking a relaxing time away from home, Car Rentals available upon Request. The space Fully equipped kitchen Microwave Electric kettle Air condition Fan Wifi Netflix Hulu Smart Tvs Coffeemaker Iron/Iron Board Hairdryer Queen size bed

5 out of 5 average rating, 19 reviews

A private outdoor area features a rectangular plunge pool surrounded by lush green grass. Comfortable seating areas are arranged under a wooden pergola and gazebo, complemented by pool lounge chairs. The bright sky and light clouds create an inviting ambiance.

Home in Hellshire

Vista Oasis | 2BR | Shared Pool & Gym | Hellshire

Escape the city and unwind in your ideal Jamaican getaway. This comfortable 2-bedroom, 1-bath section sleeps up to 4 guests and is perfect for couples, small families, or returning residents. Enjoy access to a shared, bespoke plunge pool & gazebo oasis, an air-conditioned gym with a Smart TV and a shower, a games room, a BBQ area, and outdoor seating. We have everything you need for a relaxing and memorable stay. Includes 1 designated garage parking space.

4.79 out of 5 average rating, 126 reviews

A spacious bed is adorned with a textured white quilt, complemented by two pillows. A bedside lamp casts a soft glow, while a small potted plant adds a touch of greenery to the nightstand. Neutral walls create a serene backdrop.

Condo in Portmore

City/Ocean View, Pool, Beach: Resort Like Vacation

Step into your dream getaway! This luxurious studio apartment blends coastal charm with city vibes, offering killer views of both skyline, beach and mountains. Splash in the pool, hit the beach, or chill in the lobby—whatever floats your boat! Elevator? Check. Meeting room? Got it. Plus, an epic mix of city buzz and mountain zen. Ready for an unforgettable escape? Let's do this! Nb. The wine on the picture is not included with your stay

Popular amenities for Hellshire family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.97 out of 5 average rating, 31 reviews

A tall, gated wall is seen, featuring a decorative pattern and adjacent palm trees. Soft lighting highlights the entrance, creating a welcoming effect. A small grassy area is visible in front of the gate, contributing to the overall inviting exterior of the property.

Home in Harbour View

Home away from home

Townhouse in Beverly Hills

A serene pool area is seen, featuring a clear blue swimming pool with an integrated hot tub. Lounge chairs are positioned nearby, offering a view of the surrounding hills. The patio is surrounded by decorative planters, enhancing the outdoor ambiance.

4.82 out of 5 average rating, 180 reviews

5 star comfort and environment at best cost

4.83 out of 5 average rating, 24 reviews

Home in Old Harbour

Harmony Suites @ The Concierge 4BD RM.

4.86 out of 5 average rating, 102 reviews

The image presents a modern condominium building featuring multiple stories with distinct color patterns. Large windows offer ample natural light, while balconies extend from the upper floors. The rooflines are elegantly designed, contributing to the contemporary aesthetic of the architecture.

Condo in Kingston

Kingston - Centrally located luxury apartment

A spacious jacuzzi is set against a modern wall design featuring light tiles with decorative accents. Two cushioned black headrests are visible, enhancing comfort. Natural light enters through a small window, illuminating the inviting space.

4.85 out of 5 average rating, 71 reviews

Simm's Estate lux with Jacuzzi

Guest suite in Constant Spring

A serene pool area is surrounded by lounge chairs and tropical plants. A shaded gazebo is positioned nearby, and a scenic view of distant mountains is visible in the background. The clear water of the pool reflects the sunlight, creating a calming atmosphere.

4.89 out of 5 average rating, 27 reviews

Ridgeview suite 4

5 out of 5 average rating, 17 reviews

A modern cabin features a dark wooden exterior with large windows, allowing views of the surrounding greenery. Steps lead up to the entrance, which is framed by small plants. A sign indicating 'Cottage Blu' is prominently displayed near the door.

Cabin in Mulleth Hall

Cottage Blu

The exterior of a single-story home is displayed, featuring a warm yellow façade with decorative white columns. A small seating area with two chairs is positioned under a covered porch. Lush green grass borders the pathway leading to the entrance.

4.71 out of 5 average rating, 38 reviews

CHEERFUL TROPICAL 4BEDROOMs Villa Security 24hour

Family- and pet-friendly home rentals

4.92 out of 5 average rating, 26 reviews

A spacious living area features a modern sectional sofa adorned with decorative cushions in various colors. A glass coffee table sits in the center, topped with a floral arrangement. Natural light filters in through large windows, draped with stylish, dark curtains.

Condo in Portmore

Bayfront Villas and Apartment - Portmore

4.77 out of 5 average rating, 102 reviews

A swimming pool is set against a backdrop of natural greenery and a multi-story building. The pool features a light blue surface with grey stone tiling along the edges. Large windows line one side, allowing for natural light and views of the surrounding area.

Condo in Kingston

Penthouse w/ Free Wifi/ Pool/ Gym/ Great Location

4.79 out of 5 average rating, 121 reviews

The bedroom features a spacious queen-sized bed with a light-colored patterned coverlet. Two wooden nightstands with lamps are positioned on either side. A comfortable chair is placed in the corner, and a TV is mounted on the wall. Soft light filters through sheer curtains.

Apartment in Kingston 10

Peaceful 1BR Apt near Devon House

The dining area features a glass table set with two white cups and accented by a decorative placemat. A large mirror leans against the wall, while a door leads to another room. Green plants and minimal decor enhance the modern aesthetic.

4.8 out of 5 average rating, 40 reviews

Solace at Phoenix Park

4.87 out of 5 average rating, 31 reviews

Home in Spanish Town

Cool & Cozy Retreat in Jacar Homes

Apartment in Constant Spring

A parking area is visible in the foreground, surrounded by multi-story buildings with a tropical landscape in the background. Palm trees add greenery, while a guardhouse stands at the entrance. The sky is partly cloudy, providing a bright and open atmosphere.

4.76 out of 5 average rating, 129 reviews

Kingsley's Hillman Apartment

4.9 out of 5 average rating, 173 reviews

An outdoor sitting area is visible, featuring a small patio with a mix of potted plants including flowering species. A white chair and small table complement the space, providing a serene entrance to the garden apartment. The surrounding greenery adds a natural touch.

Guest suite in Kingston

Garden apartment @ Charlemont

4.88 out of 5 average rating, 320 reviews

A private balcony offers a serene view of the Caribbean Sea, showcasing gentle waves lapping against a rocky shore. The landscape features a mix of sandy and rocky terrain, set against a cloudy sky that hints at the upcoming sunset.

Guest suite in Bull Bay

Rustic Beauty Beach Front Hideaway

Family-friendly home rentals with a pool

4.73 out of 5 average rating, 41 reviews

Apartment in Portmore

The Shoreline Suite | Pool • Beachfront • Relax

4.96 out of 5 average rating, 163 reviews

Vibrant purple orchids are prominently displayed in the foreground, with a lush garden environment surrounding a clear swimming pool in the background. Tropical plants and trees are seen throughout the scene, contributing to a serene outdoor atmosphere.

Guesthouse in Norbrook

Orchid Cottage

Home in Saint Catherine Parish

A comfortable living area is presented, featuring two gray sofas with decorative cushions in shades of green and blue. A large flat-screen television sits atop a sleek glass stand. Bright curtains in alternating colors frame the windows, enhancing the room's cheerful ambiance.

4.99 out of 5 average rating, 106 reviews

Sleep Easy, Relax in Comfort

Apartment in Beverly Hills

A cozy sleeping area is highlighted by a spacious bed adorned with a soft white quilt. Natural light is filtered through large glass doors leading to a balcony, which is surrounded by greenery. A wall-mounted television is visible, alongside a bedside lamp on a wooden table.

4.97 out of 5 average rating, 151 reviews

Modern flat with a view

4.73 out of 5 average rating, 129 reviews

Home in Spanish Town

Comfort Cottage: Private Oasis w/Pool & Security

4.94 out of 5 average rating, 126 reviews

A dining area is seen with a glass table set for four, featuring colorful bowls and glassware. The living space is furnished with a dark sofa, highlighted by vibrant cushions. Light filters in through sheer curtains, adding warmth to the inviting atmosphere.

Apartment in Portmore

Phil's Hideaway*Spacious, 2 BR Apt*Gated + Pool*

4.83 out of 5 average rating, 316 reviews

The modern exterior of the gated complex is displayed, featuring a blend of light and dark blue facades. The entrance sign indicates 'Harloe's Place,' while multiple balconies are visible on the upper floors, enhancing the structure's contemporary design.

Apartment in Kingston

One bedroom, one bathroom Apt Kingston

A heart-shaped pool is surrounded by a stone patio featuring a mix of grey, white, and beige stones. Lush greenery is visible in the background, complemented by clear skies. The area is enclosed by a wooden fence, ensuring privacy.