Holiday rentals in Cockpit

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Top-rated holiday rentals in Cockpit

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

A single-story home with a welcoming front porch is showcased. Light yellow and creamy white exterior walls are complemented by a manicured lawn and garden. A small outdoor table and chairs are set on the porch, with a pathway of stones leading to the entrance.

Home in Old Harbour

4.83 out of 5 average rating, 24 reviews

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.

Superhost

The exterior of the house is showcased, featuring a vibrant green facade with a covered porch. A white door is framed by large windows, while plants are positioned near the entrance. The pathway is paved, leading to a well-defined entrance.

Home in Old Harbour

4.71 out of 5 average rating, 31 reviews

Polly Dreams Vacation Home.

Relax with the whole family at this peaceful place to stay.Whether it’s a couple’s retreat or with the entire family, come enjoy the quiet and comfort of this oasis that lies within walking distance of Old Harbor Square. Inside you will find a luxuries two bedrooms, a kitchen/dining room, bathroom state-of-the-art furniture and appliances to facilitate the comfort of your stay. Privacy and safety is a priority w/outdoor cameras, fence & grilled. You also have the luxury of relaxing outdoors.

Guest favourite

Home in Old Harbour

4.94 out of 5 average rating, 81 reviews

Nicely Furnished-1BR/24hr Sec./AC/Fast Wi-Fi/ NHV4

Come relax a while at this centrally-located place in New Harbour Village. Located on a quiet street this home is clean, comfortable and cozy with a stylish design. Enjoy waking up in a comfy queen-size bed, having a warm rain shower bath, eating your choice of foods and selecting your choices for entertainment. You will be two minutes away from the Old Harbour Town Centre where you can enjoy local foods, shopping and round town travels. What are you waiting for? Come! You will love it here.

Guest favourite

The exterior of the home features a secure metal gate adorned with a sunburst design. Light-colored walls contrast with the gray driveway. A large window allows for natural light, complementing the modern architectural lines of the structure.

Home in Old Harbour

4.87 out of 5 average rating, 23 reviews

The Cherryhill of Old Harbor

Welcome to The Cherryhill – Your Home Away from Home in Old Harbor. Escape to comfort and convenience at The Cherryhill, a modern 2-bedroom, 1-bathroom home located in the brand-new Whim Estates gated community in Old Harbor, St. Catherine. Perfect for families, couples, or small groups. This cozy retreat offers everything you need for a relaxing stay. Enjoy a clean, secure environment just a short drive from both Spanish Town and May Pen, Clarendon, an ideal base for exploring Jamaica.

Guest favourite

A cozy living area features a gray sofa adorned with yellow cushions, paired with a glass coffee table holding decorative items. A dining table with black chairs is visible in the background, framed by sunny yellow drapes that enhance the light-filled space.

Home in Old Harbour

4.82 out of 5 average rating, 17 reviews

Exquisite Village

Exquisite Village is a centrally located, peaceful, and stylish Airbnb home! Nestled in the heart of Old Harbour, our residence offers the perfect blend of convenience and tranquility. Enjoy a restful stay in our comfortable and thoughtfully designed space, where every detail has been curated to provide a serene and stylish retreat. Whether you're here for business or leisure, our home promises comfort and elegance, ensuring a memorable stay. It's 3 minutes drive from the town centre.

Superhost

A living area is presented with neutral-colored tiled flooring and bright walls. A dark grey sofa occupies one side, while a small round coffee table complements the space. A television is mounted on a wall unit, and a decorative entrance door is visible in the background.

Home in Spanish Town

4.82 out of 5 average rating, 95 reviews

Irie Getaway - House in gated community

One bedroom newly built and furnished home in very peaceful and quiet residential, gated community, with 24 hour security, in St. Catherine. House is ideally located just a few minutes from the Spanish Town Toll road, which makes it easy to access without having to encounter heavy traffic. Kingston is 25 minutes away and Portmore is 10 minutes away. House is nicely furnished and has ac in the bedroom (only) and other amenities to make your stay feel like a home away from home!

Guest favourite

The living room features a spacious sectional sofa with a combination of colored cushions. A center table is placed in front, complemented by two high chairs. Two large windows with dark curtains allow natural light to enter, enhancing the room's openness. A wall-mounted Smart TV is visible.

Home in Old Harbour

4.89 out of 5 average rating, 72 reviews

Serene 2 Bedroom House With AC in Gated Community

This property is in a gated community which offers 24 hr security and patrolling. The community is 2 minutes from the Old Harbour town center and 3 minutes from the highway. The property has 2 bedrooms and 1 bathroom with an open plan kitchen and living room setting. The property has Wifi and air conditioner (AC) which is located in both rooms as well as fans in both rooms and the living room. Smart TV is located in the living room which gives access to cable TV and Netflix.

Guest favourite

The kitchen features modern cabinetry in navy blue and white, complemented by a marble countertop. A gas stove and stainless steel refrigerator are visible. Colorful decor, including sunflowers and pineapples, adorn the island. LED lighting along the ceiling adds a contemporary touch.

Home in Old Harbour

5 out of 5 average rating, 5 reviews

Modern Home ( Gated Community) NHV3 Old Harbour 1

Modern Home Gated. 1 King size bed, 1Q-B, 2baths located in Old Harbour with GAZEBO and BAR. This amazing home also decked with LED Lighing, 1 fancy Kitchen an laundry. It's fully A/C and 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 the Town, Restaurant, Jerk Centre, KFC, Juici Beef, High 2000, 30mins portmore spanish Town 1 hour to Ocho Rios.

Top guest favourite

Home in Old Harbour

4.96 out of 5 average rating, 68 reviews

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.

Guest favourite

Home in Old Harbour

4.92 out of 5 average rating, 12 reviews

The Oasis at Whim

Welcome to your relaxing retreat in the quiet and secure community of Whim Estates. This cozy home is ideal for families, couples, or solo travelers looking for comfort and convenience. You’ll also enjoy easy access to the town centre, where you’ll find a variety of restaurants, shops, and local amenities—all just a short drive away. The nearby highway ensures quick connections to surrounding areas, making it easy to explore the island or commute if needed.

Guest favourite

A well-appointed bedroom features a spacious bed with a cozy blanket and decorative pillows. The green curtains frame the window, while a sleek dresser is positioned against the wall. An air conditioning unit is mounted above, providing comfort during warm days. Inset is an image of the pool area.

Home in Old Harbour

4.92 out of 5 average rating, 48 reviews

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.

Superhost

A modern living area features a dark blue sofa adorned with colorful cushions. A round coffee table is set with decorative items. Soft lighting accentuates the textured walls, while a patterned rug adds visual interest. A small armchair and air conditioning unit complete the space.

Bungalow

4.69 out of 5 average rating, 13 reviews

Andre's Manor

Escape to Andre’s Manor, a cozy and secure retreat in Whim Estate’s gated community with 24/7 security. Nestled on a quiet street, this clean and comfortable space is perfect for relaxation while being less than 5 minutes from Old Harbour Town Centre. Enjoy authentic Jamaican food, shopping, and local amenities nearby, then return to the peace and comfort of your private getaway.