Holiday rentals in Middlesex County

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Top-rated holiday rentals in Middlesex County

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Guest favourite
A serene outdoor space is showcased, featuring a shaded gazebo surrounded by palm trees and manicured greenery. In the background, a swimming pool is visible, with residential buildings partially framed by the lush hillside.
Apartment in Ocho Rios
4.92 out of 5 average rating, 112 reviews

The Ocean Ridge - Ocho Rios, Stunning Sea Views

The Ocean Ridge Apartment (K1), Sky Castles, Columbus Heights, in Ocho Rios. With jaw-dropping views of the sea & cruise ships, this studio unit was renovated in 2023 & is ideally located for a relaxing getaway, remote work, or a long vacation. The unit is bright & uncluttered with a tastefully modern décor. K1 is located in a gated hillside complex, close to all major attractions, some walkable. The area provides unparalleled scenic views of the sea, mountains & flora of a tropical paradise.

Top guest favourite
The spacious suite features a comfortable bed with soft linens, complemented by a decorative throw. A large glass door offers views of greenery outside, while a modern seating area and dining table are visible. Natural light filters through sheer curtains, enhancing the bright, clean space.
Flat in Mandeville
5 out of 5 average rating, 22 reviews

Premium Studio with Pool View

This exclusive luxury suite offers the perfect blend of elegance and convenience. Located 3 minutes from the town center, it features a private pool with a serene sundeck, a fully equipped gym, and a jogging trail. The suite boasts a spacious interior and premium amenities, including concierge services. Its proximity to the town center allows easy access to fine dining, shopping, and entertainment, making it an ideal retreat for those seeking relaxation, luxury, and an overall great experience!

Top guest favourite
Apartment in Mandeville
5 out of 5 average rating, 11 reviews

Penthouse Apartment in Mandeville

Welcome to The DelaGrace at Avista – your perfect retreat in the heart of Manchester, Jamaica. Blends comfort, convenience, and style, featuring two balconies to unwind and enjoy the cool Manchester nights. Wide range of amenities, including a swimming pool, clubhouse, gym, jogging trail, assigned parking, and 24-hour security. Ideally located, just minutes from grocery stores, banks, restaurants, and shopping centers—making it the ideal home base for both business and leisure travelers.

Top guest favourite
A bright bedroom features a spacious bed adorned with a yellow throw blanket and decorative pillows. Natural light floods the room through large sliding glass doors, which lead to a balcony. A ceiling fan and a bedside table complement the modern décor.
Flat in Mandeville
5 out of 5 average rating, 27 reviews

Cozy Haven Apartment with Gym, Pool and WiFi

Kick back and relax in this calm space at Avista! This modern apartment offers the perfect retreat, blending comfort and convenience. Guests can enjoy a range of amenities, including a swimming pool, clubhouse, gym, jogging trail, assigned parking and 24-hour security. The property is ideally situated close to essential facilities such as banks, restaurants and shopping centers. Whether you're visiting for business or leisure, this serene space is the perfect base for exploring Jamaica!

Guest favourite
A shaded gazebo offers comfortable seating surrounded by lush greenery. Palm trees and vibrant foliage frame a view of the expansive lawn leading to the beach. The sea glimmers in the distance under a clear blue sky, creating a serene outdoor retreat.
Bungalow in Laughlands District
4.88 out of 5 average rating, 191 reviews

Kling Kling Beach House

Kling Kling is a beach house with a family feel, set within a large lawn running down to an almost fully private beach, a river for freshwater swimming, a reef for snorkelling, a fantastic housekeeper cook and a one of a kind man about the place. Just mins drive to shops or tourist facilities. Nearby scuba facilities, waterfalls, water parks, markets, tennis , golf, riding, the list goes on, both mainstream and off piste local. For more pics follow our Instagram: klingklingbeachhouse.

Guest favourite
A private gazebo offers a spacious seating area with a glass-top table and dark wicker chairs. The structure features a white lattice design, framing sweeping ocean views and a vibrant sunset. Surrounding greenery enhances the tranquil atmosphere.
Apartment in Ocho Rios
4.88 out of 5 average rating, 251 reviews

One of Ocho Rios Best Getaway Airbnb!

Welcome to Marazul, a picturesque vacation condo at upscale Columbus Heights in the hills of Ocho Rios. The perfect gateway with postcard-like panoramic ocean views and all the amenities to make your stay feel right at home. Surrounded by beautifully manicured rainforest gardens and direct access to 1 of 5 community pools. For your convenience, we are centrally located near restaurants, beaches, and the most popular attractions in the area only minutes away. Do you see yourself here?

Guest favourite
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, 94 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 exterior of a single-story house is seen under a partly cloudy sky. It features a light beige façade with white trim around the windows and door. Two large windows flank the central entrance, offering a welcoming appearance, while a flat, paved area leads to the entrance.
Home in Portmore
4.97 out of 5 average rating, 38 reviews

"Exquisite, holiday home in Portmore".

Set in the beautiful sunshine community of Portmore, Phoenix Park is a beautiful, tranquil gated community in Portmore. This community is newly built and boast amenities such as gazebo, kiddies park, football field, and 24hrs security. The house has 1 bedroom and 1 bathroom, dining room, living room and kitchen. The house has an open concept with wireless internet, HD smart television with cable and air conditioning units in the bedroom.

Top guest favourite
A cozy bedroom features a spacious bed with a light-colored quilt and decorative pillows. Air conditioning is provided above, while large windows are adorned with teal curtains. A wooden dresser with a blue decorative vase and a mirror complement the room's serene atmosphere.
Home in Portmore
5 out of 5 average rating, 16 reviews

Gated Home 2: A/C, Airport Pickup, 15 min to Beach

Your Cozy Escape! Welcome to your second home in Phoenix Park Village 2! This stylish 2-bedroom stay is ideal for families or friends. Enjoy comfy air-conditioned rooms, a full kitchen, washer, free parking, and 24/7 security. Wheelchair accessible with airport pickup available (extra cost). Close to shops, restaurants, and entertainment. Hosted by a Superhost, you’ll feel right at home—comfort and convenience guaranteed!

Guest favourite
A decorative entrance sign displaying 'Colbeck Manor' is mounted on a beige wall. Surrounding greenery features well-maintained flowering plants, adding a touch of color against the background of a clear blue sky.
Home in Old Harbour
5 out of 5 average rating, 19 reviews

Colbeck364 Comfort Stay

Colbeck364 Comfort Stay – Relax in Style! Welcome to Colbeck364 Comfort Stay, a fully air-conditioned retreat in Colbeck Manor, Old Harbour, St. Catherine. Enjoy a community pool, gym, high-speed Wi-Fi, and Smart TV. The home features a fully equipped kitchen, stylish interiors, and a secure gated community. Just minutes from Old Harbour town, shopping, and major highways. Book now for a relaxing and comfortable stay!

Top guest favourite
The bright living area features a single day bed with striped bedding, accented by floral pillows. A light-colored coffee table sits in front, surrounded by modern furniture. A large window offers a view of the Caribbean Sea, while greenery adds a fresh touch to the space.
Apartment in Ocho Rios
4.99 out of 5 average rating, 223 reviews

Carib Escape Water-Front Condominium Ocho Rios

Hurricane Melissa update - All services are up and running. Most restaurants and attractions are open in Ochi and eastern parishes and we are ready to welcome you back.❤️❤️❤️ 180 degree view of the Caribbean Sea. Fully refurbished, modern chic Ocean Front Condo. Great Location in the Heart of Ocho Rios. Close to Restaurants, Attractions, Shops and right next to Mahogany Beach. Gated community with 24 hours security.

Guest favourite
A modern kitchen is presented with dark cabinetry and a granite countertop. Kitchen appliances, including a microwave, stove, and double-door refrigerator, provide functionality. A dining table set for two is featured, with a glass and decorative elements, enhancing the space's practical appeal.
Flat in May Pen
4.89 out of 5 average rating, 44 reviews

Home

Kick back and relax in this calm, stylish space. Home is centrally located in a gated secure premises in May Pen, Clarendon. It is 2 mins from the nearest hospital. Doctors offices, restaurants, shopping, spas, salons, etc. Attractions in Clarendon includes, the Milk River Mineral bath, Farquahar beach, salt River mineral spring and other hidden gems. Home is also 2 mins away from the high way 2000.

Popular amenities for Middlesex County holiday rentals