Holiday rentals in Middlesex County

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Top-rated holiday rentals in Middlesex County

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Superhost
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.
Home in Portmore
4.86 out of 5 average rating, 214 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

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, 25 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!

Guest favourite
A semi-open living area is presented with white walls and modern furnishings. A wooden coffee table sits in front of a comfortable sofa. Large windows overlook the sea, revealing two loungers on the balcony, creating a serene atmosphere with natural light.
Apartment
4.83 out of 5 average rating, 276 reviews

Seafront Apartment nxt to Beach

My place is in Ocho Rios Jamaica , walking distance from Ocho Rios Town centre . Its a homely seafront, split level apartment within a traditional 1960s style past resort directly next to Mahogany beach. Breathtaking sea views, set within a beautiful garden. The people are lovely and the sea and beach/bar are so relaxing. You can book and set sail from the beach on a Cool Runnings catamaran cruise. My place is good for couples, solo adventurers, business travellers, and families (with kids)

Top 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, 117 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 renovated studio apartment is ideally located for a relaxing getaway or a longer remote working vacation. The unit is bright & uncluttered with a tastefully modern décor. K1 is located in a gated hillside community, 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
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
4.89 out of 5 average rating, 192 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.

Superhost
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, 257 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?

Top guest favourite
Home in Old Harbour
4.96 out of 5 average rating, 68 reviews

Luxury 2BR Escape with Pool, Gym & Games Room

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.

Top guest favourite
Villa in Ocho Rios
5 out of 5 average rating, 47 reviews

Tropical Paradise | Cozy, Modern 1BR

Welcome to Grand Island Villa II. Nestled in a serene setting just five minutes from the heart of Ocho Rios town. This modern villa offers the perfect blend of relaxation and convenience. Whether you’re lounging by the pool, enjoying breathtaking views, or exploring the nearby beaches and attractions, Grand Island Villa II is designed for an unforgettable island experience. With spacious interiors, stylish décor, and all the comforts of home.

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, 227 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.

Superhost
Home in Portmore
5 out of 5 average rating, 3 reviews

The Royal Villa - Portmore

Your family will be close to everything when you stay at this centrally-located gated-community property. This brand new unit offers a quality, safe and secure space with major shopping areas and entertainment options less than 5 minutes away. If you are more the adventurous traveler, you have ease of access to Helshire or the major Toll roads for ease of access to the north, west or even east of the island.

Guest favourite
A cozy bedroom features a dark wood bed with crisp white linens and a vibrant yellow throw blanket. A decorative floral artwork hangs above the headboard. Two bedside lamps provide soft lighting, and a ceiling fan ensures airflow. A small yellow chair is positioned in the corner.
Home in Portmore
4.93 out of 5 average rating, 56 reviews

Modern Cozy Haven

Modern Cozy Haven☘️ RENTALS & AIRPORT PICKUP AVAILABLE. Step into "Cozy Haven," a 2-bed, 1-bath sanctuary in a gated community, blending homey comfort with a zesty twist! Air-conditioned, perfect for game nights or movies, it's not just a stay but a haven where family memories are made. Dive into this unique blend of warmth and adventure, and let "Cozy Haven" be the start of your unforgettable journey.

Top guest favourite
A welcoming entrance features a charming archway and decorative columns, leading to a well-maintained facade. The property is set against a backdrop of rolling hills, with a paved driveway and lush greenery surrounding the area, creating a tranquil and inviting first impression.
Home in Mandeville
5 out of 5 average rating, 64 reviews

RUSTIK INN cozy home away from home

I’m pleased to welcome guests to my cozy abode dubbed Rustik Inn. Nestled in lush green vegetation, you’ll find the perfect little getaway in Jamaica’s coolest parish. Here you will find tranquility & peace if you’re seeking a perfect relaxation get away. I am very happy to be able to share a piece of my home with you and I am definitely eager to help you create the BEST memories during your stay!

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