Vacation rentals in Middlesex County

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Middlesex County

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

0 of 0 items showing

1 of 3 pages

Guest favorite

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.

Condo in Ocho Rios

4.92 out of 5 average rating, 109 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.

Guest favorite

A cozy bedroom features a queen-size bed with a light gray quilt and decorative pillows. Natural light filters through sheer curtains on either side of two windows. A bedside table holds a lamp and a vase of flowers, while an air conditioning unit is mounted above.

Home in Old Harbour

4.95 out of 5 average rating, 77 reviews

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

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.

Top guest favorite

The exterior of the home features a welcoming entrance with a spacious driveway paved with stone. Surrounding greenery includes neatly trimmed plants and decorative rocks. The structure is set against a clear blue sky dotted with clouds, and white gates provide access to the property.

Home in Portmore

4.93 out of 5 average rating, 15 reviews

The Pearl @ Phoenix Pk Village 2 - Gated, 1Bedroom

Welcome to our aesthetically pleasing and thoughtfully decorated home. Situated at Phoenix Park Village II, a newly built gated community with 24/7 security. Every aspect of this home has a touch of luxury that adds to its uniqueness, we want you to indulge, relax and enjoy your home away from home. While 'The Pearl' is the perfect getaway for you and yours, its location makes it easy for you to get around. You will be close to beaches, restaurants, movie theater, shopping plazas & lounges.

Top guest favorite

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.

Apartment in Mandeville

5 out of 5 average rating, 22 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 favorite

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.

Condo in Ocho Rios

4.89 out of 5 average rating, 243 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 favorite

A spacious bedroom features a plush headboard and a neatly made bed topped with a yellow throw. Two nightstands with lamps flank the bed, and light filters through sheer curtains, illuminating the bright and airy space.

Apartment in Mandeville

5 out of 5 average rating, 37 reviews

Luxury suite with gym/ pool

Nestled in the cool hills of Mandeville this newly constructed apartment offers everything you have been looking for in your stay. It has an amazing view of this beautifully landscaped property with amenities that include swimming pool, gym, jog trail, assigned parking, club house and 24 hours security. The enviable location of this property allows for easy access to Mandeville town center, banks, hospital and shopping centers which are all within five minutes walking distance.

Guest favorite

A cozy bedroom features a queen-sized bed adorned with a light-colored bedspread and decorative pillows. Bright yellow walls create a warm ambiance, complemented by artwork above the headboard. Natural light enters through sheer curtains, and a bedside table holds a small arrangement of flowers and a book.

Home in Portmore

4.9 out of 5 average rating, 153 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!

Guest favorite

A comfortable bedroom is furnished with a spacious bed adorned with soft pillows and a light blanket. Black-out curtains frame the window, while artwork featuring palm trees decorates the walls. A bedside table offers storage and a remote control is placed on the bed.

Home in Old Harbour

5 out of 5 average rating, 11 reviews

JayA Suite2: Apartment in Old Harbour

A peaceful, relaxing 1 bedroom apartment. Apartment has a gate in a quiet friendly neighborhood, however the community is NOT gated. 5 mins drive into Old Harbour town and easy access to the highway. Equipped with your everyday essentials. Family friendly home away from home. IG @jayasuite876 35 minutes from Kingston Norman Manley airport via Highway 2000 Please feel free to ask any questions, for further details about the property.

Guest favorite

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

4.92 out of 5 average rating, 52 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.

Guest favorite

The exterior of the apartment is adorned with lush green vines, showcasing a welcoming front porch. A wooden door is framed by two windows, and a small dining set is placed on the tiled surface. Tropical plants and colorful flowers enhance the inviting entrance.

Guesthouse in Summerfield

4.8 out of 5 average rating, 25 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.

Guest favorite

A modern bedroom features a spacious bed dressed in crisp white linens and yellow accents. A decorative mirror and framed artwork adorn the walls. A cozy seating area includes a light-colored bench and a gray chair, while a ceiling fan contributes to the airy atmosphere.

Apartment in Bog Walk

5 out of 5 average rating, 6 reviews

Church Road Haven

Relax in this modern 1-bedroom, 1-bathroom apartment, just 3 minutes from Linstead and Bog Walk. Offering privacy, comfort, and all amenities, it’s perfect for solo travelers or couples. Enjoy a stylish, cozy retreat in a central yet peaceful location. Whether for business or leisure, this space provides the ideal blend of convenience and relaxation. Book now and make it your home away from home!

Guest favorite

A serene bedroom features a spacious bed covered in a navy blue patterned bedspread. A comfortable armchair is positioned beside a wooden wardrobe, and a small dining table is set for two. Natural light floods the room through bright windows, complemented by a TV mounted on the wall.

Home in Spanish Town

4.91 out of 5 average rating, 47 reviews

The Kool escape @Angels estate

Relax and enjoy your stay at this peaceful and centrally-located home. located minutes away from the Angels shopping center which houses a multitude of restaurants KFC & PIZZAHUT, clothing stores, doctors offices, supermarkets and knutsford express. the north-south highway is located only two mins away and the town of Ocho Rios only 30minutes.