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.

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Guest favourite

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 favourite

Home in Old Harbour

4.8 out of 5 average rating, 20 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.

Top guest favourite

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 favourite

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 favourite

Apartment in Mandeville

5 out of 5 average rating, 35 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 favourite

Apartment in Ocho Rios

4.92 out of 5 average rating, 26 reviews

Ocean View Sunset-5mins Blue Hole|10mins Beach

Unwind in Paradise Ocean View and Sunset Bliss Our place is a tranquil retreat that offers breathtaking views of the ocean and stunning sunsets. * With the Panoramic Ocean Views and Breathtaking Sunsets that the sky transform into a kaleidoscope of colours as the sun dips into the ocean * Serene Ambiance of our place is designed to provide a peaceful and calming atmosphere, perfect for relaxation and rejuvenation Experience the Best of Oceanview Living!

Guest favourite

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.

Top guest favourite

Apartment in Linstead

4.96 out of 5 average rating, 24 reviews

SG Apartment Complex (Apt #1)

Kick back and relax in this calm, stylish space. We are only 30 minutes away from Ocho Rios and 45 minutes outside of Kingston via toll. Not to mention, we are 5 minutes or walking distance from the famous Grant's Jerk Center, 5 mins from Fj's Smokehouse, and 25 mins away from Bush Trails Excursions Tours. The apartment is ultra-modern with all the amenities for the comfort of you and yours. Come, stay with us, we are here to serve you!

Guest favourite

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 favourite

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 favourite

Home in Old Harbour

4.89 out of 5 average rating, 44 reviews

Colbeck Villa

Relax with the whole family at this peaceful place to stay. The Colbeck Villa located in a gated community with pool gym. The home is a beautiful 2 bedroom 1 bathroom house with all modern amenities. The home is fully Air Condition with ceiling fans. Clean and spacious bedrooms living room and kitchen. Comfortable beds, sofa and chairs. You will enjoy you stay at the Colbeck Villa.

Guest favourite

Tiny homes in Oracabessa

4.93 out of 5 average rating, 46 reviews

Papa Curvin's Cottages & Seaside Tropical Garden

Quite small but very cosy - you will love it! Our newly build Umbrella Hut on Real Jamaica´s big property is waiting for you. Have a look at the pictures, they will tell you everything :-) There are two other houses to book, just have a look on Airbnb for: Real Jamaica - Cabin right beside the sea; and: Real Jamaica - The Artist House