Vacation rentals in Middlesex County

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Top-rated vacation rentals in Middlesex County

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

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Guest favorite

A swimming pool is visible, featuring clear water and a mosaic floor with the phrase 'HIDDEN GEMS' submerged. The pool is bordered with blue tiles, creating a modern and inviting atmosphere.

Home in Portmore

4.86 out of 5 average rating, 191 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

Guest favorite

A modern kitchen area features a stainless steel gas stove with five burners and an oven below. A countertop extends alongside a microwave and a sink, complementing the warm wood cabinetry. A small potted plant and a decorative sign add subtle touches to the space.

Home in Old Harbour

4.97 out of 5 average rating, 70 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.

Guest favorite

A beach scene is depicted with individuals lounging on sunbeds along the shoreline. Turquoise waters are visible in the background, complemented by a clear blue sky. The sandy beach provides a spacious area for relaxation, with gentle waves lapping at the shore.

Guest suite in Ocho Rios

4.84 out of 5 average rating, 122 reviews

HiddenTreasure Suite I 24h Sec Pool *AC *Hot Water

This suite is ideal for friends, couples, solo/business travelers which is located in upscale well sought-after Community of Draxhall Country Club which is one of the best gated communities in Jamaica. It's located close to the airport, city center and tourist attractions: Dunns River Falls Dolphine Cove Mystic Mountains Bamboo Blu Beach Draxhall Cove Ocho Rios Town Center Jerk Centers Seafood and Italian/American Restaurants Montego Bay Kingston Knutsford Express 24hrs medical services

Guest favorite

A scenic view is framed by a yellow window, showcasing the ocean and a cruise ship in the distance. Lush palm trees and vibrant greenery are visible in the foreground, enhancing the natural beauty of the surrounding area.

Condo in Ocho Rios

4.89 out of 5 average rating, 219 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?

Superhost

A serene coastal view is displayed from a private balcony, featuring a glass table and two modern chairs. The turquoise water gently meets the sandy shore, surrounded by lush greenery and rocky cliffs under a clear blue sky.

Guest suite in Boscobel

4.75 out of 5 average rating, 160 reviews

Beach bungalow beside Ochi Rios /Ian Flem Airport

Relax in a very comfortable self contained villa 10 minutes from the town of Ochi Rios and 3 minutes from Ian Fleming Airport on your very own Private beach. Walking distance from super markets, markets, Beaches Boscobel resort and golf club hotel, drinking saloons with friendly local people. Private enclosed parking with monitored security. The beach sits on a ocean wildlife protected sanctuary so pardon us if its not more refined, it is still great for swimming and relaxation.

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, 25 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 modern refrigerator features an external panel with settings for water, cubed ice, and crushed ice. The sleek design includes a lock feature for added convenience, while a brushed stainless steel finish enhances its contemporary appearance.

Home in Galina

4.97 out of 5 average rating, 34 reviews

Oasis Getaway in Saint Mary

Escape to OD’s Oasis, a charming one-bedroom retreat in Galina, St. Mary! Just 10 minutes from Ian Fleming Airport and minutes from the iconic Galina Lighthouse, this cozy getaway is perfect for two. Tucked in the community of Lighthouse, it features an open-concept kitchen and living area for ultimate comfort. The road has a few bumps, but the peace, charm, and convenience make it worth it. With Ocho Rios and Port Maria nearby, your dream island escape starts here!

Guest favorite

A textured wall is illuminated by a modern light fixture, casting warm rays of yellow and orange. Two windows frame the light, enhancing the structure's design with a subtle contrast to the illuminated area.

Apartment in Linstead

4.95 out of 5 average rating, 21 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!

Superhost

A modern bathroom features a glass-enclosed shower with a rainfall showerhead. A white vanity with a sink is against one wall, alongside a toilet. Natural light enters through a small window, and decorative rugs with a leaf pattern add a touch of comfort.

Apartment in Bog Walk

5 out of 5 average rating, 4 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!

Top guest favorite

A dedicated games room is showcased, featuring a pool table at the center. To one side, classic arcade machines offer nostalgic gaming experiences, while a foosball table occupies the opposite side. Two gaming chairs are positioned facing a wall-mounted TV, creating an inviting space for entertainment.

Home in Old Harbour

4.96 out of 5 average rating, 49 reviews

Entertainment, Comfortable + A Pool - Book Now!

Airport Pickup & Drop Off Available! When you book this Airbnb, don't forget to schedule your round-trip airport pickup & drop off. This service comes with this Airbnb - A dedicated service that is 100% reliable. Schedule your pick up and drop off times with the host. This Airbnb is 3-5 minutes away from the town, extremely close to supermarkets, restaurants, gas stations, banks and atm etc.

Guest favorite

A clear blue pool is framed by a sunbathing area, featuring a few lounge chairs. A shaded structure is visible in the background, providing a space for relaxation. The surrounding landscape includes open green areas and distant homes under a bright sky.

Home in Old Harbour

4.93 out of 5 average rating, 30 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 favorite

A clear, shallow river gently flows over smooth stones, reflecting sunlight that creates sparkling patterns on the water's surface. Lush greenery flanks the riverbank, providing a natural backdrop that captures the serenity of the environment.

Loft in Summerfield

4.85 out of 5 average rating, 13 reviews

Hershy B's -'The Cottage'

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 accessible by steps, it , there is no wheelchair access