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 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

Superhost

A laundry area features a modern washing machine positioned beside a decorative window grille. Outside, lush greenery and flowering plants can be seen through the window, providing a view of the serene surroundings.

Apartment in Ocho Rios

5 out of 5 average rating, 4 reviews

White River Ocho Rios Suite

Looking for a comfortable, budget-friendly escape just minutes from Ocho Rios? This charming 1-bedroom unit is the perfect spot offering everything you need for a relaxing getaway.Located just 8 minutes from Ocho Rios , you’ll be close to all the top attractions Dunn’s River Falls, Dolphin Cove, Mystic Mountain. After a day of exploring, unwind with access to a private beach just 2 mins away.A cozy atmosphere ideal for couples or solo travelers Unbeatable convenience at a budget-friendly price

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 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, 220 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 favorite

A wall-mounted light fixture casts a soft glow along textured paint. The design creates dual rays of light that extend outward, highlighting the surrounding wall. Two vertically oriented windows are visible on either side, showcasing a simple yet modern aesthetic.

Apartment in Linstead

5 out of 5 average rating, 25 reviews

S.G Apartment complex.

Take it easy at this unique and tranquil getaway. S.G apartment complex is nestled in the tranquil community of Charlemont Housing Scheme. We are only 30mins away from Ocho Rios and 45mins outside of Kingston via toll. Not to mention, we are 5mins or walking distance from the famous Grant's Jerk Centre and 25mins 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 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, 161 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, 26 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

The exterior of a modern one-bedroom retreat is framed by lush greenery and palm trees. A smooth driveway leads to the entrance, highlighted by minimalist architecture and large windows, inviting guests to enjoy the serene surroundings.

Home in Galina

4.97 out of 5 average rating, 35 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 modern bathroom is displayed, featuring a glass sink set on a dark marble countertop. Circular mirror hangs above the sink, and a wall-mounted organizer holds toiletries. A white toilet sits adjacent, surrounded by elegant marbled walls that enhance the room's clean aesthetic.

Apartment in May Pen

4.89 out of 5 average rating, 37 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.

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!

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

4.94 out of 5 average rating, 31 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.

Top guest favorite

A compact sink with a unique flower-shaped basin is present, surrounded by tiled walls featuring an intricate geometric pattern. A clear cup is placed beside a pump bottle of hand soap, providing essential amenities for guests.

Home in Spanish Town

4.94 out of 5 average rating, 47 reviews

Studio Serenity

Modern, peaceful studio in Angels Grove, perfect for your Jamaican getaway. Minutes from restaurants and the Knutsford Express depot. Easy toll road access to north coast attractions. Equipped with WiFi, AC, and kitchenette. Ideal for solo travelers, couples, or business trips. Your serene home base for island exploration.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Middlesex County vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Middlesex County

Top guest favorite

A bathroom shelf displays essential toiletries and decorations. A black sign labeled 'Bathroom' hangs above. Two small plants and a candle are positioned on the top shelf. The middle shelf holds a roll of bathroom tissue, while the bottom shelf contains cleaning supplies and personal care items.

Home in Portmore

4.93 out of 5 average rating, 45 reviews

Modern Cozy Haven

ChrisRating, 5 stars1 month ago

This place was perfect for us. We felt right at home in this cozy home. It was clean and had everything that you could look for in an Airbnb. We didn’t have to go and purchase anything that we wouldn’t have had in our own home. This home was perfect for our needs and we appreciate the attention to detail and responsiveness of the host.

Top guest favorite

A sandy beach stretches along the coastline, with gentle waves lapping at the shore. People can be seen enjoying the water, while palm trees sway in the breeze. Umbrellas and rustic structures are positioned in the background, creating a relaxed coastal atmosphere.

Home in Portmore

4.98 out of 5 average rating, 54 reviews

The Palms at Phoenix

NadineRating, 5 stars2 weeks ago

This was my second time staying at Ken’s home, and once again, it truly felt like my home away from home. Ken is the best of the best—patient, caring, and always going above and beyond to make your stay unforgettable. The house is warm, inviting, impeccably clean, and cool—everything you could ask for. I didn’t miss a thing from home because Ken’s home had it all. Thank you, Ken, for your incredible hospitality, kindness, and understanding. If you’re ever visiting Jamaica, I highly recommend booking this property—you won’t regret it. Looking forward to my next stay! Nadine Chambers

Guest favorite

A sectional seating arrangement is presented with light-colored cushions featuring contrasting piping. The furniture is positioned on a textured tile floor, surrounded by large windows with decorative patterns that allow natural light into the space.

Apartment in Spanish Town

4.89 out of 5 average rating, 45 reviews

Home in St. Catherine

FijauhnRating, 5 stars3 weeks ago

Is the best and will always be the best I’ll recommend anyone using this Airbnb app to stay right here

Home in Old Harbour

4.67 out of 5 average rating, 3 reviews

Modern Home New Harbour (Village Old Harbour)

KevinRating, 5 stars1 month ago

The host at Modern Home Old Harbour was incredibly friendly and helpful the responded to my messages promptly. The place was clean elegant and nice and I felt like I was being treated like a valued customer, and I appreciate that. I would recommend this place to anyone

A modern kitchen features grey cabinets and granite countertops, with a gas stove, microwave, and kettle visible. The kitchen island includes seating for three. Natural light enters through a window adorned with decorative glass, illuminating the space.

Home in Crooked River

4.83 out of 5 average rating, 6 reviews

Livingwell Homes Jamaica

QuintonRating, 5 stars2 months ago

if you haven't booked yet... DO IT!! Jodyanns place is remarkable and she is the best host ever. Jodyanns place is very remote and exactly the vibes I was looking for. The place is huge and clean, it comes with dishes pots pans cutlery everything you need to disconnect and have some quality time or family time. The community vibe was some icing on the cake. The host has several resources very close to help with anything you need. I was taken to a local grocery to purchase food items that I would have never found by myself. Directions to a local waterfall and llocation of the center of the island... which you can see from their farm. We were given sugar cane and food items LIKE CACAO pineapple oranges and mango from a farm located on the same street as jodyanns place (actually a family farm). We were in direct and responsive communication with resources that made our trip even better.

Guest favorite

Apartment in Mandeville

4.93 out of 5 average rating, 14 reviews

Luxury Oasis of Toni’s Estate

NeseanRating, 5 stars2 months ago

all positives no negatives. feels like home away from home.

Guest favorite

Home in Bog Walk

4.88 out of 5 average rating, 41 reviews

Serenity Breezy Hillview

AvaRating, 5 stars3 days ago

Yuen took such great care of me ! He took me too and from the airport and the instructions for the house are very clear and simple. The house looks ever better in person and Is so spacious. Overall I had a great time and I was even given coconut water :-) will be coming back for sure!

Guest favorite

A modern bathroom is presented with a sleek design, featuring a glass-enclosed shower, a stylish vanity with a bowl sink, and a large mirror with integrated lighting. Neutral colors create a calm atmosphere, complemented by plush rugs on the floor.

Villa in Ocho Rios

4.83 out of 5 average rating, 35 reviews

Onyx Villa @The Cove, Ocho Rios

JulianRating, 5 stars5 days ago

This place was breathtaking!!!! The ambience was everything !!!! Definitely my vibes clean classy and captivating. Happy cove stand to its name my family and I surely felt happy we didn’t want to leave ; what I loved the most is how well kept this gated community was, very quiet and peaceful. I will definitely go back to this property loved my stay here.

Show all

Vacation rentals in Middlesex County

Top-rated vacation rentals in Middlesex County

Vacation rentals for every style

Popular amenities for Middlesex County vacation rentals

Other great vacation rentals in Middlesex County

Destinations to explore