Vacation rentals in Middlesex County

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Top-rated vacation 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

4.87 out of 5 average rating, 200 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 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, 108 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.

Top guest favorite

A charming exterior of a single-story home is highlighted by soft outdoor lighting. A small seating area with two chairs is positioned by the entrance, framed by well-maintained landscaping. Lush greenery and gravel paths lead up to the welcoming front door.

Home in Portmore

4.94 out of 5 average rating, 51 reviews

Gated Cozy Urban Luxe Retreat

Phoenix V is your city oasis. Find serenity in our secure haven, blending luxury & tranquility. setting the stage for a peaceful escape from the bustling urban landscape. Our home invites you to unwind while enjoying a cozy ambiance. Enjoy a luxurious bedroom as the living area opens to a contemporary, fully-equipped kitchen. Central location, minutes from cultural gems & vibrant life. Relax on the private verandah with lush views. Perfect for business or leisure, book your home away from home!

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, 20 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!

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, 34 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 image captures a vibrant sunset over a landscape, showcasing a blend of warm orange and pink hues filling the sky. Lush greenery is visible in the foreground, while distant hills are faintly outlined against the dramatic backdrop of colors.

Apartment in Ocho Rios

4.92 out of 5 average rating, 24 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!

Top guest favorite

An open concept kitchen is showcased, featuring a stainless steel refrigerator and an oven with a hood. A round glass dining table is surrounded by four metal chairs. Natural light is filtered through a window adorned with patterned curtains, illuminating the modern cabinetry.

Home in Portmore

5 out of 5 average rating, 6 reviews

Sher Cozy 1 BR Suite @ Phoenix Park II

Retreat to our luxurious 1 bedroom 1 bath home unit conveniently located in the peaceful and gated community of Phoenix Park Village II with 24hrs security for peace of mind. This newly built unit is equipped with all the necessities for a comfortable and peaceful stay and is perfect for couples or solo travelers. You will be in close proximity to Hellshire Beach, Fort Clarence Beach, Starbucks, Restaurants, Movie Theatre, Pricesmart and Fontana Pharmacy.

Guest favorite

A well-appointed bedroom features a spacious bed with a cozy blanket and decorative pillows. The green curtains frame the window, while a sleek dresser is positioned against the wall. An air conditioning unit is mounted above, providing comfort during warm days. Inset is an image of the pool area.

Home in Old Harbour

4.91 out of 5 average rating, 44 reviews

Chillax Manor Your Private Oasis for Relaxation

Get this entire space with Pool access! Nestled in a gated community, Chillax Manor is perfect for your next getaway. The Manor offers you a luxury hotel feel. It is the getaway that your family will enjoy while being centrally located place to everything. You deserve to chill in this impeccable two-bedroom, one-bathroom peaceful spot with a pergola. Chillax Manor is also equipped with the necessary toiletries and a few complimentary beverages/snacks.

Guest favorite

The living room displays a modern ambiance with gray sofas and a blue accent chair. A round coffee table sits on a soft area rug, complemented by natural light streaming through large windows, and decorative plants enhance the space's fresh feel.

Home in Ocho Rios

4.92 out of 5 average rating, 26 reviews

Pyramid Springs

Our luxurious home in a gated Jamaican community with 24-hour security offers an array of complimentary amenities, including a tennis court, gym, community pool, playground, air conditioning, Wi-Fi, Netflix, YouTube, Electric stove with oven, Air fryer, and a large refrigerator/freezer. Located central to all airports, 10 min to Dunns River Falls/Dolphin Cove; 15 min to Chukka & Plantation Cove, and 5 minutes’ drive to beaches in Ocho Rios.

Guest favorite

A cozy bedroom features a spacious bed with a light-colored quilt and decorative pillows. Air conditioning is provided above, while large windows are adorned with teal curtains. A wooden dresser with a blue decorative vase and a mirror complement the room's serene atmosphere.

Home in Portmore

5 out of 5 average rating, 7 reviews

Gated Home 2: A/C, Airport Pickup, 15 min to Beach

Your Cozy Escape! Welcome to your second home in Phoenix Park Village 2! This stylish 2-bedroom stay is ideal for families or friends. Enjoy comfy air-conditioned rooms, a full kitchen, washer, free parking, and 24/7 security. Wheelchair accessible with airport pickup available (extra cost). Close to shops, restaurants, and entertainment. Hosted by a Superhost, you’ll feel right at home—comfort and convenience guaranteed!

Guest favorite

A modern kitchen is presented with dark cabinetry and a granite countertop. Kitchen appliances, including a microwave, stove, and double-door refrigerator, provide functionality. A dining table set for two is featured, with a glass and decorative elements, enhancing the space's practical appeal.

Apartment in May Pen

4.9 out of 5 average rating, 41 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.

Guest favorite

A spacious living area features a comfortable grey sofa positioned on a soft rug. Natural light fills the room from nearby windows. A modern kitchen is visible in the background, complemented by dark wood cabinetry and sleek appliances. A television is mounted on the wall, adding entertainment options.

Home in Old Harbour

4.9 out of 5 average rating, 42 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.