Holiday rentals in Middlesex County

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Top-rated holiday 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
4.86 out of 5 average rating, 214 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

Top guest favourite
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
4.95 out of 5 average rating, 64 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!

Guest favourite
A serene ocean view is presented, with gentle waves lapping at the shore. Lush green lawn stretches towards the water, bordered by ornamental shrubs. A large tree provides shade, enhancing the natural beauty of the tranquil landscape under a clear blue sky.
Flat in Ocho Rios
4.85 out of 5 average rating, 187 reviews

Precious Studio with a Vast Ocean View

We are fully operational post Hurricane Melissa with power, water & wifi Unwind at this stunning ocean-view studio only 5 minutes away from the heart of Ocho Rios. The studio is freshly renovated with granite counter tops in the kitchen and bathroom, and porcelain tile throughout for a luxurious yet homey feel. Enjoy the vast ocean view and dip your toes in the water only a few steps out from the patio. This studio is the perfect place for relaxing, listening to the ocean and enjoying the breeze

Guest favourite
A semi-open living area is presented with white walls and modern furnishings. A wooden coffee table sits in front of a comfortable sofa. Large windows overlook the sea, revealing two loungers on the balcony, creating a serene atmosphere with natural light.
Apartment in Ocho Rios
4.83 out of 5 average rating, 277 reviews

Seafront Apartment nxt to Beach

My place is in Ocho Rios Jamaica , walking distance from Ocho Rios Town centre . Its a homely seafront, split level apartment within a traditional 1960s style past resort directly next to Mahogany beach. Breathtaking sea views, set within a beautiful garden. The people are lovely and the sea and beach/bar are so relaxing. You can book and set sail from the beach on a Cool Runnings catamaran cruise. My place is good for couples, solo adventurers, business travellers, and families (with kids)

Top guest favourite
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.
Apartment in Ocho Rios
4.92 out of 5 average rating, 119 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 renovated studio apartment is ideally located for a relaxing getaway or a longer remote working vacation. The unit is bright & uncluttered with a tastefully modern décor. K1 is located in a gated hillside community, close to all major attractions, some walkable. The area provides unparalleled scenic views of the sea, mountains & flora of a tropical paradise.

Superhost
A verandah offers a serene space with two comfortable chairs and a small table. A stack of books rests on the table beside a cup, with views of the ocean and palm trees in the background, enhancing a peaceful atmosphere.
Apartment in Tower Isle
4.84 out of 5 average rating, 190 reviews

2 bedroom Oceanfront condo with a pool

Kick back and relax in this calm, stylish 2 bedroom Condo on the ocean with an infinity pool. 5 minutes east of Ocho Rios, within walking distance to a beachfront restaurant, local jerk centre, bar and grocery store. We can host up to four guests. As we have many couples traveling we offer a discounted base rate for two guests and then each additional guest comes with an additional fee up to a maximum of four. For two guests we will often close the second bedroom unless otherwise requested

Guest favourite
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.
Apartment in Ocho Rios
4.88 out of 5 average rating, 260 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 living area is presented with neutral-colored tiled flooring and bright walls. A dark grey sofa occupies one side, while a small round coffee table complements the space. A television is mounted on a wall unit, and a decorative entrance door is visible in the background.
Home in Spanish Town
4.82 out of 5 average rating, 95 reviews

Irie Getaway - House in gated community

One bedroom newly built and furnished home in very peaceful and quiet residential, gated community, with 24 hour security, in St. Catherine. House is ideally located just a few minutes from the Spanish Town Toll road, which makes it easy to access without having to encounter heavy traffic. Kingston is 25 minutes away and Portmore is 10 minutes away. House is nicely furnished and has ac in the bedroom (only) and other amenities to make your stay feel like a home away from home!

Guest favourite
Apartment in Portmore
5 out of 5 average rating, 14 reviews

Beachfront Condo w|Amazing Views |2Pools & Gated.

Enjoy a stylish experience at this centrally-located place. We have carefully designed this unit to be your escape from reality. This condo sits on a beachfront property with large windows that showcase breathtaking views of the Kingston Harbor and Port Royal. Guests have access to a private beach and a large pool deck facing the sea. This complex is gated community and provides 24hrs security. The unit is equipped with everything you need for a memorable stay.

Guest favourite
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
4.92 out of 5 average rating, 48 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.

Top guest favourite
A decorative entrance sign displaying 'Colbeck Manor' is mounted on a beige wall. Surrounding greenery features well-maintained flowering plants, adding a touch of color against the background of a clear blue sky.
Home in Old Harbour
5 out of 5 average rating, 21 reviews

Colbeck364 Comfort Stay

Colbeck364 Comfort Stay – Relax in Style! Welcome to Colbeck364 Comfort Stay, a fully air-conditioned retreat in Colbeck Manor, Old Harbour, St. Catherine. Enjoy a community pool, gym, high-speed Wi-Fi, and Smart TV. The home features a fully equipped kitchen, stylish interiors, and a secure gated community. Just minutes from Old Harbour town, shopping, and major highways. Book now for a relaxing and comfortable stay!

Superhost
Home in Portmore
5 out of 5 average rating, 3 reviews

The Royal Villa - Portmore

Your family will be close to everything when you stay at this centrally-located gated-community property. This brand new unit offers a quality, safe and secure space with major shopping areas and entertainment options less than 5 minutes away. If you are more the adventurous traveler, you have ease of access to Helshire or the major Toll roads for ease of access to the north, west or even east of the island.

Popular amenities for Middlesex County holiday rentals