Vacation rentals in Middlesex

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Top-rated vacation rentals in Middlesex

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Top guest favorite
A spacious living room features a large, cushioned sectional sofa adorned with light throw blankets. A round wooden coffee table is positioned in front, surrounded by a light geometric area rug. Wall-mounted shelves display decorative items, and a flat-screen TV is visible on the wall, framed by natural elements.
Home in Lucea
4.97 out of 5 average rating, 59 reviews

Kelly’s Ocean Paradise

Unwind in this gorgeous modern yet rustic decorated coastal home in a quiet gated community. Fully equipped to be your home away from home. The home boasts 3 beautiful bedrooms and 2 bathrooms. Plenty of space to keep up with your daily routine. The kitchen features stainless steel appliances. Enjoy your meals around our dining table or take it to the backyard lounge area. Enjoy a view of the sea and the mountains just looking from the veranda. End the day with a movie in our comfy living room.

Guest favorite
Home in Hanover Parish
4.85 out of 5 average rating, 138 reviews

Private & Cozy two bedroom Oceanpointe House

Escape to Home away from home in a private and cozy two bedroom, two bathrooms, kitchen, laundry, living and dining room House. This recently built house is located in a new modern gated community. Air condition and ceiling fan in both bedrooms and living room, , solar electricity & hot water, water tank , Starlink internet, Granite kitchen and bathroom countertop, washer, dryer, sliding door closet, rear fencing, large patio, driveway and open floor plan. These are some of the many features.

Guest favorite
A modern living area is designed with comfortable gray sofas adorned with patterned cushions. A sleek coffee table is positioned in front, and large windows allow natural light to illuminate the space. A flat-screen TV is mounted on the wall, contributing to a relaxed atmosphere.
Home in Lucea
4.93 out of 5 average rating, 15 reviews

OceanBreeze

BOOK WITH CONFIDENCE Welcome to ocean-breeze your cozy stylish family friendly vacation home. Ocean-breeze’s located in the Paris of Hanover in the middle between Montego Bay and Negril across the street from Grand Palladium Jamaica Resort. At ocean-breeze you will find everything to make your vacation memorable. Check in any time remotely! Get 24/7 gated security and customers support with helpful tips. Car rental service and certified local tour guides are available for additional charges

Guest favorite
A serene bedroom is presented with light-colored walls and a plush bed covered in a textured white quilt. Framed artwork featuring architectural motifs adorns the wall above the bed. Soft curtains frame a window, allowing natural light to brighten the space.
Home in Hanover Parish
4.79 out of 5 average rating, 61 reviews

Serenity Get Away-solar powered, starlink

2 bedroom 2 bathroom tastefully decorated home filled with modern amenities. Take Advantage of the pool, tennis and basketball courts that the property has to offer. Take morning runs using the jogging trail or take a dip in the beautiful Caribbean sea located within walking distance of the house. Whatever you fancy Serenity get away is right for you, as we aim to please with comfort, style and cleanliness. 30 mins from Montego Bay airport. Shuttle and private transport at additional cost.

Top guest favorite
A spacious outdoor patio features a dining table and chairs, complemented by a shaded umbrella. A BBQ grill is positioned nearby, and a heated plunge pool with a tiled backdrop reflects the clear sky. Lush greenery borders the wooden decking, creating a serene atmosphere.
Home in Oceanpointe, Lucea
4.93 out of 5 average rating, 29 reviews

Best Vacation Ever/Private Pool/Local Beach

The cottage at Oceanpointe is exquisite, stylish, relaxing and designed as the ultimate getaway. Highlights: Private chef available to book, full kitchen and BBQ grill, heated pool, king size beds, WiFi and cable, AC in every room, 2 twin size daybeds on back patio, option to purchase day/night pass to Grand Palladium, walk to beach for a quick swim, gated, 2 community pools, event space, tennis and basketball courts, close to Montego Bay and Negril, gorgeous garden and amazing decor.

Guest favorite
A bright living and dining area features a spacious seating arrangement with a light grey sofa and an oversized chair. A wooden dining table accommodates six people, complemented by modern decor. Large windows framed with soft curtains allow natural light to illuminate the space.
Home in Lucea
4.86 out of 5 average rating, 29 reviews

SunKiss Paradise/Family 4 home/ Btw Negril & Mobay

Welcome to our now SOLAR EQUIPPED, charming two-bedroom, two-bathroom home in an exclusive oceanfront gated community. Situated between the world-renowned seven-mile beaches of Negril and the bustling cruise ship destination of Montego Bay, our home offers a haven of tranquility with 24-hour security. Just minutes away from the historic town of Lucea, where part of the famous movie Cool Runnings was filmed. Let this cozy solar packed home serve as the perfect setting for your vacation.

Guest favorite
A modern living space is displayed, featuring a comfortable sectional sofa with a yellow accent pillow. Light-colored curtains frame large windows, allowing natural light to fill the room. A flat-screen TV is mounted on a minimalist console, with a dining area visible in the background.
Home in Lucea
4.85 out of 5 average rating, 20 reviews

Grand 180° Sea View OceanPointe

Welcome to The Grand 180 Degrees Sea View at Ocean Pointe, the Perfect Relaxing Vacation home located in a quiet gated community in Lucea, Hanover. Centrally located just 30mins between Montego Bay and The Beautiful Negril. Experience the Clean and Airy Beach Vibe for a Family Getaway, Business Trip or Staycation. Enjoy the Sea and Mountain views, Unique Eco-Friendly front yard, and a Private Back Yard with a 180-degree Ocean View you Cannot resist. Your home away from Home Awaits!

Guest favorite
A light-colored house is depicted with a pointed roof, featuring a front porch and large windows. Landscaped greenery surrounds the house, including a small garden and well-maintained lawn. A paved driveway leads up to the home, with a white picket fence in the background.
Home in Lucea
4.92 out of 5 average rating, 105 reviews

Sunflower Escape Deluxe Pool/Beach/Gym/AC

Escape to relaxation at this two bedroom home located halfway between two of our islands most popular tourist destinations Montego Bay and Negril. Sunflower Escape Delux has all the basic modern amenities, privacy, comfort and style. Our community is gated with free access to a pool, gym, tennis and basketball courts and jogging trail. Chukka Adventures and Dolphin Cove are just minutes away. We also offer airport transfers and a nice car for rent at affordable rates.

Top guest favorite
A refreshing swimming pool is surrounded by a neatly landscaped area, featuring palm trees and low shrubs. The pool is bordered by a light-colored stone deck, and a white fence provides privacy. Green hills are seen in the background under a partly cloudy sky.
Home in Lucea
5 out of 5 average rating, 27 reviews

The Ultimate SeaClusion/Pools/GYM/Solar/1 Parking

Have fun with the whole family at this stylish place. Newly gated community with amenities: Two Swimming pools, gym, tennis court, soccer field, basket court, table tennis and WiFi. The home is 35 minutes from Montego Bay Airport and 45 minutes from the home to Negril. We are directly across from the sea so it is nice and breezy. You can enjoy watching the sunset across the street by the sea. The home has everything you need to make it a home away from home.

Top guest favorite
The entrance features a charming pathway of manicured grass leading to a wooden door, surrounded by vibrant flowers and lush greenery in decorative pots. The exterior is characterized by light-colored walls and a spacious balcony above, providing a welcoming ambiance.
Apartment in Sandy Bay
4.95 out of 5 average rating, 107 reviews

Oleander Staycation

Just 30 minutes from Sangster International Airport and the lively resort town of Montego Bay, Oleander Staycation is your perfect island escape any time of the year. In only five minutes on foot, you can be at the beach, and when you return, you’ll enjoy the comfort of a safe, welcoming neighborhood. For everyone’s comfort, we kindly ask that only registered guests stay overnight. Need a ride? A vehicle is available for rent at an additional cost.

Top guest favorite
A modern living area features a light gray sectional sofa adorned with orange cushions. Two lamps illuminate the space alongside a wooden coffee table. Large windows are framed with sheer and dark gray curtains, while decorative plants and white flowers add a touch of elegance.
Home in Lucea
4.95 out of 5 average rating, 105 reviews

Paradise Oasis at Oceanpointe

Have fun and relax at Paradise Oasis at Oceanpointe. A tranquil yet luxurious home away from home. Nestled in the beautiful island of Jamaica, halfway between two popular tourists’ destinations – Negril and Montego Bay. This chic yet warm beauty, promises to appeal to your need for relaxation while satisfying your desire for comfort. It is simply an ideal space for solace, business trips, family vacations or a couple’s hideaway.

Guest favorite
The living area features a comfortable sofa beneath a ceiling fan, complemented by light from large windows adorned with light curtains. A smart TV is mounted on the wall, while a dining table set with decorative placemats and vibrant flowers is visible in the foreground.
Home in Hanover Parish
4.87 out of 5 average rating, 102 reviews

Comfort Suite:

Comfort Suite is a two-bedroom, two-bathroom home located at Oceanpointe in Lucea Hanover with 24-hour security. The community is nestled between Jamaica's tourist capitals, Montego Bay and Negril. Soak up the sunshine by the pool or enjoy a fun games night at the community clubhouse. Enjoy a swim with the dolphins' meters away at Dolphin Cove or horseback riding and ATV rides at Chukka Adventure Tours 10 minutes away.

Popular amenities for Middlesex vacation rentals

  1. Airbnb
  2. Jamaica
  3. Hanover
  4. Middlesex