Vacation rentals in Middlesex

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Top-rated vacation rentals in Middlesex

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Guest favorite
A spacious patio area is shown with a built-in pool, featuring a ladder leading into the water. A retractable awning extends above large glass doors that open to the interior. Sun loungers are positioned for relaxation beside the pool, with clear skies in the background.
Home in Hanover Parish
4.85 out of 5 average rating, 144 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
4.89 out of 5 average rating, 19 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 cozy living area is presented with a sectional sofa featuring soft cushions. A glass coffee table sits in front of the sofa, complementing the light-colored walls. A flat-screen TV is mounted on the wall above a decorative shelf, while sunlight filters through sheer curtains.
Villa in Lucea
4.87 out of 5 average rating, 83 reviews

Natalia’s Sweet Oasis

Natalia’s Sweet Oasis in the gated community of Oceanpointe is ideally located 30km between Jamaica’s 2 most popular tourist destinations: Montego Bay the tourist capital and Negril the capital of casual, famous for its seven miles of white sandy beach and pristine waters. Take a quick 1 minute drive to Dolphin Cove OR a 5 minutes drive to Chukka Adventure Park for a day of fun activities. This gem is an ideal space for family vacations, business trips, group travel or a getaway by yourself.

Guest favorite
Home in Hanover Parish
4.8 out of 5 average rating, 66 reviews

Serenity Get Away-beach access, solar, 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.

Guest favorite
Home in Lucea
4.84 out of 5 average rating, 31 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 bright living area features a spacious sectional couch and a sleek coffee table. A large television is mounted on the wall, above a modern electric fireplace. Ambient lighting is provided by a ceiling fan and decorative fixtures, with soft colors enhancing the interior's design.
Home in Lucea
4.92 out of 5 average rating, 51 reviews

Scenic Cozy Casa- between Mobay & Negril

Solar powered and Starlink ready! Scenic Cozy Casa is a tropical retreat located in the beautiful, gated community of Oceanpointe (midway between Negril and Montego Bay). Enjoy sea views to the north and lush mountains to the south, offering a serene escape. The community features two pools, a gym, jogging trail, tennis court and multi-purpose court. Relax at the clubhouse or explore the amenities. With 24-hour security, Scenic Cozy Casa is the ideal base for relaxation and adventure.

Top guest favorite
Home in Lucea
5 out of 5 average rating, 19 reviews

Island Breeze Escape

Island Breeze Escape is your cozy getaway where comfort meets island charm. Whether you’re here for relaxation, adventure, or a little of both, our space is designed to make you feel right at home—just with a fresh sea breeze and tropical vibes all around. Wake up to the gentle sound of birds chirping, enjoy nearby beaches and attractions, and end your day unwinding in a space curated for peace and ease, inside or by the pool. Perfect for solo travelers, couples, or small families!

Top guest favorite
Condo in Lucea
5 out of 5 average rating, 13 reviews

FOUR (4) new modern-minimalistic style apartments.

Experience a memorable vacation at our tropical oasis located right on the water. Waking up to the sound of ocean waves outside your door, spectacular waterfront views and a spacious courtyard fit for relaxing, Chateau Bleu embodies the essence of 'Fun in the sun!' Imagine, unwinding on lounge chairs, or sipping a cocktail in a hammock, all whilst being at your own private seaside retreat! Local attractions: 5 mins walk to Downtown Lucea 10 mins walk to the Historic Fort Charlotte.

Guest favorite
A tranquil swimming pool is situated in the center of a spacious outdoor area, surrounded by light-colored stone tiles. Sunlight reflects off the calm water, while the backdrop features a modern two-story home with large windows and a covered patio area.
Home in Lucea
4.92 out of 5 average rating, 106 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 spacious bedroom features a large wooden bed with a decorative headboard and light-colored bedding. A dresser displays a wooden finish, complemented by a mirror on the wall. Natural light enters through an open door, enhancing the bright and airy feel of the room.
Apartment in Green Island
4.93 out of 5 average rating, 28 reviews

Stunning Nature-Views StudioApt

Welcome! Make this stunning studio apartment your home away from home. Nestled on 2 acres, the villa is surrounded by luscious nature with sunset and partial sea views. You will be only 15mins drive away from the resort town of Negril and 45mins drive away from Montego Bay, the second city, with a direct highway connection. The studio is self-contained with private, self-check in access, ample parking and 24/7 surveillance. We speak English, Italian and Spanish!

Top guest favorite
A serene outdoor area features a clear swimming pool surrounded by a spacious patio. White lounge chairs with blue cushions are arranged around the pool, while vibrant tropical plants add a touch of greenery. A covered pergola provides shade and enhances the relaxing environment.
Home in Lucea
4.95 out of 5 average rating, 107 reviews

Paradise Oasis at Oceanpointe (Solar Powered)

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
A spacious outdoor area features a crystal-clear pool surrounded by stone tiles and tropical plants. Lounge chairs are positioned nearby for relaxation. The covered patio area provides shade, enhancing the charming setting for outdoor gatherings.
Home in Hanover Parish
4.87 out of 5 average rating, 107 reviews

Comfortsuite: Cozy/Solar-Powered/Gym/Pool

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