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Holiday rentals in Middlesex

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Top-rated holiday rentals in Middlesex

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Guest favourite
A view of a beachfront scene featuring a straw-roofed gazebo surrounded by palm trees. The blue Caribbean Sea shines in the background, with a parachute glider visible in the distance. A grassy area is framed by a white fence, enhancing the serene outdoor atmosphere.
Townhouse in Negril
4.9 out of 5 average rating, 147 reviews

'Sunset Vista' - Negril Seafront Home w/Solar - Se

Sunset Vista is located within Little Bay Country Club, an upscale, beachfront community in Negril. The gated community sits on a peninsula that is surrounded by the Caribbean Sea on both sides and features a private beach, infinity pool, clubhouse, tennis courts, basketball, and 24-hour security. Sunset Vista sleeps 4 very comfortably and up to 6 (4 adults max). The home is fully solar powered with wifi and a/c throughout and is perfect for couples or families. This relaxing 2 Bedroom and 2 an

Superhost
A montage showcases various areas of the Wabi-Sabi Villa. The pool area features a lap pool with lounge floats, while the interior highlights a modern kitchen, a cozy living room with bookshelves, and a luxurious bedroom with a plush king-sized bed.
Villa in Hanover Parish
4.96 out of 5 average rating, 26 reviews

All-Inclusive Jamaica Getaway| Pool| Chef| Gym|Car

Welcome to Wabi-Sabi, a beautifully designed accessory dwelling unit that includes the modern amenities you need for an epic holiday. The luxury villa has two units, each with its own bedroom, bathroom, and living area. We offer an experience unlike any other, with a personal chef, free rental car, rooftop terrace with ocean views. Alcoholic beverages not included. 2 Min Drive to Park Beach 5 Min Drive to Fort Charlotte 16 Min Drive to Dolphin Cove Experience Lucea With Us & Learn More Below!

Guest favourite
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 favourite
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.

Top guest favourite
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
4.81 out of 5 average rating, 67 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 favourite
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.

Top guest favourite
A spacious living area features a comfortable beige sofa adorned with decorative pillows. A vibrant area rug with intricate patterns covers the tiled floor. Green curtains frame the window, while a stylish coffee table sits in the center, enhancing the inviting atmosphere.
Home in Lucea
4.94 out of 5 average rating, 113 reviews

I love Lucea Nestled between Montego Bay & Negril

A secured, gated community nestled between the cities of Montego Bay and Negril. This little piece of paradise is all you need to relax and unwind. If you’d prefer an adrenaline boost, we’ve got you! The community is equipped with a gym, clubhouse, multipurpose court, tennis court, football field, running track and a private beach. We provide other services such as airport transfer, city tours, grocery deliveries, spa, housekeeping, manicure and pedicure services at an additional cost.

Guest favourite
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
4.84 out of 5 average rating, 25 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!

Top guest favourite
Apartment 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 favourite
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, 109 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 favourite
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.
Flat in Green Island
4.94 out of 5 average rating, 31 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 favourite
A clear view of the coastline is visible, showcasing a wide expanse of blue ocean under a bright sky. Palm trees frame the scene, swaying gently in the breeze. The sandy beach is present in the background, suggesting a serene atmosphere.
Home in Lucea
5 out of 5 average rating, 32 reviews

Starlink/Solar/Pool/1 Parking/Gym

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.

Popular amenities for Middlesex holiday rentals

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