Holiday houses in Middlesex

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Top-rated holiday rentals in Middlesex

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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
A dining area features a dark wooden table surrounded by four matching chairs and a bench. A simple centerpiece of faux flowers adds elegance. Soft, neutral curtains frame a window, and modern wall art complements the space. The open doorway leads to a kitchen area.
Home in Lucea
5 out of 5 average rating, 20 reviews

Sea Breeze Villa

Welcome to Sea Breeze Villa! This luxurious and spacious abode is the perfect retreat for those seeking a tranquil and relaxing escape. You'll be captivated by the elegant styling and attention to detail that has been put into every aspect of this home. Located in a quiet and peaceful neighborhood, this property offers the perfect blend of seclusion and convenience.We can't wait to welcome you to our stunning Sea Breeze Villa and help you create unforgettable memories that will last a lifetime!

Top Guest favourite
A serene pool area is visible, featuring lounge chairs arranged beside a clear blue pool. Palm trees and lush greenery frame the space, while a covered gazebo is provided in the background, enhancing the outdoor relaxation experience.
Townhouse in Montego Bay
4.98 out of 5 average rating, 195 reviews

2BR Townhouse with staff, gym, pool & beach access

Escape@20 is a lovely townhome that guarantees a truly relaxing and memorable experience. A friendly housekeeper/cook is included at NO EXTRA COST!! You just need to purchase the groceries. The townhome has an open floor plan with living and dining room opening out to a covered patio and a backyard. Guests can enjoy breathtaking views of the neighboring yacht docking area, swimming pool, gazebo/bbq grill space, gym, playground for kids, 24 hour security and complimentary beach access nearby.

Guest favourite
A blue metal ladder leads into clear turquoise water, which reflects sunlight. The surrounding rocky shore features lush greenery along the edge, and a distant view of a residential area is visible on the cliffs above.
Cottage in Westmoreland Parish
4.93 out of 5 average rating, 331 reviews

Little Bird Cottage @ High Cove

We are operating as normal after Hurricane Melissa! The West End is in top shape! Little Bird is located on High Cove property, nestled on a pristine swimming cove on the famous West End. There are 2 other cottages on the property that can be rented separately, or jointly for groups of up to 15. A stone's throw away from the world-renowned Rick's Cafe, restaurants/watering holes, and has incredible sunsets. 10mins drive to Negril's vibrant Seven Mile Beach. A secluded and romantic getaway.

Top Guest favourite
Home in Lucea
5 out of 5 average rating, 14 reviews

Turquoise Escapes, Hanover Jamaica

Turquoise Escapes is a luxurious retreat at Oceanpointe. This beautifully designed and getaway features 2 bedrooms and 2 bathrooms, combining rustic charm with modern comfort. Accommodating up to four guests, it includes a king suite and a queen suite. Amenities include a washer, dryer, air fryer, coffee maker, 3 televisions, air conditioning, fans, and Wi-Fi access. It boasts a prime location, just a five-minute drive to Dolphins Cove. Public beach access is conveniently a 10 minutes walk.

Top Guest favourite
Loft in Negril
5 out of 5 average rating, 9 reviews

Seafront Modern Loft w/ Pool - Negril’s West End

Experience the best of Negril from this stylish loft studio perched on the area’s famous cliffs. With sweeping ocean views, modern design, and resort-style amenities, this seafront escape is perfect for couples, friends, or small families seeking both relaxation and adventure. Good to Know: The property is part of a newly developed condo-hotel, with certain areas still under construction. Guests may notice light construction during their stay, but all private areas of the loft are ready.

Guest favourite
Home in Lucea
4.84 out of 5 average rating, 32 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 favourite
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
4.91 out of 5 average rating, 53 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.

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
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 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, 110 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.

Guest favourite
A bright bedroom is featured, showcasing a spacious bed adorned with colorful pillows and a soft green throw. Large glass doors open to a balcony, offering a view of the tranquil water and lush greenery beyond. Natural light enhances the airy atmosphere.
Townhouse in Negril
4.9 out of 5 average rating, 109 reviews

Private Oasis in Negril: Beachfront Luxury!

Escape to this gorgeous two-bedroom townhouse, your ideal Negril getaway! This unit boasts every amenity you could desire. Nestled within the tranquil, gated Little Bay Country Club, you'll enjoy 24-hour security. Our waterfront gem overlooks a mesmerizing fish sanctuary, offering breathtaking views! The expansive porch is simply divine for all-day relaxation – from your morning coffee to lazy afternoons, or vibrant evenings with cocktails. An unforgettable stay awaits!

Popular amenities for Middlesex holiday rentals

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