Holiday rentals in Middlesex

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Top-rated holiday rentals in Middlesex

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
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
4.89 out of 5 average rating, 76 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.

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, 206 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 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
5.0 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 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, 30 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.

Superhost
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, 26 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
5.0 out of 5 average rating, 24 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 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, 110 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!

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
4.95 out of 5 average rating, 40 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!

Guest favourite
A bright living space features a soft grey sofa adorned with colorful cushions. A round coffee table, topped with decor and a small plant, occupies the center. Natural light floods the room through sheer curtains, illuminating the cozy atmosphere.
Home in Lucea
4.94 out of 5 average rating, 36 reviews

CasaLamar Beachside Retreat

Bright, Breezy Beachside Retreat conveniently located between 2 popular tourist destinations- Montego Bay and Negril, Jamaica. This coastal beauty inside Oceanpointe’s safe & secure gated community is appointed with everything you need for a relaxing stay. Get inspired by an interesting read, catch a refreshing ocean breeze from the patio, restore with a good nights sleep, and embark upon one of many nearby adventures like Dolphin Cove or Chukka Adventure Park!

Top guest favourite
Home in Lucea
5.0 out of 5 average rating, 42 reviews

Pools/Starlink/Solar/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.

Guest favourite
A modern living area features a comfortable gray sofa with bright yellow accent pillows. A round black coffee table sits centrally, complemented by stylish seating. The space is brightened by natural light from large windows, showcasing a well-appointed dining area and kitchen in the background.
Home in Lucea
4.92 out of 5 average rating, 26 reviews

Welcome to our Ocean View Villa Solar/Starlink/Gym

Welcome to your dream getaway in Jamaica – this newly constructed 2-bedroom, 2-bathroom spacious ocean view villa is located in the quiet and peaceful gated community of Oceanpointe, just between Negril and Montego Bay. You will immerse yourself in the beauty of the Caribbean with breathtaking views of the ocean from your front door and a mountainous landscape from your backyard. This villa offers the beauty and wonder Jamaica has to offer just steps away!

Top guest favourite
Home
4.82 out of 5 average rating, 78 reviews

Oceanpointe Serenity Get Away-solar pool WiFi

Welcome to Serenity Getaway! Relax in our stylish 2-bedroom, 2-bathroom home with modern comforts. Enjoy access to swimming pools, a gym, tennis and basketball courts, and a scenic jogging trail. Unwind in the private backyard pergola featuring a bar and grill, perfect for entertaining or relaxing. Just 30 minutes from Montego Bay Airport, with solar power and a backup water tank for added peace of mind.

Popular amenities for Middlesex holiday rentals

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