Vacation rentals in Middlesex

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Top-rated vacation rentals in Middlesex

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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

4.78 out of 5 average rating, 59 reviews

Serenity Get Away-solar powered, pool

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.

Superhost

A light-filled living area features a spacious sectional couch adorned with colorful throw pillows. A dining table with modern chairs sits nearby, and large windows are framed with soft curtains, allowing natural light to brighten the space.

Home in Lucea

4.91 out of 5 average rating, 88 reviews

Summer Dreams at Oceanpointe - Private Villa

Unwind in this gorgeous and modern decorated coastal home in a quiet gated community. Fully equipped to be your home away from home. The home boasts 2 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

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 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

4.95 out of 5 average rating, 39 reviews

Scenic Cozy Casa- between Mobay & Negril

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 on Jamaica’s stunning western coast.

Guest favorite

Home in Hanover Parish

4.84 out of 5 average rating, 134 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 hot water, Granite kitchen and bathroom countertop, washer and dryer, complete closet with sliding doors, rear and side fencing, large patio, paving stone driveway, open floor plan , these are some of the many features.

Guest favorite

Home in Lucea

5 out of 5 average rating, 7 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!

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 charming two-story pink house is surrounded by lush green grass and tropical plants. Tall palm trees provide shade, and a walkway leads to the front entrance. A water tank is visible on the roof, enhancing the functional aspect of the property.

Guesthouse in Montego Bay

4.97 out of 5 average rating, 104 reviews

Always Home

This cozy and private hideaway is located in Bogue Village Montego Bay minutes away from Sangster International Airport, restaurants and shopping center. Although off the beaten path you'll want for nothing. Fantastic for first time or returning vacationers. The outdoor area is equipped with seasonal fruits, BBQ area, swing,hammock, green area, outdoor dining and privacy. The chirping birds, awesome sun rise and sunset add tranquility and peace of mind to each day.

Top guest favorite

An outdoor patio is shaded by a gazebo, featuring comfortable seating arrangements with red cushions. A low table is centrally positioned on the paved floor, surrounded by neatly trimmed grass and tropical plants, with a clear blue sky visible above.

Home in Lucea

5 out of 5 average rating, 25 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.