Vacation rentals in Middlesex

Rohi's Relaxing Haven

Kick back and relax in this calm and stylish space where your comfort is my priority. Enjoy the beautiful seaview from the front bedroom and verandah, the cool sea breeze and beautiful sunsets. The community is gated with 24 hours security, swimming pools, fully equipped gym, clubhouse and tennis court. About half hour away is the very vibrant city of Montego Bay and the capital of casual, Negril, where you will find seven miles of prestine beach, restaurants and a host of other attractions.

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.

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.

Ocean Escape| Beach, Pools, Gym, Courts, Clubhouse

Relax at our stunning, luxury two-bedroom, two-bathroom home on Jamaica’s breathtaking north coast. Just 40-45 minutes from Sangster International Airport and 30 minutes from Montego Bay and Negril, it’s perfect for families or groups. The gated community features pools, gym, sports courts, and nearby beaches. Enjoy local restaurants, beach clubs, and vibrant attractions. Prefer staying in? The home is fully equipped with entertainment for your comfort. Your ideal island getaway awaits!

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.

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.

Turquoise Escapes, Hanover Jamaica

Turquoise Escapes is a luxurious retreat at Oceanpointe. This beautifully designed 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-minute walk.

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.

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!

Starlink/Pools/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.

Luxury Oceanview 4BR Villa w/ Balcony, Pool & BBQ

Welcome to BayWatch Villa – a 4BR luxury retreat in Montego Bay. Marvel at breathtaking views of the harbor and Caribbean Sea both day and night. Share unforgettable moments with family and friends. Enjoy spacious living spaces, a modern kitchen, and laundry convenience on premises. Stay connected with Wi-Fi throughout, even by the pool. With solar backup, you’ll always have power for the essentials. Note: AC is not available on backup power.

Paradise Oasis – Solar Powered/Starlink WiFi

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.