Vacation rentals in Middlesex

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.

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!

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.

Lovely Tree House w Ocean Views

Escape to our amazing Tree House in Negril! Nestled in nature with stunning ocean views, this timber and thatch gem features an open-plan layout, connecting kitchen, living, and dining areas. The main bedroom boasts a double bed and en-suite bathroom, while the loft offers two twin beds. Start your day on the balcony, enjoy the outdoor shower, and relax in hammocks. Immerse yourself in nature, explore nearby restaurants n bars and enjoy cliff jumping in the Caribbean. An unforgettable getaway!

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.

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!

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!

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!

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.

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.