Holiday 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.

Whiterock Pink Bougainvillea Villa

Spend memorable moments at our quiet oasis with Royal Palm trees, gardens, Jerk grills for outdoor cooking or just sit in the garden and enjoy the wind chime as it's soothing melody chimes as the winds blow. View of the Courtyard and open skies. Take a stroll down hill then up our spiral stairs to our elevated pool. Enjoy stunning ocean, mountain and city views from the pool deck. Or watch the sunset from the Floating Deck. Whatever your choice, you will enjoy the natural beauty. Whiterock.

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.

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!

Neptune Cottage @ High Cove

We are operating as normal after Hurricane Melissa! The West End is in top shape! Neptune 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 14. It's 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.

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.

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.

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!

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!

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.

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.