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.

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.

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.

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!

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!

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.

Snorkeler's Cove - Negril, Jamaica

Welcome to your Jamaican paradise, a hidden gem perched atop a picturesque cliff overlooking the breathtaking Caribbean Sea. Nestled within the exclusive gated community, Little Bay Country Club, this newly renovated home offers a slice of island heaven. Your own private furnished cabana beckons, as well as the leisurely stroll to the world-famous 7-mile beach. With every sunrise at Snorkeler's Cove, you'll be greeted by a barrage of colors painting the horizon.

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!

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.

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.