
Vacation rentals in Middlesex
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Top-rated vacation rentals in Middlesex
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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.

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.

3BR in Lucea btwn Montego Bay & Negril -SeaJam Vac
Welcome to SeaJam Vacation Home, your luxurious retreat nestled within the secure confines of Oceanpointe, Lucea, Jamaica. This beautifully furnished 3-bedroom, 2-bathroom house offers a serene escape for up to 6 guests, providing ample space and comfort for families or groups seeking a tropical getaway. Conveniently located adjacent to the Grand Palladium Hotel, 30 min from MBJ Airport. Gated Community with 24 hrs security. Beach access. SeaJam offers easy access to exciting attractions.

I love Lucea Nestled between Montego Bay & Negril
A secured, gated community nestled between the cities of Montego Bay and Negril. This little piece of paradise is all you need to relax and unwind. If you’d prefer an adrenaline boost, we’ve got you! The community is equipped with a gym, clubhouse, multipurpose court, tennis court, football field, running track and a private beach. We provide other services such as airport transfer, city tours, grocery deliveries, spa, housekeeping, manicure and pedicure services at an additional cost.

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.

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 50mins 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!

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.

Pools/Solar/Starlink/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!

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.
Popular amenities for Middlesex vacation rentals
Other great vacation rentals in Middlesex

Sea Breeze Villa

Summer Dreams at Oceanpointe - Private Villa

Modern 2BR | 3 Beds | Private Gazebo | Starlink

"Smallah" 4-br seaside villa own pool, resort area

AUG & SEP Special, Designer Villa on top of Negril

Best Vacation Ever/Private Pool/Local Beach

CasaLamar Beachside Retreat

Private & Cozy two bedroom Oceanpointe House
Destinations to explore
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- Montego Bay Vacation rentals
- Negril Vacation rentals
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