
Holiday rentals in Middlesex
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Top-rated holiday rentals in Middlesex
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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.

All-Inclusive Jamaica Getaway| Pool| Chef| Gym|Car
Welcome to Wabi-Sabi, a beautifully designed accessory dwelling unit that includes the modern amenities you need for an epic holiday. The luxury villa has two units, each with its own bedroom, bathroom, and living area. We offer an experience unlike any other, with a personal chef, free rental car, rooftop terrace with ocean views. Alcoholic beverages not included. 2 Min Drive to Park Beach 5 Min Drive to Fort Charlotte 16 Min Drive to Dolphin Cove Experience Lucea With Us & Learn More Below!

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.

Serenity Get Away-beach access, solar, starlink
2 bedroom 2 bathroom tastefully decorated home filled with modern amenities. Take Advantage of the pool, tennis and basketball courts that the property has to offer. Take morning runs using the jogging trail or take a dip in the beautiful Caribbean sea located within walking distance of the house. Whatever you fancy Serenity get away is right for you, as we aim to please with comfort, style and cleanliness. 30 mins from Montego Bay airport. Shuttle and private transport at additional cost.

Turquoise Escapes, Hanover Jamaica
Turquoise Escapes is a luxurious retreat at Oceanpointe. This beautifully designed and 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 minutes walk.

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.

SunKiss Paradise/Family 4 home/ Btw Negril & Mobay
Welcome to our now SOLAR EQUIPPED, charming two-bedroom, two-bathroom home in an exclusive oceanfront gated community. Situated between the world-renowned seven-mile beaches of Negril and the bustling cruise ship destination of Montego Bay, our home offers a haven of tranquility with 24-hour security. Just minutes away from the historic town of Lucea, where part of the famous movie Cool Runnings was filmed. Let this cozy solar packed home serve as the perfect setting for your vacation.

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.

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.

Sunflower Escape Deluxe Pool/Beach/Gym/AC
Escape to relaxation at this two bedroom home located halfway between two of our islands most popular tourist destinations Montego Bay and Negril. Sunflower Escape Delux has all the basic modern amenities, privacy, comfort and style. Our community is gated with free access to a pool, gym, tennis and basketball courts and jogging trail. Chukka Adventures and Dolphin Cove are just minutes away. We also offer airport transfers and a nice car for rent at affordable rates.
Popular amenities for Middlesex holiday rentals
Other great holiday rentals in Middlesex

Gorgeous Beachfront Villa @ Paradise Point

Ocean Blue Villa in Lucea

Scenic Ocean View Home (in Gated Community)

Oceanfront 1BR SkyView Lux Condo Pool/Gym/Beach

Welcome to our Ocean View Villa Solar/Starlink/Gym

Grotto House at Brimhole

Little yellow house

Ocean Breeze | Near Beach + Palladium | Gated
Destinations to explore
- Kingston Holiday rentals
- Montego Bay Holiday rentals
- Ocho Rios Holiday rentals
- Trinidad Holiday rentals
- Negril Holiday rentals
- Portmore Holiday rentals
- Mandeville Holiday rentals
- Treasure Beach Holiday rentals
- Old Harbour Holiday rentals
- Holguín Holiday rentals
- Guardalavaca Holiday rentals
- Port Antonio Holiday rentals




