Vacation rentals in Middlesex

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Top-rated vacation rentals in Middlesex

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

A spacious living room features a large, cushioned sectional sofa adorned with light throw blankets. A round wooden coffee table is positioned in front, surrounded by a light geometric area rug. Wall-mounted shelves display decorative items, and a flat-screen TV is visible on the wall, framed by natural elements.

Home in Lucea

4.9 out of 5 average rating, 78 reviews

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.

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Top guest favorite

A serene pool area is visible, featuring lounge chairs arranged beside a clear blue pool. Palm trees and lush greenery frame the space, while a covered gazebo is provided in the background, enhancing the outdoor relaxation experience.

Townhouse in Montego Bay

4.98 out of 5 average rating, 210 reviews

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.

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Guest favorite

A dining area features a dark wooden table surrounded by four matching chairs and a bench. A simple centerpiece of faux flowers adds elegance. Soft, neutral curtains frame a window, and modern wall art complements the space. The open doorway leads to a kitchen area.

Home in Lucea

5.0 out of 5 average rating, 22 reviews

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!

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Guest favorite

Treehouse in Negril

4.84 out of 5 average rating, 38 reviews

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!

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Guest favorite

Cottage

4.85 out of 5 average rating, 109 reviews

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.

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Guest favorite

An aerial view captures the serene beachfront villa surrounded by lush greenery and clear turquoise waters. Light blue buildings are seen dotting the landscape, while rocky outcrops frame the peaceful shoreline, contributing to the tranquil atmosphere of the property.

Townhouse in Negril

4.93 out of 5 average rating, 73 reviews

Gorgeous Beachfront Villa @ Paradise Point

This beachfront villa promises to deliver an unforgettable escape into an oasis of beauty and tranquil. Wake up to panoramic views of the Caribbean Sea, captured perfectly from our balconies while inhaling the sweet aroma of Jamrock. This charming island retreat is located within a gated property moments away from a private beach and 4 minutes walk to access the famous 7 Mile Beach. With attractions and shopping within your reach, your perfect Jamaican getaway awaits you at Paradise Point.

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Guest favorite

Condo in Montego Bay

5.0 out of 5 average rating, 5 reviews

Oceanfront Lux 2Bdr Condo Private Patio Beach Pool

Experience a luxurious oceanfront retreat in our stunning new two-bedroom condominium. Designed with sophistication in mind, this space features uninterrupted ocean views, soaring high ceilings, and a serene coastal ambiance that instantly invites relaxation. Step onto your private, spacious patio with an extended waterfront terrace, where the ocean is literally at your feet. This idyllic setting is perfect for soaking up the sun, spa treatments, or just taking in the endless ocean views.

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Guest favorite

A spacious living area features a comfortable beige sofa adorned with decorative pillows. A vibrant area rug with intricate patterns covers the tiled floor. Green curtains frame the window, while a stylish coffee table sits in the center, enhancing the inviting atmosphere.

Home in Lucea

4.94 out of 5 average rating, 120 reviews

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.

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Top guest favorite

Condo in Lucea

5.0 out of 5 average rating, 26 reviews

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.

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Guest favorite

A bright bedroom is featured, showcasing a spacious bed adorned with colorful pillows and a soft green throw. Large glass doors open to a balcony, offering a view of the tranquil water and lush greenery beyond. Natural light enhances the airy atmosphere.

Townhouse in Negril

4.9 out of 5 average rating, 111 reviews

Private Oasis in Negril: Beachfront Luxury!

Escape to this gorgeous two-bedroom townhouse, your ideal Negril getaway! This unit boasts every amenity you could desire. Nestled within the tranquil, gated Little Bay Country Club, you'll enjoy 24-hour security. Our waterfront gem overlooks a mesmerizing fish sanctuary, offering breathtaking views! The expansive porch is simply divine for all-day relaxation – from your morning coffee to lazy afternoons, or vibrant evenings with cocktails. An unforgettable stay awaits!

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Guest favorite

A modern living area features a comfortable gray sofa with bright yellow accent pillows. A round black coffee table sits centrally, complemented by stylish seating. The space is brightened by natural light from large windows, showcasing a well-appointed dining area and kitchen in the background.

Home in Lucea

4.93 out of 5 average rating, 27 reviews

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!

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Guest favorite

An infinity edge swimming pool glistens under a clear blue sky, offering expansive views of the ocean and distant shoreline. Sun loungers are positioned along the poolside, inviting relaxation and enjoyment of the breathtaking scenery.

Home

4.98 out of 5 average rating, 134 reviews

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.

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