Holiday houses in Jamaica

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Top-rated holiday rentals in Jamaica

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Guest favourite

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, 203 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 favourite

Home in Ocho Rios

4.91 out of 5 average rating, 58 reviews

4BR Oceanfront Villa Pool Chef Option Nr Ocho Rios

Wake up to sweeping Caribbean sea views at this private 4-bedroom oceanfront villa, just 15 mins from Ocho Rios. * Perfect for families and groups, it features en-suite bedrooms, a private pool, and inviting outdoor spaces for dining and relaxing. * Enjoy the ideal mix of seclusion and convenience — peaceful and tucked away, yet close to beaches, restaurants, and attractions. * We can arrange a private chef, housekeeping, airport transfers, and grocery pre-stocking so you can arrive and unwind.

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Guest favourite

A tranquil swimming pool offers crystal-clear water, framed by lush tropical plants. The serene ocean view stretches beyond, showcasing gentle waves and distant hills under a partly cloudy sky. Lounge chairs are positioned nearby, inviting relaxation by the water's edge.

Home in Montego Bay

4.92 out of 5 average rating, 65 reviews

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

Welcome to Smallah Villa, our spacious and elegantly designed 4-bedroom, 4.5-bathroom oceanfront townhouse in the Freeport Area of Montego Bay! This stunning property is the perfect getaway for families or groups of friends looking for a relaxing retreat in Caribbean Paradise. It comfortably accommodates up to 10 guests. With private infinity pool and a pier for private boat pickup. Premium Services ($ - Additional Fee) • Grocery Shopping & Delivery Service ($) • Cook & Clean ($) • Driver ($)

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Guest favourite

Condo in Montego Bay

4.89 out of 5 average rating, 28 reviews

Oceanfront Panoramic Views 3br Beach Pool Gym

Your Caribbean dream escape awaits in our spacious oceanfront 3br/3.5ba condo with private corner balcony and sweeping ocean views. Lounge by the pool, stay fit in the gym/pickleball court or unwind at the sandy beach. Highlights- Large Waterfront Pool & Pool Deck * Private Beach Access * Gym * Tennis/Pickleball * Kids Play Area * Fast WiFi* Gated Waterfront Community * Chef on request * Spa Services * Concierge Services * Driver Upon Request* Add our listing to your favorites by clicking❤️

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Guest favourite

A bright blue door stands open, offering a view of the clear turquoise water and distant boat on the horizon. Lush greenery frames the entrance, enhancing the connection between the interior space and the inviting beach just outside.

Cottage in Runaway Bay

4.94 out of 5 average rating, 134 reviews

Bahia - Charming seaside cabin, loft/wood shutters

Bahia is a 1 bedroom cottage located directly on a beautiful beach which is perfect for swimming.* Ideal for a couple, or a family with children who can be accommodated in a loft. Beachside patio with hammocks and outdoor furniture. Air-conditioned and fans. Cook included. Nightly security guard. 50 minutes from MBJ Airport. Popular attractions nearby. A truly memorable, rejuvenating beach holiday. $300 per night for 2 persons, for additional persons see below. *Beach/water subject to weather

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Guest favourite

Villa in Treasure Beach

4.92 out of 5 average rating, 51 reviews

Private | Beach | Pool | Luxury | Culinary Escape

Villa Blanca, our airy white-on-white modern beach villa, is part of the ONLY Villas Collection — a curated blend of boutique-hotel service and private barefoot luxury above a secluded sandy beach. Designed primarily as an adults-oriented escape focused on peaceful, elevated, culinary-driven experiences. Enjoy complete privacy in your villa, plunge pool, and outdoor living spaces with private chef and villa hostess services. Guests 18+ preferred. Younger children only with prior approval.

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Guest favourite

Loft in Negril

5 out of 5 average rating, 15 reviews

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.

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Top Guest favourite

An infinity pool cascades gently into a lower plunge pool, surrounded by lush greenery. The sparkling water reflects the sunlight, while the shimmering sea is visible in the background, enhancing the serene outdoor setting.

Villa in Treasure Beach

5 out of 5 average rating, 102 reviews

Summer Special Treasure Beach Sanguine Villa

Sanguine's spacious fully staffed beachfront Villa with an infinity pool is located in Treasure Beach on Jamaica's South Coast. Treasure Beach is where one comes to get away from the hustle and bustle of everyday life and happily ensconce themselves in our laid-back community. Latoya will be here to ensure that you have a holiday of memorable meals, you sit back and relax while we do the grocery shopping and look after you. Message me re airport and transport options

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Guest favourite

A serene outdoor seating area is presented with two dark wood chairs positioned on a wooden deck. A small table supports a guidebook and a potted plant, offering a view of lush green mountains and a distant blue expanse of water under a partly cloudy sky.

Cabin in Port Antonio

4.93 out of 5 average rating, 30 reviews

Modern Nature's Escape at the Falls

Welcome to your peaceful getaway at Cabin at the falls where nature meets comfort, as the sound of cascading water sets the perfect backdrop for your stay. This cozy, cabin is perched just a hike away from the falls, offering a rare blend of seclusion, comfort, and natural beauty. Whether you are hiking to the base of the falls,or soaking in the sights and sounds of nature, this cabin is your perfect escape into the wilderness without giving up the comforts of home.

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Top Guest favourite

A spacious sleeping area features a large bed draped in a light-colored coverlet. Floor-to-ceiling windows showcase lush greenery and the distant landscape, complemented by wooden furniture including a table and chairs for enjoying the view.

Guest suite in Port Antonio

4.97 out of 5 average rating, 230 reviews

Starfish Cottage

IMPORTANT NOTE: This property does not accept children under 13. Experience tranquility and beauty at our cottage, perfectly positioned for stunning views of the Blue Mountain peak, the Port Antonio coastline, and a nearby waterfall. Delight in the frequent visits from hummingbirds to our feeders, adding a touch of nature’s charm to your stay. Conveniently located, you'll find yourself at the heart of all the attractions that the area has to offer.

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Guest favourite

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 in St. James Parish

4.99 out of 5 average rating, 129 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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Superhost

An infinity-edge pool is framed by modern lounge chairs and plush seating. Lush greenery and an expansive lawn create a serene environment, while the Caribbean Sea is visible in the distance under a clear blue sky.

Villa in Montego Bay

4.81 out of 5 average rating, 148 reviews

Hospitality Expert EL1: Private Pool, Beach, Chef

Eden Luxe 1 is set on a beautiful hillside offering panoramic views of the sparkling Caribbean Sea. This 2 BR ultra luxurious villa is part of the HOSPITALITYEXPERT Eden Estate, set in the heart of Spring Farm, an upscale Montego Bay community, right above the Half Moon Golf Club. Luxe 1 sleeps up to 6 guests, a private chef is available for hire and we offer pre-stocking services. Includes complimentary access to Tropical Bliss Beach Club.

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