Holiday houses in Caledonia

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Top-rated holiday rentals in Caledonia

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Superhost
Two lounge chairs are positioned by a private pool, offering views of the coastline and lagoon. The chairs feature bright, colorful fabrics, inviting relaxation under clear blue skies. Lush greenery and vibrant flowers adorn the surrounding area, enhancing the tranquil setting.
Condo in Montego Bay
4.82 out of 5 average rating, 409 reviews

Modern apartment with a pool & amazing views!

Modern, 1BR, ground level apartment with all the modern amenities you will need for a perfect stay. Start your day having coffee on the patio gazing at the awe-inspiring coastline and turquoise lagoon. The property is part of a secure, gated development with a private community pool for guests to laze away while perfecting their tan, or hide in the shade sipping on a cold drink. You're close enough to the airport, shopping malls and nightlife - but nestled on the outskirts for quiet relaxation.

Top 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, 195 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.

Guest favourite
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
4.86 out of 5 average rating, 140 reviews

Hospitality Expert EL1: Private Pool, Beach, Chef

This property has electricity, water and internet. 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.

Guest favourite
Cottage in Westmoreland Parish
4.85 out of 5 average rating, 108 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.

Superhost
A tranquil bedroom is highlighted by a spacious bed draped with sheer canopies. Large sliding glass doors open to an ocean view, while lush greenery is visible outside. Soft textiles and textured decor are present, contributing to a serene environment.
Apartment in White House
4.81 out of 5 average rating, 31 reviews

Ivy's Cove Beach Side Condo

“At Last,” one of four villas that comprise Ivy’s Cove. This idyllic, 2 bedroom/2 bathroom beachfront villa with PRIVATE BEACH, is located in the heart of Whitehouse, Westmoreland, Jamaica and is walking distance from the small-town square where you can find a local market, rum bars, grocery stores, and restaurants. The villa features ocean views from the living room, kitchen, and master bedroom . The property also includes a large Varanda that overlooks both the ocean and a mini lagoon.

Top Guest favourite
Loft in Negril
5 out of 5 average rating, 11 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.

Superhost
Two white lounge chairs are positioned on the sandy beach, facing a charming villa in the background. A picnic table is visible nearby amongst the lush greenery. The villa features a covered porch with outdoor seating, inviting relaxation and outdoor enjoyment.
Villa in JM
4.8 out of 5 average rating, 110 reviews

Bel Cove Villa

Bel Cove is a modern Caribbean villa with its own private beach, a lush 3/4 acre property, and pool built into an old Lime mill. Hotspots such as Negril and Montego Bay are an hour a way. You’ll love Bel Cove because of the quaint charm, the unique people, picturesque location, and the tranquility that a hidden beach front villa affords to the weary. Bel Cove is great for families and groups looking to get away. (Please note that hurricane Melissa has damaged the over-water gazebo)

Top Guest favourite
The vibrant exterior of a villa features a decorative stone façade and a landscaped front garden. A charming porch is framed by ornate railings, and a stone pathway leads to the entrance. Lush greenery and a fountain add to the inviting appearance of the home.
Home in Savanna la Mar
4.94 out of 5 average rating, 64 reviews

Roans Villa Airbnb Peaceful home with A/C

Welcome to Roan's villa. Situated in a nice quiet neighborhood where you can enjoy peace and quiet. You can enjoy having a nice cool drink on the verandah or outdoor patio overlooking the Mountainview. You can enjoy watching your favourite movies and TV shows in livingroom. Hot water is available Location Waterworks Carmel Westmoreland 15 minutes to Savannah la mar 30-40 minutes to Negril 15 minutes to Bluefield Beach 5 minutes to police station 40 -45 minutes to Montego Bay

Top Guest favourite
A spacious living area features an oversize sectional sofa adorned with colorful cushions. Complementary orange armchairs provide additional seating. A large ottoman rests in front of the seating arrangement, with a modest coffee table placed nearby. Soft lighting from a decorative pendant illuminates the room.
Home in Montego Bay
4.98 out of 5 average rating, 147 reviews

Villa Ginger: Food paradise/Beach/Pool/keycode

Private Retreat for close friends and family in the safety of a pristine garden-like gated community. New and dazzlingly beautiful, the oversize sectional will be your favorite place to lounge. Linger on the patio for breakfast, go across the street for snorkeling, tour the nearby beaches and waterfalls, or make your birthday celebration extra special with a spectacular private dinner. Savor the candlelight reflecting from wine glasses as you toast your amazing good luck.

Top 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, 126 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.

Guest favourite
The charming blue exterior of the cottage is surrounded by well-maintained foliage and flowers. A welcoming pathway leads to the front entrance, accentuated by a covered porch with decorative railing and large windows, providing ample natural light.
Home in Savanna la Mar
5 out of 5 average rating, 24 reviews

Entire property in Westmoreland - ‘Something Blue’

A charming Savanna-la-Mar villa perfect for relaxing Caribbean escapes and quiet evenings under the stars. The home accommodates up to 6 overnight guests and offers a comfortable indoor space with an inviting outdoor patio to enjoy the tropical atmosphere. Small private events of up to 20 guests may be considered with prior approval. Event fees and a refundable deposit apply.

Superhost
The exterior of the villa features a warm, terracotta-colored facade, complemented by decorative ironwork around the arches. A single large window allows natural light to illuminate the interior. Lush greenery can be seen in the background, enhancing the inviting atmosphere.
Home in Amity
4.86 out of 5 average rating, 14 reviews

Zed's Villa Entire home

Welcome to Zed's Villa! Our stylish 2 bedrooms, 1 bathroom home is the epitome of modern comfort and convenience. Perfect for both business and leisure travelers. Location Amity, Westmoreland 15 minutes to Savannah La Mar 20 minutes to Bluefield Beach 25 minutes to Mayfield Falls 25 minutes to Benta Falls 30 minutes to Roaring River

Popular amenities for Caledonia holiday rentals

  1. Airbnb
  2. Jamaica
  3. Westmoreland
  4. Caledonia