Holiday houses in Caledonia

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Top-rated holiday rentals in Caledonia

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

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Superhost
A serene view is captured from a pool area, showcasing lush tropical plants and a glimpse of the ocean in the distance during sunset. The sky is adorned with soft hues, reflecting on the water's surface, creating a calming atmosphere.
Home in Reading
4.81 out of 5 average rating, 47 reviews

Whiterock Pink Bougainvillea Villa

Spend memorable moments at our quiet oasis with Royal Palm trees, gardens, Jerk grills for outdoor cooking or just sit in the garden and enjoy the wind chime as it's soothing melody chimes as the winds blow. View of the Courtyard and open skies. Take a stroll down hill then up our spiral stairs to our elevated pool. Enjoy stunning ocean, mountain and city views from the pool deck. Or watch the sunset from the Floating Deck. Whatever your choice, you will enjoy the natural beauty. Whiterock.

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, 205 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
Treehouse in Negril
4.81 out of 5 average rating, 32 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!

Guest favourite
A bright living area is presented with large windows that allow natural light to filter in. A neutral-colored sofa is paired with textured cushions, and a textured wooden coffee table adds warmth to the space. A ceiling fan contributes to air circulation, enhancing comfort.
Cabin in Anchovy
4.99 out of 5 average rating, 84 reviews

Turn Plantain Cabin

Turn Plantain Cabin offers 180 degrees view of lush mountainsides. The cool breeze, whistling wind, fresh crisp air provide the perfect condition to rest, relax and recharge. Off the main, a short ride up the bumpy hill leads to the perfect escape. This oasis is ideally located off the beaten track giving a break from the hustle and bustle of everyday living yet it is in close proximity to some of Jamaica’s finest attractions. Be sure to relax by the pool and make memories by the firepit.

Guest favourite
A serene outdoor space is depicted, featuring a private pool surrounded by lush greenery and coastal views. The ocean's vibrant blue stretches into the horizon. A decorative arch and terracotta pots enhance the tropical ambiance, creating an inviting area for relaxation.
Villa in Hopewell
4.86 out of 5 average rating, 7 reviews

Sea Glass: The Seaside Sanctuary

Named for treasures shaped by the sea, this suite features an open-concept kitchen, dining, and living area. It has 3 bedrooms: the Rocksteady Bedroom, celebrating Jamaica’s musical heritage; the Bush Bedroom, inspired by countryside calm; and the Oasis Bedroom, offering a stunning seaside vista. Find your spot to relax: under an almond tree, by the shoreline or poolside. Offload the cooking duties w/ our complimentary private chef service; just bring groceries or let us source them for you.

Guest favourite
A blue metal ladder leads into clear turquoise water, which reflects sunlight. The surrounding rocky shore features lush greenery along the edge, and a distant view of a residential area is visible on the cliffs above.
Cottage in Westmoreland Parish
4.93 out of 5 average rating, 332 reviews

Little Bird Cottage @ High Cove

We are operating as normal after Hurricane Melissa! The West End is in top shape! Little Bird 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 15. 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.

Guest favourite
Loft in Negril
4.81 out of 5 average rating, 16 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.

Guest favourite
A modern villa exterior is showcased, featuring sleek architecture and a stone accent wall. Lounge chairs are positioned beside a private swimming pool. An umbrella provides shade, and a stairway leads to the upper level. Lush greenery complements the outdoor space.
Home in Sandy Bay
4.83 out of 5 average rating, 60 reviews

SBS Seaview 5BD Pool Villa - 5 min from Excursions

Serenity By the Sea (SBS) is a 5 bedroom Villa overlooking the Caribbean Sea. This modern villa is perfect to host a large group of friends or family and includes breakfast labor fees for up to two days. In a prime location, we're nestled between Montego Bay and Negril (less than an hour)! Chukka Sandy Bay Outpost is a short minute drive from excursions, 25 Minutes from Montego Bay's hip strip, nightlife and airport. Only a day trip away from Ocho Rios, the South Coast and Kingston.

Superhost
A modern living room features a sectional sofa, a coffee table, and decor items. Large windows allow natural light to fill the space, offering views of the ocean beyond. Sliding glass doors lead to an outdoor dining area, enhancing the open-concept living experience.
Condo in Montego Bay
4.95 out of 5 average rating, 44 reviews

Modern & Serene Oceanfront MoBay Retreat

Experience refined coastal living at Soleil, located in the prestigious Sept Mers enclave of Freeport, Montego Bay. Just 20 minutes from the airport, this beautifully designed condo offers panoramic ocean views, a modern kitchen, and luxurious finishes throughout. Guests can enjoy a pool, gym, tennis court, playground, and outdoor dining area. The property also offers a private beach within walking distance, a tranquil spa room, and 24-hour gated security for your peace of mind.

Guest favourite
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, 110 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!

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, 130 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.

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
4.82 out of 5 average rating, 17 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