Vacation rentals in Caledonia

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Top-rated vacation 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 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, 206 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 favorite
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
4.93 out of 5 average rating, 67 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 ($)

Guest favorite
Apartment in Montego Bay
5 out of 5 average rating, 6 reviews

Ocean Endless Views 2Br Lux Condo | Beach Pool Gym

Welcome to Montego Bay’s most exclusive waterfront address. This breathtaking 2 bedroom oceanfront condo features sweeping panoramic ocean views, majestic mountains, yachts, the Bogue Islands & much more. From your condo enjoy the rare spectacular sight of massive cruise ships docking at the pier, an extraordinary event that can only be experienced at Soleil. This condo offers premium amenities and a sophisticated atmosphere designed for comfort, relaxation, and unforgettable seaside escapes.

Guest favorite
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.

Superhost
Two wooden lounge chairs with blue cushions are positioned on a stone terrace, overlooking calm blue waters. A thatched gazebo is visible to the right, and lush greenery frames the scene, enhancing the serene coastal setting.
Cottage in Westmoreland Parish
4.86 out of 5 average rating, 138 reviews

Sea Bird Cottage @ High Cove

We are operating as normal after Hurricane Melissa! The West End is in top shape! Sea 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 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 or romantic getaway.

Superhost
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.

Superhost
An open-plan living area features modern furnishings and a large skylight, allowing natural light to fill the space. A sleek kitchen island provides a convenient dining area, while sliding glass doors open to reveal a view of the sea and lush greenery beyond.
Apartment in Westmoreland Parish
4.69 out of 5 average rating, 16 reviews

Whitehouse 2-Bed Apartment Sea View Balcony

Welcome to the luxurious 2 bedroom apartment nestled in a peaceful community in Whitehouse. Escape the big-city crowds and immerse yourself in the lavish ambiance of the sun-soaked pool backyard while being close to numerous local attractions and sunny beaches. Here's a glimpse of our fantastic offer: ✔ 2 Spacious Bedrooms With Queen Beds ✔ Open-Plan Living ✔ Fully Equipped Kitchen ✔ Sea-view balcony ✔ Smart TV ✔ Wi-Fi ✔ Maid Service (additional cost) ✔ Free Parking Learn more below!

Guest favorite
Home in Black River
4.96 out of 5 average rating, 82 reviews

Entire home + Complimentary CAR Included

🚗 Complimentary Car Included A complimentary 2022 Toyota Corolla Fielder is included with your stay to make exploring St. Elizabeth easy and stress-free. No rental arrangements, no daily fees, no taxis, just enjoy the freedom to explore on your own schedule. Car is provided exclusively with your booking for local use. Fuel is the guest’s responsibility. A valid driver’s license is required. Additional terms shared inquiry or booking. *Offer activated for 2 or more guests booked.

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, 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!

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 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 vacation rentals

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