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Vacation rentals in Portland Cottage

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Portland Cottage

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

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Superhost
An outdoor seating area features dark wicker furniture with bright turquoise cushions, providing a comfortable space for relaxation. The view includes a landscaped yard with palm trees and a swimming pool, outlined by a wooden pergola and surrounded by vibrant greenery.
Home in Portmore
4.86 out of 5 average rating, 229 reviews

🏝🏝HIDDEN GEMS 💎 💎 🏝🏝 Vacation Home 🏡🏞

This carefully designed house is ideal for persons looking for a cool refreshing modern and comfortable vacation stay . It is perfectly located in quiet and secure gated community Phoenix park village ,in the well developed sunshine city of portmore st catharine . It is most suitable for you because of its convenient access to all it has to offer around it ,its famous helshure beach, movie theater ,shopping malls ,clubs ,restaurants etc . it is the place for families ,couples, or just friends

Superhost
The exterior of the apartment is showcased, featuring a two-story white structure with blue accents. A secure fence and electric gate provide safety. Surrounding greenery enhances the peaceful environment, while a covered porch area offers a shaded space to relax.
Home in Sandy Bay
4.79 out of 5 average rating, 53 reviews

PAARJ Peaceful Escape with Pool, Garden&Parking #1

This spacious retreat is located in a quiet neighborhood, minutes from the Millennium Mall, May Pen Town Centre and close to the highway. ✨Features Swimming Pool Two electric/remote-control gates for easy, secure access Solar water heating system Grilled windows and doors for added safety 8-lens, 24-hour security camera system (external) Off-street parking for up to 4 cars. Well kept garden This retreat is safe, spacious, peaceful and relaxing. Ideal if you're visiting for work or leisure.

Guest favorite
Home in Old Harbour
4.94 out of 5 average rating, 87 reviews

Nicely Furnished-1BR/24hr Sec./AC/Fast Wi-Fi/ NHV4

Come relax a while at this centrally-located place in New Harbour Village. Located on a quiet street this home is clean, comfortable and cozy with a stylish design. Enjoy waking up in a comfy queen-size bed, having a warm rain shower bath, eating your choice of foods and selecting your choices for entertainment. You will be two minutes away from the Old Harbour Town Centre where you can enjoy local foods, shopping and round town travels. What are you waiting for? Come! You will love it here.

Superhost
A spacious outdoor area features a crystal-blue pool with built-in seating and a hot tub. Surrounding the pool, several lounge chairs are positioned under an umbrella, while a well-maintained garden with vibrant flowers offers a natural border.
Villa in Lionel Town
4.86 out of 5 average rating, 92 reviews

Country Villa

Villa de Campaña is a breath taking 3 bedroom,3 bathroom with a exquisite private crystal ocean blue pool and gym. If you adore nature and privacy then this is the place to be . Salt river mineral bath is just 15 mins away and also the wonderful white sand beach seafood restaurant Villa de Campaña is ideally located along the south coast. The property is fitted with a 35ft pool, gym, fish pond and indoor design for comfort. No visitors - only the 6 guests on booking permitted in the villa

Top guest favorite
Home in Old Harbour
4.97 out of 5 average rating, 30 reviews

Camerons Cove-378 Home in Whim Estates Old Harbour

A cozy and well-appointed space designed for comfort and relaxation in a gated and secured community. Located in a convenient and desirable area, you’ll love the warm and welcoming atmosphere, perfect for families, couples, or solo travelers. What makes it so special is the thoughtful amenities, stylish decor, and personalized touches that make you feel right at home. Whether you’re looking for a peaceful retreat or easy access to local attractions, we offer you an unforgettable stay.

Guest favorite
A living area is presented with neutral-colored tiled flooring and bright walls. A dark grey sofa occupies one side, while a small round coffee table complements the space. A television is mounted on a wall unit, and a decorative entrance door is visible in the background.
Home in Spanish Town
4.82 out of 5 average rating, 108 reviews

Irie Getaway - House in gated community

One bedroom newly built and furnished home in very peaceful and quiet residential, gated community, with 24 hour security, in St. Catherine. House is ideally located just a few minutes from the Spanish Town Toll road, which makes it easy to access without having to encounter heavy traffic. Kingston is 25 minutes away and Portmore is 10 minutes away. House is nicely furnished and has ac in the bedroom (only) and other amenities to make your stay feel like a home away from home!

Guest favorite
Home in Hellshire
5 out of 5 average rating, 17 reviews

Luxurious 6 bed villa w/own pool

Your whole group will be comfortable in this spacious, tastefully furnished and unique villa. Chill at the private plunge pool or stroll to the pristine waters of hellshire for sand, sun and sea. Gather as a family or a as a group to make memories in this hidden paradise. Equipped with fast free WiFi, smart TVs, large kitchens, many seating areas, you will have everything you need for a weekend, family reunion, and small events. Don't hesitate to book early for the best prices.

Guest favorite
A modern living area is highlighted by a large sectional sofa adorned with decorative pillows. Soft ambient lighting runs along the ceiling. A wooden coffee table sits in front of the sofa, and a television is mounted on the wall opposite the seating area.
Apartment in Kingston
4.94 out of 5 average rating, 148 reviews

Fresh Oasis City View

Welcome to your perfect getaway that is centrally-located in Kingston! This modern and stylish apartment offers breathtaking panoramic views of Kingston city, its vibrant surroundings, and the shimmering Caribbean Sea. Whether you’re visiting for business or leisure, this exclusive Airbnb rental promises comfort, convenience, and an unforgettable experience. The building has 24/7 security, gated entry, and controlled access, ensuring your safety and peace of mind.

Guest favorite
Home in Old Harbour
4.94 out of 5 average rating, 18 reviews

The Oasis at Whim

Welcome to your relaxing retreat in the quiet and secure community of Whim Estates. This cozy home is ideal for families, couples, or solo travelers looking for comfort and convenience. You’ll also enjoy easy access to the town centre, where you’ll find a variety of restaurants, shops, and local amenities—all just a short drive away. The nearby highway ensures quick connections to surrounding areas, making it easy to explore the island or commute if needed.

Top guest favorite
Home in Clarendon
5 out of 5 average rating, 38 reviews

Step into TRENZ …Airbnb

Step into Trenz Airbnb. A luxurious vacation home conveniently and centrally located in the gated community of Paisley Place. Trenz offers 3 modern bedrooms, each outfitted with its own en-suite bathroom, air conditioning, and hot water to sleep 6 persons comfortably. You’ll be 5 minutes away from : *May Pen Town Centre * The major highways * Millennium Mall. * Knutsford Express You’ll be 15-20 minutes away from: * Fyah Side *Murrays Fish & Jerk

Superhost
Home in Old Harbour
4.7 out of 5 average rating, 10 reviews

Casamara

Casamara is located in the new harbor village 3 gated community, it's a safe and comfortable environment. the place is equipped with all the amenities that you would need for a relaxing stay. there are two 55 inches tv in both bedrooms, there's 65 inches tv in the living Room with complimentary Netflix, washer/dryer, hot water, air conditioner, security camera around the premises.

Guest favorite
A modern living space is presented, featuring a comfortable sectional sofa and an ottoman. An entertainment unit displays a large screen showcasing the Netflix logo. The kitchen area is visible, with bar stools arranged at a sleek counter, and natural light filters through the window.
Home in Old Harbour
4.96 out of 5 average rating, 50 reviews

Great Price, Modern, Video Games, All Inclusive!

Enjoy a stylish 2-bedroom retreat just minutes from town, with modern décor, a full kitchen, and a cozy living space. Unwind with PS4 entertainment or explore the nearby shops, dining, and attractions all within easy reach. With thoughtful touches, tasteful design, and unbeatable convenience, this home is the perfect blend of comfort and style for your next stay in Old Harbour.

Popular amenities for Portland Cottage vacation rentals

  1. Airbnb
  2. Jamaica
  3. Clarendon
  4. Portland Cottage