Portland holiday homes

We found 175 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Portland by choosing from 68 houses, 43 apartments and other holiday rentals. Holiday rentals provide the best amenities for your family, friends or furry companion, such as Wi-Fi and cable TV. You'll be sure to find a property to rent that has what everyone needs, including options that are accessible or non-smoking.

Popular Portland destinations on Bookabach

Why visit Portland

  • Pristine Beaches: Portland offers stunning, unspoilt coastal stretches perfect for a relaxing day by the sea.
  • Majestic Waterfalls: Explore cascading waterfalls set against lush, tropical backdrops for an invigorating outdoor adventure.
  • Cultural Landmarks: Discover historical sites that reveal the rich heritage of this laid-back Jamaican town.
  • Scenic Trails: Wander through verdant, picturesque landscapes ideal for hiking and nature walks.
  • Local Vibe: Enjoy the vibrant, welcoming atmosphere of downtown Portland, filled with local charm and cultural flair.

Top attractions in Portland

Portland, Jamaica is a paradise for outdoor, scenic adventures. Enjoy pristine beaches, majestic waterfalls, and even a castle that hints at the island’s rich history. Whether you're exploring cultural landmarks or seeking an adrenaline rush with outdoor activities, Portland offers a diverse range of attractions for every traveller.

  • Boston Bay Beach: Enjoy the laid-back beach vibes at Boston Bay Beach, where you can relax on the sands and savour local flavours along the shoreline.
  • Trident Castle: Experience a touch of romance and culture at Trident Castle, a historic landmark that enchants with its storied past and scenic settings.
  • Portland Parish Church: Discover heritage and community spirit at Portland Parish Church, a cultural cornerstone offering a glimpse into local traditions.

Things to do recommended for couples

Planning a romantic getaway in Portland, Jamaica? Explore the stunning beaches of Frenchman’s Cove, take a scenic hike to the Blue Lagoon, or indulge in a candlelit dinner at a local seafood restaurant. Embrace the vibrant culture and serene landscapes for an unforgettable couples' experience.

Things to do recommended for families

Families visiting Portland, Jamaica, can explore the beautiful Blue Lagoon, enjoy a thrilling day at the nearby Dunn's River Falls, or relax on the stunning beaches of Frenchman's Cove, perfect for swimming and sunbathing. Don't miss the local markets for a taste of authentic Jamaican cuisine.

Things to do recommended for groups

Explore the stunning Blue Lagoon with a boat tour, then savour authentic Jamaican cuisine at local eateries. Experience a lively visit to the vibrant town of Port Antonio or relax on the beautiful Frenchman’s Cove beach with your mates.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Portland

When planning your trip—be it with friends, family, pets, or for an extended stay—be sure to use the appropriate filters to suit your needs. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Portland with a group: Think about how many bedrooms you’ll require, along with features like a full kitchen or outdoor areas suitable for group gatherings. Luckily, you can easily filter for these options and much more on Vrbo.
  • Traveling to Portland with young kids: Traveling with young children can be demanding. You must prioritise their comfort and safety, along with suitable amenities like a private pool. It’s also wise to consider how near you are to attractions that are family-friendly.
  • Taking your pets with you to Portland: For many, a family holiday isn’t truly complete without their furry companion. If that resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Portland: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Portland

Portland, Jamaica offers a unique blend of adventure, culture, and relaxation. Experience the vibrant local scene in downtown areas, explore lush landscapes and scenic trails, and immerse yourself in the friendly, laid-back atmosphere. The region promises an engaging mix of outdoor activities and cultural excursions, making it an ideal destination for a diverse and memorable holiday experience.

  • Buff Bay: Buff Bay is a charming city nestled within the scenic expanse of Portland. Its geographic setting offers travellers an abundance of outdoor and adventure opportunities, where one can enjoy the natural beauty and pristine beaches. The area is ideal for those seeking a blend of exploration and relaxation, with nearby national parks and state parks providing ample space for hiking and wildlife spotting. Visitors can immerse themselves in the stunning local scenery while partaking in various outdoor activities.
  • Hope Bay: Hope Bay is a delightful city within Portland, celebrated for its picturesque outdoor and adventurous appeal. This destination is particularly attractive for those in search of a romantic escape, where the combination of cascading waterfalls, serene parks, and expansive beaches creates a truly captivating atmosphere. Whether hiking through the lush landscapes or simply enjoying the calm coastal environment, Hope Bay is a perfect retreat for nature lovers and couples alike.
  • Boston Bay: Boston Bay, a vibrant city in the heart of Portland, is renowned for its outdoor charm and stunning beachside scenery. The local attractions include family-friendly beaches and a historic church, all contributing to a culturally enriching experience. With educational venues nearby, Boston Bay offers a unique blend of relaxation and intellectual engagement, making it a well-rounded destination for travellers seeking both leisure and cultural exploration.

Best time to go to Portland

If you're planning a trip to Portland, it's a good idea to check both the weather and property rates. The warmest month is August.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January76.6°F (24.8°C)Light RainMostly SunnyAverage
February76.6°F (24.8°C)Light RainMostly SunnyAverage
March76.6°F (24.8°C)Light RainMostly SunnySlightly High
April78.1°F (25.6°C)Light RainMostly SunnySlightly High
May79.5°F (26.4°C)Light RainMostly CloudySlightly Low
June80.8°F (27.1°C)Light RainMostly SunnyAverage
July81.5°F (27.5°C)Light RainMostly SunnySlightly High
August81.9°F (27.7°C)Light RainMostly SunnyAverage
September81.7°F (27.6°C)Light RainMostly SunnyAverage
October80.8°F (27.1°C)Moderate RainMostly CloudySlightly Low
November79.3°F (26.3°C)Light RainMostly CloudySlightly Low
December77.9°F (25.5°C)Light RainMostly SunnyAverage

Booking with Vrbo is a breeze

Looking to cut costs on your next adventure? Being flexible with your travel dates may help you snag a better deal, as prices often fluctuate. You can also secure substantial savings by booking a longer stay. To find a Vrbo property that suits your budget, simply use our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's Trip Board offers a handy platform for you to plan new adventures, resume your previous trips, or keep track of your travel arrangements. You can easily find your saved or booked properties sorted into categories like Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply head over to: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Take in the beachside beauty of Portland

The area's live music and culture are just some of the reasons to come on holiday to Portland. Renowned for its beaches, rafting and restaurants, this city welcomes all visitors. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in and around Portland

Are you hoping to find things to do in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that Portland has to offer. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Constant Spring Golf Club (24.6 mi / 39.6 km)
  • Hardwar Gap (20.1 mi / 32.3 km)
  • Hope Zoo (22.3 mi / 35.9 km)

Exploring the natural features in Portland

Whether you're looking for adventure or just want to spend some time taking in the scenery, Portland is a great place to get out in nature. These are some of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Rio Grande (0.2 mi / 0.4 km)
  • Frenchman's Cove Beach (3 mi / 4.8 km)
  • San San Beach (3.4 mi / 5.4 km)
  • Blue Lagoon (4 mi / 6.4 km)
  • Winnifred Beach (4.7 mi / 7.6 km)
  • Boston Bay Beach (6.1 mi / 9.8 km)

Frequently asked questions

What is the best area to stay in Portland when booking a holiday home?
One of the more popular areas to find a Portland holiday home is Fairy Hill. When you book your stay with Bookabach, you will have the whole place to yourself. This means you don't have to share it with anyone apart from your people.
What is the most popular type of holiday home accommodation in Portland?
The most in-demand types of holiday homes in Portland are villas. Hoping for something different? Bookabach has numerous options to match the needs of our guests, so you'll see holiday properties in loads of sizes and shapes. The ideal fit is ready and waiting for you — lock in yours today.
How much does it cost to rent a holiday home in Portland?
Property type, length of stay and time of year are some of the conditions that can affect the price of a holiday home. Simply add your travel dates to find your perfect fit. From cosy cabins to expansive luxury villas, all Bookabach holiday homes provide unbeatable value.
How much does it cost to rent a beach house in Portland?
Prices for beach houses in Portland may differ depending on the size and type of the property and when you're travelling. Just enter your travel dates into Bookabach and the number of guests to view your holiday home options and prices. From there you can use our filters to tailor your search by amenities, ratings, nearby activities and more.
Are there pet-friendly holiday homes in Portland?
With 96 holiday homes that welcome four-legged guests, your furry little friend can join in on your Portland holiday. Use the filter tool to search our pet-friendly holiday homes and find your pawfect pad on Bookabach.
Can I rent a house with a pool in Portland?
Tick the "pool" box in our filter tool and you can choose from 22 houses with private pools in Portland on Bookabach. Morning swim, sunset soak or midnight dip? Leisure activities are up to you when your Bookabach holiday home comes with its own swimming pool.
What are popular home amenities in Portland?
Some of the most popular home amenities people are searching for in Portland include a lake view, ski-in/ski-out facilities and a nearby river. Whether you're hitting the road with pals, family or even pets, Bookabach holiday properties include the best amenities for fun and relaxation with the people closest to you.
Are there large group holiday homes in Portland?
With 18 holiday homes that can sleep 10 or more people in Portland, you won't have to leave anyone off your guest list. From extended family holidays to special events like anniversary parties and weddings, Bookabach can help you find a large group home that fits the occasion.
Are there holiday homes in Portland that welcome kids?
Bring the whole group together for fun-filled adventures in Portland at one of our 86 family-friendly holiday properties. Lots of these stays come with conveniences that are perfect for getaways with children, including laundry facilities, bunk beds and patios. Just check the "Properties good for families" filter box and choose your favourite option.
What are the top attractions for families in Portland?
Keeping the kiddos entertained during your stay in Portland is easy with these top family-friendly attractions:

  • Trident Castle
  • Frenchmans Cove Beach
  • Boston Bay Beach

Are there one-bedroom holiday homes in Portland?
Take your pick from 34 one-bedroom homes in Portland. Whether you're searching for a cosy cottage or a condo, our one-bedroom homes are just right if you don't need lots of room. One of the major perks of having your own place? You'll never need to share your holiday with strangers.
Can I find two-bedroom holiday homes in Portland?
Take your pick of 25 two-bedroom properties in Portland. Put your little ones in the second room or fill it with a couple of your favourite people. There's enough space for whoever's lucky enough to be joining your adventure.
Are there holiday homes with WiFi in Portland?
Choose from 31 holiday homes with WiFi in Portland. If you'd like to disconnect from daily life on your trip, but still need to be connected to the web, these getaways have just what you need. Narrow your search by applying the WiFi filter on Bookabach.
How can I find holiday homes with air conditioning in Portland?
Portland has 49 holiday homes where you can chill out in air-conditioned comfort. To book a property on Bookabach that comes with this amenity, enter your preferred travel dates and use the handy filter tool to select the "air conditioning" box.
How old do you have to be to rent a holiday home in Portland?
The minimum age requirements can differ between properties on Bookabach, so check the rules of the holiday home in Portland you want to book. But in general, it's 16, 18 or 21.
How long can I rent a holiday home in Portland for?
The length of time you can book a holiday home in Portland is up to the property. Just enter your preferred dates to see a list of options offering extended stays. With a range of features such as air conditioning and laundries, as well as some offering discounted weekly or monthly prices, you're sure to discover someplace just right to call your home away from home in Portland.