Portland vacation rentals

We found 171 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Portland by choosing from 76 houses, 33 apartments, and other vacation rentals. Vacation rentals provide the best amenities for your family, friends, or furry companion, such as parking and a washer and dryer. What you'll find is a rental that has what everyone needs, including options that are accessible or non-smoking.

Popular cities in Portland

Find out more about Portland

Find out more about Portland

Why visit Portland

  1. Stunning Beaches: Portland boasts beautiful beaches that offer a perfect spot for relaxation and water activities.
  2. Breathtaking Waterfalls: Experience the natural beauty of the region with its captivating waterfalls, ideal for hiking and photography.
  3. Rich Cultural Experience: Immerse yourself in local culture, enjoying the warmth of friendly locals and vibrant traditions.
  4. Picturesque Landscapes: Explore the lush landscapes of Portland Parish, ideal for outdoor enthusiasts and nature lovers.
  5. Diverse Accommodation Options: Choose from charming villas, cozy cabins, and private homes for a comfortable stay.

Popular types of accommodation in Portland

If you’re considering a getaway to Portland, you’ll find a variety of vacation rental options to suit your needs. Our most popular choices include charming villas, houses, and cozy cabins. Whether you're searching for Portland parish vacation rentals, holiday cottages, or properties featuring pools and outdoor jacuzzis, we've got you covered. Enjoy a comfortable stay with competitive room rates that offer great savings and peace of mind.

  • Villas: The top choice for visitors to Portland, these luxurious accommodations offer spacious living and stunning views.
  • Houses: A close second, these homes provide a home-away-from-home experience, ideal for families and groups.
  • Cabins: Perfect for nature enthusiasts, these rustic retreats offer a cozy escape amidst beautiful surroundings.
  • Apartments: A convenient option for solo travellers or couples, providing comfort in urban settings.
  • Cottages: This charming choice offers a quaint and intimate atmosphere for a delightful stay.**

Top attractions in Portland

Portland, Jamaica, is perfect for outdoor enthusiasts and adventure seekers, offering stunning scenery and a vibrant culture. Popular attractions include beautiful beaches, breathtaking waterfalls, and historic castles. Visitors can immerse themselves in the local culture while enjoying a range of outdoor experiences, making it an ideal destination for those looking to relax or explore the natural beauty of the area.

  1. Frenchman's Cove Beach: A stunning beach known for its crystal-clear waters and lush surroundings. This tranquil spot offers a perfect blend of relaxation and beach vibes, ideal for sunbathing, swimming, or enjoying a picnic by the shore.
  2. Trident Castle: A romantic castle that exudes culture and history, featuring stunning architecture and beautiful gardens. It's a unique venue for weddings and events, with breathtaking views of the Caribbean Sea.
  3. Portland Parish Church: A historic place of worship that reflects the rich cultural heritage of the area. Its beautiful architecture and serene atmosphere make it a peaceful spot for reflection and appreciation of local traditions.

Things to do recommended for groups

Experience the vibrant atmosphere at Musgrave Market, where you can explore local crafts and fresh produce. Engage with the friendly vendors and soak up the lively city vibes as you sample traditional Jamaican cuisine with your group.

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

If you're planning a trip with a group, family, or pets, or if you're considering an extended stay, it's important to prioritize your preferences when searching. Here are some helpful Vrbo booking tips for you.

  • Traveling to Portland with a group: Think about how many bedrooms you require, along with features like a fully-equipped kitchen or outdoor areas for group gatherings. Luckily, you can easily refine your search for all of these options and more on Vrbo.
  • Traveling to Portland with young kids: Traveling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, along with ensuring access to suitable amenities, like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Portland: For many families, a trip isn't truly fulfilling without their furry companions. If that resonates with you, consider exploring Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Portland: If you're seeking vacation rentals with special offers 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 rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay in Portland

Portland, Jamaica, is a hidden gem for adventurous travellers seeking a blend of culture and natural beauty. Explore the lush landscapes of Portland Parish, where friendly locals welcome you to experience Jamaican town life. From breathtaking nature spots to relaxing excursions, this region offers a vibrant atmosphere perfect for unwinding and immersing yourself in local culture. Discover the lovely beaches and picturesque scenery that make Portland an unforgettable vacation destination.

  • Port Antonio: Port Antonio is a vibrant city located in the heart of Portland, Jamaica. Renowned for its stunning natural scenery and adventure-filled opportunities, this destination is perfect for outdoor enthusiasts. Visitors can enjoy activities such as golfing and various adventure sports, all while being surrounded by breathtaking landscapes. Noteworthy attractions include beautiful beaches and tranquil water features, making it an ideal spot for families and nature lovers alike. The laid-back atmosphere, coupled with a rich cultural heritage, provides an unforgettable travel experience.
  • Long Bay: Situated in the picturesque area of Portland, Long Bay is a charming city that offers a delightful blend of outdoor activities and pristine beaches. Known for its relaxing environment, visitors can indulge in spa treatments and body care, ensuring a rejuvenating experience. The stunning shoreline and inviting water features make it a popular destination for beach lovers and families seeking fun in the sun. Long Bay's serene ambience and natural beauty create the perfect backdrop for a memorable vacation.
  • Drapers: Drapers is a quaint village nestled in Portland, offering a unique experience for those looking to unwind in a scenic setting. Known for its beautiful beaches and lush surroundings, this village is an excellent choice for outdoor enthusiasts and families. Visitors can explore the local water features while enjoying the tranquil beach atmosphere. With its charming community and proximity to natural attractions, Drapers serves as a serene retreat for those wanting to connect with Jamaica’s stunning landscapes and vibrant culture.

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. Peak season runs in March to April and July, while off-peak times, like May and October to November tend to have fewer bookings and better deals.

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

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can change significantly. Moreover, extending your stay often results in substantial savings. To discover the ideal Vrbo property that fits your budget, make use of our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly platform for planning your journeys. Whether you're starting a new adventure, continuing from where you last paused, or organizing your travel plans, this feature has you covered. You can easily access your saved or booked properties, neatly sorted into categories like Potential, Upcoming, or Current Trips. To explore and make the most of Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Take in the beachside beauty of Portland

The area's live music and culture are just a few of the reasons to vacation in Portland. Renowned for its beaches, rafting and restaurants, this city welcomes all visitors. Whether you're planning a family vacation, friends trip or romantic retreat, Vrbo has a great selection of vacation 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

Do you want to discover things to do in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Portland a fun place to get away. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city center:

  • 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 an outdoor enthusiast or just want to take in the scenery, Portland is a great place to spend some time outside. These are some of the area's most stunning natural features, all within 30 miles (48.2 km) of the city center:

  • 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)
  • Somerset Falls (9.3 mi / 15 km)

Frequently asked questions

What is the best area to stay in Portland when booking a vacation rental?
One of the more popular areas to find a Portland vacation home is Fairy Hill. When you book your stay with Vrbo, 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 vacation rental accommodation in Portland?
The most in-demand types of vacation rentals in Portland are villas. Hoping for something different? Vrbo has numerous options to match the needs of our guests, so you'll see vacation 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 vacation rental in Portland?
Property type, length of stay and time of year are some of the conditions that can affect the price of a vacation home. Simply add your travel dates to find your perfect fit. From cozy cabins to expansive luxury villas, all Vrbo vacation rentals 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 traveling. Just enter your travel dates into Vrbo and the number of guests to view your vacation rental 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 vacation rentals in Portland?
With 96 vacation rentals that welcome four-legged guests, your furry little friend can join in on your Portland vacation. Use the filter tool to search our pet-friendly vacation rentals and find your pawfect pad on Vrbo.
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 Vrbo. Morning swim, sunset soak or midnight dip? Leisure activities are up to you when your Vrbo vacation home comes with its own swimming pool.
What are popular rental amenities in Portland?
Some of the most popular rental 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, Vrbo vacation properties include the best amenities for fun and relaxation with the people closest to you.
Are there large group vacation rentals in Portland?
With 18 vacation rentals that can sleep 10 or more people in Portland, you won't have to leave anyone off your guest list. From extended family vacations to special events like anniversary parties and weddings, Vrbo can help you find a large group rental that fits the occasion.
Are there vacation rentals in Portland that welcome kids?
Bring the whole group together for fun-filled adventures in Portland at one of our 86 family-friendly vacation 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 favorite 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 vacation rentals in Portland?
Take your pick from 34 one-bedroom rentals in Portland. Whether you're searching for a cozy cottage or a condo, our one-bedroom rentals 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 vacation with strangers.
Can I find two-bedroom vacation rentals 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 favorite people. There's enough space for whoever's lucky enough to be joining your adventure.
Are there vacation rentals with WiFi in Portland?
Choose from 31 vacation rentals 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 Vrbo.
How can I find vacation rentals with air conditioning in Portland?
Portland has 49 vacation rentals where you can chill out in air-conditioned comfort. To book a property on Vrbo 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 vacation rental in Portland?
The minimum age requirements can differ between properties on Vrbo, so check the rules of the vacation home in Portland you want to book. But in general, it's 16, 18 or 21.
How long can I rent a vacation rental in Portland for?
The length of time you can book a vacation rental 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.

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