Portland holiday lettings

We found 143 holiday rentals — enter your dates for availability

your current months are April, 2024 and May, 2024.
April 2024
May 2024
Discover a selection of 70 homes, 44 villas and holiday rentals in Portland that are perfect for your trip. 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 cities in Portland

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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:

  • Hope Zoo (22.3 mi / 35.9 km)
  • Constant Spring Golf Club (24.6 mi / 39.6 km)
  • Hardwar Gap (20.1 mi / 32.3 km)
  • Sunshine Amusement Complex (25.5 mi / 41 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 rental?

One of the more popular areas to find a Portland holiday 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 holiday rental accommodation in Portland?

The most in-demand types of holiday rentals in Portland are villas. Hoping for something different? Vrbo 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 rental 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 Vrbo holiday 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 travelling. Just enter your travel dates into Vrbo and the number of guests to view your holiday 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 holiday rentals in Portland?

With 96 holiday rentals 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 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 holiday 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 holiday properties include the best amenities for fun and relaxation with the people closest to you.

Are there large group holiday rentals in Portland?

With 18 holiday rentals 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, Vrbo can help you find a large group rental that fits the occasion.

Are there holiday rentals 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 rentals in Portland?

Take your pick from 34 one-bedroom rentals in Portland. Whether you're searching for a cosy 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 holiday with strangers.

Can I find two-bedroom holiday 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 favourite people. There's enough space for whoever's lucky enough to be joining your adventure.

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