Portland holiday lettings

We found 1,452 holiday rentals — enter your dates for availability

Discover a selection of 147 homes, 173 apartments and other holiday rentals in Portland that are perfect for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday rentals have the amenities that you expect for your stay, including parking and a TV. No matter what you're looking for, you'll be able to choose a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Portland

Showing deals for:3 Oct - 10 Oct

Why visit Portland

  • Stunning coastal beauty: Portland boasts beautiful beaches and picturesque coastal scenery, perfect for relaxation and outdoor activities.
  • Cultural immersion: Explore historic houses and vibrant neighbourhoods that reflect the city's rich heritage and charm.
  • Family-friendly activities: The city offers a variety of attractions suitable for families, ensuring an enjoyable experience for all ages.
  • Outdoor adventures: Engage in numerous outdoor pursuits, from hiking to beachcombing, in a scenic environment.
  • Charming accommodations: Choose from quaint cottages, modern condos, and beachfront rentals to enhance your stay.

Popular types of accommodation in Portland

You've chosen Portland for your getaway, and now it's time to select the perfect accommodation. Explore our top picks, including houses, charming cottages, and modern condos. Whether you're seeking beachfront rentals, cosy cottage retreats, or rentals with beach access, Portland, Maine, has something to suit every traveller's needs. Enjoy your stay with complete transparency and reassurance while making the most of your holiday.

  • Houses: The top pick among travellers to Portland, these homes offer spacious accommodations ideal for families or groups seeking a home-from-home experience.
  • Cottages: A delightful option, these charming cottages provide a quaint atmosphere perfect for those wanting a peaceful getaway.
  • Condos: These modern apartments are a popular choice, offering convenience and comfort in the heart of the city.
  • Apartments: A versatile option, these self-contained living spaces cater to various needs, whether for short or extended stays.
  • Cabins: For a taste of rustic charm, our cabins offer a serene escape surrounded by nature.**

Top attractions in Portland

Portland, Maine, is an ideal destination for outdoor enthusiasts and families seeking scenic experiences. With a rich array of attractions, visitors can explore beautiful beaches, vibrant entertainment venues, and historic houses. The city's points of interest cater to those looking for cultural immersion and outdoor adventures, ensuring a delightful holiday filled with diverse activities for all ages.

  • University of Southern Maine: A historic university that offers a vibrant cultural atmosphere, perfect for those interested in education and community engagement. Stroll through its scenic campus and enjoy the various events and activities that reflect the local culture.
  • Portland Museum of Art: This art museum showcases an impressive collection of American and European art, providing a rich cultural experience. Its exhibitions frequently change, ensuring there's always something new to discover.
  • Cross Insurance Arena: A dynamic entertainment venue that hosts a variety of events, from concerts to sports. Ideal for families, it offers an exciting atmosphere and a chance to enjoy live performances.

Things to do recommended for couples

For a romantic getaway in Portland, Maine, indulge in live music at Thompson's Point, enjoy luxury at the Portland Club, or embark on an adventurous water sports experience with Capt Lyman Stuart, only five miles away. Each offers a unique atmosphere perfect for couples.

Things to do recommended for families

Families will have a fantastic time at Hadlock Field, soaking in the sports atmosphere, exploring the Portland Observatory for entertaining insights into the stars, and enjoying thrilling moments at Bayside Bowl, a vibrant arcade adventure zone perfect for all ages.

Things to do recommended for groups

Enjoy a show at the historic State Theatre, shop at Maine Mall for a mix of local and brand-name goods, or unwind with a round of golf at Riverside Municipal Golf Course, where you can soak in the beautiful outdoors and engage in some friendly competition.

Booking with Vrbo is a breeze

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, opting for a longer stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, make use of our filters to refine your search by price, location, and type of holiday rental.

Where to stay in and around Portland

Portland, Maine, is a splendid destination for those seeking a mix of urban charm and coastal beauty. With its friendly atmosphere and family-friendly activities, visitors can explore stunning beaches and vibrant neighbourhoods. The city offers a delightful blend of outdoor adventures and romantic spots, perfect for creating lasting memories. Just a short drive away, you’ll find even more picturesque areas ideal for a beach vacation, ensuring your stay is both relaxing and enriching.

  • South Portland: Situated a mere 1.2km from Portland, South Portland is a vibrant city that caters to families, business travellers, and those seeking a city-themed experience. This area offers a variety of attractions, including shopping centres and educational venues, making it ideal for a leisurely day out. Visitors can enjoy the picturesque beaches, family-friendly lakes, and scenic waterfronts, all while soaking in the local atmosphere. The close proximity to Portland makes it a convenient stop for those looking to explore the greater region.
  • Downtown Portland: Nestled in the heart of Portland, Downtown Portland is the city's bustling hub, perfect for families, outdoor enthusiasts, and couples looking for a romantic getaway. A plethora of activities awaits, from spectacular theatre performances and lively music concerts to engaging arena entertainment. The area’s charming streets are lined with eateries and shops, while nearby beaches and lakes provide a serene escape. Whether you’re enjoying a sunset stroll or immersing yourself in the local arts scene, Downtown Portland offers a delightful blend of experiences.
  • Old Port: Old Port is a historic neighbourhood that exudes charm and character, attracting families and those seeking outdoor entertainment. This vibrant area is well-known for its lively atmosphere, featuring a range of venues including theatres and shopping centres. The waterfront is a highlight, with its beautiful beaches and lakes, providing an ideal backdrop for leisurely walks. Visitors can indulge in the local cuisine, explore unique shops, or simply soak in the coastal views, making Old Port a must-visit destination during your stay.

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 July. Peak season runs from June to August, while off-peak times, like January to March tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January26.1°F (-3.3°C)Light RainMostly SunnyLowSlightly Low
February27.0°F (-2.8°C)Light RainMostly SunnyLowSlightly Low
March33.4°F (0.8°C)Light RainMostly SunnyLowSlightly Low
April43.9°F (6.6°C)Light RainMostly SunnyAverageAverage
May54.0°F (12.2°C)Light RainMostly SunnyAverageAverage
June61.9°F (16.6°C)Light RainMostly SunnyHighSlightly High
July68.9°F (20.5°C)Light RainMostly SunnyHighSlightly High
August68.5°F (20.3°C)Light RainMostly SunnyHighSlightly High
September62.2°F (16.8°C)Light RainMostly SunnyAverageAverage
October52.2°F (11.2°C)Light RainMostly SunnyAverageAverage
November41.2°F (5.1°C)Light RainMostly SunnyAverageAverage
December32.9°F (0.5°C)Light RainMostly SunnyAverageAverage

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

If you're travelling with a group, family, pets, or planning an extended stay, be sure to refine your search according to your specific needs. Here are some helpful booking tips for using Vrbo.

  • Traveling to Portland with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor space for social gatherings. Thankfully, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Portland with young kids: Travelling with young children can indeed be quite demanding. It’s important to prioritise their comfort and safety, along with 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, a family holiday wouldn't feel complete without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortably at home.
  • Planning for a long term stay visiting Portland: If you’re in search of holiday rentals that offer deals 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 a private pool in your search as well.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a practical area for you to plan new holidays, resume your previous arrangements, or simply organise your travel plans. You can easily find the properties you’ve saved or booked, sorted into categories such as Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Delight in the waterfront landscape of Portland

Enjoy the area's live music, museums and theatre scene with a rental holiday home in Portland. This cosmopolitan city attracts visitors thanks to its seafood restaurants and shopping. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Portland

Do you want to discover attractions to visit during your stay? Venture out of your holiday home and experience everything that makes Portland a fun spot to go on holiday. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Aquaboggan Water Park (10.8 mi / 17.3 km)
  • Dunegrass Golf Club (11.8 mi / 18.9 km)
  • Pirate's Cove (12 mi / 19.3 km)
  • Funtown Splashtown USA (12.7 mi / 20.5 km)
  • Old Orchard Beach Parasail (15.1 mi / 24.2 km)
  • Happy Wheels Skate Center (4.2 mi / 6.7 km)

Exploring the natural features in Portland

Whether you're an adventurous traveller or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Portland. Here are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Eastern Promenade (0.8 mi / 1.3 km)
  • East End Beach (0.9 mi / 1.4 km)
  • Willard Beach (1.8 mi / 2.9 km)
  • Thompson's Point (2 mi / 3.2 km)
  • Sand Beach (2.2 mi / 3.5 km)
  • Higgins Beach (7 mi / 11.2 km)

Travelling to and around Portland

Fly into Portland, ME (PWM-Portland Intl. Jetport), the closest airport, located 2.9 mi (4.7 km) from the city centre. If you're unable to find a flight that fits your schedule, you could also fly into Auburn, ME (LEW-Auburn - Lewiston Municipal), which is 26.8 mi (43.2 km) away.

If you prefer train travel, the main station is Portland Transportation Center.

Frequently asked questions

What is the best area to stay in Portland when booking a holiday rental?
One of the more popular neighbourhoods to experience a holiday home in Portland is Downtown Portland. Base yourself here and you won't be too far from leading visitor attractions like Portland Museum of Art and Wadsworth-Longfellow House.
What is the most popular type of holiday rental accommodation in Portland?
Apartments are the most popular style of holiday rental in Portland, according to our data. Even if you've got a different idea about what you'd like, Vrbo has holiday homes in a variety of shapes and sizes. Compare our options to find your perfect match.
How much does it cost to rent a holiday rental in Portland?
The average price for a holiday rental in Portland is based on several factors, including season, property type and length of stay. Whether you prefer a sprawling villa with room to move around or a quaint cabin for just you and the kids, just enter your travel dates to discover some great-value stays.
How much does it cost to rent a beach house in Portland?
The average price for a holiday home by the beach in Portland will depend on when you're going and the style and size of property you're looking for. You can easily and quickly find prices on Vrbo by entering the dates you'll be travelling. Then use our filters to pick the number of bedrooms and amenities important to you, like WiFi, air conditioning and a pool.
Are there pet-friendly holiday rentals in Portland?
Yes, there are. Take your pick of 189 holiday rentals that allow pets in Portland on Vrbo. Our cuddly best friends need a getaway too, so simply use our search function for pet-friendly holiday rentals to find a pad where your pup can get in on the fun.
Can I rent a house with a pool in Portland?
Mark the "pool" box in our handy filter tool and select from 17 houses with private pools in Portland on Vrbo. Morning soak, afternoon splash or midnight swim? How you spend your free time is up to you when your holiday home has a swimming pool.
What are popular rental amenities in Portland?
When it comes to rental amenities that people are searching for in Portland, mountain views, an electric car charging station and a garden rank highest. With Vrbo holiday homes, there are choices to match your taste and style, whether you're travelling with your partner, your family or even pets.
Are there large group holiday rentals in Portland?
Portland has 17 holiday properties that can accommodate 10 or more people. These stays come with all the space you need to share good times with your favourite people.
Are there holiday rentals in Portland that welcome kids?
Portland has 185 family-friendly holiday homes. And securing a stay that welcomes kiddos is a breeze with Vrbo's "Properties good for families" filter. As well as having the whole place to yourselves, you'll get access to conveniences and perks like bunk beds, kitchens and private pools.
What are the top attractions for families in Portland?
There are tons of exciting things to see and do with the family in Portland, including:

  • Higgins Beach
  • East End Beach
  • Pine Point Beach

Are there one-bedroom holiday rentals in Portland?
You can choose from 65 one-bedroom rentals in Portland. Whether you'd prefer a townhouse or a condo, our one-bedroom properties are perfect if you don't require a lot of space. One of the main perks of having your own digs? You'll never need to share your getaway with strangers.
Can I find two-bedroom holiday rentals in Portland?
Take off with your loved ones and experience complete comfort and privacy in one of the 57 two-bedroom holiday rentals Portland has to offer.
Are there holiday rentals with WiFi in Portland?
Portland has 95 holiday rentals with WiFi, so you can stay connected while you're on holiday. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming movies with the family to sending emails, these Vrbo homes make it a breeze to get online.
How can I find holiday rentals with air conditioning in Portland?
You can pick from 161 holiday homes with air conditioning in Portland giving you that gentle, cool breeze and extra level of comfort. Simply enter your desired travel dates and then use our handy filter tool to help you book properties with air conditioning.
How old do you have to be to rent a holiday rental in Portland?
It's a good idea to check with the Portland holiday rental you want on Vrbo as the age limit varies. However, generally it's 16, 18 or 21.
How long can I rent a holiday rental in Portland for?
The amount of time you can book a Portland holiday home for differs depending on the property. Simply tap in your preferred travel dates to see available options offering longer term stays. They include all you require to make your extended holiday more enjoyable and convenient, like laundries and air conditioning. Some Vrbo holiday homes may also offer weekly or monthly discounted prices, so you can stay longer for less money.

Explore destinations around Portland

More Holiday Rentals ideas

People also search for