Portland holiday lettings

We found 1,372 holiday rentals — enter your dates for availability

Discover a selection of 88 homes, 170 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:13 Mar - 20 Mar

Image gallery for Spacious Ocean View Getaway, 3 min walk to beach with large fenced in yard

Our private neighborhood path to the beach, lined with beach roses!
10 out of 10, Exceptional, (60 reviews)
Exceptional
(60 reviews)

Spacious Ocean View Getaway, 3 min walk to beach with large fenced in yard

Scarborough, ME

19% off
Price is £3,801
for 7 nights, 1 home
£543 per night
includes taxes & fees
Spacious Ocean View Getaway, 3 min walk to beach with large fenced in yard

Find spaces that suit your style

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.

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.

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

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.

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:

  • 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)
  • Aquaboggan Water Park (10.8 mi / 17.3 km)
  • Land's End Gift Shop (13.3 mi / 21.3 km)
  • Old Orchard Beach Parasail (15.1 mi / 24.2 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:

  • 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)
  • Scarborough Beach State Park (8.6 mi / 13.8 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?
When planning a holiday rental in Portland, Maine, the Old Port district stands out as a popular area to stay. This charming waterfront neighbourhood is famed for its cobblestone streets, vibrant atmosphere, and an array of boutique shops and restaurants. Visitors can enjoy the stunning views of the harbour and take leisurely strolls along the picturesque piers. Notable attractions in the Old Port include the Portland Head Light, a historic lighthouse located just a short drive away, and the bustling Portland Museum of Art, which showcases a diverse collection of American and European art.

Another excellent option is the West End, known for its beautiful Victorian architecture and a more residential feel. This area is home to several parks and the scenic Western Promenade, where one can take in panoramic views of the city and the waterfront. The West End is also close to the Maine Medical Centre and offers a variety of delightful eateries and cafes to explore. The availability of holiday rentals in these areas is quite ample, providing a range of choices from quaint apartments to larger homes, ensuring a comfortable stay while immersing yourself in the local culture.
How much does it cost to rent a holiday home in Portland?
Prices for holiday rentals in Portland vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Portland to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Portland holiday house rentals?
You can find great discounts on house rentals in Portland on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Portland?
For renting a beach house in Portland, Maine, head towards the scenic coastline of Cape Elizabeth, particularly near the iconic Two Lights State Park. This area features holiday rentals that provide stunning views of the Atlantic Ocean and easy access to rocky beaches and coastal trails. Many properties here come with amenities like outdoor decks, private gardens, and fully equipped kitchens, superb for enjoying the fresh seafood that the region is known for.

Another excellent option is the area around Old Orchard Beach, which is famous for its sandy shores and vibrant boardwalk. Rentals in this vicinity often include family-friendly amenities such as beach access, BBQ grills, and spacious living areas, making them ideal for groups looking to soak up the sun and enjoy beach activities. The nearby amusement park adds an extra layer of fun for families.
Where are the best Portland ski resort rentals?
For those seeking ski resort rentals near Portland, Maine, the nearby area of Sunday River is a prime destination, located roughly 50 miles northwest of the city. Here, travellers can find diverse lodging options in the Bethel and Newry regions, which cater to various group sizes and budgets. Many of these properties are ski-in/ski-out lodges or condos, providing direct access to the slopes. Expect amenities such as hot tubs, fireplaces, and fully equipped kitchens or kitchenettes, making it easy to unwind after a day on the mountain.

In addition to Sunday River, the nearby area of Mount Abram offers another excellent skiing choice with accommodations in the surrounding towns. Here, visitors can find charming cabins and lodges that often feature rustic decor, spacious living areas, and outdoor decks with views of the mountains. Many properties in this region also provide easy access to local dining options and shops, enhancing the overall experience.
What is the most popular type of holiday rental accomodation in Portland?
In Portland, Maine, apartments are the most popular type of holiday rental, with around 144 available in various vibrant neighbourhoods, including the Old Port and the Arts District. These apartments typically feature fully equipped kitchens, comfortable living areas, and modern amenities, great for both short and extended stays.

Holiday houses come next in popularity, with approximately 112 options available. These properties often boast multiple bedrooms, private gardens, and outdoor spaces ideal for enjoying the fresh coastal air. For those seeking a more compact option, about 30 condominiums are also on offer, providing convenience and access to local attractions.
Are there any family house rentals in Portland?
In Portland, Maine, there are numerous family-friendly house rentals available, with approximately 162 options to choose from. Popular neighbourhoods such as the Old Port and Munjoy Hill offer a variety of spacious homes, great for families looking to explore the vibrant local culture. Many of these properties come equipped with full kitchens, allowing for convenient meal preparation, as well as comfortable living areas where families can gather after a day of adventure.

Visitors staying in the Old Port can enjoy being close to the waterfront, where they can find charming shops, restaurants, and scenic views. Meanwhile, Munjoy Hill boasts stunning vistas of Casco Bay and is not far from parks, providing ample outdoor space for children to play. Some properties even feature private yards or outdoor seating areas, enhancing the family experience.
Can I rent a holiday home with a pool or hot tub in Portland?
In Portland, Maine, there are several holiday homes available for rent that feature pools and hot tubs, with about 17 options to choose from. The city is known for its picturesque waterfront and vibrant arts scene, making it an attractive destination for travellers. In neighbourhoods such as the Old Port, visitors can find charming homes that often come with amenities like private pools, hot tubs, and outdoor patios, ideal for enjoying the coastal climate. Many of these properties also feature fully equipped kitchens, spacious living areas, and comfortable bedrooms, ensuring a relaxing stay.
Can I find long-stay holiday rentals in Portland?
A long-stay holiday rental in Portland is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Portland?
In Portland, Maine, there are numerous pet-friendly house rentals available, offering a welcoming environment for travellers with furry companions. Many of these rentals are situated near the vibrant Old Port district, where visitors can enjoy cobblestone streets lined with shops, restaurants, and waterfront views. Properties in this area often come equipped with modern amenities such as fully stocked kitchens, comfortable living spaces, and outdoor areas where pets can relax.

Additionally, the East End neighbourhood is a popular choice, featuring holiday homes that may include private gardens or patios, superb for enjoying the fresh air with pets. This area is close to several parks, including the scenic Eastern Promenade, which boasts walking trails and stunning views of Casco Bay, making it an ideal spot for leisurely strolls with pets.
Are there any remote work holiday rentals in Portland?
In Portland, Maine, there are numerous remote work holiday rentals available, with around 256 options to choose from. This vibrant city offers a mix of historic charm and modern amenities, making it an excellent choice for those looking to blend work and leisure. Many properties come equipped with dedicated workspaces, including desks and ergonomic chairs, as well as high-speed Wi-Fi to support your remote work needs. Some rentals may even feature additional amenities such as computer monitors and laptop workspaces, ensuring a comfortable and productive environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Portland holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Portland with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Portland?
In Portland, Maine, holiday rentals frequently feature a variety of amenities that enhance the travel experience. Most properties include a fully equipped kitchen, allowing guests to prepare their own meals, along with essential appliances like a refrigerator and microwave. Additionally, complimentary Wi-Fi is commonly available, ensuring connectivity for both leisure and work needs. Cookware, dishware, and utensils are typically provided, making it easy for visitors to feel at home.
When is the best time to visit Portland for a holiday rental?
The most popular time to visit Portland, Maine, is in March, when the city's vibrant culture begins to awaken after winter. This month marks the transition into spring, offering a delightful mix of mild temperatures (averaging around 5°C) and the exciting anticipation of seasonal events. As the snow melts, visitors can enjoy outdoor activities and the city's charming streets lined with quaint shops and cafes.

From June to August, Portland experiences its peak tourist season. Warm weather and a bustling atmosphere attract visitors eager to explore the stunning coastline, indulge in fresh seafood, and partake in numerous festivals and events. This lively period is great for those who thrive on social experiences and want to immerse themselves in the local culture.

For those looking for a more budget-friendly option, consider visiting in October. This month showcases the beauty of fall foliage, with vibrant colours painting the landscape. The pleasant temperatures and fewer crowds make it an ideal time for leisurely strolls along the waterfront or visiting the iconic lighthouses without the hustle and bustle of peak season.
How early should I book a Portland holiday rental?
Book your Portland holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Portland?
In Portland, Maine, visitors can enjoy a variety of attractions throughout the city. The Old Port district is a charming area filled with cobblestone streets, historic buildings, and a vibrant waterfront. Here, you can explore local shops, seafood restaurants, and the iconic Portland Head Light, one of the most photographed lighthouses in America. Holiday rentals in this neighbourhood often provide easy access to the bustling atmosphere and scenic views of the harbour.

Another popular area is the Arts District, which includes the Portland Museum of Art and numerous galleries showcasing local talent. This neighbourhood is superb for those interested in culture and the arts, with holiday apartments typically offering a blend of modern amenities and artistic flair.
Can I change or cancel my Portland home rental booking on Vrbo?
To find Portland holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Portland holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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