Portland holiday rentals

We found 1,398 holiday rentals — enter your dates for availability
Discover a selection of 90 homes, 165 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:18 Dec - 25 Dec

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

2nd Floor: Spiral stairs lead to ocean view attic bunk room.
10 out of 10, Exceptional, (72 reviews)
Exceptional
(72 reviews)

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

Scarborough

20% off
Price is AU$8,154
for 7 nights, 1 home
AU$1,165 per night
includes taxes & fees
Spacious Ocean View Getaway, 3 min walk to beach with large fenced in yard

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Why visit Portland

  • Stunning coastal scenery: Explore breathtaking beaches and picturesque waterfront views that showcase the natural beauty of Maine.
  • Historic charm: Discover well-preserved historic houses and landmarks that reflect Portland's rich cultural heritage.
  • Outdoor activities: Enjoy various outdoor pursuits, from hiking in nearby parks to leisurely strolls along the scenic coastline.
  • Vibrant local culture: Experience the bustling downtown area filled with eclectic shops, eateries, and lively cultural events.
  • Iconic lighthouses: Visit Portland's famous lighthouses, iconic symbols of the city's maritime history.

Popular types of accommodation in Portland

Discover Portland, Maine – a charming coastal city offering seaside stays and cosy holiday rentals. Enjoy a selection of private holiday homes, quaint cottages, and stylish condos, each promising a quintessential Maine experience. From scenic waterfront views to vibrant local culture, your stay in this historic city is sure to be both refreshing and memorable.

  • Private Holiday Homes: These are standalone residences offering privacy and exclusivity, making them the top choice for visitors seeking a unique holiday retreat in Portland.
  • Cottages: Quaint and charming, cottages provide a cosy escape, ideal for those desiring a picturesque stay in the city.
  • Condos: Modern and convenient, condos offer a blend of style and comfort for holidaymakers exploring Portland.
  • Apartments: Well-appointed apartments deliver practicality and ease, perfect for a comfortable urban experience.
  • Cabins: Rustic and intimate, cabins offer a distinctive getaway for travellers looking for a more laid-back escape.**

Top attractions in Portland

Portland, Maine, is a charming city perfect for outdoor enthusiasts and families alike. Visitors can enjoy stunning beaches, explore historic houses, and admire iconic lighthouses. The city offers a rich cultural experience alongside beautiful scenery, making it an ideal destination for those seeking adventure or relaxation. With its blend of history and nature, Portland promises memorable experiences for every traveller.

  • Sand Beach: Experience the tranquil beauty of Sand Beach, where soft sands meet gentle waves, perfect for sunbathing and beach activities. Enjoy picturesque views and a relaxed atmosphere, ideal for unwinding amidst nature.
  • Victoria Mansion: Step back in time at Victoria Mansion, a stunning example of Italianate architecture. This historic house museum offers a glimpse into 19th-century opulence, showcasing exquisite furnishings and rich cultural history.
  • International Cryptozoology Museum: Delve into the world of the unknown at the International Cryptozoology Museum, where you can explore fascinating exhibits on mythical creatures and legendary beasts, blending curiosity and culture in a unique setting.

Things to do recommended for couples

Seeking a romantic escape in Portland? Explore the charming Old Port district with its cobblestone streets, indulge in a sunset cruise along Casco Bay, or share a candlelit dinner at a waterfront restaurant, savouring fresh seafood and stunning views. Perfect for couples looking to connect.

Things to do recommended for families

Families will love exploring the Children's Museum & Theatre of Maine, where interactive exhibits spark creativity. A visit to the Portland Head Light offers stunning coastal views, while the scenic ferry ride to Peaks Island provides a delightful day out with beaches and bike rentals for all ages.

Things to do recommended for groups

Experience the thrill of racing at Beech Ridge Motor Speedway, located 11km from Portland. Perfect for groups, this venue offers an exhilarating atmosphere filled with sports and adventure vibes, ensuring an unforgettable outing for everyone in your party.

*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

Regardless of whether you're travelling with a group, as a family, bringing your pets along, or seeking longer stays, it's important to refine your search according to your key priorities. Here are some helpful booking tips for Stayz.

  • Traveling to Portland with a group: Think about how many bedrooms you require, along with amenities like a fully equipped kitchen or outdoor space for group gatherings. Luckily, you can easily filter for all these options and more on Stayz.
  • Traveling to Portland with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, alongside ensuring access to suitable amenities, such as 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 be the same without their furry companion by their side. If this resonates with you, explore Stayz properties that welcome pets. The majority 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 place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding amenities such as a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay in and around Portland

Portland, Maine, is a vibrant city brimming with charm and unique experiences. Explore the bustling downtown area, where eclectic shops and eateries await, or stroll along the picturesque waterfront, taking in stunning views of the harbour. Outdoor enthusiasts can enjoy camping in nearby parks, while families can discover local attractions that cater to all ages. With a friendly atmosphere and rich culture, Portland promises a delightful holiday for every traveller.

  • South Portland: South Portland is a vibrant city situated a short 3km from Portland. Ideal for families, business travellers and those seeking a city-themed experience, it offers an enticing blend of urban charm and seaside leisure. Explore a range of shopping centres and malls, or take advantage of nearby educational venues. The city's coastal allure is enhanced by its proximity to a family beach, a traditional beach, and a scenic lake, promising a diverse travel experience.
  • Downtown Portland: Downtown Portland is a bustling neighbourhood at the very heart of the city. It caters to visitors who enjoy outdoor activities, family outings and scenic vistas. Within this lively area, you'll find entertainment hubs such as arenas, alongside popular shopping centres and malls. The surrounding landmarks include a family beach, a standard beach and a picturesque lake, all contributing to a dynamic urban escape.
  • Old Port: Old Port is a charming neighbourhood known for its vibrant outdoor, family and scenic appeal. It is home to cultural venues such as theatres, arenas for entertainment and music concert spaces. The area's rich ambience is complemented by its close proximity to a family beach, a traditional beach and a serene lake, ensuring a well-rounded experience for all visitors.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 Stayz is a breeze

Are you eager to save on your upcoming journey? Being flexible with your travel dates can lead to considerable savings, as prices often fluctuate. Additionally, booking an extended stay can unlock even greater discounts. To discover a Stayz property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Effortless planning

Stayz’s Trip Board provides a dedicated area to initiate new journeys, continue your plans, or review and arrange your bookings. Properties you have either saved or reserved are now categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.stayz.com.au/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)
  • 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)
  • Dunegrass Golf Club (11.8 mi / 18.9 km)
  • Seacoast Adventure (16.4 mi / 26.5 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?
When considering the best area to stay in Portland, Maine for a holiday rental, the Old Port neighbourhood is an excellent choice. This vibrant area boasts a charming blend of cobblestone streets, historic architecture, and a lively waterfront atmosphere. Visitors can enjoy a plethora of boutique shops, artisanal eateries, and delightful cafes, all while being just a stone's throw from the scenic harbour. A top attraction in Old Port is the Portland Head Light, an iconic lighthouse that offers stunning views of the Atlantic Ocean and is steeped in maritime history.

Another fantastic option is the Arts District, which is home to a thriving creative community. This area features an array of galleries, theatres, and cultural venues, making it great for those who appreciate the arts. The Portland Museum of Art is a significant highlight, showcasing an impressive collection of American and European works.

In terms of holiday rentals, both Old Port and the Arts District have a good selection of properties, ranging from quaint apartments to larger homes, ensuring that visitors can find accommodation that suits their needs.
Where are the best areas for renting a beach house in Portland?
For renting a beach house in Portland, consider the picturesque area of Cape Elizabeth, just a short drive from the city centre. This coastal community features stunning beachfront properties near Crescent Beach State Park, where visitors can enjoy sandy shores and beautiful ocean views. Many rentals in this area come with amenities such as private decks, outdoor grills, and access to walking trails, making them great for families and groups looking to relax by the sea.

Another excellent option is the Old Port district in downtown Portland, which offers a vibrant setting with waterfront access. Here, travellers can find charming lofts and apartments with modern amenities, including gourmet kitchens and rooftop terraces, ideal for enjoying the lively harbour views. The proximity to local seafood restaurants, boutiques, and cultural attractions adds to the appeal of staying in this area.

Additionally, the nearby Scarborough area provides further beach house options, especially around Pine Point Beach, known for its long stretches of sand and calm waters. Many properties in Scarborough feature family-friendly amenities such as outdoor showers, game rooms, and easy beach access, allowing guests to fully embrace the coastal lifestyle.
Where are the best Portland ski resort rentals?
For those seeking ski resort rentals near Portland, Maine, the closest major ski area is Sunday River, located approximately an hour's drive northwest of the city. In the Bethel area, which is near Sunday River, travellers can find a variety of rental options, including spacious lodges and cosy cabins that cater to families and groups. Many properties in this area come equipped with amenities such as full kitchens, fireplaces, and in some cases, hot tubs, providing the ideal setting for relaxation after a day on the slopes.

Additionally, the nearby town of Bethel offers a quaint New England atmosphere, with local shops and restaurants enhancing the experience. Some rentals may also feature easy access to hiking trails and stunning views of the surrounding mountains, ideal for those looking to explore the beautiful outdoors outside of skiing.

For a more rustic experience, consider properties in the surrounding rural areas, where you can find charming chalets and log cabins, often set in serene, wooded settings. These accommodations typically include modern conveniences like Wi-Fi and laundry facilities, ensuring a comfortable stay.
What is the most popular type of holiday rental accomodation in Portland?
In Portland, apartments are the most prevalent type of holiday rental, with around 548 available throughout the city. These can be found in lively neighbourhoods close to the waterfront, the Historic Old Port, and various cultural attractions. Most apartments come equipped with modern amenities such as fully fitted kitchens, comfortable living areas, and often a dedicated workspace, suiting both leisure and business travellers.

Holiday houses are also a popular choice, with about 248 options that provide more space and privacy for families or larger groups. These homes typically feature multiple bedrooms, private outdoor spaces, and full kitchens, allowing guests to enjoy a home-like experience. Additionally, there are around 136 condos available, which often include shared facilities like pools and fitness centres.

For those seeking a quaint and charming stay, there are about 20 cottages scattered around the area, providing a unique character and often set in picturesque locations. Villas are also present, although they are less common.
Are there any family house rentals in Portland?
In Portland, Maine, there are numerous family-friendly house rentals available—about 132 in total. The city boasts a variety of neighbourhoods, each offering unique attractions for families. The Old Port area, known for its cobblestone streets and waterfront views, features spacious homes with amenities like full kitchens, multiple bedrooms, and outdoor areas, superb for family gatherings. Visitors can easily access local highlights such as the Portland Head Light and the bustling shops and eateries along Commercial Street.

Additionally, the West End is another great option, featuring Victorian-style houses that often come with gardens and cosy living spaces. Families can enjoy nearby parks like Deering Oaks, which offers playgrounds and open spaces for picnics. Many properties in this area include conveniences such as laundry facilities and Wi-Fi, enhancing the comfort of your stay.
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, providing a great option for travellers seeking relaxation during their stay. The city's charming neighbourhoods, such as the historic Old Port and the picturesque East End, offer a variety of rental properties that cater to different preferences and budgets.

Many of these holiday rentals come equipped with amenities such as private pools, inviting hot tubs, outdoor decks, and well-appointed kitchens, making them ideal for family gatherings or group getaways. Some properties may also include additional conveniences like barbecue areas, spacious living rooms, and even proximity to local attractions, enhancing the overall holiday experience.
Are there pet-friendly house rentals in Portland?
In Portland, Maine, there are numerous pet-friendly house rentals available, with a total of 92 options to choose from. Many of these rentals are situated in charming neighbourhoods like the historic West End, where you can find beautifully restored Victorian homes equipped with modern amenities such as gourmet kitchens, private gardens, and spacious living areas.

The East End is another popular area, featuring coastal views and proximity to the waterfront. Properties here often include features like outdoor decks, superb for enjoying the fresh sea air, and are close to pet-friendly parks such as the Eastern Promenade, which offers scenic walking trails and stunning vistas of Casco Bay.

Travellers can also expect comfortable accommodations that cater to both humans and pets, including fenced yards, easy access to pet-friendly dining options, and nearby beaches where leashed dogs are welcome.
Are there any remote work holiday rentals in Portland?
In Portland, Maine, there are a substantial number of remote work holiday rentals available—around 832 in total. This vibrant city is not only known for its picturesque waterfront and historic architecture but also offers a range of amenities suited for those working remotely. Many properties come equipped with dedicated workspaces, high-speed Wi-Fi, and comfortable office setups, allowing guests to maintain productivity while enjoying their stay.

Travellers can expect to find a mix of modern apartments and charming homes, often featuring amenities such as fully equipped kitchens, laundry facilities, and outdoor spaces to unwind after a day of work. The Old Port area is particularly appealing, with its cobblestone streets, boutique shops, and waterfront views, providing a lovely backdrop for breaks during working hours. Additionally, the presence of local cafes and co-working spaces nearby further enhances the remote working experience. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Portland?
In Portland, Maine, popular holiday rental amenities cater to a variety of traveller needs. Most rentals typically feature a kitchen, allowing guests to prepare their own meals, which is especially convenient for families or those looking to save on dining out. Additionally, many properties include a coffee and tea maker, ensuring that guests can enjoy their morning brew at their leisure. Onsite parking is commonly available, offering convenience for those travelling by car. Many rentals also boast a deck or patio, providing a lovely space to relax outdoors and enjoy the fresh air. Furthermore, several options permit pets, making it easier for those wishing to travel with their furry companions.
When is the best time to visit Portland for a holiday rental?
March is a fantastic time to visit Portland, Maine, as it marks the beginning of the spring season. During this month, visitors can enjoy the city's vibrant setting as the winter chill starts to fade, making it ideal for outdoor activities and sightseeing. With temperatures ranging from around -1 to 10 degrees Celsius, it's a comfortable time to explore Portland's beautiful waterfront, historic Old Port district, and local parks.

The peak tourist season in Portland typically runs from June to August, when the weather is warmest, and visitors flock to the area for its famous festivals, outdoor markets, and stunning coastal views. This bustling period is superb for those who thrive in lively environments and want to experience everything Portland has to offer, from food truck delicacies to live music events.

For travellers looking for a budget-friendly option, October presents a wonderful opportunity to experience the fall colours without the summer crowds. The crisp air and stunning autumn foliage create a picturesque backdrop for exploring the city's parks and scenic coastal drives.

Ultimately, the best time to book a holiday rental in Portland depends on your preferences. If you enjoy a vibrant setting and the buzz of summer activities, plan for June through August. Alternatively, if you favour a quieter experience with beautiful autumn scenery, consider October for your visit.
What are the top attractions in Portland?
In Portland, Maine, visitors can explore a variety of attractions that highlight the city's coastal charm and vibrant culture. The Old Port district features cobblestone streets lined with boutiques, galleries, and restaurants, offering a picturesque setting along the waterfront. Here, travellers can enjoy fresh seafood and local craft beers while taking in views of the working harbour.

The Portland Head Light, located in Fort Williams Park, is an iconic lighthouse and a must-see for its stunning views and historical significance. This area also provides ample opportunities for picnicking and scenic walks along the coastline.

For art enthusiasts, the Arts District showcases the Portland Museum of Art, which houses an impressive collection of American, European, and contemporary works. Nearby, the historic Victoria Mansion offers insight into 19th-century architecture and design.

Additionally, the Eastern Promenade provides a beautiful park space with walking paths, picnic areas, and access to sandy beaches, great for enjoying the outdoors and the ocean breeze.
Are all fees included in the Portland holiday homes prices shown on Stayz?
Stayz 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.
Are there any Portland holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Portland holiday homes?
You can find great discounts on holiday homes in Portland on Stayz, 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.
Can I change or cancel my Portland holiday home booking on Stayz?
To find Portland holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Portland?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Portland holiday home?
Book your Portland holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Portland?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Portland to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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