Downtown Portland holiday homes

We found 232 holiday rentals — enter your dates for availability
Discover a selection of 16 apartments, 12 flats and other holiday rentals in Downtown Portland that are perfect for your trip. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll find the best amenities for hanging out with the people that matter most, which might include air conditioning and a pool. At the end of the day, you'll be able to choose a property to rent for everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Downtown Portland

Showing deals for:30 Oct - 6 Nov

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Why visit Downtown Portland

  • Stunning waterfront views: Downtown Portland boasts picturesque coastal scenery, perfect for leisurely strolls along the water.
  • Historic charm: Explore the neighbourhood's rich history through its beautifully preserved houses and iconic lighthouses.
  • Vibrant local culture: Enjoy the lively atmosphere filled with local art, music, and friendly faces that characterise the area.
  • Delicious dining: Savor a variety of culinary delights at charming eateries offering fresh, local seafood and other regional cuisines.
  • Outdoor adventures: Take advantage of scenic parks and recreational activities ideal for families and nature lovers.

Top attractions near Downtown Portland

Downtown Portland is a vibrant neighbourhood offering a mix of cultural and outdoor experiences perfect for families and beach lovers. Enjoy exploring historic houses and lighthouses, along with scenic coastal views and outdoor adventures that truly capture the local charm. It’s an ideal destination for travellers seeking a blend of history, culture, and nature in a relaxed urban setting.

  • East End Beach: A lovely sandy spot perfect for relaxing and soaking up the sun, East End Beach offers stunning views of Casco Bay, making it an ideal place for a leisurely stroll or a picnic.
  • Victoria Mansion: This exquisite historic house showcases opulent architecture and stunning interiors, reflecting the grandeur of the 19th century. A visit here immerses you in the rich cultural heritage of Portland.
  • Willard Beach: Known for its tranquil atmosphere, Willard Beach is a fantastic place for beachcombing and enjoying picturesque sunsets, perfect for a peaceful getaway.

Things to do recommended for couples

Downtown Portland is perfect for a romantic getaway. Enjoy a leisurely stroll along the picturesque waterfront, explore charming local shops, or share a cozy meal at a waterfront restaurant. Don’t miss a sunset cruise for breathtaking views of the harbour and city skyline.

Things to do recommended for families

Families visiting Downtown Portland can explore the fascinating Children's Museum & Theatre of Maine, enjoy the scenic waterfront at the Eastern Promenade, and experience hands-on exhibits at the Maine Discovery Museum, all within a short walk from each other, making for a delightful family adventure.

Things to do recommended for groups

Groups visiting Downtown Portland, Maine can enjoy the thrill of Beech Ridge Motor Speedway, just 11km away, where adrenaline-pumping motor racing takes centre stage. It's a fantastic spot for those seeking adventure and a vibrant atmosphere.

*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 around Downtown Portland

Whether you're travelling with a group, as a family, with your pets, or seeking extended stays, be sure to filter by your key priorities. Here are some Vrbo booking tips for you.

  • Traveling to Downtown Portland with a group: Think about how many bedrooms you’ll require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Downtown Portland with young kids: Traveling with little ones can be a challenge. You must prioritise their comfort and safety, ensuring they have age-appropriate facilities, like a private swimming pool where available. It’s also wise to consider how close you are to attractions that are family-friendly.
  • Taking your pets with you to Downtown Portland: For many families, a holiday isn’t truly complete without their furry companion. If that resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that your four-legged friend feels just as comfortable as you do.
  • Planning for a long term stay visiting Downtown Portland: If you're after holiday rentals that offer deals for month-long or longer stays, you've come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Also, think about including options like a parking bay, a well-equipped kitchen, or your own private pool in your search.

Where to stay near Downtown Portland

Downtown Portland, Maine, is a vibrant neighbourhood perfect for exploring with family and friends. With its walkable streets, you'll uncover stunning waterfront views, charming boutiques, and delightful eateries. The urban atmosphere is enriched by local art, culture, and friendly faces. Enjoy scenic parks and waterfront strolls, making it an ideal destination for outdoor adventures. Experience the best of urban life while soaking in the unique charm that makes Downtown Portland a must-visit location.

  • Portland: Portland, Maine, is a vibrant coastal city offering a delightful blend of outdoor activities and urban charm. Located right in the heart of the city, Downtown Portland is renowned for its stunning waterfront views, beautiful beaches, and family-friendly attractions. Visitors can enjoy thrilling arena entertainment, captivating theatre performances, and live music concerts throughout the year. The picturesque local landmarks, including scenic beaches and tranquil lakes, provide ample opportunities for relaxation and recreation, making it a perfect destination for outdoor enthusiasts and families alike.
  • Ferry Village: Just 1km from Downtown Portland, Ferry Village is a charming neighbourhood known for its inviting beaches and stunning coastal scenery. It is an ideal spot for those seeking outdoor adventures and picturesque views. The area features various venues for education and golf, as well as an arena entertainment facility for sports and events. Visitors can explore local attractions, including a historic lighthouse and beautiful family beaches, making it a great choice for a leisurely day out by the water.
  • Oakdale: Oakdale, located 2km from Downtown Portland, is a lovely neighbourhood that offers a romantic atmosphere and scenic outdoor experiences. It is perfect for couples and nature lovers who enjoy music concerts and educational activities. The area provides access to beautiful trails, along with nearby beaches and lakes that invite visitors to immerse themselves in nature. Whether you're strolling hand in hand or exploring the local scenery, Oakdale is a delightful escape from the hustle and bustle of city life.

Best time to go to Downtown Portland

If you're planning a trip to Downtown Portland, it's a good idea to check both the weather and property rates. The warmest month is July.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January26.1°F (-3.3°C)Light RainMostly Sunny
February27.0°F (-2.8°C)Light RainMostly Sunny
March33.4°F (0.8°C)Light RainMostly Sunny
April43.9°F (6.6°C)Light RainMostly Sunny
May54.0°F (12.2°C)Light RainMostly Sunny
June61.9°F (16.6°C)Light RainMostly Sunny
July68.9°F (20.5°C)Light RainMostly Sunny
August68.5°F (20.3°C)Light RainMostly Sunny
September62.2°F (16.8°C)Light RainMostly Sunny
October52.2°F (11.2°C)Light RainMostly Sunny
November41.2°F (5.1°C)Light RainMostly Sunny
December32.9°F (0.5°C)Light RainMostly Sunny

Booking with Vrbo is a breeze

Are you keen to save on your next adventure? Being flexible with your travel dates can really help, as prices can vary quite a bit. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, feel free to use our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a handy platform for you to plan new adventures, easily resume your previous arrangements, or manage your travel itinerary. You can find your saved or booked properties neatly sorted into categories such as Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of holiday home accommodation in Downtown Portland?
Apartments are the most popular kind of holiday home in Downtown Portland, according to our data. Even if you've got a different idea about what you want, Bookabach has holiday homes in a variety of sizes and shapes. Filter our options to find your perfect pad.
How much does it cost to rent a holiday home in Downtown Portland?
Length of stay, season and property type are some of the things that can affect the price of a holiday home. Simply add your dates of travel to find your dream escape. From cosy chalets to plush villas, all Bookabach holiday homes provide amazing value.
How much does it cost to rent a beach house in Downtown Portland?
Prices for beach houses in Downtown Portland can differ depending on the size and type of the property and time of year you're travelling. All you need to do is enter your travel dates into Bookabach and how many guests to see available options and prices. From there you can use the filters to refine your search results by nearby activities, ratings, amenities and more.
Are there pet-friendly holiday homes in Downtown Portland?
With 46 properties that welcome four-legged guests, your furry best friend can also come along on your Downtown Portland break. Use our filter tool to browse our pet-friendly holiday homes and find the pawfect pad on Bookabach.
What are popular home amenities in Downtown Portland?
Nearby museums, an electric car charging station and a firepit are the most popular home amenities in Downtown Portland. Whether you're planning to travel by yourself, with your better half or as a family, Bookabach can help you find a holiday home that fits your style with all the features you need.
Are there large group holiday homes in Downtown Portland?
With two properties that can sleep 10 people or more in Downtown Portland, there's no need to cross anyone off the invite list. From family holidays to special events like Christmas or New Year's Eve parties, Bookabach can help you find a large group home that fits the occasion.
Are there holiday homes in Downtown Portland that welcome kids?
With 44 family-friendly holiday homes available in Downtown Portland, there's never been a better time to introduce your little ones to the pleasures of travel. Just click on our "Properties good for families" filter to search for stays loaded with amenities ideal for families on the move, like living rooms, swimming pools, entertainment areas and bunk beds.
What are the top attractions for families in Downtown Portland?
Keeping the kids occupied during your stay in Downtown Portland is a cinch with these exciting family-friendly attractions:

  • East End Beach
  • Sand Beach
  • Portland Observatory

Are there one-bedroom holiday homes in Downtown Portland?
Take your pick from 23 one-bedroom homes in Downtown Portland. Whether you want a townhouse or an upmarket condo, Bookabach's one-bedroom properties are just right if you don't need a lot of space. One of the perks of having your own digs? You'll never need to share your getaway with strangers.
Can I find two-bedroom holiday homes in Downtown Portland?
Pick from 16 two-bedroom homes in Downtown Portland. Settle the kids into the second room or maybe fill it with a couple of your favourite people. There's plenty of space for whoever's fortunate enough to be joining your journey.
Are there holiday homes with WiFi in Downtown Portland?
Pick from 29 holiday homes with WiFi in Downtown Portland. If you'd like to disconnect from the world during your break, but still need to be connected to the web, these getaways have what you need. Narrow your search by applying the WiFi filter on Bookabach.
How can I find holiday homes with air conditioning in Downtown Portland?
Downtown Portland has 43 holiday homes where you'll be able to wind down in air-conditioned comfort. To book a stay on Bookabach that offers this amenity, enter your preferred travel dates and use the filter tool to select the "air conditioning" box.
How old do you have to be to rent a holiday home in Downtown Portland?
Age restrictions can differ between properties on Bookabach, so be sure to look at the rules of the holiday home in Downtown Portland you want to book. But in general, it's 16, 18 or 21.
How long can I rent a holiday home in Downtown Portland for?
The amount of time you can rent a Downtown Portland holiday home for is down to each property. Just tap in your travel dates to view available options offering longer term stays. They come with all you require to make your extended trip more comfortable and convenient, like kitchens and yards. Some properties might also offer weekly or monthly discounted prices, so you can have a longer stay for less.