Downtown Portland holiday lettings

We found 228 holiday rentals — enter your dates for availability

Discover a selection of 17 apartments, 11 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.

Find spaces that suit your style

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Why visit Downtown Portland

  • Scenic waterfront: Enjoy picturesque views along the waterfront, perfect for leisurely strolls and relaxing outings.
  • Historic attractions: Discover the rich history of the area through its charming historic houses and landmarks.
  • Local cuisine: Indulge in delightful local eateries offering fresh seafood and regional specialties.
  • Vibrant markets: Explore bustling markets brimming with unique crafts, artisanal goods, and local produce.
  • Outdoor activities: Engage in various outdoor adventures, from beach outings to scenic parks, ideal for families and couples.

Popular types of accommodation around Downtown Portland

Discover the charm of Downtown Portland with an array of vacation rentals tailored to suit your needs. Whether you're seeking a private vacation home, a quaint cottage, or a modern condo, we have options that cater to every traveller. Explore our selection of Downtown Portland apartments and rentals, perfect for immersing yourself in the vibrant local culture. Your ideal Portland getaway awaits!

  • Houses: The top choice for accommodation in Downtown Portland, offering spacious and comfortable settings ideal for families or groups.
  • Cottages: A quaint option, perfect for those seeking a charming and cosy stay with a touch of character.
  • Condos: A popular selection, providing modern amenities and convenience, often located in vibrant areas.
  • Apartments: A versatile lodging choice, suitable for solo travellers or couples looking for a home-away-from-home experience.
  • Cabins: A delightful retreat for those wanting a rustic feel while still enjoying access to the city.**

Top attractions in and around Downtown Portland

Downtown Portland, Maine, is an ideal destination for families, couples, and outdoor enthusiasts alike. Visitors can enjoy a variety of attractions, including beautiful beaches, engaging entertainment venues, and historic houses. This vibrant area offers a rich cultural experience, perfect for those seeking adventure and memorable family outings. Make the most of your trip by exploring the diverse points of interest that Downtown Portland has to offer.

  • Portland Museum of Art: This vibrant art museum showcases a rich collection of American, European, and contemporary works, set within a beautifully designed space that encourages cultural exploration and appreciation.
  • Cross Insurance Arena: A lively venue for entertainment, hosting various events from concerts to sporting activities, making it a perfect spot for family fun and excitement.
  • University of Southern Maine: A historic college campus just 1.6km from downtown, offering a blend of educational and cultural experiences, with beautiful architecture and engaging community events.

Things to do recommended for couples

Looking for a romantic getaway in Downtown Portland? Experience the lively atmosphere at Thompson's Point for a concert, indulge in luxury at the Portland Club, or embark on an adventurous outing with Capt Lyman Stuart for some water sports. Perfect for couples seeking memorable moments together!

Things to do recommended for families

Families visiting Downtown Portland, Maine, can enjoy a thrilling day at Hadlock Field, catch stunning views from the Portland Observatory, and unleash their competitive spirit at Bayside Bowl, all within easy reach and offering fantastic family-friendly vibes.

Things to do recommended for groups

Experience the vibrant culture at the State Theatre, perfect for entertainment and romance. Enjoy a shopping spree at the Maine Mall, offering a bustling atmosphere, or explore the iconic LL Bean Flagship Store, a short drive away, for a taste of local retail charm.

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

If you're travelling with a group, family, pets, or seeking longer stays, it's important to use the appropriate filters to suit your needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Downtown Portland with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily apply filters for all of this and more on Vrbo.
  • Traveling to Downtown Portland with young kids: Travelling with young children can present its challenges. It's essential to prioritise their comfort and safety, along with suitable facilities, like a private swimming pool. Additionally, it's wise to think about your closeness to family-friendly attractions.
  • Taking your pets with you to Downtown Portland: For many, a family holiday isn’t quite the same without their furry companion. If you can relate, take a look at Vrbo properties that welcome pets. Most 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 Downtown Portland: If you're in search of holiday rentals with discounts for stays of a month or more, you've come to the perfect destination. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include options such as a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Downtown Portland

Downtown Portland, Maine, offers a delightful mix of urban charm and friendly vibes, making it an ideal destination for families, couples, and outdoor enthusiasts alike. Stroll through its vibrant streets, explore quaint neighbourhoods, and indulge in local eateries. The area is rich in attractions, from bustling markets to scenic waterfronts, ensuring a memorable experience for every traveller. Whether you're here for business or leisure, Downtown Portland promises a warm and inviting atmosphere.

  • Portland: Nestled a mere 249m from Downtown Portland, this vibrant city offers a delightful blend of outdoor activities and scenic beauty. Visitors are drawn to its picturesque beaches and lovely lakes, making it perfect for family outings. Portland boasts an array of attractions such as theatres and shopping centres, where you can indulge in local cuisine or catch a live performance. Whether you're enjoying a leisurely stroll along the waterfront or exploring the lively shopping scene, Portland's charm is undeniable.
  • South Portland: Located 621m from Downtown Portland, South Portland is an excellent destination for families and business travellers alike. The city features expansive shopping centres and educational venues, catering to a variety of interests. Its close proximity to beautiful beaches and lakes makes it an ideal spot for a relaxing day out. South Portland offers a unique blend of city life with easy access to nature, ensuring that visitors enjoy both urban and outdoor experiences.
  • Old Port: A mere 0.621m from Downtown Portland, Old Port is a charming neighbourhood known for its historic waterfront and lively atmosphere. Families and visitors flock here for its array of entertainment options, including theatres and arena venues. The area’s cobblestone streets are lined with delightful shops and eateries, providing a perfect backdrop for a leisurely day out. With its stunning views of the water and nearby beaches, Old Port is a must-visit for anyone looking to experience Portland's vibrant culture.

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. 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 simple

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

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board provides you with a convenient platform to plan new getaways, pick up right where you left off, or review and organise your travel arrangements. You can easily access the properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

How much does it cost to rent a holiday home in Downtown Portland?
Prices for holiday rentals in Downtown 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 Downtown 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 Downtown Portland holiday house rentals?
You can find great discounts on house rentals in Downtown 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.
Are there any Downtown Portland holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Downtown 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.
Can I find long-stay holiday rentals in Downtown Portland?
A long-stay holiday rental in Downtown 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.
When is the best time to visit Downtown Portland for a holiday rental?
July marks the peak season for visiting Downtown Portland, where visitors can enjoy the vibrant setting and a lot of outdoor experiences. From July to September, the city comes alive with an array of festivals, events, and an abundance of opportunities for sightseeing along the picturesque waterfront.

During this time, the weather is typically warm and pleasant, with temperatures averaging between 20 and 30 degrees Celsius. This creates ideal conditions for exploring the city's renowned food scene, visiting local markets, or simply soaking in the sun at one of the many parks.

For those looking for a more budget-friendly option, consider planning your trip in May. This month offers a quieter experience with fewer crowds, allowing you to fully appreciate the beauty of spring blooms and enjoy leisurely walks through the charming streets. Plus, you can still partake in delightful local events and enjoy the city's culinary delights without the peak season bustle.

Ultimately, your ideal time to visit Downtown Portland will hinge on whether you wish to immerse yourself in the lively option of summer or prefer a more relaxed experience during the spring.
How early should I book a Downtown Portland holiday rental?
Book your Downtown 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 Downtown Portland, Maine, United States of America?
In Downtown Portland, Maine, visitors can enjoy a vibrant mix of attractions and experiences. The Old Port district is renowned for its cobblestone streets, historic buildings, and a variety of boutique shops and restaurants. Here, you can explore the bustling waterfront and indulge in fresh seafood at local eateries. The Portland Head Light, located a short drive away in Cape Elizabeth, is a must-see lighthouse offering stunning coastal views.

The Arts District, home to the Portland Museum of Art, showcases an impressive collection of American and European art, making it a great stop for culture enthusiasts. Nearby, the historic State Theatre hosts various live performances and events.

For those interested in local history, the Wadsworth-Longfellow House offers a glimpse into the life of the famous poet Henry Wadsworth Longfellow. Additionally, the Eastern Promenade provides picturesque walking trails along the waterfront, ideal for enjoying the scenic beauty of Casco Bay.
Can I change or cancel my Downtown Portland home rental booking on Vrbo?
To find Downtown 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 Downtown 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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