Downtown Portland vacation rentals

We found 222 vacation rentals — enter your dates for availability

Select from 13 houses, 12 condos, and other vacation rentals to find the perfect place for your stay in Downtown Portland. Whether you’re staying in a vacation home with friends, family, or even just your pets, you'll find the amenities you need and want, which might include WiFi and a fireplace. Whatever you're looking for, you'll be able to choose a rental that has what everyone needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Downtown Portland

Showing deals for:Nov 14 - Nov 21
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more
  • More for less

    More space, more privacy, more amenities — more value

Find out more about Downtown Portland

Find out more about Downtown Portland

Why visit Downtown Portland

  1. Scenic waterfront: Enjoy the stunning views and vibrant atmosphere along the picturesque waterfront, perfect for leisurely strolls.
  2. Cultural experiences: Immerse yourself in the local art scene with galleries and cultural venues showcasing Portland's creativity.
  3. Outdoor activities: Explore beautiful beaches and parks, ideal for outdoor enthusiasts and families alike.
  4. Historic charm: Discover historic houses and architecture that reflect Portland's rich heritage and character.
  5. Diverse accommodation: Choose from a range of vacation rentals, from cozy cottages to modern condos, ensuring a comfortable stay.

Popular types of accommodation around Downtown Portland

Planning a getaway to Downtown Portland? The excitement begins with selecting the perfect place to unwind. Explore our top picks for vacation rentals, including houses, charming cottages, and modern condos. With a range of options to suit your needs, we’ve curated the best Portland vacation rentals to ensure a memorable stay. Experience the vibrant city with transparency and reassurance, knowing you’ve found the ideal vacation home in the heart of it all.

  • Houses: The top choice among visitors to Downtown Portland, offering spacious and comfortable settings for families or groups.
  • Cottages: These delightful, quaint retreats provide a charming atmosphere, perfect for a peaceful getaway.
  • Condos: A popular option, condos blend convenience and modern amenities, ideal for city explorers.
  • Apartments: Offering a home-like feel, apartments are a great choice for those wanting to immerse themselves in local life.
  • Cabins: For those seeking a rustic escape, cabins offer a cozy connection to nature.**

Top attractions around Downtown Portland

Downtown Portland, Maine, is a fantastic vacation spot for families, couples, and outdoor enthusiasts alike. Visitors can enjoy a variety of attractions, including beautiful beaches, historic houses, and entertainment venues. The area offers enriching cultural experiences and great outdoor activities. For those looking to explore further, consider day trips or sightseeing options that showcase Portland's charm and vibrant atmosphere.

  1. Cross Insurance Arena: This vibrant arena in Downtown Portland hosts a variety of events, from thrilling sports games to captivating concerts. It's a family-friendly venue where you can experience the excitement of live entertainment in a dynamic atmosphere.
  2. Portland Museum of Art: A cultural gem in the heart of the city, this museum showcases an impressive collection of American and European art. Its beautifully curated exhibits provide a profound insight into the art world, making it a must-visit for culture enthusiasts.
  3. East End Beach: Located a mile from Downtown, this charming beach offers stunning views of Casco Bay. Perfect for a relaxing day by the water, it's an ideal spot for sunbathing, picnicking, or simply enjoying the serene coastal vibe.

Things to do recommended for couples

For a romantic getaway in Downtown Portland, explore the lively vibes at Thompson's Point for a concert, indulge in luxury at the Portland Club, or embark on an adventurous water sports experience with Capt Lyman Stuart. Each destination offers unique experiences to create lasting memories together.

Things to do recommended for families

Your family will have a fantastic time exploring Hadlock Field's sports atmosphere, enjoying the fun at Bayside Bowl's arcade adventures, and taking in stunning views from the Portland Observatory, all within a short distance from Downtown Portland.

Things to do recommended for groups

Groups visiting Downtown Portland, Maine, can enjoy a show at the historic State Theatre, indulge in shopping at the Maine Mall, or explore the iconic LL Bean Flagship Store. Each location offers unique experiences that capture the vibrant spirit of the area.

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

If you're travelling with a group, your family, pets, or planning an extended stay, be sure to prioritise your preferences when filtering your options. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Downtown Portland with a group: Think about how many bedrooms you require, along with additional features like a complete kitchen or outdoor space for group gatherings. Luckily, Vrbo allows you to filter for all these options and more.
  • Traveling to Downtown Portland with young kids: Travelling with young children can present its challenges. It's important to prioritize their comfort and safety, along with ensuring access to age-appropriate amenities 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 vacation isn’t truly fulfilling without their furry companion by their side. If this resonates with you, explore Vrbo listings that are pet-friendly. Most of these properties offer essentials like feeding bowls and beds, ensuring that every member of the family feels comfortable and welcome.
  • Planning for a long term stay visiting Downtown Portland: If you're seeking vacation rentals with discounts 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 consider including amenities like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay around Downtown Portland

Downtown Portland, Maine, offers a delightful blend of urban charm and coastal beauty, perfect for families, couples, and outdoor enthusiasts. Explore the vibrant waterfront, indulge in local art, and enjoy the friendly atmosphere. Nearby, Northwest Portland beckons with its unique attractions, while the city's romantic vibe makes it an ideal getaway. Whether you crave a bustling business environment or a laid-back family-friendly experience, Downtown Portland has something for everyone to enjoy.

  • South Portland: Located a mere mile from Downtown Portland, South Portland is a vibrant city that offers a delightful blend of family-friendly activities and urban experiences. With its convenient shopping centres and educational venues, visitors will find plenty to explore. South Portland is also known for its beautiful beaches and serene lakes, making it an ideal spot for outdoor enthusiasts and families looking to spend quality time together. Enjoy a leisurely stroll along the waterfront or indulge in some retail therapy at the local shopping mall.
  • Old Port: A mere 161m from Downtown Portland, Old Port is a charming neighbourhood that captures the essence of coastal Maine. This historic district is a hub for family activities, outdoor adventures, and entertainment. With its vibrant theatre scene and numerous shopping options, Old Port offers something for everyone. Visitors can explore the waterfront, enjoy fresh seafood at local restaurants, or take in a show at an arena entertainment facility. The nearby beaches and family-friendly parks provide excellent spots for relaxation and recreation.
  • Portland Arts District: Just 483m from Downtown Portland, the Portland Arts District is a cultural haven that showcases the city’s artistic flair. This neighbourhood is perfect for families, outdoor lovers, and culture enthusiasts alike. Explore the local theatres, enjoy a round of golf, or visit one of the many museums that highlight the area's rich history and creativity. The proximity to beautiful beaches ensures you can enjoy both art and nature, making your visit to the Portland Arts District a truly enriching experience.

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.

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 Vrbo is simple

Are you hoping to save on your upcoming journey? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that aligns with your budget, make use of our filters to sort by price, location, and the type of vacation rental that suits your needs.

Vrbo Trips: Planning made easy

Vrbo's unique Trip Board offers you a dedicated space to plan new adventures, pick up right where you left off, or manage your travel arrangements with ease. You can easily access the properties you've saved or booked, now categorized under Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Downtown Portland?
In Downtown Portland, vacation houses are the most popular type of rental, with around 21 available throughout the area. These properties often feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces where guests can relax and enjoy the vibrant city atmosphere. Many are located near the waterfront, offering easy access to local attractions like the Old Port district and the Portland Museum of Art.
Are there any beach house rentals in Downtown Portland?
In Downtown Portland, Maine, there are about 19 beach house vacation rentals available. These properties are typically located near the waterfront, providing easy access to stunning views of Casco Bay and the bustling Old Port area. Most beach houses come equipped with multiple bedrooms, fully stocked kitchens, and spacious living areas, making them superb for families or groups. Many also feature outdoor decks or patios where guests can relax and enjoy the coastal atmosphere.
How much does it cost to rent a vacation home in Downtown Portland?
Prices for vacation 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 travelling 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.
Are there any discounts for Downtown Portland vacation 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 vacation rentals with parking?
Vrbo offers a wide selection of vacation 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 vacation rentals in Downtown Portland?
A long-stay vacation 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 vacation rental?
The best time to book a vacation rental in Downtown Portland is during the peak season from July to September. This period draws visitors eager to embrace the vibrant atmosphere of the city, as the warm summer temperatures typically range from 20 to 27 degrees Celsius. With the sun shining, it's an ideal time for outdoor activities like exploring the waterfront, visiting local parks, and enjoying the lively street fairs and festivals that characterise this bustling season.

July stands out as the most popular month, when tourists flock to enjoy everything from food events to live music performances. The city's parks and gardens are in full bloom, providing a picturesque backdrop for leisurely strolls or picnics with friends and family. In this lively environment, you'll also find plenty of opportunities to sample Portland's renowned food scene, with numerous food trucks and restaurants offering delicious local cuisine.

For travellers seeking a more budget-friendly option, May is an excellent time to consider. The crowds are thinner, allowing for a more relaxed exploration of the city's attractions, and the weather is still pleasantly mild. This quieter month is superb for those who appreciate a more laid-back experience, while still enjoying the charm and beauty of Downtown Portland.
Are there any remote work vacation rentals in Downtown Portland?
In Downtown Portland, Maine, there are numerous remote work vacation rentals available, with around 38 options to choose from. This vibrant area offers a fantastic blend of urban living and scenic beauty, making it an ideal choice for those looking to work remotely. Many of these properties come equipped with essential amenities for remote work, including high-speed WiFi, dedicated desks, and comfortable office chairs, ensuring a productive environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Downtown Portland vacation rental?
Book your Downtown Portland vacation 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 vacation 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?
In Downtown Portland, Maine, visitors can engage in a vibrant mix of attractions. The Old Port district, known for its cobblestone streets, offers a charming atmosphere with a variety of boutique shops, galleries, and restaurants serving fresh seafood. Key highlights include the historic Portland Head Light, just a short drive away, and the scenic waterfront, where guests can enjoy views of the harbour and the bustling marina.

The Arts District is another focal point, featuring the Portland Museum of Art and several theatres, great for those interested in culture and the performing arts. Here, vacation rentals often provide easy access to local cafes and artisanal shops, enhancing the overall experience.
Can I change or cancel my Downtown Portland home rental booking on Vrbo?
To find Downtown Portland vacation 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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Downtown Portland vacation 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.

More Vacation Rentals ideas

People also search for