Downtown Portland holiday rentals

We found 231 holiday rentals — enter your dates for availability
Discover a selection of 16 apartments, 13 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:18 Dec - 25 Dec

Interior
Outdoor dining
Exterior detail
Private kitchen
Exceptional
(43 reviews)

Modern & Sunny House Steps from the Promenade.

Portland

8% off
AU$3,976
for 7 nights, 1 home
AU$568 per night
includes taxes & fees
Modern & Sunny House Steps from the Promenade.
Lobby can be accessed from Patton Ct or Exchange St. Door code will be provided.
Large open concept living space with tall sloped celling and a loft.
View from inside unit.
Oven, Keurig, microwave, fridge, toaster, and dishwasher.
Exceptional
(7 reviews)

Exchange Street Skylight Loft

Portland

8% off
AU$3,950
for 7 nights, 1 apartment
AU$564 per night
includes taxes & fees
Exchange Street Skylight Loft
Interior
Living area
Private kitchen
Off-street parking behind building dedicated to this unit only.
Exceptional
(41 reviews)

Eastbayside/Munjoy - Charming Downtown Escape

Portland

8% off
AU$2,700
for 7 nights, 1 apartment
AU$386 per night
includes taxes & fees
Eastbayside/Munjoy - Charming Downtown Escape
Living area
Interior
Dining
Exterior detail
Exceptional
(99 reviews)

2 Bedroom Apartment Unit In Portland's Historic West End Neighborhood

Portland

8% off
AU$2,854
for 7 nights, 1 apartment
AU$408 per night
includes taxes & fees
2 Bedroom Apartment Unit In Portland's Historic West End Neighborhood
Pia Men Miyake, the best place for lunch!
Smalls! A short walk from the house.
Dining
Room
Exceptional
(23 reviews)

West End Bright Spot with Parking.

Portland

8% off
AU$2,024
for 7 nights, 1 apartment
AU$289 per night
includes taxes & fees
West End Bright Spot with Parking.
Living area
Tour the Victorian Mansion at the bottom of the street.
Scales! The best spot in town for a delish dinner.
Interior
Exceptional
(63 reviews)

Historic Home in the West End. Private Parking.

Portland

8% off
AU$2,537
for 7 nights, 1 apartment
AU$362 per night
includes taxes & fees
Historic Home in the West End. Private Parking.
Outdoor dining
Private kitchen
Living area
Room
Exceptional
(14 reviews)

Harborview - Curated East End Escape w/ Parking

Portland

8% off
AU$7,324
for 7 nights, 1 apartment
AU$1,046 per night
includes taxes & fees
Harborview - Curated East End Escape w/ Parking
Living area
Interior
Room
Interior
Exceptional
(22 reviews)

West End's Diamond in the Rough 2-bedroom Apartment with Parking & WiFi

Portland

8% off
AU$4,486
for 7 nights, 1 apartment
AU$641 per night
includes taxes & fees
West End's Diamond in the Rough 2-bedroom Apartment with Parking & WiFi
Room
Interior
Living area
Interior
Exceptional
(43 reviews)

Fresh East End Apartment Walkable to Downtown Portland

Portland

8% off
AU$4,267
for 7 nights, 1 apartment
AU$610 per night
includes taxes & fees
Fresh East End Apartment Walkable to Downtown Portland
The State Theater is a 5 minute walk away.
Scales in the Old Port for the best seafood
Interior
Discover Victoria Mansion at the bottom of the street.
Exceptional
(53 reviews)

Charming West End Hideaway. Private Parking

Portland

8% off
AU$2,724
for 7 nights, 1 apartment
AU$389 per night
includes taxes & fees
Charming West End Hideaway. Private Parking

  • 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, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

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.
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.
Are all fees included in the Downtown 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 Downtown Portland holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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 Downtown Portland holiday homes?
You can find great discounts on holiday homes in Downtown 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 Downtown Portland holiday home booking on Stayz?
To find Downtown 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 Downtown Portland?
A long-stay holiday home 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 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 Downtown Portland holiday home?
Book your Downtown 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 Downtown Portland?
Prices for holiday homes 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. Stayz offers something for every taste and budget, from affordable homes in Downtown 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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