Holiday houses in Portland Downtown

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Top-rated holiday rentals in Portland Downtown

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Top Guest favourite
A charming outdoor patio space is presented, featuring two white lounge chairs positioned on a gray rug. A neutral planter holds green plants, while a small vase with fresh flowers adds a touch of color. The wooden wall provides a natural backdrop.
Home in Ladd's Addition
5 out of 5 average rating, 245 reviews

New Home Near it All on Division w/ EV Charger

Welcome to The Eloise — a bright, art-filled home centrally-located in the bustling Division/Clinton district of SE Portland. This beautiful ADU has it all. A suite with king bed & bathroom with a luxurious shower; workspace w/ speedy wi-fi; lounge; two TVs a full kitchen, & EV charger. Premium amenities & local treats await you. Tucked into a quiet street just off Division, you’re within walking distance to restaurants, shops, bars, venues, bus & TriMet lines & a 5-minute drive to Downtown.

Top Guest favourite
The exterior of a two-story studio is framed by lush greenery and trees. The building features a spiral staircase leading to a private balcony with black railings. A shared garden area is visible below, with a hammock and various plants around the space.
Guesthouse in Piedmont
4.98 out of 5 average rating, 243 reviews

Spacious, bright garden studio on Peninsula Park

Explore the world-class restaurants, coffee shops and bars in the nearby Williams and Mississippi districts. Take a stroll around the award winning (and oldest) rose garden in the City of Roses across the street in Peninsula Park. At home, this second story studio has extra space in the meditation loft, a full kitchen, fast internet, and projector for streaming. Enjoy your private deck over the shared garden with hammock and H/C outdoor shower. Bus and train nearby with ample on-street parking.

Top Guest favourite
Apartment in Portland
4.94 out of 5 average rating, 140 reviews

Spacious 1BR+ by NW 23d. Free parking & cleaning!

If you're looking for a great value and a convenient location (no car needed!), you have found the place! Steps away from NW 23rd St, this is a spacious 700 sq. ft., 1 BD/1BA private apartment. PLENTY of room to play with fido, cook, hang out, work, etc. Free street parking, your own outdoor balcony, fast wifi, plus easy access to all things shopping and food. Whether it's your first or fiftieth visit to Portland, this apartment has all you and your family/friends need for a comfortable stay.

Guest favourite
Apartment in Pearl District
4.88 out of 5 average rating, 103 reviews

Luxurious king bed suite! Free Garage Parking

This high-end downtown apartment on the 6th floor offers breathtaking views of the city. The apartment is furnished with modern furniture and features a spacious living area with ample natural light. Equipped with underground parking, and access to nearby restaurants, entertainment venues, and shopping areas all within walking distance, this lofts prime location make this contemporary style apartment an ideal choice for those seeking a sophisticated and comfortable urban living experience.

Top Guest favourite
Apartment in Northwest District
4.96 out of 5 average rating, 478 reviews

Pet Friendly NW Nob Hill High End Private Apt.

Beautiful high end modern private apartment built in a historic 1904 Craftsman in Nob Hill. Walk two blocks to NW 23rd for a wide variety of stellar restaurants and shopping or take a 10min walk to get to the heart of the city or to the famous trails of forest park. Easy access to transportation all over the city just steps away. View Mt. Hood from the front porch or relax with your own large private yard and let your pets run. Listed on VRBO 395585, excellent reviews.

Top Guest favourite
A charming two-story house is framed by lush greenery and blooming plants. Tall windows allow natural light to fill the interior, while stone steps lead up to the welcoming entrance. Bright sunlight filters through the leaves overhead, enhancing the inviting atmosphere of the home.
Apartment in Kerns
4.96 out of 5 average rating, 388 reviews

Studio in Walkable Foodie Heaven

We're on a quiet side street – right around the corner from a dynamic restaurant scene in Kerns, the 5th coolest neighborhood in the world. Stroll to parks, live music, vintage shops, and a vintage movie theater. Walk, Lyft/Uber, bicycle, or use Portland’s amazing public transportation everywhere. Tall windows overlook greenery and a cozy porch. Our family's 1900 house has been divided into separate apartments. Its like an artsy hotel room, but much more homey!

Guest favourite
The historic four-story home is presented in a charming green exterior with intricate detailing. Tall trees and colorful shrubs frame the front yard, while a decorative fence surrounds the property. Large windows and a welcoming porch are visible, showcasing the architectural character of the residence.
Guesthouse in Portland
4.93 out of 5 average rating, 184 reviews

Queen Anne Guest Apt. In Historic District

Discover a charming guesthouse apartment in the heart of Portland! This private retreat, nestled in a historic home, offers easy access to the city's vibrant scene. Explore the nearby NW 21st/23rd commercial districts, the Pearl District, and downtown Portland. Enjoy delicious dining, unique shops, and exciting entertainment, including the Timbers and Thorns soccer stadium. Perfect for leisure or business travelers seeking a comfortable and convenient stay.

Top Guest favourite
A warm sleeping area features a spacious bed framed by two wooden nightstands with lamps. A bright yellow throw blanket lays across the bed. The walls are painted a deep teal, and natural light enters through a window with a beige shade. A decorative piece on the wall adds character.
Guesthouse in Sullivan's Gulch
4.99 out of 5 average rating, 468 reviews

Cozy, Stylish Bungalow w/ Fireplace & Full Kitchen

Enjoy a comfy retreat in this cozy and bright studio with a private bathroom, air conditioning, fireplace, full kitchen and work desk. Conveniently located within walking distance to local restaurants, coffee shops, retail stores, and parks. Centrally located in Portland and just 3 miles from downtown. Take a stroll through Historic Irvington and enjoy some of the most beautiful homes and old growth trees that Portland has to offer.

Top Guest favourite
A well-lit outdoor patio area is visible, featuring a round table and two striped chairs. Soft blue and warm ambient lights illuminate the space. A hot tub can be seen in the background, surrounded by greenery, creating a serene and inviting environment.
Guesthouse in Ladd's Addition
4.95 out of 5 average rating, 253 reviews

Portland at your doorstep

Newly built studio space above garage, one queen bed and a futon couch for extra sleeping space. Shared backyard with owners who love to host, beautiful patio and hot tub! Enjoy the beauty of one of Portland's oldest and most beautiful neighborhoods with modern conveniences. Very comfortable and an easy walk, bike or ride share to anywhere in Portland's center. Food carts, restaurants, bars and entertainment are all within minutes.

Top Guest favourite
The historic Isam White House features a striking blue exterior with intricate details and large windows. Lush greenery surrounds the property, complemented by seasonal foliage. The well-maintained garden is enclosed by a decorative black iron fence, adding to the home's charm.
Guest suite in Portland
4.92 out of 5 average rating, 430 reviews

Large Studio in Historic Isam White House

Super Clean third floor suite in the historic Isam White House. Includes bed area, living and dining area, kitchenette with microwave, hot water kettle, dishes and small fridge and private bathroom with tub/shower. This is one of the last grand mansions downtown that hasn't been converted to condos or offices. We are at the shopping and restaurant districts of Northwest 21st and 23rd Avenues. Walkability score of 97!

Guest favourite
Apartment in Ladd's Addition
4.9 out of 5 average rating, 573 reviews

Stylish Hawthorne 1BR w 90 WalkScore

✨ Sleek SE Portland Retreat in the Hawthorne District ✨ 🛏️ Cozy 1-bedroom with queen bed 🍳 Full kitchen with dishwasher & coffee maker 🛋️ Cable TV & fast WiFi 💻 Laptop-friendly workspace for remote work 🐾 Pet-friendly — bring your furry friend ❄️ AC & heating for year-round comfort 🔒 Private entrance — entirely yours 🍽️ Steps from Hawthorne's best cafes, brewpubs & shops. Free street parking.

Top Guest favourite
Guesthouse in Buckman
4.98 out of 5 average rating, 897 reviews

Cozy Portland Studio Apartment

The space is a well appointed, comfortable studio apartment. It is an ADU at the back of the main house. All the amenities that one would desire are provided (wifi, internet, TV, washer & dryer, fridge, dishwasher, stove, microwave, AC, cooking utensils, etc., etc). It is also very modern and clean, with a private entrance and keyless entry. Close to many restaurants, bars and coffee shops.

Popular amenities for Portland Downtown holiday rentals

When is the best time to visit Portland Downtown?

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Avg. price$226 AUD$208 AUD$228 AUD$242 AUD$254 AUD$238 AUD$261 AUD$257 AUD$239 AUD$219 AUD$223 AUD$209 AUD
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Quick stats about holiday rentals in Portland Downtown

  • Total holiday rentals

    Explore 250 holiday rentals in Portland Downtown

  • Nightly prices starting at

    Portland Downtown holiday rentals start at $56 AUD per night before taxes and fees

  • Verified guest reviews

    Over 7,130 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 130 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    210 properties have a dedicated workspace

  • Wi-Fi availability

    250 of Portland Downtown holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Portland Downtown rentals

  • 4.7 Average rating

    Portland Downtown stays receive an average rating of 4.7 out of 5 from guests

  • Nearby attractions

    Portland Downtown's top spots, include Powell's City of Books, Tom McCall Waterfront Park, and McMenamins Crystal Ballroom

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