Holiday houses in Portland Downtown

4.84 out of 5 average rating, 342 reviews

Bright 1BR - Walk to Coffee, Food & Shopping

✨ Bright 1BR in Walkable NW 23rd — Steps to Everything ✨ 🏙️ Heart of Portland's trendiest shopping & dining district 🛏️ Queen bed in private bedroom 🍳 Full kitchen with oven, stove & coffee maker 📺 Smart TV & fast WiFi throughout 💼 Laptop-friendly workspace for remote work 🐾 Pet-friendly — bring your furry friend ❄️ AC & heating for year-round comfort 🔑 Private entrance, no shared spaces — entirely yours 🪜 Steep exterior stairs to enter (not step-free) 🍽️ Steps from NW 23rd's top resta

Apartment in Portland Downtown

A well-lit living area is viewed through an open doorway, showcasing large floor-to-ceiling windows that reveal lush green hills and vibrant cityscapes. A cozy seating arrangement, including a light-colored chair and dark ottoman, complements the inviting atmosphere of the space.

Luxury Living in Prime Location FREE Airport Rides

FREE AIRPORT [pickups/drop offs] get personally picked up, no wait on Lyft or Uber. Incredible city views! Centrally located studio. Walk straight to world famous Powells Bookstore on the iconic Burnside Street! Or simply enjoy southwest hills sunsets from the comfort of your living room with floor to ceiling windows! Portland Street Car station is located across the street, a block from WholeFoods Markets! Lots of iconic clubs, bars, restaurants, and entertainment within walking distance.

4.94 out of 5 average rating, 18 reviews

Guest suite in Southwest Portland

A spacious deck features a round table surrounded by four chairs. The view captures a vibrant sunset over the Portland skyline, with a blend of city buildings and natural greenery in the foreground. The sky displays hues of orange, pink, and gray.

Magnificent finishes and views!

A rare opportunity to get to stay in Portland's most coveted view neighborhood, full of multi-million dollar homes, and under 200 feet away from the house with the highest listing price in Portland (at $7mil). This is an every surface touched renovation in 2023/2024, utilizing Italian tile, Oregon black walnut, rare mid-century modern furniture pieces and decades old original works of art. We renovated this space in the vision of the finest boutique hotels we have stayed at throughout Europe.

4.98 out of 5 average rating, 59 reviews

5.0 out of 5 average rating, 82 reviews

2 Bedroom Apt. in Historic NW Portland Warehouse

Historic Renovation of a NW Portland brick warehouse that was originally built in 1911. The location is near the heart of the City close to dozens of restaurants and Providence Park stadium is a block away. No need for a car as you can walk 4 blocks to the entrance of the Arboretum with over 30 miles of hiking trails in Forest Park. 5 blocks to the Pearl District with a new pedestrian path. This space is heavily insulated from any sound so you will sleep peacefully through the night.

4.76 out of 5 average rating, 197 reviews

Historic 2BR | Walk to NW 23rd Shops & Eats

✨ Charming Northwest Portland Flat in Alphabet District ✨ 🏙️ Heart of NW 23rd — walk to top shops & cafes 🛏️ 2 cozy bedrooms, sleeps 4 guests comfortably 🍳 Full kitchen with coffee maker & wine glasses 🛋️ Smart TV & fast WiFi throughout 💻 Laptop-friendly workspace for remote work 🌿 Private entrance & porch for your morning coffee ❄️ AC & heating for year-round comfort 🔒 Entire apartment — no shared spaces 🍽️ Steps from NW 23rd's best dining & shopping. Free street parking.

Home in Southwest Portland

A panoramic view of the city skyline is captured during sunset, showcasing vibrant orange and pink hues in the sky. Modern buildings stand prominently against the colorful backdrop, with trees framing the scene in the foreground.

Urban Oasis with Spectacular Views

The downtown and mountain views are a showstopper! Peaceful and centrally located place with many amenities and an easy walk to downtown. Stylish and charming studio apartment attached to the home where the host lives. It has its own private entrance and balcony. This apartment is perfect for the business traveler, longer-term stays, artist's retreat or a weekend urban get-away. Super close to downtown, PSU, OHSU, shopping and tourist destinations. Easy on and off the highway too.

4.88 out of 5 average rating, 74 reviews

Home in Northwest Portland

Cozy artist's bungalow steps from NW 23rd

Designed for comfort by 10-year Superhosts, this 1+ bedroom single-level bungalow is recently renovated, filled with original art and period furnishings, and steps away from Portland’s beloved 23rd Ave. Stroll the quiet, tree-lined streets to the best restaurants, shops, bars and coffee, or hop the streetcar to the Pearl or downtown. Home includes a large gourmet kitchen, off-street parking, and a covered deck overlooking a cottage garden certified as a Backyard Bird Sanctuary.

4.95 out of 5 average rating, 21 reviews

A workspace is positioned by large windows, allowing natural light to fill the area. A stylish desk with a lamp is accompanied by white chairs. The room features warm wooden flooring and modern furnishings, contributing to a comfortable environment for work or relaxation.

4.96 out of 5 average rating, 507 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.

4.97 out of 5 average rating, 73 reviews

Elegant NW Portland Suites - Central Walkable Stay

✨ Bright NW Portland Loft Near 23rd Avenue ✨ 🏠 Private entrance, soaring ceilings & modern design 🛏️ Cozy 1-bed setup, perfect for couples 🍳 Full kitchen with coffee maker & wine glasses 🛋️ Smart TV, dining table & fast WiFi 💻 Laptop-friendly workspace for remote workers 🌀 AC, ceiling fan & room-darkening shades 🧺 In-unit washer & dryer — pack light 🔒 Entire loft to yourself, no shared spaces 📍 Steps from NW 23rd shops, cafes & restaurants. Paid parking available.

4.98 out of 5 average rating, 41 reviews

Cozy Apartment in NW District

The apartment is nestled in the heart of the NW 23rd Ave shopping/dining area. Washington park, home to the International Rose and Japanese Gardens is also just a 5 min walk away. This cozy basement apartment is in a 1896 Shingle-style victorian home. The large living room flows into a dining area and full kitchen. The bright bedroom has a window facing the outdoor patio which is perfect for outdoor dining day or night. A laundry room and full bathroom complete the space.

Guesthouse in Northwest Portland

An open bedroom features a spacious bed with a light blue quilt and matching accent pillows. A textured wall art piece is displayed above the headboard. Natural light illuminates the neutral-toned carpet, complemented by a small wooden nightstand and a mirror reflecting the inviting space.

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.

4.93 out of 5 average rating, 226 reviews

Home in Northwest Portland

A three-story home is depicted with a distinctive dark exterior and a peaked roof. The entrance is framed by a landscaped area featuring bushes and steps leading to the front door. A garage is visible beneath the living space, and a fence encloses the property.

Old Portland Charmer

Nestled in one of Portland's most desirable neighborhoods, this charming home beautifully combines the character of the early 1900s with modern style and amenities. Walk to some of Portland's best restaurants, shops, and attractions just a short walk away. The completely remodeled home features a spacious backyard, abundant natural light, and the added convenience of off-street parking— simple luxuries that make all the difference.

4.99 out of 5 average rating, 72 reviews

Popular amenities for Portland Downtown holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Portland Downtown

4.82 out of 5 average rating, 136 reviews

Mark Spencer Hotel, Standard queen

Superhost

4.77 out of 5 average rating, 196 reviews

Near Portland Art Museum + Café & Fitness Center

Superhost

The entrance of the Heathman Hotel is depicted, showcasing a stylish sign above the door. Planters with neatly trimmed greenery flank the entrance. Pedestrians walk along the sidewalk, reflecting the lively atmosphere of downtown Portland, with shops and trees lining the street.

4.71 out of 5 average rating, 7 reviews

Steps to Powell’s & Art Museum | Pet-friendly. Gym

4.89 out of 5 average rating, 109 reviews

The Clyde by Kasa | King Suite

Hotel room in Portland

KEX Hotel Portland, Standard Queen Ensuite

4.85 out of 5 average rating, 115 reviews

Hotel room in Pearl District

Harlow Hotel, Deluxe queen courtyard view

4.86 out of 5 average rating, 14 reviews

5.0 out of 5 average rating, 4 reviews

Heathman Hotel, Heathman king accessible