Apartment holiday rentals in Portland

Charming Classic Ladd's/Hawthorne Gem/Sleeps 4

You will stay in an historic neighborhood with 100 year old trees, in a home with character and beauty fitting of this lovely, walkable and friendly part of Portland called Ladd's Addition, where it intersects with Hawthorne Blvd. Steps from restaurants, food carts, pubs, coffee houses, bike rentals, a comedy club and more! Vintage shopping? Yes. Easy public transit? Yes. You can also spend time relaxing;there is a modern kitchen, living and dining room, and even a piano if you like to play.

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

Casita Sarita, Your Urban Escape! NO Cleaning Fee!

Welcome to Casita Sarita, Your Urban Escape! A large, beautiful, light-filled studio in the heart of SE Portland, walking distance to everything. I have eliminated my cleaning fee for 1-2 night stays because I understand the frustration of so many fees, and short stays tend to need less cleaning time. This is the only fee I can control, so I hope it's helpful. On site professional MASSAGE(by me!) available. Please make yourself at home, relax, and rejuvenate. I look forward to hosting you!

Bamboo & Lavender Luxury Container Retreat w/ View

Tucked inside a private bamboo grove and lavender field, Black Box Retreat is a brand-new luxury container home with sweeping valley views. Watch hummingbirds nest in the bamboo, deer graze at dusk, and sunsets turn golden from your private deck and fire pit. Inside, enjoy luxury finishes, room-darkening shades, a full kitchen, and dedicated workspace — perfect for couples, solo travelers, or groups of up to 3. World-class hiking, wineries, and the Oregon coast are just a short drive away.

Close-in, private Overlook retreat.

The Overlook neighborhood is one of Portland's hidden gems. Quiet, tree lined, yet only a few minutes from all the action Portland serves up. Walk or ride to meals, brewpubs or shopping in the Mississippi and Williams districts. Hop a train (three blocks away) to all quarters. Or, to unwind, walk to Overlook or Mocks Crest parks for sweeping views of downtown Portland, Forest Park and the Willamette River. Please read on to see if the studio's lower ceiling is the right fit for you.

Retro artist's loft on Belmont

Newly renovated attic apartment in a Victorian home right on bustling Belmont street with shopping, food, coffee, and bars just a block away! This attic apartment features hand-painted retro wall details and three skylights for plenty of natural light even on grey winter days. Our cozy loft embodies the funky, creative vibe found in Southeast Portland and is a stone's throw from all the entertainment that the Hawthorne district has to offer.

Dogwood Loft -cozy neighborhood, pet friendly

This pet-friendly ground floor apartment is in the heart of Portland's Southeast Laurelhurst neighborhood. It's just 5 blocks away from a hub of amazing restaurants and Whole Foods Market. There are cafes, shops, breweries and parks all within walking distance and it's just one block off of the famous East Burnside Street. The one time multiple pet fee is $50 for up to 7 nights. Inquire about longer stays.

Historic Mississippi - Live Music & Local Shops

✨ Bright 1BR Steps from Vibrant Mississippi Ave ✨ 🛏️ Cozy 1-bedroom with queen bed 🍳 Full kitchen with dishwasher & coffee maker 🛋️ Cable TV, fast WiFi & laptop workspace 🐾 Pet-friendly — bring your furry friend ❄️ Bedroom A/C + heating; living area can run warmer 🔒 Private entrance — entire place is yours 🍽️ Walk to Mississippi shops, cafes, bars & music. First-come rear lot + street parking.

Sunny Buckman Studio • Walk to Food & Coffee

✨ Cozy SE Oak Studio in Portland's Buckman District ✨ 🛏️ Studio with queen bed, sleeps 2 🍳 Full kitchen with stove, oven & coffee maker 💻 Laptop-friendly workspace with fast WiFi 🧺 In-unit washer & dryer ❄️ AC & heating for year-round comfort 🔒 Private entrance — entire studio is yours 🍽️ Heart of Buckman — walk to top restaurants, bars & vintage shops. Free street parking.

Stylish Hawthorne 1BR w 90 WalkScore

✨ Walkable Hawthorne 1BR with Fast WiFi ✨ 🛏️ 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 ❄️ Living-room mini-split A/C + heat 🔒 Private entrance - entirely yours 🍽️ Steps from Hawthorne cafes, brewpubs & shops. Free street parking.

1BR - Walk to Coffee, Brews & NW 23rd Shops

✨ Sunlit Suite Steps from NW 23rd Ave ✨ 🌇 Natural light floods this stylish retreat 🛏️ Queen bed & plush living space 🍳 Full kitchen with coffee maker & cookware 🐾 Pet-friendly — bring your furry friend 💻 Laptop-friendly workspace with fast WiFi ❄️ AC & heating for year-round comfort 🔒 Private entrance — entirely yours 🍽️ Heart of NW 23rd boutiques & top restaurants.

Modern Home in Foodie District - 2BR - Sleeps 4

✨ Stylish SE Portland Apartment Near Hawthorne ✨ 🛏️ 2 bedrooms, sleeps 4 with queen beds 🍳 Full kitchen with dishwasher & dining table 🛋️ Cable TV, fast WiFi & laptop workspace 🐾 Pet-friendly with private entrance 🧺 In-unit washer & dryer ❄️ Living-room mini-split A/C + heat 🚗 Steps from Hawthorne cafes, brewpubs & shops. Free street parking.