Holiday rentals with outdoor seating in Portland Downtown

Accessible, AIA-Award Winning, Urban Garden Oasis

A nurturing place with abundant light, garden views, & access to the best Portland food. “The best Airbnb I’ve ever stayed in!” - frequent guest comment. - American Institute of Architects Award to designer Webster Wilson - Upscale amenities & European fixtures - Quiet NoPo neighborhood tree-lined street, minutes from downtown - Fully equipped kitchen w/ fresh local coffee - Indoor & outdoor dining - See photo captions for more details - Trained Service Animals welcome; no pets nor ESAs

Cozy modern staycation workplace close to downtown

Entire space is very private. Enjoy the cozy modern 1 bedroom queen bed, 2 large sofas that are comfortable to sleep on, oversize soaking tub large walk-in closet , 2 TVs, Blue Ray player, stereo, gorgeous private garden with table seating & tranquil water feature, & private entry. 5 minute drive to downtown, 2 minute walk to Forest Park & Marquam trails. Several amazing restaurants just minutes away. There is a pet fee of $40 each pet. Preferably just one pet or the fee is $70 for two.

Chic Belmont retreat w/tree views & king bed!

Experience weird and wonderful SE Portland from a serene, newly-built home in a walkable/bikeable neighborhood with king bed and lots of light! Wake up well rested and open curtain on floor to ceiling windows to morning light. Enjoy the full kitchen & soaker tub in a breathtaking architect-designed home perfect for foodies, couples, and remote work. Great location just steps from bakeries, shops, parks and taprooms. Discover the quirky character and trendy eats of Belmont-Hawthorne-Tabor!

Cozy Bungalow in Ladd’s Addition • Walk/Dine/Shop

Welcome to “Happy Place”, your cozy retreat that feels like a home-away-from-home in the vibrant heart of Portland! Our sanctuary in the bustling SE Clinton/Division area offers fast internet, perfect for work-from-home needs, and is a short stroll from top restaurants, bars, and boutiques. Boasting a walkability score of 92, city exploration is a breeze. Ideal for foodies, culture lovers, and outdoor adventurers, we provide FREE on-site parking and embrace the spirit of Portland living.

Cozy Private Portland Studio Near Food & Downtown

Quiet retreat near food, cafés & easy downtown access. Welcome to your comfortable, thoughtfully designed private studio suite tucked inside a welcoming Portland home. Perfect for solo travelers, couples, or business guests looking for a peaceful place to recharge after exploring the city. Enjoy the privacy of your own space while staying in one of Portland’s most loved neighborhoods—close to local restaurants, coffee shops, parks, and convenient transit to downtown.

The Green Door PDX: A European Inspired Cottage.

A bolthole created from passion by Kaemingk Collection, The Green Door PDX was designed to provide a unique respite from the energy of Portland while being conveniently located only minutes from downtown and popular shopping/eating districts. We have taken queues from Europe and built a traditional field cottage tucked into the landscape at the front of the property and surrounded it with mature greenery for an inviting welcome and ultimate privacy for our guests.

Romantic Casita. HotTub and Firepit. Pets Welcome!

Come and stay in our romantic, Mediterranean Casita. This private cabin is built for singles and couples. Featuring a hot tub, fenced courtyard, fire pit, covered patio, white Linens, handmade ceramics, rustic furniture, peaceful art and off street parking. Though secluded, you're just a short walk from the vibrant Woodstock BLVD. Enjoy a unique, tranquil retreat designed for relaxation and intimacy, comfortably fitting two guests. Pet's are welcome.

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.

Modern Guesthouse in Portland's Central Eastside

Tall ceilings, an open staircase and walls of windows flood the space with light (even in Portland), while molded plywood Eames chairs add mid-century style. Located in the heart of Portland within walking distance to great restaurants, coffee and parks. Fast, gigabit fiber internet, full kitchen, large table, and private outdoor spaces help maximize your stay and comfort, whether you're alone or with a group. Editor's pick in Dwell.

Portland Modern

Welcome to our Midcentury Modern, a true masterpiece inspired by the iconic Frank Lloyd Wright. Nestled on a lush 1/3 acre private retreat, this architectural gem is just minutes away from Multnomah Village and Gabriel Park. Immerse yourself in the timeless beauty of this renovated mid-mod marvel, where high vaulted open beamed wood ceilings adorn every room on the main floor. License number is 26ASTR-REN-00301

Ankeny Loft Just a Block From East Burnside

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. Pet fee is $35 for one night; $50 for 2-7 nights. Higher fee with longer stays.

Free Parking/Gym/Rooftop/Pearl District/Downtown

Tahitian, one of the four types of Pearls in the world. Welcome to Pearl District in PDX! Simple yet elegant, the Tahitian Stay combines convenience and style. Location is extremely walkable and offers quick access to Whole Foods and the MAX Light Rail. Simply step out of the building and get lost in the brewery blocks, fine dining, entertainment & premier retail shopping.