Smoking-friendly holiday rentals in Portland Downtown

Mama J's

For whatever brings you through/to Oregon, stay at Mama J’s comfortable, peaceful, safe and convenient spot. Portland is just ten miles away, the closest beaches, Columbia River Gorge and Mt. Hood are all about an hour, and there are numerous hikes from the forest right down the street to Silver Falls and beyond. The neighborhood is peaceful and your private patio is the perfect place for a beverage and some bird and squirrel watching. If it rains, hang out in the gazebo! Hope to host you here!

a/c ~ {Petite Palazzo VlLLA} ~ Small+Stylish!

Quality & Design in a smaller space Entirely for Yourself! Centrally Located in one of Portland's best Neighborhoods! ★ Includes STARBUCKS COFFEE, Tea & an Oatmeal Breakfast ★ Enter through your own PRIVATE OUTDOOR ENTRANCE & Arrive Anytime! ★ ENTIRE SPACE is PRIVATE, Bath too! ★ LUXURIOUS Stearns & Foster Mattress ★ KITCHENETTE: Refrigerator, Microwave, Mr Coffee, Water Kettle, Wine Glasses & More! ★ Natural Stone Shower + Rain Head ★ KOI POND in the Tranquil Tropical Garden Oasis

Hawthorne Hobbit Hole A Unique Portland Experience

Welcome to the "Hobbit Hole" a one of a Kind Portland Experience! This enchanting oasis is crafted with love and guests in mind! This is a walking, biking, and transit paradise in one of the "Hottest" neighborhoods in PDX The HAWTHORNE DISTRICT! Easy curbside parking. One block from organic grocery store, ICONIC restaurants, and shopping, galore! Soo much entertainment! Top 1% of homes! An open and affirming household who welcomes all. We do allow smoking/vaping outside, including cannabis.

Yeti's Tree House: Where Dreams Come True

"Thank you for creating such a magical place..." Recent Guest "Best Tree House I've ever seen!" Recent Guest Let the kid in you come to play in this real treehouse held up by four trees, 18 feet off the ground. Zip line down or take a giant soaking tub. A magical stroll through the woods leads to the suspension bridge. You won't believe you're only minutes from town. Wear appropriate shoes as it is a short 2-minute hike to the tree house. At times, it can get a little slick.

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.

Williams Avenue Hideaway

Welcome to our charming studio nestled in the heart of NE Portland! This cozy ground floor suite on the lower level of our home offers a perfect blend of comfort and convenience, making it an ideal home base for travelers seeking a local experience. Our space features a plush king bed, ensuring a restful night's sleep. Additional amenities include a thoughtfully designed kitchenette, full bathroom, smart TV, fast WIFI, washer/ dryer and a private patio all at your disposal during your stay.

Fern Cabin

The Fern Cabin has everything to enjoy your Portland stay. There's a private bedroom, living space w/ (small) sleeper sofa/kitchen/table. Full bath & jetted tub. WiFi and cable. Heating/air conditioning keeps you comfortable all seasons. Fully equipped kitchen. Private patio. Cozy lodging for 4. Located in SE Portland between Hawthorne & Division close to Mt Tabor park. Shops, cafes, food carts & restaurants abound. walk to everything. $20 pet fee per night. Cannabis friendly, outside only.

Art Filled Historic Craftsman • Inner Eastside

An artist’s home filled with pieces I’ve created and collected, each chosen with intention. Two serene bedrooms with soft cotton bedding and 1.5 baths offer quiet comfort, while the house itself holds a calm, creative magic. In the heart of Portland yet peaceful and sheltering, it’s a short walk to the Convention Center, Lloyd Center, and the future Lloyd Center Music Venue. Come stay where beauty, artistry, and ease naturally meet. 420 OK in designated outdoor area — please be respectful

Artistic Boho Romantic Woodshed

This warm and cozy close-in country sanctuary is like nothing you've EVER seen! If you like affordable ultimate glamping, then look no further! The fire pit, creative décor, heat pump, table/chairs, weekly serviced private portapotty (equals most of cleaning fee), sink, HD TV, WiFi, Alexa, outdoor covered heated shower w/view, AND 2 friendly Scottish Highland cows you can feed and interact with! We welcome ALL colors, religions, LGBTQ , Cannabis friendly! Cigs OK by fire pit only.

Modern Urban Barn Guesthouse

Featured in Portland Monthly Magazine, the Urban Barn Guesthouse is a two bedroom gem in culinary-rich Division St. where you'll mix with quirky neighbors, track down nearby food finds and experience SE Portland's cultural richness. The Barn has cathedral-height ceilings in 800 sf of style and comfort - a full stocked gourmet kitchen and private, gated patio and yard. Because you're on vacation the cleaning fee covers all cleaning. You don't have to strip the beds or empty trash

Garden Home Backyard Yurt Experience

Our cozy-comfy 4 season yurt is nestled under majestic trees on a beautifully landscaped 1/3 acre. Located in a quiet, safe SW Portland neighborhood with a park, hike/bike trail a block away. We are 6 miles from downtown, with beaches, gorge and Mt. Hood accessible for day outings. There is a full kitchen, a natural gas fireplace and complete electrical and plumbing service. The guests full bathroom is located in the home's utility room a short lighted pathway walk from the yurt.

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.