Family-friendly holiday rentals in Portland Downtown

Hawthorne Hobbit Hole: special Portland experience

The Hobbit Hole is a cozy, comfortable sculpted suite to stay. It's an enchanting oasis, crafted with love and with guests in mind. This is a walking, biking, and transit paradise with easy curbside parking. We are around the corner from an organic grocery store, iconic restaurants, shopping, bike share programs and entertainment on perfectly Portland Hawthorne and Division streets. We are an open and affirming household who welcomes all. We do allow smoking/vaping outside, including cannabis

The Westmoreland Lighthouse - Private studio in SE

We've dubbed this stunning, newly constructed detached studio the "Lighthouse" because of the way natural light pours through the 550-square-foot studio's many windows and dances off its walls and vaulted ceilings. An open loft offers soothing views. We are tucked into the Westmoreland neighborhood's quiet residential area, but are only a five minute walk from more than 20 restaurants and entertainment features. Westmoreland Park, Reed College and downtown Portland are just minutes away by car.

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.

The Nest: Very Clean & Peaceful N Portland Studio

Guest Testimonial: “If I could give this place 6 stars I would. I literally wanted to move in.” “Our favorite Airbnb ever. Very clean. Great location in an awesome neighborhood.” The Nest is nestled in N Portland, 15 minutes from downtown and 15 minutes from the airport. The space is a cozy 512SF studio with beautiful open floor plan, full kitchen and laundry. Solar powered home with 40amp EV charger. Walking distance to Portland’s famous food and historic districts. All are welcome here.

Brand New Tiny Home/Pottery Studio in Cute Village

Welcome to DARK MODE, the tiny home/pottery studio 2 blocks from adorable Multnomah Village. Find peace in this serene hidden backyard oasis. Unit is 200 square feet plus loft and deck, behind the main house. Features include: - Jetted tub - Sleeping loft (queen) - Pull out bed (full) - Fire pit - Porch swing - Work desk - Cascading water feature - Outdoor dining table No kitchen but has a sink, fridge, microwave, water boiler, and plenty of wonderful food options within a few blocks.

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.

Spacious Forest Retreat w/ Hot Tub & Views

In the woods, next to a creek, but still in Portland! Forget your worries in this spacious and serene space. There is a private entrance to this large two story guest suite, which includes a family room, living area with dining area and kitchenette, bedroom and bathroom, central AC, and private balcony. Located in a quiet neighborhood, close to hiking trails in Woods Memorial Park. A 3-minute drive or 1 mile walk to popular Multnomah Village; 15 minutes from Downtown Portland.

Central Historic NE Portland – Irvington Suite

Charming, remodeled 1-bed/1-bath basement suite in a 1905 historic home! Includes living room with sleeper sofa, kitchenette, and laundry. Walk score 87, bike 98, transit 71—20 min to the Oregon Convention & Moda Centers. Squeaky clean with no cleaning fee or checkout chores. Please read the full listing before booking to understand the joys and quirks of this historic home. Your stay supports a local public school teacher!

Monta-Villa Garden Cottage & Furry Farmstead

Private cottage with views of the garden & cats. High ceilings, lots of natural light & warm accents. 🥰 Four, friendly cats and four, suspicious hens in the garden chickens coop. 🐈‍⬛🐓 Tranquil garden with bubbling fountain, chimes, & sheltered, cozy seating. ⛲️ Nearby food, drink, shopping & recreation options. 🍷 Local recommendations. 🌟 Ask about renting our Toyota Sienna. 🚐 Your home away from home! 🏡

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, cable 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.

Garden hideaway steps from classic PDX favorites

Tucked away in a secret community of old Portland classic homes, we are perfectly situated for your visit to the Rose Garden, Japanese Garden, Providence Park, shopping on 23rd street or imbibing on 21st street. We are a are a nice walk from the culinary delights of the Pearl District and 7 minutes afoot from the Goose Hollow light rail stop.

Hawthorne Wisteria Retreat

A private studio in a garden courtyard located in the heart of bustling Hawthorne and Division neighborhoods, this retreat offers walking access to countless top restaurants, boutiques, vintage stores, book stores independent movie theaters and more. There is ample street parking right infront of the house or very near.