Family-friendly holiday rentals in Southeast Portland

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

Woodstock Tiny House

Detached, very small (300 sq ft) guest house in the Southeast Portland neighborhood of Woodstock. Lots of walkable eateries as well as New Seasons and Safeway within a 5 minute walk. Close to Reed College, Woodstock Village, Springwater Trail, Southeast Portland Neighborhoods, Public Transportation. You’ll love the location, the outdoors space, and the ambiance. Good for couples, solo adventurers, and business travelers. TV (Netflix enabled!), A/C (summer months), heat, coffee, fridge/freezer.

Cozy Guest Cottage in Woodstock Neighborhood

A bright and cozy cottage located near Reed College, Woodstock's restaurants/coffeehouses, Trader Joe's and public transit. This residential neighborhood is ideal for a quiet retreat for all visitors. The private guesthouse is outfitted to make your stay comfortable including a spacious bathroom with a walk in shower and a heated floor. Plus, you may want to enjoy a cup of coffee on your own patio located behind the Airbnb. As an added bonus, breakfast items and home baked treats are provided.

Mi casa Es Tu Casa (near SE 52nd and Holgate)

Family friendly spacious basement apartment (700 square feet) with living, bath, kitchenette and bedroom, close to Creston park. Our house is a 5-7 minute drive from Reed College. It is within walking distance to several restaurants including Gladstone Street Pub and Food Carts on Foster. It is a 15 minute walk to Trader Joes; a 20 minute walk to many restaurants and shops on Woodstock Blvd. We have two security cameras on our property - one in the driveway and one on the front porch.

Architect-designed house in SE Portland’s MtTabor

Our modern guesthouse is a clean, private space filled with natural light. The front gate opens into a private, landscaped courtyard landscaped with jasmine, a Japanese maple tree, rhododendrons, and ferns. We are conveniently located near Mt Tabor Park that has walking trails and a spectacular view of the city. We are also close to several popular neighborhoods with shops, cafés, and restaurants. We welcome people of all backgrounds to stay here and enjoy beautiful Portland.

Projector/Spacious/Airy ★ Walk to everything!

A modern-elegant 1000 sq ft guest suite, a few minute walk from a gorgeous, 26 acre park and all the restaurants, bars and shopping you could want. The space is complete with a private guest bedroom with luxury, organic bedding, private bath with locally-made products, a fully loaded kitchenette, an 8-seat dining table, a 100" screen with access to every streaming service, lightning-fast wifi, and even a baby-grand piano! Perfect for couples, business travelers or families.

Fresh & Modern, Spacious 1 Bed/1 Bath Condo

Large, modern 700 sq ft condo with private entrance & lots of natural light. Free washer & dryer, A/C, and king-size memory foam bed. Cook’s kitchen with quartz countertops & full size appliances. Lovely outdoor stone patio with picnic table. We're excited to host you at our Earth Advantage energy efficient home that's convenient to downtown, the airport, and many nearby restaurants. Just steps away from walking paths on Mt. Tabor with panoramic views!

Spacious Loft in the Heart of Southeast PDX

Enjoy Portland in this cozy and spacious bungalow in the heart of southeast PDX. Come stay in a private, loft apartment in our home with a separate entrance, keyless entry, 50'' smart TV, laundry and a kitchenette/bathroom. Public transit is easily accessible, city center 2.5 miles away & Division street - a restaurant and food cart hub - is a 10 min walk. Permitted by the City of Portland Bureau of Development Services - Permit #17-156319-HO

Cozy and Walkable 1 bedroom daylight basement

Our basement has been newly renovated. Brand new bedroom, beautiful bathroom and living space. The living space includes a 57” Smart TV and couch. The wet bar features a mini fridge, sink and Keurig Coffee maker. The bedroom has 1 queen sized bed with hotel luxury 1800 bedding sheets, a dresser, full length mirror and natural light window. Our house is centrally located with dozens of restaurants, bars and coffee shops just a short walk away!