Family-friendly holiday rentals in Southeast Portland

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.

Eastmoreland Private Guest Suite by Reed College

Private Guest House Studio Apartment in one of SE Portland's historic neighborhoods - Eastmoreland. With quick access to all the best things Portland has to offer. Situated two blocks from Reed College entrance and a short walk to golfing, Sellwood, Westmoreland, and Woodstock restaurants as well as bus lines and the Trimet MAX Orange Line. If you are looking to explore the wonderful city of Portland, or if you are looking for a quiet comfortable tiny home retreat you have found your getaway!

Bar 3728

An open 850 sq ft. studio w/ a queen bed, living space with a modern smart TV & gas fireplace, bar/kitchenette, private entrance & bathroom. The space is intended for solo travelers only. I live in the Richmond neighborhood & am located 1 block from 37th & Division Street, which is surrounded by great restaurants & shops. My home is a 1910 Bungalow & I’ve owned it for 30 years. If you may be looking for a longer term August stay, please see "other details to note" in my description.

The Westmoreland Lighthouse - Private studio in SE

We've dubbed this stunning, fully 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.

SE Portland Guest Cottage

The guest cottage offers self check-in. It is located in a quiet neighborhood in SE Portland. High ceilings make this studio airy and bright. We think of it as a perfect hotel room without the hotel. The small galley kitchen has everything you need to cook a gourmet meal including filtered water. There is a full bathroom with tub and shower. The cottage stands on its own making it perfect for coming and going as you please. City of Portland Permit #24 013532

Award-Winning Guest House with Private Entrance

Featured in Dwell Magazine; Winner of “Best Whole House Design” by Oregon Home Magazine, this spacious urban garden retreat has one-bedroom with a luxurious king bed, full bathroom, and fully equipped kitchen. Tucked away in a tranquil urban oasis, the space is filled with natural light and boasts a private garden entrance. Wake up refreshed in the crisp, white bedroom and slide open the rustic barn door for a coffee on the patio of this zen retreat.

The Kenilworth Guest House

Showcased in the Modern Home tour of Portland, this newly built ADU is the amazing creation of Portland architect Webster Wilson. A private, airy and elegant oasis set in urban Portland. A glass house with intentional frosted glass to ensure privacy. Escape and experience the elegant grace of this unique guesthouse. Threading the needle of a city lot, the Kenilworth House lives along side a 1905 Victorian, where the host resides.

Modern Studio - Steps to Hawthorne Shops & Eats

✨ Walkable Hawthorne Studio with Full Kitchen ✨ 🛏️ Studio layout with queen bed, sleeps 2 🍳 Full kitchen with stove, oven, microwave & dishwasher 💻 WiFi and laptop-friendly workspace ❄️ Mini-split A/C + heat in the living/sleeping area 🧺 In-unit washer & dryer 🐾 Pet-friendly - bring your furry friend 🚪 Private entrance - no shared interior spaces 🍽️ Steps from Hawthorne cafes, breweries & 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.

Sunset Porch House - Inner SE Portland

We would love to host you in our recently renovated bungalow. Architect designed with all new finishes, cabinetry, appliances and furniture will make you feel pampered in your home away from home. Nestled between Division Street and Hawthorne Blvd, this is one of the most walkable neighborhoods in the city. You'll never run out of new places to eat, drink, shop, or explore!

Cozy Clinton Cottage (close-in SE off Division)

Our lovingly renovated, light-filled guest cottage is detached from the main house, with a private entrance and outdoor seating area. Our central location is great for exploring all of the best that Portland has to offer, with easy access to public transit and bike routes. The space is very cozy and has everything you need for a fantastic Portland vacation or work trip.

Mt. Tabor Private Apartment

The apartment is close to trendy upper Hawthorne business district and Mt. Tabor Park. You’ll love the studio because of the location (close to downtown), the people, and the neighborhood. Perfect for walking, biking, and the use of public transportation to get you where you need to be. It is ideal for couples, solo adventurers, and business travelers.