Guesthouse holiday rentals in Southeast Portland

Private Oasis! Cozy & Close to Everything!

Beautiful, one of a kind guest house nestled in one of Portland's most desirable locations! This chic and cozy space features vaulted ceilings, all new appliances, comfortable furniture, and tons of natural light! A quiet street, peaceful atmosphere (and awesome soaking tub) make this the perfect spot for relaxation. Enjoy exploring the surrounding neighborhood and easily walk to shops, restaurants, bars and Laurelhurst Park! Central location allows quick travel to other areas of the city!

Value · Location · Air conditioning

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!

Value · Family · Bathroom

Willow Tree Guesthouse

Pet friendly guest house in SE Portland 1 block from the heart of SE Division street. Located on a quiet dead-end street, with a full kitchen, ground floor bedroom/bathroom, spacious walk-in shower, and super cozy upstairs loft makes for the perfect work remote office. Grocery stores in every direction, neighborhood wine shop, and weed shop, restaurants and bars right around the corner. Location and walk score - 100! Gigabit fiber internet - good bandwidth for the digital nomads!

Value · Family · Outdoor spaces

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.

Location · Value · Parks

Bright, Private & Cozy with Yard

Relax in this private, bright and cozy studio space with fully fenced back yard. Nestle up by the outdoor fire, or enjoy a sunset under the covered patio. Equipped with TV, WiFi, and FireStick so you can connect to your favorite shows easily. Kitchen has microwave, mini-refrigerator, induction stove, dishwasher, and all of the supplies you would expect! Enjoy cozy Brooklinen bedding (it's the best!). Full bathroom with washer/dryer, walk-in shower, and ultra soft bath towels!

Location · Family · Outdoor spaces

Château Woodstock – Cozy Stay Near Cafés & Parks

This detached studio home is located in the Woodstock neighborhood, which is one of the few remaining ungentrified areas in Portland. Located a short drive from highway 205 you can get to any part of the city quickly or explore the local bars, restaurants, and parks of SE Portland. There is a private entrance where you can come and go as you please. We're happy to interact with you as little or as much as you prefer, so don't be a stranger or be as private as you like.

Value · Location · TV

Newly built studio in perfect SE location

A cozy newly renovated space with a modern motif. Plenty of natural light, high ceilings. Large walk in shower,walk in closet, washer +dryer and kitchenette with microwave. Queen size bed with European style bedding:fitted sheet, pillows and king size duvet with duvet cover, NO FLAT SHEET or TOP SHEET. The apartment is located in one of the best neighborhoods on the east side.Close to downtown, bus lines, bikes and scooters rental,shopping,casual and fine dining.

Value · Location · Heating

The Loft in Hawthorne Tabor

Loft style guest house with private entrance & private porch in a quiet and convenient Hawthorne Tabor neighborhood. Location: Explore the many restaurants, bars, boutiques, etc in less than 10 min walk along SE Hawthorne Blvd including: Por Que No?, Tabor Bread, New Seasons, Farmhouse Kitchen Escape to the tranquility of Mt Tabor park & trails after an enjoyable 20 min walk through West Tabor neighborhood 15 min drive to PDX Airport 15 min drive to Downtown

Family · Location · Nearby

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.

Family · Location · Access

Romantic Casita. Hot Tub, 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.

Value · Family · Sleep quality

Urban Oasis Retreat + sauna

Our guest house is a completely private space, accessible by an outdoor walkway, and has an outdoor patio. We designed the space to be light-filled, feel cozy yet roomy, fitting a lot into a small space. Vaulted ceilings, a ceiling fan, full kitchen, bathroom, a bed alcove with a comfy queen mattress and soft bedding and lots of extra touches. Our 335 sq ft guest house is fitted with all you'll need for your time in Portland.

Value · Location · Breakfast

Walkable Guesthouse - Inner SE Portland

Private one bedroom ADU in the walkable SE Division and Clinton neighborhood. Second story unit with queen bed (firm mattress) walk-in shower, and easy access to shops, food, and parks. Parents and grandparents return often for the quiet setting. The backyard sitting area is not included in the rental. There are two small dogs on the property, but they do not have access to the guest pathway.

Value · Family · Hiking