Guesthouse holiday rentals in Southeast Portland

We had an absolutely wonderful stay at this apartment — truly one of the best rentals we’ve ever experienced. From the moment we arrived, we were impressed by the impeccable cleanliness. Every room was spotless, and it was clear that a lot of care and attention had gone into preparing the space for guests. The apartment was very well equipped, with everything we could possibly need during our stay. Every appliance and amenity was in excellent condition, and nothing was missing. Whether it was the kitchenware, linens, or electronics, everything was thoughtfully chosen and clearly well-maintained. One standout feature was the beautiful backyard. It was a lovely spot to relax! Great for kids!! The location was ideal, in a quiet yet convenient area, and parking was very easy — a huge plus when traveling. We also want to highlight how friendly, kind, and responsive the hosts were. Communication was smooth from start to finish! We will absolutely return if we’re in the area again! Thanks!!

Perfect studio in the heart of Division! Easy parking in front of the house, powerful AC and dehumidifier in the studio, which was perfect during the first Portland heat wave of the Summer. Very functional space with nice light, and a nice little porch for hanging out. Host was a pro with check ins and offering assistance if needed. If you want to be walkable to Division and have a quiet street, this is an ideal spot!

The Little House was peaceful & quiet, with a nice private yard for me & my dogs! Chris was helpful and friendly, I would recommend his place to anyone!

Absolutely loved our stay! The space was incredibly cozy — felt like a home away from home. Everything clearly well cared for and the kitchen was fully stocked, which made us feel right at home. Highly recommend the cottage for anyone wanting a cute and cozy stay while in Portland!

Sari was an amazing host, responsive to all our requests and very accommodating! We wouldn't have had such a lovely stay without her. Highly recommend!

I always stay at The LIghthouse when in Portland. It's cozy in a charming neighborhood and Dana is the perfect host, there when you need him and not when you don't.

The farmhouse was quiet, cute, and cozy with a well-appointed kitchen and thoughtful touches. It felt very spacious with the high ceilings. Hosts were responsive and the location was great for us. Bed pillows were a bit lumpy but we would stay here again!

This was an excellent Airbnb. The bed was super comfortable and I slept like a rock. A nice private place close to restaurants and a fun neighborhood. The host was super responsive and helpful.

Our 3rd stay here in the last 3 months and it continues to be a favourite. Bright, clean, private and close to the University of Portland, where we watched Pilots Baseball’s last home series of the season. Janine is a gracious and accommodating host. We look forward to coming back to stay here when we visit our son next school year.

Great location with easy access no matter your preferred mode of transportation. Super quiet and restful space during my visit. Small space but well laid out, didn’t feel small at all!

The location is quiet and neighborly. Folks are out walking their dogs in the morning and evening and are friendly in the neighborhood. It is a peaceful street and easy to walk a block or two to catch a bus into nearby shops and restaurants. A close drive to downtown or an easy day trip to the Columbia Gorge, Coast, or Mt. Hood. Nice, clean, relaxing space. Hot tub is excellent and well-maintained, kitchen is stocked with quality gadgets and table settings. Hosts are friendly and knowledgeable about the area. But they do not expect/require extended in-person pleasantries upon arrival or departure or at any point throughout. They are available when needed, but mostly just gave us space to do our thing. In our case, we had a multi-day, large family gathering so solo decompression time at the Airbnb was much appreciated. Even got some work done over WiFi. It was also a nice spot to have a family member or two at a time over for lunch or a soak in the hot tub.

A great spot, super close to a local park and with easy access to downtown Portland and local highways. The apartment is set in a private situation, away from the main house. All the facilities were perfect for the stay and we could have happily spent more time in this spot. 10 out of 10 recommend.

My stay here was incredible! The private hot tub surrounded by beautiful foliage was perfect!

We loved our 1 night stay. They have thought of everything you might need for a comfortable stay. Friendly and flexible hosts! The studio was spotless, quiet, cozy and in a walkable neighborhood. Would highly recommended and would definitely return!

We had a truly wonderful stay at Drusilla Airbnb! The home was spotless, beautifully decorated, and had all the amenities our family needed for a comfortable and relaxing small vacation. The kitchen was fully equipped, the beds were super cozy, and the outdoor space was perfect for us to unwind in the evenings. The host was incredibly responsive. The neighborhood was peaceful and safe, with easy access to local attractions, restaurants, and grocery stores. We would absolutely love to come back and highly recommend it to anyone looking for a relaxing and memorable stay in Portland

Very cute well decorated ADU with small private back porch. Super cute neighborhood. Walkable to coffee, food, and public transport. Great place if you want to experience what it’s like to live in Portland.

Wonderful place to stay while visiting my son !! Would definitely stay again!

This was our second time staying here. Nothing but good things to say. The owners are friendly and the place is nice, modern, and clean. The neighborhood is cute and close to everything.

The Owl’s Nest was one of the best Airbnbs where my husband and I have ever stayed! John’s place was pristine with beautiful wood details and decor was tastefully thematic. (He displays a beautiful map collection!) We really appreciated the attention to detail - they provide little things like extra toothbrushes, toiletries, and first aid that demonstrate thoughtfulness and care for their guests! The kitchen was very well stocked, too — we enjoyed some nighttime snacks and a slow morning with the coffee provided ☕️ John’s instructions and guest book were clear and thorough. We simply loved our short stay here! It was the perfect reprieve from a busy trip :)

It was a great stay for my time in Portland. It was close to lots of fun things and also very quiet and private.

This was a fantastic spot in a great location! 10 minute walk to the amazing Jacqueline restaurant (don’t miss the 5pm oyster happy hour). Easy public transportation is a block away. The studio was spotless and features top notch fixtures and an amazing shower. Great host, would definitely re-book.

We had such a great stay! It was my sister’s first time in Portland. The location was incredibly walkable, we didn’t even need to rent a car. It was easy to get to restaurants, shops, and everything we wanted to see. The hot tub and sauna were a perfect way to wind down at the end of the day. Would definitely stay here again!

Trust the reviews of this place as they’re perfectly accurate! The space was great and the check in and out was easy. Do not be nervous about street parking as there was always parking available with little to no walk to the house. Thank you very much, we loved the space!

Laura’s guest house is the cutest, cleanest, most modern place. We’ve stayed in since we started using Airbnb’s years ago. Laura and her husband Joe are super hosts! The location is amazing. Close to everything! You can walk to Whole Foods, the Human Bean, another local coffee shop, and Fremont Street, which has amazing stores, restaurants. Try the Little Griddle on Fremont Street! Best breakfast brunch foods ever! We will definitely stay here again, as long as it’s available!