Holiday rentals with a pool in Southeast Portland

Large 2 Bdrm Designer Guesthouse: Pool & Fireplace

Beautifully renovated with a professional interior designer. This large, private, light & bright 1300 sqft 2-bedroom unit with a separate entrance overlooks the pool. Designed for long-term stays; guests love the total comfort, privacy, and design touches. Pool available during stays from mid-May to mid-Oct. Working remotely? Fully furnished with fast WiFi. Great for traveling nurses, relocations, etc. Close to Downtown Portland, Beaverton, Nike, Intel, OHSU, St Vincent Hospital, etc.

Rose City Hideaway

Oasis for the traveler seeking culture, nightlife, music, food, and ease of access to the Oregon Convention Center, Moda Center, Kaiser and Legacy Hospitals, and Portland Expo Center. This tucked away space, with views of the public park with art installations, is located in the entertainment district. The Hideaway is the ideal landing pad for business and pleasure. After exploring, return to RCH for time in the swim spa, gym, outdoor kitchen, or relax by the gas fire pit to end your day!

Garden Apartment in the Heart of Portland

Beautiful and bright basement apartment with AC in relaxing Northeast Portland. The neighborhood has everything you could want with NE Williams Street a short walk away, easy access to the Rose Garden and the Convention Center, and a 10-minute bike ride to Powell's Books in downtown Portland. The community center across the street offers a full-sized pool and gym. Enter through your own gate into a backyard food forest, and enjoy a private entrance to your apartment. Easy checkout.

Cascadia Cabana | Poolside Suite with Spa

Modern Scandi Guest Suite located on a 1/3 of an acre within the Powell Butte Natural Area. Equipped with a Heated Pool, Oversized Hot Tub Spa, Water Slide, Outdoor Shower, & plenty of privacy and room for activities. A grand sculpture arches over the large pool displaying a gorgeous disco ball! It is the perfect feature to swim under or use as a backdrop for a unique photo. The large deck and pool get full sun almost all day. This space boasts total privacy and all the amenities!

Oasis Between City, River & Mountain. Damascus OR

A large & private guest house on lower level of home only 30 min. to Portland. Mt. Hood, Gorge Waterfalls & Scenic hikes within 60 min drive. Super comfortable bed, quiet nights, recliner sofa & relaxing atmosphere make this an ideal place to hang out and rest. We welcome ALL colors, LGBTQ. Must Read all info, house rules & details prior to booking please. Informed guests are happy guests. Can accommodate 3pm check in every day of the week except Tuesdays.

Quaint Tiny House In The Trees. Damascus, Oregon.

150 ft. walk down a steep driveway takes you to a unique private little studio with everything an adventurous spirit needs. You must be in physically good shape to handle this location. We have friendly dogs you may see outside. 30 min. to SE Portland, 45 to PDX, One hour to Mt. Hood, 40 min to waterfalls in the Columbia Gorge. Pool open June 15 through September 5th. Can accommodate a 3pm check-in all days except Tuesdays.

Quiet Casita with sauna! Pool Opening April 22!

Palm Springs meets Portland in this private guesthouse with a private fenced yard and sauna. The whole group will be comfortable in this spacious and unique space. The pool is currently closed until about April, but the yard is private and there is plenty of space to spread out. With proximity to great shopping, parking and easy access to 205 or 99, you'll be able to get anywhere in Portland in about 20 minutes.

Sellwood Sanctuary Guest House

The Sellwood Sanctuary guesthouse complete with its own fully stocked bathroom, kitchen and queen sized bed with Dreamcloud Premier mattress that includes a luxurious foam topper. Half a block from one of Portland's best parks and Springwater Bike Trail. Great shopping, coffee shops, bakeries, food carts and restaurants all within walking distance. New Seasons grocery store is a few blocks away.

Piedmont Pied-à-terre (Basement Unit)

Remodeled basement apartment, with all the amenities one needs for a perfect getaway in Portland. With just the right amount of space for your group! Our basement apartment is great for short and long term stays. Did we mention we have a Pool and Spa? We have availability throughout the year. You are just 3 blocks from one of Portland’s best parks that has a fun kid play space.