Holiday rentals with a pool in Sherwood

Luxury Wine Country Estate

Welcome to Luxury Wine Country Estate, an oasis where luxurious refinement meets the epitome of wine country indulgence. Revel in unmatched hositality, thoughtfully designed to include Tempur-Pedic suites, therapeutic hot tub, rejuvenating sauna, invigorating cold plunge, and the most stunning valley and vineyard views. Every touch is meticulously crafted, from heated stone floors and Dyson innovations to dual gourmet kitchens, Yeti picnic essentials, EV charging capabilities, and so much more.

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!

Secluded Suite Surrounded in Beauty

* Queen bed * Private bath * No smokers * Quarters on first floor of house* Shared hallways * Quiet location * 3-room suite in non-smoking home up long driveway not visible from st. Walking distance to WSU-V w/hiking trails and 3 min. drive to Legacy Hosp. 1-acre home w/heated pool during summer. Adjacent private livingroom has sink, frig, microwave and eating area. Shared laundry room -keypad for secure entry. Second bedroom available per request and registration.

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.

Rose City Retreat

Newly constructed basement studio with private entry in 100+ year old NE Portland home in park-like setting. Trendy Beaumont Village neighborhood, walking distance to restaurants and shops, 90 minutes to the coast, one hour to skiing on Mt. Hood. Triple lot, gardens, swimming pool, and patio with BBQ. Non-smoking household. If you are into cold plunging, use our pool during the cooler months for this experience!

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.