Vacation rentals with a pool in Portland Downtown

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Top-rated rentals with a pool in Portland Downtown

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Vancouver

4.95 out of 5 average rating, 110 reviews

The Starburst Inn

Bring your family to the luxurious 5 BR 3 Bath oasis in the tranquil and friendly Old Evergreen Highway waterfront area. Visit the exciting attractions, natural landmarks, restaurants, shops, and much more, and then retreat to the lavish oasis that will leave you in awe with its starburst MCM design, backyard, and rich amenity list. ✔ 5 Comfortable BRs ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Swimming Pool ✔ Hot Tub ✔ Game Room ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Free Parking See more belo

Top guest favorite

Home in Newberg

4.96 out of 5 average rating, 236 reviews

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.

Top guest favorite

Home in North Plains

5 out of 5 average rating, 10 reviews

Private house retreat & acres of forest trails!

Only 30 minutes from Portland you will find your private, cozy, comfortable cottage in the 100 acre woods! Enjoy a private spa & pool (in season) out your back door. Gaze in awe at the breathtaking views of Williamette valley farms and coastal mountains. Glimpse the wildlife of bald eagles, hawks, owls, elk, deer, and songbirds. Explore many hiking and walking trails in the forest with your dog. Relax in the quiet peace of the country. Enjoy our resident herd of Scottish Highland cattle.

Top guest favorite

Home in North Portland

4.96 out of 5 average rating, 116 reviews

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!

Top guest favorite

Guest suite in Sherwood

4.93 out of 5 average rating, 116 reviews

Sherwood Bella Retreat / close to GFU - Newberg

Nestled on a quiet mountaintop, offers a welcoming spot for relaxation. Located in country setting surrounded by vineyards between Sherwood and Newberg, while still being close to Portland and Beaverton. 3 miles from Devonwood Equestrian Center. Enjoy the entire 4BR/2BA downstairs apartment with a private entrance, parking area and your own patio and BBQ. This property also features a salt water pool/June-Sept pool available depending on weather. Firepit for relaxing in the evening

Top guest favorite

Guest suite in Vancouver

4.98 out of 5 average rating, 163 reviews

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.

Guest favorite

Guest suite in Damascus

4.92 out of 5 average rating, 584 reviews

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.

Guest favorite

Home in Cedar Mill

4.89 out of 5 average rating, 35 reviews

Portland Pool Lodge

Portland Pool Lodge was made for creating memories. A covered heated pool w/ waterslide, BBQ, and 3 fireplaces. An all age entertainment paradise with a theater room, ping pong, rod hockey and arcades. Safe suburban location in Cedar Mill area near Forest Park. The local food scene, zoo, Rose Gardens and NIKE Headquarters are all just 10 minutes away with a short 25 minute drive to PDX airport. Bring Your friends & Family and enjoy the best of Portland!

Superhost

Villa in Gresham

4.85 out of 5 average rating, 13 reviews

Luxury 7-Bedroom Villa with Pool, Hot Tub & Sauna

**Luxury 7-Bedroom Villa with Pool, Hot Tub, Sauna, Gym, Pool Table & Entertainment Room, – Perfect for Large Groups** Experience ultimate relaxation in this stunning 7-bedroom villa, perfect for family reunions, corporate retreats, or group getaways. This spacious property 6,721 sqft offers high-end amenities, including a private outdoor pool (seasonal), hot tub, sauna, and gym, ensuring your stay is as comfortable as it is memorable.

Guest favorite

Tiny home in Damascus

4.92 out of 5 average rating, 733 reviews

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.

Top guest favorite

Guest suite in Central Northeast Portland

4.96 out of 5 average rating, 437 reviews

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!

Guest favorite

Home in Newberg

5 out of 5 average rating, 6 reviews

Private Wine Country Carriage House

With views of gardens, orchards, and vineyards, this restored and perfectly private 1912 Carriage House is secluded, restful, and beautifully restored. Luminous with hardwood floors, clawfoot tub, new linens, new appliances, and tasteful appointments. Walk to vineyards and a farmhouse brewery through orchards. Stroll the pond area bustling with wildlife. Enjoy the private pool in season and tennis court.