
Holiday rentals with a pool in Willamette Valley
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Top-rated rentals with a pool in Willamette Valley
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

The blueberry villa spa & heated pool
Welcome, 1981 farmhouse, top of Prune Hill neighborhood. Fully renovated modern farmhouse on 1acre, surrounded by trees. Heated, pool, hot tub, sauna, outdoor deck, patio and dining. Large yard, garden, blueberry orchard. LUXURY mattresses and bedding for optimal sleep. By far the most unique property on the hill and guaranteed to be a serene retreat and entertain all guests. Centrally located with quick access to downtown, local dining, Columbia river beaches, most amazing CR gorge & airport.

An Entertainment Oasis!
An open floorplan greets you & your friends. The island invites you into the kitchen with a full sized fridge & range. With drinks in hand, take the entertainment outdoors! The oversized covered patio is spacious enough for grilling, chilling, a tabletop firepit with seating galore. Soak up the sunshine with additional seating - or just soak in the jacuzzi. Take a summer dip & cool off in the pool, cozy up by the wood firepit or the sauna - or break a sweat at the adjacent gym. Your choice!

The Zen Den- Sauna, Hot Tub, Fireplace & Game Room
Welcome to The Zen Den! Beautifully updated private family cabin located steps away from the Sandy River and less than 30 minutes to ski resorts, mountain lakes, and hiking. Warm modern decor, gorgeous wood accents, and thoughtful touches to enjoy with family and friends. Two living areas with a downstairs theater and game room perfect for kids. A spacious, modern kitchen make cooking/relaxing at home dreamy. The backyard is equipped with a sauna, hot tub, fire pit, BBQ, and outside dining area!

Brand new "Safari tent" with pool/hot tub
This luxury safari-inspired tent site puts the glamour in glamping! Thanks to our sustainable tent, this glamping experience will "wow" your friends and family. Our tent conveniently located just 30 min from Portland. Just relax in the hot tub and swim in pool. We got breakfast area with microwave and coffee/snacks. Also we offer farm breakfast ($20/pp). Perfect for escaping off the grid, you and your family can bond together at “fire circle”, walk your dogs in the wilderness behind the property

Beautiful, Magical, Treehouse
"Glamping at its' best"! 16' x 16' TreeHouse, suspended between 3 large fir trees, queen size bed, loft w/2 twin beds, composting toilet, much more, situated on 20 acres with a pond. Gas heater, mini-fridge, microwave, coffee pot. IMPORTANT: this is a Tree House! Going up the spiral staircase is an adventure in itself, so pack small bags (or packs) (large suitcases are not appropriate). Be sure to look at the pictures & read our reviews... that provides the most information. Happy Travels!

Recreational Family Fun & Adventures Await
Entertain outdoors in a covered lit patio with grill and cooler. Stay warm with 2 propane firepits or by the campfire pit. Fenced in yard is pet friendly. Nearby Rec Center offers a Gym, Splash Pad, and Indoor Pool with Water Slide ($7 Day Pass). Enjoy basketball, baseball, soccer, and tennis all walking distance with our sports equipment. Explore many nearby parks with playgrounds and trails with our bicycles. Short drive to Washington Square Mall, restaurants, grocery stores, and more!

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. We have friendly dogs you may see outside, and we do not allow pets. No smoking in the unit. There is a smoking hut on the property you are free to use should you choose to (bring a container with you to dispose the remnants). SE Portland is a 30 min drive and downtown Portland a 45 min drive. One hour to Mt. Hood, & falls in the Gorge. Pool open 6/15 through 9/5.

Modern home - Billiards, Pingpong, Sauna & Views!
Enjoy panoramic sunset views over Eugene when you stay at this modern Skyline property. This luxurious newly-remodeled 3-bedroom house has a private sauna, game room, and is centrally located, 5 minutes from the University of Oregon and Matthew Knigh Arena and 10 minutes from Autzen Stadium. It is 5 minute walk to Hendricks Park and steps away from the famous Pre's Rock! This home is ideal for travelers, reunions, bridal groups, graduations, office retreats and romantic staycations!

A Rustic, Lodge Style Retreat with Pool & Hot Tub
Perched atop Parrett Mountain, Roosters Coop Retreat is a luxurious 4500 square foot lodge style escape set on 26 private acres in the heart of Oregon Wine Country. Surrounded by peaceful countryside, the property features an equestrian arena, ponds, gardens, and friendly farm animals, offering guests a true ranch style experience while remaining just a short drive from local wineries, charming towns, and some of the valley’s most loved restaurants and tasting rooms.

The Starburst Inn: Enclosed Heated Pool, Theater
****NEW POOL COVER AND THEATER ROOM!!!**** Bring your family to the luxurious 6 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, enclosed pool, theater room, and more! (Sixth bedroom opens to groups of 15+ to keep costs down for smaller groups)

Poolhouse of Portland Architectural Gem
Private guest house adjacent to Pietro Belluschi's "Sutor House", featured in Dec 2017 Dwell Magazine. Pool-house is 750 square feet, and features a master bedroom, full bath, living area with kitchenette, and access to and shared use (With our family) of the swimming pool in summer months (June, July, August). Surrounded by private wooded garden with Japanese plantings and water features. Located in Portland's West Hills, just minutes from Downtown.

Cozy A-frame hideaway w/hot-tub, fenced backyard
If you’re looking for the quintessential 70s A-frame experience, look no further! Classic 1973 A-frame with modern updates and mid-century vibe! This cozy 928 sq ft A-frame is located on wooded property at the foothills of Mt. Hood National forest near Sandy River. Perfect for a solo getaway, a couple’s retreat, or a small family escape. Skiing/snowboarding is 20-30 mins away. Sandy Ridge mnt biking - 5 mins away. Lots of hiking around.
Popular amenities for Willamette Valley rentals with a pool
House rentals with a pool

Fun & Relaxing Getaway!

Hot Tub + River + Pool | Family Cabin Near Mt Hood

Mt Hood Cabin: River, Trails, Pool, Dog-Friendly

Luxurious Log Home Retreat on the River in Albany

Cozy Mountain Home with Hot Tub and Fireplace

Creswell Farmhouse Pool+New Spa 13min to DT Eugene

Rose City Hideaway

Centrally located home w/pool
Apartment rentals with a pool

beautiful condo setting next to the river, pool ac

2BDR Peaceful Cozy retreat Family Friendly midterm

Whispering Woods Resort Two-Bedroom Loft

Relax Poolside! All-Season Base in Mt Hood Village

7-night Mt. Hood Summer Adventure Getaway

Whispering Woods Resort, 2 bedroom

A little bit of heaven, on Mt. Hood..

➤Whispering Woods , Welches, Oregon / 1BD Suite ➤
Other holiday rentals with a pool

Mountain Retreat, Yoga, Sauna, Walk to River Beach

Oasis Between City, River & Mountain. Damascus OR

Eagle’s Nest for Happy Glampers

KERNS-CHASE COTTAGE--cozy fireplace, kitchen, W/D

Wine Country Private Villa with Pool+Hot Tub- 3 BD

Mahalo Mountain Cabin *Games, Hot Tub & Fire Pit!*

Mt. Hood Summer Getaway: 1BR Apartment

Romantic Spa Escape
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- Silver Falls State Park
- Moda Center
- Laurelhurst Park
- Oregon Zoo
- Oregon Convention Center
- Providence Park
- The Grotto
- Portland Japanese Garden
- Enchanted Forest
- Airplane Home
- Tom McCall Waterfront Park
- Wonder Ballroom
- Oaks Amusement Park
- Powell's City of Books
- Evergreen Aviation & Space Museum
- Tryon Creek State Natural Area
- Arlene Schnitzer Concert Hall
- Pittock Mansion
- Hoyt Arboretum
- Reed College
- Sellwood Riverfront City Park
- Wings & Waves Waterpark
- Washington Square
- Portland Art Museum
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