
House holiday rentals in Milwaukie
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Top-rated house rentals in Milwaukie
Guests agree: these houses are highly rated for location, cleanliness and more.

Forested Hygge House Getaway
Relax in a Gladstone oasis overlooking an untouched trail and forested area. A cozy, bright, and private spot. I hope you connect with my affinity for vintage art and clean lines! You’ll have the entire house and 1/3 acre to yourself. Less than 30 mins from most anywhere in Portland Metro, 10 mins to Oregon City, and 1 hr to Mt. Hood. This is a dog friendly (no cats), non-smoking house. The large yard is on a dead-end street, though not fenced. *Some uneven paths and slip hazards are present

Miranda's Lodge- cozy place with hot tub
Miranda's farm has been popular camping destination place in Molalla, OR during the summer. We decided to open Farm Lodge that will be welcoming guests all year around and close to the city, only 10min downtown Portland, 15min Airport. This dream home has been created with lots of love, imagination and farm style décor. Its cozy, sunny, happy, comfortable and healthy home, close to shopping and restaurants. Private entrance and fenced yard. Everything is brand new, you will want to stay forever.

Secluded Studio
This a fully private and detached guest house is quiet and relaxing. Walk down your very own pathway to a completely private, safe and secure patio with a quaint garden, a small yard and outdoor seating. With tall ceilings and a large nice bright kitchen, this place is very comfortable. Blackout curtains. Close to many desirables: Max Orange Line Commuter Train, Reed College, Woodstock, Sellwood, & East Moreland & Milwaukie Providence Hospital. Ride, walk or run along the Springwater Corridor.

1000+ sq private 2b1.5b unit in gated area
A private unit in gated resort like homesite centrally located. Kaiser hospital , Clackmas TC and Happy Valley TC are mins drive away. 25 mins to PDX, NW 23rd ave, Portland downtown and 50 mins to Mt Hood. Very quite and you can wake up to bird chirping in am. Evergreens provide nice soothing color year round. Patio and deck with dinning table give you chance to enjoy outdoor and sunset if weather permits. Full kitchen. Up to 1gb super fastinternet. Spacious for 4 no extra charges. Central a/c.

RoofTop FirePit, HotTub & Outdoor Theater
Our large (1,500sq ft) space (private access), has a bedroom, bathroom, living room w/ a fireplace, hot tub, full gym as well as a kitchenette w/ full sized fridge, keurig, microwave, air fryer, toaster oven, single burner, and laundry facility. Smart tvs, hammocks and a rooftop firepit are in the outdoor entertainment area. LGBT & BIPOC friendly. Gym, hot tub and laundry are shared with owners but guests have priority access. Close to Mt Hood Wilderness (45mins) & Downtown Portland (15mins).

Gladstone Garden Retreat
Lovely updated bungalow, private & quiet garden retreat in old Gladstone home, walking distance to Clackamas River. Gated yard with garden, grill, outdoor dining, east facing windows, private keyless entrance, off street parking. Tons of natural light; beautifully decorated; AC, HDTV, Wi-Fi, Cable TV with movie channels; Queen beds; designer appliances for gourmet meals; rock fireplace w/ gas, soaking tub upstairs, updated shower downstairs; washer & dryer. Pet friendly patio w/ doggie door.

Cozy, Modern Farmhouse, King Bed, Great Yard, Pets
Enjoy your stay in the quaint, Oak Grove neighborhood of Portland a block from the old historic trolly trail. Minutes to the river, close to downtown, ample dog parks make this spot perfect for your getaway. Our family poured our hearts into designing a modern and cozy space that our family loves to visit. We're so very excited that we get to share that with you! We've got a yard that the whole family will love and I know you'll make some priceless memories here, just as we have. Welcome!

Crossroads Country Cottage
Conveniently located at the crossroads of HWY 224 and SE Lake Road, our home, cottage and garden are the last remnants of a time gone by and what was once a large family farm. When you walk through the private gate leading to the cottage, you might feel you have stepped through a portal into another time. Everything about the cottage is secluded, peaceful and private. We are pleased to have many return visitors. The garden features a waterfall, chairs and table, BBQ and fresh herbs.

Oak Grove Easy-Centrally located w/King Bed
Welcome to this updated and comfortable, light filled home in the Oak Grove neighborhood of Portland. A short distance to the river, downtown, parks, restaurants and all things Portland-make this a perfect vacation space for your family and guests. We put a lot of love in to designing the interior to be stylish, yet comfortable and seamless to ensure you feel right at home. Ample space in our park-like backyard to relax , entertain or play a summer game of corn hole!

Multnomah Village Hideout
Explore our new, artist-built bungalow in Multnomah Village, Portland. This cozy space sleeps four with a queen bed upstairs and a pullout couch downstairs. Steps away are charming cafes, shops, and a park with hiking trails and dog parks. Enjoy local activities like bingo and dining on pet-friendly patios. Complete with essentials including laundry and a breakfast nook, this bungalow is perfect for both short and extended stays, offering a unique Portland experience.

“Sucker Creek Inn” - with partial lake view
This home is in a great location only a 10 minute walk to downtown Lake Oswego where you'll find a wide variety of restaurants, bars, and shopping. It's also just a five minute walk from the Willamette River, so bring your kayaks and SUPs to explore all that Lake Oswego has to offer, or take a short Uber ride (10 minutes) into downtown Portland. Lastly, the lot is next to one of the oldest homes in Lake Oswego- built when Lake Oswego was known as Sucker Creek

Cozy Creekside Farm House Renovated on 1/3 Acre
We have power! Private farm house on 1/3 acre with creek running through the yard. Vegetation surrounds you and neighbors are limited. Fully renovated house with new floors/plumbing/electrical. 3 cable televisions with high speed internet! Close to the Spring Water Corridor Trail for walks/runs/bike-rides. 5 minutes from Woodstock 15 minutes from downtown 20 minutes to airport Close to Cartlandia, Portland's original food carts. $30 per pet.
Popular amenities for house rentals in Milwaukie
House rentals with a pool

Frankie's Place; Walkable Craftsman luxury!

One level Entertainers Dream *Heated Pool*

The Art Farm

The Starburst Inn: Enclosed Heated Pool, Theater

An Entertainment Oasis!

3-Bed Cowboy Cabana w/ Hot Tub!

Rose City Hideaway

1BR - Private House, Pool, Hot Tub & Forest Trails
Weekly house rentals

Sunny Sellwood Studio

Central Stay w/Treehouse! Near Downtown & Nature

Spotless, Spacious & Private 2 Bedroom Guest Suite

Comfortable spacious home!

Blanton House

Beautifully Renovated 1920 Home | EV, Pets

Golden Era Reimagined

Accessible home with roll in shower
Private house rentals

Flower-Darling Guest Suite

Charming Tiny Forest Home, PDX next to Lake Oswego

Rose Meadow Oasis

Wowzaa! Theatre room, Spa&Sauna, Game room galore!

Rummer House - Stunning Mid-Century Modern

Aqua Star – Iconic Floating Home on the Columbia

Spruce Cottage

The Colton Retreat
When is the best time to visit Milwaukie?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £68 | £78 | £81 | £81 | £80 | £96 | £95 | £92 | £83 | £86 | £95 | £96 |
| Avg. temp | 5°C | 7°C | 9°C | 12°C | 15°C | 18°C | 21°C | 21°C | 19°C | 13°C | 8°C | 5°C |
Quick stats about house rentals in Milwaukie

Total holiday rentals
Explore 60 holiday rentals in Milwaukie

Nightly prices starting at
Milwaukie holiday rentals start at £30 per night before taxes and fees

Verified guest reviews
Over 3,020 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
60 of Milwaukie holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Milwaukie rentals

4.9 Average rating
Milwaukie stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
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- Rentals with a washing machine and dryer Milwaukie
- Rentals with a firepit Milwaukie
- Family-friendly rentals Milwaukie
- Rentals with a patio Milwaukie
- Rentals with a fireplace Milwaukie
- Pet-friendly rentals Milwaukie
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- Moda Center
- Columbia River Gorge National Scenic Area
- Silver Falls State Park
- Timberline Lodge
- Laurelhurst Park
- Oregon Zoo
- Mt. Hood Skibowl
- Mt. Hood Meadows
- Providence Park
- Enchanted Forest
- The Grotto
- Portland Japanese Garden
- Beacon Rock State Park
- Wonder Ballroom
- Tom McCall Waterfront Park
- Powell's City of Books
- Hoyt Arboretum
- Wings & Waves Waterpark
- Arlene Schnitzer Concert Hall
- Oaks Amusement Park
- Portland Art Museum
- Airplane Home
- Pittock Mansion
- Reed College




