
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.

Brand new 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.

Knotty Pine - Log Home
Located in the heart of historic Willamette district in West Linn is a beautiful log home situated on 1.3 acres. Short walk to Willamette park (next to the river), walk to shops & restaurants. Private entrance, easy parking. Apartment is on one level, no stairs (800 square feet). Living room, full size kitchen and two bedrooms. Master- king size bed and Guest room - double bed, no closet. Includes a laundry room . Great for extended stay. Close to I-205, 25 min. to PDX and downtown Portland.

Springwater Retreat: Relax in quiet comfort
In a tucked-away corner of Portland’s closest suburb, you will find our private duplex on a large, private park-like lot. We are located 8 blocks from the Springwater Corridor, a popular biking/walking trail on the Portland border. It is a lovingly furnished home: queen bedroom, twin-over-full bunk bedroom, bonus room that has a very comfortable queen sofa bed and foozball table, fully equipped kitchen for real cooking, dining area, and huge private yard. Only the off-street parking is shared.

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).

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. *Not ideal for those with mobility issues*

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.

#StayinMyDistrict Sellwood Coco Rose Retreat
#StayinMyDistrict Sellwood Retreat! This private garden Retreat is located in the heart of Sellwood! Live like a local and experience a vibrant SE Portland neighborhood! Known for its “walkability” and “friendly neighborhood feel”! Walk (1 block) to local hotspots, nightlife, dining, coffee, & boutique shops, from this comfortably appointed Queen Studio Suite. Relax and enjoy a glass of wine on the private patio. Kitchenette & kitchen amenities, W/D in unit, FREE street parking!

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.

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!

Paradise in Sandy, breathtaking views of Mt. Hood

The Art Farm

The Starburst Inn: Enclosed Heated Pool, Theater

Scandinavian Modern Farm House in Wine Country

3-Bed Cowboy Cabana w/ Hot Tub!

Rose City Hideaway

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

The Redwood House 2.0 Safe Cozy 2BR Pet Friendly

Luxury Craftsman | Uniquely Portland | King Beds

Central Stay w/Treehouse! Near Downtown & Nature

Comfortable spacious home!

Spotless, Spacious & Private 2 Bedroom Guest Suite

The Clinton Modern

Cozy Boho Inspired Duplex - with 4 person HOTUB!
Modern Guesthouse in Portland's Central Eastside
Private house rentals

Charming Tiny Forest Home, PDX next to Lake Oswego

Sunny Sellwood Studio

Mount Scott Skyline Views!

Blanton House

Newly Built Modern Escape | EV, Gym, Pets

Enchanting Private Bungalow in Alberta Arts

Modern Comfort Nest

Accessible home with roll in shower
When is the best time to visit Milwaukie?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $118 SGD | $135 SGD | $141 SGD | $141 SGD | $139 SGD | $167 SGD | $164 SGD | $161 SGD | $144 SGD | $149 SGD | $164 SGD | $167 SGD |
| 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 $26 SGD per night before taxes and fees

Verified guest reviews
Over 2,860 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 30 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 patio Milwaukie
- Rentals with a fireplace Milwaukie
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- Moda Center
- Columbia River Gorge National Scenic Area
- Mt. Hood Skibowl
- Silver Falls State Park
- Timberline Lodge
- Laurelhurst Park
- Oregon Zoo
- Mt. Hood Meadows
- Providence Park
- Enchanted Forest
- Portland Japanese Garden
- The Grotto
- Beacon Rock State Park
- Wonder Ballroom
- Powell's City of Books
- Wings & Waves Waterpark
- Hoyt Arboretum
- Oaks Amusement Park
- Tom McCall Waterfront Park
- Portland Art Museum
- Arlene Schnitzer Concert Hall
- Pittock Mansion
- Evergreen Aviation & Space Museum
- Council Crest Park




