
House vacation 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.

Charming Remodeled Home in SE
Unique, charming 1920's home, just minutes from Portland by bike or car, fully remodeled, w/custom handmade furnishings made w/local hardwoods. Our cozy home has a fully loaded gourmet kitchen. Master suite w/king bed and a top of the line Stearns and Foster mattress. 2nd bedroom w/brand new queen nectar mattress. King sleeper sofa w/memory foam mattress. Covered patio, plenty of outdoor seating, natural gas BBQ, and firepit. Fenced yard for pets. Local fav cafe across the street.

Milwaukie Easy-Centrally located, Close to PDX
Our home is a spacious cozy contemporary home, complete with an outdoor deck, and a beautifully decorated interior with contemporary pieces that complete the design of our home. Windows in living & dining space are across from each other bringing in ample light. Our space is furnished with various mid-century, modern and contemporary pieces that complete the home. Shared Spaces •Parking area •On site laundry shared with other tenant, tenant has a separate living area with no other shared spaces

Portland Modern
Welcome to our Midcentury Modern – a true masterpiece inspired by the iconic Frank Lloyd Wright. Nestled on a lush 1/3 acre private retreat, this architectural gem is just minutes away from Multnomah Village and Gabriel Park. Immerse yourself in the timeless beauty of this completely renovated mid-mod marvel, where high vaulted open beamed wood ceilings adorn every room on the main floor. This house is perfect for friend groups, families or corporate retreats. Note: 4 bedroom, 2 bath, 2 kitchen.

New Home Near it All on Division w/ EV Charger
Welcome to The Eloise — a bright, art-filled home centrally-located in the bustling Division/Clinton district of SE Portland. This beautiful ADU has it all. A suite with king bed & bathroom with a luxurious shower; workspace w/ speedy wi-fi; lounge; two TVs a full kitchen, & EV charger. Premium amenities & local treats await you. Tucked into a quiet street just off Division, you’re within walking distance to restaurants, shops, bars, venues, bus & TriMet lines & a 5-minute drive to Downtown.

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.

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.

Spacious Forest Retreat w/ Hot Tub & Views
In the woods, next to a creek, but still in Portland! Forget your worries in this spacious and serene space. There is a private entrance to this large two story guest suite, which includes a family room, living area with dining area and kitchenette, bedroom and bathroom, central AC, and private balcony. Located in a quiet neighborhood, close to hiking trails in Woods Memorial Park. A 3-minute drive or 1 mile walk to popular Multnomah Village; 15 minutes from Downtown Portland.

Hidden Springs Hideaway
Privacy, tranquility and views abound at this beautiful elevated home. Enjoy Mt. Hood views on a tranquil 1/2 acre lot. The open floor plan is spacious with professionally designed new furnishings. High end linens and bedding in every room including bamboo sheets, coops pillows, and nice beds. The home is completely remodeled with gorgeous aesthetics (except kitchen). Relax downstairs in the family on the extra deep couch while watching a movie on the huge flat screen.

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!

Cozy and Walkable 1 bedroom daylight basement
Our basement has been newly renovated. Brand new bedroom, beautiful bathroom and living space. The living space includes a 57” Smart TV and couch. The wet bar features a mini fridge, sink and Keurig Coffee maker. The bedroom has 1 queen sized bed with hotel luxury 1800 bedding sheets, a dresser, full length mirror and natural light window. Our house is centrally located with dozens of restaurants, bars and coffee shops just a short walk away!
Popular amenities for Milwaukie house rentals
House rentals with a pool

Frankie's Place; Walkable Craftsman luxury!

Paradise in Sandy, breathtaking views of Mt. Hood

The Starburst Inn

Scandinavian Modern Farm House in Wine Country

5bdrm,Heated Pool, Hot Tub, Sauna.

3-Bed Cowboy Cabana w/ Hot Tub!

Rose City Hideaway

Serene Oasis: Swim Spa, Sauna, huge deck and grill
Weekly house rentals

Woodlawn Retreat

Portland Southwest Suite Stay

Modern Apt | Close to Everything

Mt Tabor House Salmon Room

Modern Central Portland House

Updated Woodland Garden Retreat & Spa

RoseCity Getaway - New Modern Private Home

Charming home on private street with hot tub
Private house rentals

The Redwood House 2.0 Safe Cozy 2BR Pet Friendly

Sunny Sellwood Studio

Central Stay w/Treehouse! Near Downtown & Nature

Secluded Studio

Comfortable spacious home!

Newly Built Modern Escape | EV, Gym, Pets

Woodsy PNW A-Frame

Cozy Newly Remodeled Duplex
When is the best time to visit Milwaukie?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $128 CAD | $147 CAD | $154 CAD | $154 CAD | $151 CAD | $181 CAD | $179 CAD | $175 CAD | $156 CAD | $156 CAD | $173 CAD | $173 CAD |
| 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 vacation rentals
Explore 60 vacation rentals in Milwaukie

Nightly prices starting at
Milwaukie vacation rentals start at $28 CAD per night before taxes and fees

Verified guest reviews
Over 3,010 verified reviews to help you choose

Family-friendly vacation rentals
40 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
60 of Milwaukie vacation 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!
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- Moda Center
- Laurelhurst Park
- Oregon Zoo
- Timberline Lodge
- Silver Falls State Park
- Providence Park
- Enchanted Forest
- Mt. Hood Skibowl
- The Grotto
- Portland Japanese Garden
- Mt. Hood Meadows
- Wooden Shoe Tulip Festival
- Beacon Rock State Park
- Wonder Ballroom
- Powell's City of Books
- Hoyt Arboretum
- Tom McCall Waterfront Park
- Wings & Waves Waterpark
- Pumpkin Ridge Golf Club
- Oaks Amusement Park
- Skamania Lodge Golf Course
- Domaine Serene
- Portland Art Museum
- Bridal Veil Falls State Scenic Viewpoint




