House holiday rentals in Milwaukie

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Top-rated house rentals in Milwaukie

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Guest favourite
A cozy living area features a large area rug with a floral design in shades of blue and gray. Two elegant armchairs are positioned beside a wooden console, which has a flat-screen TV mounted above it. Natural light filters in through large windows.
Home in Ardenwald
4.93 out of 5 average rating, 214 reviews

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.

Top guest favourite
A spacious bed is framed by a wooden headboard, complemented by crisp white linens and fluffy pillows. A light beige quilt covers the bed, providing a soft texture. Next to the bed, a simple nightstand with a glass lamp adds a functional touch to the design.
Home in Portland
4.95 out of 5 average rating, 154 reviews

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

Guest favourite
A mid-century living space features high vaulted wood ceilings and large windows that invite natural light. A leather sofa and patterned rug provide comfort, while a kitchen island with bar stools enhances functionality. Artwork adorns the wall, adding a touch of character to the room.
Home in Multnomah
4.95 out of 5 average rating, 128 reviews

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.

Guest favourite
The living room features a cozy layout with a large window providing natural light. A 55" UHD Roku TV is mounted on the wall, alongside a comfortable chair and a rustic coffee table. A portable air conditioner is positioned nearby, enhancing the space's functionality.
Home in Ardenwald
4.83 out of 5 average rating, 166 reviews

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.

Guest favourite
A fire pit is illuminated in the foreground, casting warm light on the surrounding stones. In the background, a colorful sunset paints the sky with shades of orange and pink, while trees and distant hills create a serene landscape.
Home in Lents
4.88 out of 5 average rating, 105 reviews

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).

Guest favourite
The open living space features a sectional couch with cushions, a wooden dining table, and chairs in a well-lit area. A television is mounted on the wall, with kitchen and dining areas visible in the background, illuminated by natural light from large windows.
Home in Gladstone
4.92 out of 5 average rating, 145 reviews

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*

Top guest favourite
A cozy kitchen is highlighted by warm wood cabinetry and a decorative countertop. A binder titled 'Crossroads Country Cottage' is prominently displayed, accompanied by a flower vase filled with vibrant blooms. Colorful stained glass pieces allow natural light to filter in, adding charm to the space.
Home in Milwaukie
4.96 out of 5 average rating, 170 reviews

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.

Top guest favourite
A spacious family room features a large L-shaped couch with comfortable seating. A plush green ottoman rests on a striped rug, complementing a contemporary armchair. Natural light filters through multiple windows, illuminating the room, which includes a TV and a cozy gas-lit fireplace.
Home in Portland
4.94 out of 5 average rating, 256 reviews

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.

Top guest favourite
An inviting living space showcases an open floor plan with large windows offering views of the surrounding landscape. Comfortable seating options include a spacious couch and two armchairs, arranged around a coffee table. A dining area is visible, featuring a long table with chairs, illuminated by overhead lighting.
Home in West Linn
4.97 out of 5 average rating, 122 reviews

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.

Top guest favourite
A warm dining area is showcased with a wooden table at its center, surrounded by decorative plants. An archway leads into a cozy living room featuring a gas fireplace, comfortable seating, and large windows that invite natural light into the space.
Home in Milwaukie
4.98 out of 5 average rating, 109 reviews

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!

Guest favourite
A bright and modern living area features a comfortable brown sofa paired with a light blue area rug. A small coffee table sits nearby, and a wall-mounted map of Portland adds character. The open kitchen showcases white cabinetry and stainless steel appliances, enhancing the functional space.
Home in Portland
4.91 out of 5 average rating, 120 reviews

Newer Built Fopo Gem, Close to Everything!

Our newly built bright and modern guest house is fully equipped with all the modern amenities you need to relax and recharge after a day of adventuring in the city. It is located in the popular FoPo (Foster-Powell) district and is the perfect location for exploring Portland. Heaps of local coffee shops, bakeries, food carts, bars and breweries are just minutes of walks away. Also easy access to local parks, shopping districts. We would love to host you!

Top guest favourite
A modern living space is presented, featuring a comfortable couch and an accent chair in blue. A small dining table accommodates four. A wet bar area is equipped with a sink and microwave. Warm lighting enhances the inviting atmosphere of the room.
Home in Richmond
4.96 out of 5 average rating, 302 reviews

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 house rentals in Milwaukie

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Avg. price$120 SGD$137 SGD$143 SGD$143 SGD$141 SGD$169 SGD$167 SGD$163 SGD$146 SGD$146 SGD$161 SGD$161 SGD
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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 3,010 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!

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