House vacation rentals in Milwaukie

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Top-rated house rentals in Milwaukie

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Guest favorite
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, 220 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.

Guest favorite
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, 140 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.

Top guest favorite
A modern living space features a teal sectional sofa adorned with vibrant throw pillows. A glass coffee table rests atop a textured rug, and the kitchen showcases wooden cabinetry and stainless steel appliances, with natural light enhancing the atmosphere.
Home in Ladd's Addition
5 out of 5 average rating, 245 reviews

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.

Top guest favorite
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
4.97 out of 5 average rating, 172 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.

Guest favorite
Home in Westmoreland
4.9 out of 5 average rating, 294 reviews

#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!

Guest favorite
A modern living space features a comfortable gray sofa adorned with patterned throw pillows. Two tables in varying heights are placed in front. A large window allows natural light in, and a nearby plant adds a touch of greenery. Laundry appliances are accessible through a door.
Home in King
4.91 out of 5 average rating, 199 reviews

Modern Apt | Close to Everything

Located within the trendy Boise neighborhood and only minutes to central Portland is this chic sun-filled apartment that offers all the modern comforts of home. With stylish décor and bright open plan living, the apartment features a fully equipped kitchen, soft comfortable furnishings, a spacious master bedroom and a sparkling modern bathroom. Walk to the popular Williams and Mississippi streets with its top restaurants, coffee shops and Portland’s world-famous food carts.

Guest favorite
An open-plan studio features a spacious layout with a comfortable bed dressed in soft linens, a plush sofa facing a wall-mounted Smart TV, and a dining table set for two. A modern kitchenette and a full bathroom are positioned in the background, enhancing convenience.
Home in Westmoreland
4.86 out of 5 average rating, 186 reviews

Stylish Open Studio | Mins to ❤ of Portland

Located within a charming Westmoreland bungalow home is this separate private studio just a short 7-minute drive to the heart of Portland. The studio features soft comfortable furnishings, access to streaming apps on the Smart TV, a fully equipped kitchenette, a sparkling full bathroom, and a spacious living area with a modern open plan design. Walk or bike to coffee shops, grocery stores, restaurants, breweries and the popular Westmoreland Park all right on your doorstep.

Guest favorite
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
4.97 out of 5 average rating, 118 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!

Top guest favorite
A charming outdoor area is visible, featuring a stone pathway leading to a cozy seating arrangement with two black chairs. The bungalow is framed by lush greenery, with warm light emanating from the windows, inviting a peaceful ambiance.
Home in Multnomah
4.96 out of 5 average rating, 130 reviews

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.

Superhost
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
4.88 out of 5 average rating, 140 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!

Superhost
The exterior of a renovated farmhouse is showcased, featuring a red wooden façade with a sloped roof. Surrounding vegetation is visible alongside a gravel driveway leading to the home. A garage structure is seen nearby, complementing the tranquil outdoor environment.
Home in Milwaukie
4.79 out of 5 average rating, 316 reviews

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.

Top guest favorite
A cozy living area includes a tufted teal couch with bright yellow pillows, complemented by a round dining table and chairs. A kitchen area with dark cabinetry and stainless steel appliances is visible in the background, illuminated by soft overhead lighting.
Home in South Tabor
4.93 out of 5 average rating, 239 reviews

Charming South Tabor Apartment!

Charming, remodeled, clean one-bedroom basement apartment with some natural light. Private entrance and patio. In a quiet, safe SE neighborhood central for exploring Portland. Walk to Mt. Tabor Park. Furnished in mid-century style, with high-end cotton linens, bedding and towels; full kitchen and bathroom. Large flat-screen TV, full Cable, HBO, etc. Very reliable WiFi. We welcome all nationalities, ethnicities and creeds. We are LGBT-friendly.

Popular amenities for Milwaukie house rentals

When is the best time to visit Milwaukie?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$19,243 GYDG$21,962 GYDG$23,007 GYDG$23,007 GYDG$22,589 GYDG$27,191 GYDG$26,772 GYDG$26,145 GYDG$23,426 GYDG$24,262 GYDG$26,772 GYDG$27,191 GYD
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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 G$4,183 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,860 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Milwaukie vacation rentals include wi-fi 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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