Vacation rentals in Milwaukie

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Milwaukie

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A modern farmhouse exterior is presented with striking red siding and white trim, complemented by a manicured lawn. Two garage doors and a side entrance door are visible, framed by potted plants. Large windows allow natural light, enhancing the exterior's welcoming appearance.
Guesthouse in Portland
4.95 out of 5 average rating, 332 reviews

Woodstock Farmhouse

Modern farmhouse in the heart of Woodstock featuring 1 bedroom, 1 bathroom, living room, a fully stocked kitchen, AC, and a private deck. This space is a new construction farmhouse with lots of privacy. Enjoy off street parking with a private garden path leading to your front door. Just a short walk to some of SE Portland's hottest spots including Double Mountain Brewing, New Seasons Market, Otto's Sausages, Cloud City Ice Cream, Grand Central Bakery, The Woodstock Farmer's Market, and more.

Top guest favorite
A detached guest house is highlighted, featuring a blue exterior with large windows and a front door. A small patio area with a wooden table is visible, surrounded by lush greenery and decorative plants. A wooden fence provides additional privacy.
Home in Milwaukie
4.96 out of 5 average rating, 114 reviews

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.

Guest favorite
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 Happy Valley
4.9 out of 5 average rating, 135 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).

Top guest favorite
Apartment in Happy Valley
4.98 out of 5 average rating, 421 reviews

All the Views: A Private airbnb Near Portland!

Guests tell us they love this view! They also mention this downstairs apartment is very clean, spacious, comfortable and relaxing, with great wifi too. • 750 square feet of privacy, including the large private deck • Full kitchen, queen size bed and fast wifi • Leather furniture, large screen TV with HDMI capability (streaming only) • Private staircase leads to your garage entrance. No shared spaces. Level 2 EV charger Clackamas County License #108 No children or infants, sorry.

Top guest favorite
A bright, modern room features a Queen Murphy bed with crisp white linens and yellow accent pillows. Two windows allow natural light, with views of a fenced outdoor space, enhancing the airy atmosphere. A small built-in sofa is positioned beside the bed, offering additional seating.
Guest suite in Milwaukie
4.99 out of 5 average rating, 325 reviews

Room In Between

Private and secure entrance to this modern and 5-Star space! Comfortable Queen Murphy bed that converts to a sofa. Fast Wifi and Smart TV w/access to Netflix & Prime Video. Fenced yard with security gate entrance, off of private paved driveway, to lead you to your own private patio & room entrance. Self check-in is at 2pm or later. Check out is 11am. No pets. Smoking allowed on the outside patio only. Flat entrance pathway is well lit from your parking space to your room & patio.

Top guest favorite
The guest home is set behind a picturesque entrance adorned with an elegant gate and carefully arranged greenery. Paved stone pathways guide visitors through the lush surroundings, leading to the welcoming facade of the home, seamlessly integrated with the tranquil, tree-lined environment.
Guest suite in Portland
4.99 out of 5 average rating, 591 reviews

IndigoBirch: Luxurious Zen Garden Retreat: Hot Tub

Look no further- as a member of The IndigoBirch Collection™️, our guest home stands as a top-tier experience on Airbnb. Located two blocks away from Reed College, IndigoBirch is nestled on a quiet tree-lined street in the highly desired & historic neighborhood of Eastmoreland. Our location is perfect for the adventurer looking to explore Portland. The guesthouse is two blocks away from public transportation, 12 minute drive to downtown Portland, and 20 minutes to PDX Airport.

Top guest favorite
A vibrant area features a comfortable gray couch paired with a glass coffee table. A colorful rug with bold patterns adds warmth to the space, while a potted plant and wall art enhance the cheerful atmosphere.
Apartment in Milwaukie
4.94 out of 5 average rating, 342 reviews

Peaceful Oasis in Portland Neighboring Milwaukie

Our names are Danusia and Ron. Welcome to our world. We have done the best with our resources to create a welcoming oasis . Portland is a great place to live and we're glad to invite you. We are offering a light, sunny second story apartment. Portland is known for its eclectic food carts, brew pubs, music venues, theatres,restaurants and its special brand of quirkiness. Upon your arrival,you will not have to travel far, we are 20 minutes from the airport,15 from downtown.

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 Southwest Portland
4.97 out of 5 average rating, 160 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.

Top guest favorite
An open-space studio features high ceilings with wooden beams, enhancing the airy feel. A queen-sized bed is set against the wall with soft linens. A small kitchenette and dining area are visible, with a full bathroom enclosed in glass. Natural light brightens the interior.
Guesthouse in Woodstock
4.96 out of 5 average rating, 505 reviews

SE Portland Guest Cottage

The guest cottage offers self check-in. It is located in a quiet neighborhood in SE Portland. High ceilings make this studio airy and bright. We think of it as a perfect hotel room without the hotel. The small galley kitchen has everything you need to cook a gourmet meal including filtered water. There is a full bathroom with tub and shower. The cottage stands on its own making it perfect for coming and going as you please. City of Portland Permit #24 013532

Superhost
The cabin, nestled among towering cedar trees, features a rustic exterior with warm lighting from the windows. A serene creek flows nearby, with smooth stones and mossy patches lining the water's edge. A wooden bridge connects to the surrounding natural landscape.
Cabin in Milwaukie
4.88 out of 5 average rating, 753 reviews

Rustic Creekside Cabin

This tranquil hideaway feels like you're in the middle of the forest, but is just minutes from Portland. Relax next to the burbling creek surrounded by towering cedar trees. The MAX Orange line and downtown Milwaukie are only five minutes away. Built in 1928, the cabin has one bedroom and bathroom, living room, full kitchen and central heat. The bedroom has one queen bed and an en suite bathroom. There is a pull-out queen futon in the living room.

Top guest favorite
A modern yellow carriage house is set in a park-like backyard, surrounded by greenery. The structure features a second floor balcony with outdoor seating, and stairs leading down to a landscaped yard. Mature Douglas Fir trees provide shade, while a garage is located below.
Guesthouse in Portland
5 out of 5 average rating, 118 reviews

Stellar Sellwood Carriage House

Whether your here for business or pleasure, come and stay in one of Sunset Magazine's Best Places to Live in the West neighborhoods. A modern 650 sq. ft. 1-bedroom carriage house tucked in the heart of Sellwood is perfect for the solo guest or couples. Lots of natural light, hardwood floors, A/C, full equipped kitchen, plus washer/dryer - all within walking distance to restaurants, local attractions, and public transit.

Top guest favorite
A comfortably appointed studio features a queen bed with decorative pillows and a soft blanket. A seating area includes a modern chair beside a sleek storage unit, with a coffee setup and a mini refrigerator. Natural light filters through sheer curtains, enhancing a relaxed atmosphere.
Guest suite in Milwaukie
4.96 out of 5 average rating, 283 reviews

Cozy, Private Studio

This beautifully remodeled studio with private bathroom, entrance and off-street parking is nestled in a quiet, relaxed neighborhood in Milwaukie- a neighborhood south of Portland. Extremely comfortable queen bed will provide you with an excellent nights sleep. Great atmosphere for those traveling for business or vacation. Located 5 minutes from I-205 and a 10-minute drive to downtown Portland.

Popular amenities for Milwaukie vacation rentals

When is the best time to visit Milwaukie?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$21,765 GYDG$21,975 GYDG$20,928 GYDG$19,882 GYDG$20,719 GYDG$21,347 GYDG$22,184 GYDG$21,975 GYDG$20,928 GYDG$21,765 GYDG$21,975 GYDG$22,603 GYD
Avg. temp5°C7°C9°C12°C15°C18°C21°C21°C19°C13°C8°C5°C

Frequently Asked Questions

  • What are the best places to stay in Milwaukie?

    Stays in downtown Milwaukie or in residential neighborhoods near parks are frequently suggested. Many accommodations have easy access to the river, green spaces, and a walkable local dining scene.

  • What are the best things to do in Milwaukie with kids?

    Families can explore riverside parks, playgrounds, and community gardens in Milwaukie. Seasonal farmers markets, public art walks, and family-focused events frequently draw visitors of all ages.

  • What are some of the best things to do in Milwaukie?

    Explore public art downtown, walk along riverside trails, and visit local farmers markets or craft breweries. Community events and green spaces invite visitors to connect with local culture and nature.

  • How is the weather in Milwaukie?

    Milwaukie has cool, wet winters averaging 36–47°F (2–9°C), and mild to warm summers with afternoons up to 82°F (28°C) and lighter rainfall. Layered clothing and a rain jacket are suggested, especially in the rainier months.

  • When is the best time to visit Milwaukie?

    Late spring through early autumn is often recommended in Milwaukie, when days are milder and rainfall is lighter. July and August have warm afternoons around 82°F (28°C), which are popular for outdoor events and activities.

  • What are the best places to visit in Milwaukie?

    Explore downtown Milwaukie for shops, eateries, and public art, or visit local parks along the river for open green spaces. Farmers markets and community gardens are often recommended for a glimpse into local life.

  • What are some hiking trails in Milwaukie?

    Milwaukie has riverside paths and greenway trails, often recommended for casual walks and family outings. Nature areas nearby invite exploration through shaded forests and local wildlife habitats.

  • What are some family activities we can do in Milwaukie?

    Visit riverside parks for play and picnics, attend community festivals, or stroll through the farmers market together. Family-friendly attractions and public art spaces are popular with visitors traveling with children.

  • What are some of the best day trip ideas from Milwaukie?

    Day trip ideas include exploring Portland’s cultural neighborhoods, hiking in local forests, or visiting regional wineries and farm stands. Many travelers enjoy experiencing gardens, wildlife centers, or scenic walks just outside the city.

  • Are there any pet friendly accommodations available in Milwaukie?

    Milwaukie has a variety of pet-friendly vacation rentals, so you can bring your companion along. Many hosts in residential neighborhoods are open to pets—be sure to check each listing’s policies before booking.

  • What are some local tips for visiting Milwaukie?

    Bring comfortable shoes to explore parks and neighborhoods, and consider a reusable bag for farmer’s market finds. Locals appreciate early mornings for quieter walks, and rain gear is useful outside summer months.

  • What is Milwaukie known for?

    Milwaukie is known for its riverside parks, community-driven farmers markets, and its legacy in agriculture. The city is also recognized for a vibrant downtown, hosting locally owned shops and public art installations.

  • What are the best hidden gems to explore in Milwaukie?

    Look for community gardens, smaller parks tucked in neighborhoods, and independent shops for unique finds. Locally curated art spaces and historic buildings around downtown often surprise visitors seeking quieter spots.

  • What are the best foods to try in Milwaukie?

    Milwaukie’s food scene celebrates Pacific Northwest flavors, including locally roasted coffee, fresh produce, and artisanal baked goods. Many visitors enjoy seasonal farmers markets, craft breweries, and independent restaurants serving contemporary American dishes.

  • What should I bring for a trip to Milwaukie?

    Pack layered clothing, a light rain jacket, and comfortable shoes for outdoor walks. A reusable bag is handy for farmers market purchases, and if visiting in summer, include sunscreen and a hat.

  • What is the nightlife in Milwaukie like?

    Milwaukie has casual bars, craft breweries, and live music venues, especially around downtown. Evening events and community gatherings bring a relaxed, social atmosphere, often centered on local food and drinks.

  • What are the most popular events or festivals in Milwaukie?

    Milwaukie has community farmers markets throughout the warmer months, along with arts and music festivals in late spring and summer. Seasonal celebrations and street fairs are often highlights for visitors and locals.

  • Are there family friendly vacation rentals in Milwaukie?

    Milwaukie has many family-friendly vacation rentals, often located in quiet neighborhoods or near parks. Parents can filter for amenities such as kitchens, multiple bedrooms, and outdoor spaces to suit their family’s needs.

Quick stats about vacation rentals in Milwaukie

  • Total vacation rentals

    Explore 120 vacation rentals in Milwaukie

  • Nightly prices starting at

    Milwaukie vacation rentals start at G$6,279 GYD per night before taxes and fees

  • Verified guest reviews

    Over 9,090 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wi-Fi availability

    120 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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