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.

1 of 1 pages1 / 1
Guest favorite
Home in Gladstone
4.93 out of 5 average rating, 158 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. *Some uneven paths and slip hazards are present

Top guest favorite
Apartment in Portland
4.97 out of 5 average rating, 349 reviews

Comfortable and Quiet Sellwood Apartment

Modern 1BR Apt. Located on a quiet street in historic Sellwood. This apartment puts you just one block from 13th Ave, where you will find restaurants, cafés, and boutiques. Couple blocks from Sellwood Park with its pool, tennis courts, and beautiful river views. Walk just 5 minutes to the Willamette River or Oaks Bottom Natural Area. The bus stop is one block away and light rail within a 15-minute walk. With direct access to the Springwater Trail and easy connectivity across the Sellwood Bridge.

Top guest favorite
A detached guest house is presented with a deep blue exterior and white trim, featuring multiple windows that invite natural light. A wooden deck leads to a door, complemented by a small plant display and outdoor seating in a brick-paved area surrounded by greenery.
Home in Milwaukie
4.96 out of 5 average rating, 113 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.

Superhost
A spacious driveway leads to a two-level duplex, featuring a garage and lush greenery along the side. Steps ascend to the front entrance of the upper unit, framed by potted plants adding a touch of nature.
Guest suite in Milwaukie
4.79 out of 5 average rating, 376 reviews

Clean & Cozy "Private" Studio Suite

Private studio suite (500 sq ft). The unit is on the lower half of this 2 level duplex (host lives upstairs), private entry is on the ground level, self check-in, off street parking. There is a kitchenette, private bathroom with a stand-up shower, washer & dryer, queen bed, high speed internet, expanded cable, Netflix/Amazon Prime. Also, there is a lovely private patio for your enjoyment with a fire table. The space is warm and inviting, very safe location, great neighborhood and dog friendly.

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
Home in Milwaukie
4.97 out of 5 average rating, 177 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 favorite
Guest suite in Milwaukie
4.99 out of 5 average rating, 323 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
Guest suite in Portland
4.99 out of 5 average rating, 589 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
Guesthouse in Woodstock
4.96 out of 5 average rating, 504 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

Top guest favorite
Guest suite in Milwaukie
4.96 out of 5 average rating, 282 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.

Top guest favorite
A spacious wooden deck features a dining set with four chairs and a large, turquoise umbrella. Bright green plants surround the area, including flowering shrubs in the background and potted plants on the deck, creating a serene outdoor space.
Home in Milwaukie
4.97 out of 5 average rating, 286 reviews

Lovely Art Filled Home 15 min to Downtown

This comfortable and newly remodeled home sits on a quiet residential street in the Ardenwald neighborhood a few blocks from the Portland border in Milwaukie. It's thoughtfully decorated throughout with local original artwork that's been curated by us, also artists! The trendy Sellwood and Woodstock neighborhoods are a little over a mile away filled with locally owned shops, bars, and restaurants.

Guest favorite
Apartment in Milwaukie
4.89 out of 5 average rating, 177 reviews

1st floor, Sleek, Nature Lover's Studio

Kick back and relax in this calm, stylish, non-smoking studio. Because of our allergies, it is an animal free listing. Allergy safe, smoke free. There is no smoking, vapping, dabbing, or loud noise permitted. This is a quiet place to unplug. Lay by the lake or under the tall trees. Watch eagles, herons, and wild life.

Popular amenities for Milwaukie vacation rentals

When is the best time to visit Milwaukie?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$21,757 GYDG$21,966 GYDG$20,920 GYDG$19,874 GYDG$20,711 GYDG$21,339 GYDG$22,175 GYDG$21,966 GYDG$20,920 GYDG$21,757 GYDG$21,966 GYDG$22,594 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$6,276 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!

  1. Airbnb
  2. United States
  3. Oregon
  4. Clackamas County
  5. Milwaukie