Vacation rentals in Milwaukie

4.93 out of 5 average rating, 203 reviews

A covered patio features two green lounge chairs with patterned cushions facing a small side table. A gas BBQ is positioned nearby on the left, with a decorative side table against the wall. Wooden beams provide support overhead, surrounded by a lush, green hedge.

Home in Milwaukie

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.

4.96 out of 5 average rating, 136 reviews

An outdoor wooden staircase leads upward, featuring sturdy railings on one side. The steps are clear and well-maintained, with a backdrop of green foliage hinting at the surrounding urban forest. Natural light enhances the inviting pathway to the entrance.

Guesthouse in West Linn

Charming one bedroom apartment in the forest.

This unique apartment above a garage/shop , detached from the main house. Tucked away into a urban forest. I call it Our Robin's Nest because you look out on to branches of large fir trees. It is very private , yet Starbucks is right next door. Private entry and off street parking. This space has everything you need full kitchen, washer&dryer, queen size bed and fold out couch , plus a Play and Pack for the Littles. Walkable neighborhood , parks market and restaurants within walking distance.

4.92 out of 5 average rating, 130 reviews

A retro-inspired refrigerator in a soft blue hue is positioned against the wall, topped with a decorative pot. Nearby, a microwave and dark cabinets complement the kitchen's functionality.

Guesthouse in Milwaukie

Spacious Studio near Historic Milwaukie/Sellwood

No cleaning fees! Unique retro inspired LARGE studio Private entrance, driveway parking. One Full sized bed and a comfy twin sized cot (set up upon request). Bright sunny space with skylights and beautiful details. Uncluttered, quiet and clean. Full sized fridge and plenty of kitchen amenities. Large dining room table and sitting space. Located in peaceful neighborhood, close to Historic Downtown Milwaukie, 15 min to downtown Portland, minutes away from SE Portland attractions!

4.96 out of 5 average rating, 159 reviews

Home in Milwaukie

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.

4.94 out of 5 average rating, 303 reviews

A close-up view of a textured area rug in shades of blue and beige, featuring colorful keychains resting on its surface. The woven design enhances the tactile quality of the space, providing a warm welcome upon entry.

Apartment in Milwaukie

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.

4.95 out of 5 average rating, 170 reviews

Riverside Cottage Apartment.

Charming cottage apartment on a hill next to the Willamette River, 30 mins from downtown Portland. Relax, and enjoy the quiet and peaceful surroundings. Fully stocked kitchen. Fast wifi at 50 Mbps. Cozy inside in the wintertime, also with a park-like setting with walking access down the lush backyard to the river where you can enjoy swimming, fishing, kayaking, and bird watching. You can use the shared recreation room with ping pong, pool table, shuffleboard, and weights.

A vibrant garden space is featured, with bright yellow flowers blooming abundantly in a lush planter. Two light green Adirondack chairs are positioned on a patio, inviting relaxation and enjoyment of the surrounding greenery.

4.99 out of 5 average rating, 393 reviews

Light Filled Garden Studio

Our wonderfully bright garden studio is perfect for a short stay or for visitors looking to explore Portland for an extended visit. It has a full, well-stocked kitchen, ideal for those looking to stay in and cook, but it’s also just a 20 minute drive from downtown, for those looking to explore the wonderful restaurant scene Portland offers. Keyless entry and private entrance through the side yard gate provide renters with complete autonomy during their visit.

4.88 out of 5 average rating, 697 reviews

The exterior of a rustic cabin is framed by lush greenery and seasonal foliage. Stone accents adorn the chimney, while flowering plants and shrubs create a natural landscape border. Windows illuminate the interior, inviting a sense of warmth and comfort.

Cabin in Milwaukie

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.

A modern private bathroom is depicted, featuring a glass-enclosed shower with a silver showerhead. White tiles with a decorative border enhance the space. A small rug is positioned in front of the shower, completing the clean and tidy environment.

4.96 out of 5 average rating, 261 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.

4.97 out of 5 average rating, 257 reviews

A modern kitchen featuring a combination of wood and glass cabinetry. A double sink is positioned beneath a window, providing views of the greenery outside. Decorative plates adorn the wall, adding a touch of color. Stainless steel appliances, including a dishwasher and toaster, are visible on the countertop.

Home in Milwaukie

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.

4.97 out of 5 average rating, 184 reviews

A private outdoor area features a wooden deck with natural elements, including large trees integrated into the design. Built-in seating is positioned against the wall, and a gentle slope leads to a pathway surrounded by greenery.

Apartment in Milwaukie

Milwaukie Retreat in the Woods

Your private apartment is located on a wood filled lot with a private outdoor area, shade and even deer on occasion. We are 12 miles from the airport, near freeways with easy access to downtown, and to make your way to the coast or the Columbia Gorge, Mt Hood and the Willamette Valley for wine tasting. We have added extra cleaning procedures to help fight against Covid 19.

4.98 out of 5 average rating, 133 reviews

The back patio features a smooth concrete surface, furnished with two light-colored chairs positioned beside a small table. Sliding glass doors lead into the unit, framed by natural wood accents, creating a connection between indoor and outdoor spaces.

Guest suite in Portland

Guest Unit in Walkable Sellwood

This is a guest unit in Sellwood, a quiet and walkable neighborhood in Southeast Portland, Oregon. Located in a residential area only blocks away from grocery stores, bakeries, public library, coffee shops, and local parks, it's the perfect place for a visit! Downtown Portland is only a short drive or light rail ride away.

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Popular amenities for Milwaukie vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Milwaukie

The exterior of the modern home is visible, featuring a manicured front yard with various plants and flowers. A stone pathway leads to the entrance, framed by low stone walls. Tall evergreen trees provide a natural backdrop, and ample parking is available in the gravel driveway.

4.99 out of 5 average rating, 292 reviews

The Room In Between

KimRating, 5 stars6 days ago

Our stay was great. Appreciate how clean & comfortable the space is. We'll definitely be back.

4.97 out of 5 average rating, 571 reviews

A scenic view of the Willamette River stretches across the image, bordered by lush greenery and a hillside covered in trees. The distant skyline of Portland is visible under a bright blue sky with scattered clouds, creating a tranquil atmosphere.

Guesthouse in Portland

Dream Cottage! Springwater Bike/Walking Path!

JuanRating, 5 starstoday

Owls nest was clean, comfortable, and located in a good neighborhood. Parking was easy. Lots to do in area with biking/walking trail next to home and even had lots of recommendations in binder that host provided. Definitely recommend if you would like to be close to downtown Portland without having to stay within downtown. Downtown is about 20 minutes from location. Host made sure that he was available in case we needed anything. Highly recommend to stay at the owls nest.

4.93 out of 5 average rating, 218 reviews

A pathway leads to the entrance of a two-level guest house, framed by lush greenery and a wooden fence. The entrance features a bold red door that contrasts with the blue exterior of the house, creating an inviting approach.

Guesthouse in Woodstock

Charming, private 2-level guesthouse-Woodstock

RichardRating, 5 stars3 weeks ago

This was one of the nicest Airbnb places we've stayed in. Smartly designed, clean, with everything we needed close at hand, we enjoyed being there. Again this was one of the best. Thank you.

Vacation home in Portland

A well-lit bathroom featuring a wooden dresser with multiple drawers, a white toilet, and a sink. Large windows provide natural light. A light patterned floor adds visual interest, and a door leads to the outside, accompanied by a climbing plant for a touch of greenery.

4.87 out of 5 average rating, 155 reviews

Lovely 1-bed vacation home w/ off street parking.

ZacharyRating, 5 stars1 week ago

Stayed here for work. The price was about half what I would have paid for a similar hotel. The place was quiet, private, and matched everything advertised. Having the ability to cook meals and take care of laundry was extremely helpful. Christian is a great host with an amazing place, and I'll be recommending his place to everyone travelling to Portland!

Guesthouse in Oregon City

5 out of 5 average rating, 574 reviews

Cottage in the Country

CarynRating, 5 stars1 week ago

I can't say enough about how much I LOVED my stay at Paul and Carol's cottage! It was truly a bit of heaven on a beautiful property, and although it's only a short drive to downtown Oregon City, it felt like I was miles away nestled amongst the trees and surrounded by nature everywhere I looked. From the welcome sign to the flowers from the garden and freshly laid eggs by the very friendly chickens in the fridge, Carol's beautiful artwork and Paul's custom made furniture - I was charmed from the moment I got there. The place was lovely and oh so comfortable, and it was very clear that my hosts had thought of everything I might need or want during my time there. I slept like a baby in the comfy bed , and enjoyed their fabulous organic coffee out on the porch every morning while taking in the scenery. The icing on the cake was getting to spend a little time with my wonderful hosts. I left feeling like I made new friends and I can't wait to go back. Thank you for such a beautiful time! ❤️

4.91 out of 5 average rating, 142 reviews

The exterior of a vintage 17ft. Aljo trailer features colorful hand-painted designs with flowers and waves. A retractable awning provides shade over the outdoor area, which includes a table and an umbrella. Lush foliage surrounds the trailer, offering a serene outdoor setting.

Camper/RV in Clackamas

The "Lazy Daisy"

KierstenRating, 5 stars1 week ago

Great value for price, cute decorations, and super comfy bed!!! Be mindful that this listing is directly next to the highway, and there is the constant sound of traffic. Can get very hot on hot days too and there’s no AC - just a small fan. Overall good stay and I highly recommend!

4.94 out of 5 average rating, 407 reviews

A welcoming entrance features a vibrant red door bordered by large planters filled with green plants. Flanking the sides are bamboo and ferns, creating a calming atmosphere. The pathway leads to the entrance, showcasing a serene, nature-inspired setting.

Guesthouse in West Linn

Sunlit Oasis

ShannonRating, 5 stars2 weeks ago

We loved staying at this cozy cottage. It was perfect for us. Out of the city, but close enough to go and have dinner in Portland. We will definitely stay here again if we make it back to the Portland area. Thank you!!