Holiday rentals in Milwaukie

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Top-rated holiday rentals in Milwaukie

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

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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, 215 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
An open living area features wooden ceiling beams and large windows that offer views of the surrounding trees. A comfortable sofa sits beside a wooden table. The kitchen area includes modern appliances and white cabinetry, enhancing the space's functionality.
Guest house in West Linn
4.96 out of 5 average rating, 158 reviews

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.

Guest favourite
A spacious studio suite features a queen bed with a patterned blanket and soft lighting. A cozy seating area includes a gray couch and round coffee table. A small dining table for two is positioned near the window, enhancing the inviting atmosphere.
Guest suite in Ardenwald
4.8 out of 5 average rating, 368 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 favourite
A sunlit sunroom features large windows overlooking greenery, creating a bright space. A dark cushioned seating area is positioned against the window, complemented by a rectangular table. A patterned rug adds texture to the warm wood floor, enhancing the room's inviting atmosphere.
Guest suite in Westmoreland
4.97 out of 5 average rating, 565 reviews

A sunny separate studio w/skylights

Your own modern large studio on 2nd floor with separate entrance, full kitchen, sunroom, skylights, 14-foot ceiling, balcony, desk, full bathroom, washer/dryer, dishwasher, gas stove, lots of windows. All this in a vibrant neighborhood, short walking distance to multiple coffee shops, restaurants, a single-screen movie theater, the light rail station, an open-late grocery store, a small park with a salmon run. One mile to Reed College, where Steve Jobs took a calligraphy class.

Top guest favourite
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.
Flat in Milwaukie
4.94 out of 5 average rating, 324 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 favourite
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.
Guest house in Woodstock
4.96 out of 5 average rating, 456 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 favourite
The exterior of a garden studio is illuminated by string lights, creating a warm ambiance at night. An inviting patio features two wooden chairs and floral greenery, while blooming white flowers add a touch of natural beauty to the space.
Guest suite in Milwaukie
4.99 out of 5 average rating, 448 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.

Guest favourite
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
4.89 out of 5 average rating, 730 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.

Guest favourite
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, 272 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 favourite
The studio features a spacious layout with a queen-sized bed and a futon couch. A dining table is set with decorative bottles and a tray, while natural light filters through large windows, complementing the cozy seating area with soft furnishings.
Flat in Westmoreland
4.91 out of 5 average rating, 603 reviews

Sellwood Detached Studio Loft

Self contained cozy yet bright studio apt located above our garage in the heart of charming Sellwood! Though no interaction is required, hosts are close-by and available as needed! Steps away from shops, restaurants, coffee, bars, parks, trails, and the river. Within a few miles of both Reed and Lewis and Clark Colleges. You will have all the privacy you need in this detached unit! Sleeps 2-4.

Top guest favourite
The exterior showcases a red house featuring a bright yellow door. Two colorful chairs are placed beside a small table adorned with potted flowers. Lush greenery surrounds the area, with a stone walkway leading up to the entrance.
Home in Ardenwald
4.97 out of 5 average rating, 276 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.

Top guest favourite
An open living area is highlighted by a cozy sofa with patterned cushions and a spacious bed dressed in soft linens. A wooden dining table with chairs is set near a window, enhancing the light, airy feel of the space. An inviting side cabinet adds functionality.
Flat in Milwaukie
4.97 out of 5 average rating, 203 reviews

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.

Popular amenities for Milwaukie holiday rentals

When is the best time to visit Milwaukie?

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Avg. price$116 SGD$116 SGD$116 SGD$122 SGD$127 SGD$131 SGD$136 SGD$135 SGD$128 SGD$122 SGD$119 SGD$122 SGD
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Frequently Asked Questions

  • How much does it cost to stay in house rentals in Milwaukie?

    Experience the best of Milwaukie with our house rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • What are the most popular amenities for Apartment Rentals in Milwaukie?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with free parking, over 10 homes with wifi, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do apartment rentals in Milwaukie have free parking?

    Absolutely! We offer over 10 apartment rentals with free parking in Milwaukie. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Milwaukie have air conditioning?

    Absolutely! We offer over 50 house rentals with air conditioning in Milwaukie. Enjoy a tailored experience with all the comforts you desire.

  • Are there house rentals with a dedicated workspace in Milwaukie?

    Yes! Work meets play with ease at over 40 house rentals in Milwaukie featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Where should I stay in Milwaukie?

    Make yourself at home in Milwaukie by choosing from our most frequently booked neighborhoods. We have over 1,440 vacation rentals in Lake Road, over 1,440 vacation rentals in Historic Milwaukie, and over 1,630 vacation rentals in Island Station.

  • Are there family-friendly house rentals in Milwaukie?

    Milwaukie has more than 40 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do apartment rentals in Milwaukie have wifi?

    Absolutely! We offer over 10 apartment rentals with wifi in Milwaukie. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly house rentals in Milwaukie?

    Four-legged friends are welcome in Milwaukie. Choose from more than 20 house rentals for guests traveling with pets.

  • Do apartment rentals in Milwaukie have a kitchen?

    Absolutely! We offer over 10 apartment rentals with a kitchen in Milwaukie. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Milwaukie

  • Total holiday rentals

    Explore 120 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 8,900 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wifi availability

    120 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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