Vacation rentals in Milwaukie

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Top-rated vacation 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, 211 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 favorite
A serene entrance features a wooden archway draped with greenery, leading to a tranquil lake. The lush yard is complemented by a carved bear statue, and mature trees provide shade. The calm water reflects the surrounding greenery, creating a peaceful atmosphere.
Guest suite in Milwaukie
4.95 out of 5 average rating, 432 reviews

River Forest Lake Apt w/hot tub. HOT find!

*No smoking, no parties, no drugs or pets on premises* total/Max 4 guests; included in this total are infants/children, no more than 2 or3 children under 12, as long as only 4 total guests. FYI: Incline driveway Welcome to our newly remodeled daylight basement apartment. Tucked into the quiet peaceful River Forest neighborhood of Milwaukie on River Forest Lake. Conveniently located to shopping, restaurants, hwy 99, freeways to Portland, Oregon City, historic Sellwood, the Gorge, Mt Hood, etc.

Guest favorite
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, 359 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
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
4.96 out of 5 average rating, 168 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
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, 311 reviews

The 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
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, 559 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 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, 318 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 serene garden scene captures early morning fog enveloping vibrant fall foliage. Lush greenery is interspersed with colorful autumn leaves, providing a peaceful backdrop. The landscape features a variety of shrubs and trees, adding depth and texture to the tranquil environment.
Guest suite in Milwaukie
4.96 out of 5 average rating, 179 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.

Top guest favorite
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, 438 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 favorite
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, 720 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 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, 271 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
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, 274 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.

Popular amenities for Milwaukie vacation rentals

Quick stats about vacation rentals in Milwaukie

  • Total rentals

    120 properties

  • Nightly prices starting at

    R345 ZAR before taxes and fees

  • Total number of reviews

    8.9K reviews

  • Family-friendly rentals

    50 properties are a good fit for families

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

Frequently Asked Questions

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

    Experience the best of Milwaukie with our private suite rentals, starting at about $30 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 Guesthouse Rentals in Milwaukie?

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

  • Do house rentals in Milwaukie have free parking?

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

  • Do private suite rentals in Milwaukie have air conditioning?

    Absolutely! We offer over 20 private suite rentals with air conditioning in Milwaukie. Enjoy a tailored experience with all the comforts you desire.

  • Are there private suite rentals with a dedicated workspace in Milwaukie?

    Yes! Work meets play with ease at over 10 private suite 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 1,440 vacation rentals in Ardenwald.

  • 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 house rentals in Milwaukie have wifi?

    Absolutely! We offer over 50 house 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 house rentals in Milwaukie have a kitchen?

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

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