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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A cozy living room features a brick fireplace at the center, emanating a warm glow. The space is furnished with a dark sofa and adorned with decorative pillows. A vibrant area rug lies on the green carpet, providing contrast and comfort. Bookshelves line the walls, showcasing various items.
Flat in Milwaukie
4.77 out of 5 average rating, 119 reviews

My Cozy Place- For the Budget Traveler-29 day max!

This cozy unit is a converted rec room located on the bottom floor of a two story house that includes a living room, a separate bedroom, a bathroom with shower, and a small kitchenette /laundry room (cold water). The kitchenette includes a microwave, toaster oven, hot plate, coffee pot, utensils, and refrigerator. The unit can be locked with key. STEPS are required for entry. Not recommended for guests with mobility issues. Extra guests are each charged $5 per day. NO smoking/vape inside.

Top guest favourite
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, 435 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 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, 364 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
The kitchen features a retro blue fridge and dark cabinetry, providing a blend of modern and vintage aesthetics. Natural light enters through a window above the sink, illuminating the space. Indoor plants are placed around the room, enhancing the overall atmosphere.
Guest house in Ardenwald
4.93 out of 5 average rating, 154 reviews

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!

Top guest favourite
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, 314 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 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, 323 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
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, 444 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, 729 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 favourite
The exterior of the mid-century home is framed by lush greenery, with a clear view of the entrance pathway leading to the door. A well-maintained garden space is visible, accompanied by steps that guide visitors towards the inviting entrance.
Guest suite in Milwaukie
4.96 out of 5 average rating, 221 reviews

Trolley Trail Treasure in Oak Grove

Our mid-century home (Clean & Sanitized) is in the beautiful quiet tree lined neighborhood of Oak Grove, Oregon. Spacious 1200 sq/ft daylight basement apartment, with 1 bedroom, living-room, full kitchen & big windows, in a quiet and desirable suburb of Portland. Park in our driveway & enter through your own gate at the back of the house. The Trolley Trail bike/hike trail is across the street from our front door.

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 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, 275 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 favourite
The bedroom features two twin beds dressed in light blue and white striped linens. A small bedside table with a lamp is positioned between the beds, complemented by decorative pillows. Framed floral art is displayed on the wall, enhancing the cozy atmosphere.
Guest suite in Milwaukie
4.86 out of 5 average rating, 175 reviews

Why Not Stay?

This charming Basement Apartment is in a beautiful Ranch Style home in a quiet tree lined neighborhood of Milwaukie, Oregon. It offers it's own ground level entrance from an ample parking area. You will have a private bedroom, bath and kitchenette.

Popular amenities for Milwaukie holiday rentals

When is the best time to visit Milwaukie?

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Avg. price£68£68£68£72£75£77£80£79£76£72£70£72
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Frequently Asked Questions

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

    Experience the best of Milwaukie with our apartment rentals, starting at about $50 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 Private Suite Rentals in Milwaukie?

    Enhance your stay in our Private Suite Rentals with the most popular amenities: over 20 homes with wifi, over 10 homes with air conditioning, over 10 homes with a kitchen, over 10 homes with free parking, 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 10 private suite 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 Historic Milwaukie, over 1,440 vacation rentals in Lake Road, 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 guesthouse rentals in Milwaukie have wifi?

    Absolutely! We offer over 10 guesthouse 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 £15 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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