Holiday rentals in Milwaukie

4.93 out of 5 average rating, 204 reviews

Home in Ardenwald

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.

4.92 out of 5 average rating, 130 reviews

Guest house in Ardenwald

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!

4.99 out of 5 average rating, 292 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.

4.94 out of 5 average rating, 303 reviews

Flat 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.

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.

4.87 out of 5 average rating, 156 reviews

Holiday home in Portland

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

Welcome to the artists nook - where characters and wayfinders come to relax. A stylish, freshly remodeled 1bed, 1bath, in a quiet, serene neighborhood. 1 Private off street park space. Private Back porch with bbq. Every room has heat keeping it nice and toasty on those cold, winter nights and AC for July's sultry, sticky evenings. Kitchen comes fully equipped. Large bathroom, and don't forget to use the huge washer and dryer to get your laundry in check.

4.88 out of 5 average rating, 697 reviews

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.

4.99 out of 5 average rating, 341 reviews

Guest house in Milwaukie

River Forest Guest House, All new+Riverfront Patio

Tasteful and brand new guest house, beautiful neighborhood on the river. Guests have private deck facing yard and separate outdoor sitting area on the Willamette river (behind main house). Watch the birds, boats and riverboat cruise from the patio with fire pit. 2 miles from lightrail station, restaurants and shopping nearby and 15 mins. to downtown Portland. All are welcome! We are on the east side of the river, Milwaukie area.

4.96 out of 5 average rating, 262 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

Home in Ardenwald

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.

4.95 out of 5 average rating, 406 reviews

Guest suite in West Linn

Evergreen Escape - Relaxing South Metro Studio

Recently updated pricing and NOW NO CLEANING FEES! Quiet basement studio with efficiency kitchen and full bath with rain shower. Located a short distance south of downtown Portland, West Linn is a quiet suburb on the Willamette River. Our home is walkable to a great pub, groceries and other restaurants. This listing includes a lofted queen bed with charming barn door for privacy.

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Other great holiday rentals in Milwaukie

5 out of 5 average rating, 48 reviews

Cottage in Milwaukie

Quiet Casita with sauna! Pool Opening April 22!

StephanieRating, 5 stars1 month ago

Our stay at Ashlee’s casita was wonderful! The beds were very comfortable and the living room / kitchen area was large and expansive. My granddaughters enjoyed the pool even though the water was on the chilly side. We found everything we needed and did not contact Ashlee during our stay. I definitely recommend Ashlee’s casita and hope that we can stay in her home on a future visit when visiting my son and his family who live nearby.

Guest house in Ardenwald

4.72 out of 5 average rating, 39 reviews

Backyard Sanctuary Tinyhome

SkylerRating, 5 stars3 weeks ago

I've stayed there before and I think it's the only place I want to stay at when I'm visiting the state. Such a cozy place and area. I feel safe and at peace. love it there!

Home in Milwaukie

5 out of 5 average rating, 3 reviews

Centrally Located - Minutes to Downtown & Nature!

JennyRating, 5 stars2 days ago

This was as close to a perfect Airbnb as I’ve found. The location is excellent—in a quiet, well-kept neighborhood, but just minutes from restaurants, theaters, parks, and shopping. The home was beautifully curated, well supplied, spotlessly clean, and the backyard provides a stunning oasis for travelers. I could not think of one thing to add to make the Airbnb better—it really is THAT good. This was a home I was delighted to call home during my stay. I highly, highly, highly recommend this home and host.

4.89 out of 5 average rating, 95 reviews

Guest suite in Sellwood

Cozy Sellwood District Studio

AngelaRating, 5 stars2 days ago

Booked this for my niece and they had a wonderful stay. Everything went very smoothly. Clear communication, very friendly, and great location.

4.8 out of 5 average rating, 344 reviews

Guest suite in Ardenwald

Clean & Cozy "Private" Studio Suite

MohamedRating, 5 stars3 weeks ago

I had a great stay at Linda’s guest house! Linda was incredibly nice, responsive, and friendly throughout the entire experience. She made sure everything was smooth from check-in to check-out and was always available if I had any questions. The space was clean, comfortable, and exactly as described. I’d definitely stay here again and highly recommend it to anyone looking for a welcoming place to stay.

4.91 out of 5 average rating, 23 reviews

Home in Milwaukie

Waves Villas #1

Don & DianaRating, 5 stars2 weeks ago

Wendy's place was perfectly and conveniently located for our needs. The place was spotlessly clean and had all the amenities we needed. We would love to stay again in the future!

4.86 out of 5 average rating, 21 reviews

Flat in Ardenwald

Spacious Neighborhood Apartment

RandyRating, 5 stars3 months ago

A great stay in a quiet neighborhood. I was seeking refuge from 30+ inches of snow, and Scott’s place was a godsend.