
Vacation rentals in Milwaukie
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Top-rated vacation rentals in Milwaukie
Guests agree: these stays are highly rated for location, cleanliness, and more.

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.

Secluded Studio
This a fully private and detached guest house is quiet and relaxing. Walk down your very own pathway to a completely private, safe and secure patio with a quaint garden, a small yard and outdoor seating. With tall ceilings and a large nice bright kitchen, this place is very comfortable. Blackout curtains. Close to many desirables: Max Orange Line Commuter Train, Reed College, Woodstock, Sellwood, & East Moreland & Milwaukie Providence Hospital. Ride, walk or run along the Springwater Corridor.

Whimsical Garden Cottage Near Sellwood
Located two blocks from the Springwater Corridor — a 21-mile paved trail for walkers and bikers — in the quiet neighborhood of Ardenwald, you’ll find The Hummingbird Cottage. This whimsical 1930s garden cottage is less than one mile from the charming streets of Sellwood, home to quaint coffee shops and restaurants, boutique shopping, and the iconic Sellwood Riverfront Park. The cottage features organic cotton sheets and goose down comforters in each room and a renovated spa-like main bathroom.

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!

River Garden Cottage.
Charming cottage apartment on a garden and forest 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.

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.

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.

Oak Grove Easy-Centrally located w/King Bed
Welcome to this updated and comfortable, light filled home in the Oak Grove neighborhood of Portland. A short distance to the river, downtown, parks, restaurants and all things Portland-make this a perfect vacation space for your family and guests. We put a lot of love in to designing the interior to be stylish, yet comfortable and seamless to ensure you feel right at home. Ample space in our park-like backyard to relax , entertain or play a summer game of corn hole!

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

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.

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.

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.
Popular amenities for Milwaukie vacation rentals
Other great vacation rentals in Milwaukie

The Redwood House 2.0 Safe Cozy 2BR Pet Friendly

Central Stay w/Treehouse! Near Downtown & Nature

Comfortable spacious home!

Cozy & Quiet Creekside Home, 8 Min to Portland

Spacious and Private Place with a BIG Yard

Casa Cuatro Pinos

Golden Era Reimagined

Accessible home with roll in shower
When is the best time to visit Milwaukie?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ331 | ﺩ.ﺇ331 | ﺩ.ﺇ331 | ﺩ.ﺇ349 | ﺩ.ﺇ364 | ﺩ.ﺇ375 | ﺩ.ﺇ389 | ﺩ.ﺇ386 | ﺩ.ﺇ367 | ﺩ.ﺇ382 | ﺩ.ﺇ386 | ﺩ.ﺇ397 |
| Avg. temp | 5°C | 7°C | 9°C | 12°C | 15°C | 18°C | 21°C | 21°C | 19°C | 13°C | 8°C | 5°C |
Frequently Asked Questions
Are there family-friendly vacation rentals in Milwaukie?
Milwaukie has more than 60 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
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.
Are there pet-friendly vacation rentals in Milwaukie?
Four-legged friends are welcome in Milwaukie. Choose from more than 40 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Milwaukie?
Yes! Work meets play with ease at over 80 vacation 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 1,620 vacation rentals in Island Station, and over 1,440 vacation rentals in Historic Milwaukie.
Do apartment rentals in Milwaukie have air conditioning?
Absolutely! We offer over 10 apartment rentals with air conditioning in Milwaukie. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Milwaukie have a kitchen?
Absolutely! We offer over 60 house rentals with a kitchen in Milwaukie. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Milwaukie have wifi?
Absolutely! We offer over 60 house rentals with wifi in Milwaukie. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Milwaukie have free parking?
Absolutely! We offer over 60 house rentals with free parking in Milwaukie. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Milwaukie?
Enhance your stay in our House Rentals with the most popular amenities: over 60 homes with a kitchen, over 60 homes with wifi, over 60 homes with free parking, over 50 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about vacation rentals in Milwaukie

Total vacation rentals
Explore 120 vacation rentals in Milwaukie

Nightly prices starting at
Milwaukie vacation rentals start at ﺩ.ﺇ73 per night before taxes and fees

Verified guest reviews
Over 8,960 verified reviews to help you choose

Family-friendly vacation rentals
60 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wi-Fi availability
120 of Milwaukie vacation rentals include wi-fi 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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