
Holiday rentals in Milwaukie
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Top-rated holiday rentals in Milwaukie
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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.

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.

The Westmoreland Lighthouse - Private studio in SE
We've dubbed this stunning, newly constructed detached studio the "Lighthouse" because of the way natural light pours through the 550-square-foot studio's many windows and dances off its walls and vaulted ceilings. An open loft offers soothing views. We are tucked into the Westmoreland neighborhood's quiet residential area, but are only a five minute walk from more than 20 restaurants and entertainment features. Westmoreland Park, Reed College and downtown Portland are just minutes away by car.

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!

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.

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.

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.

Charming, private 2-level guesthouse-Woodstock
**No list of chores to do at the end of your stay!** Vaulted ceilings, fully private 2 level home. Chef’s kitchen, AC, patio, designer decor and architecture. Contact-less, private self checkin. New Guest House in quiet residential area, upscale Eastmoreland-15 mins from downtown Portland. One bedroom/one bath. Within 10 minutes’ walk is Woodstock Ave-full of cafes, bars, bakeries, and shopping. Ample parking on the street.

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 holiday rentals
Other great holiday rentals in Milwaukie

Inner SE PDX! Historic Sellwood Basement Apt

Treetop Cedar Studio

Modern Garden Studio Self Check & Private Entrance

Luxurious Cape Cod in Central Eastside

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

Whimsical Garden Cottage Near Sellwood

Charming one bedroom apartment in the forest.

Cozy Creekside Farm House Renovated on 1/3 Acre
When is the best time to visit Milwaukie?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £67 | £67 | £67 | £71 | £74 | £76 | £79 | £78 | £74 | £71 | £69 | £71 |
| 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
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 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 wifi, over 10 homes with free parking, 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 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 Historic Milwaukie, over 1,620 vacation rentals in Island Station, and over 1,440 vacation rentals in Lake Road.
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 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.
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 8,960 verified reviews to help you choose

Family-friendly holiday rentals
60 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
80 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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- Columbia River Gorge National Scenic Area
- Moda Center
- Laurelhurst Park
- Timberline Lodge
- Silver Falls State Park
- Oregon Zoo
- Mt. Hood Skibowl
- Providence Park
- Enchanted Forest
- Mt. Hood Meadows
- The Grotto
- Portland Japanese Garden
- Wooden Shoe Tulip Festival
- Beacon Rock State Park
- Hoyt Arboretum
- Wonder Ballroom
- Powell's City of Books
- Tom McCall Waterfront Park
- Wings & Waves Waterpark
- Oaks Amusement Park
- Portland Art Museum
- Arlene Schnitzer Concert Hall
- Evergreen Aviation & Space Museum
- Pittock Mansion




