Milwaukie holiday rentals

We found 1,363 holiday rentals — enter your dates for availability
Discover a selection of 49 homes, 11 apartments and other holiday rentals in Milwaukie that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll find the amenities that you need and want, which might include cable TV and a washer and dryer. At the end of the day, you're sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Milwaukie

Showing deals for:18 Dec - 25 Dec

Property grounds
Terrace/patio
Property grounds
Interior
Wonderful
(64 reviews)

Stafford River House

West Linn

8% off
AU$3,527
for 7 nights, 1 home
AU$504 per night
includes taxes & fees
Stafford River House
Private kitchen
Interior
Room
Living area
Exceptional
(142 reviews)

Zen Cottage in Close In NE Alberta Arts Area, Sleeps 2 Private and Sanitized!!

Portland

7% off
AU$1,953
for 7 nights, 1 cottage
AU$279 per night
includes taxes & fees
Zen Cottage in Close In NE Alberta Arts Area, Sleeps 2 Private and Sanitized!!
Dining
Living area
Room
Private kitchen
Exceptional
(6 reviews)

2 King Suites • Mountain Views • Near Rose Garden

Portland

8% off
AU$5,466
for 7 nights, 1 home
AU$781 per night
includes taxes & fees
2 King Suites • Mountain Views • Near Rose Garden
Formal living room with floor to ceiling curtains for privacy.
Exterior detail
Living room to entry access
36" Kitchen Aid french door fridge H20 & ice, windows to hot tub.
Excellent
(9 reviews)

Gorgeous private home! Central Air 4 beds, hot tub, patio, designer furnishings

Portland

7% off
AU$4,955
for 7 nights, 1 home
AU$708 per night
includes taxes & fees
Gorgeous private home! Central Air 4 beds, hot tub, patio, designer furnishings
Property grounds
Property grounds
Living area
Room
Exceptional
(16 reviews)

Charming and minimal with private Backyard ADU 1-bedroom, 1-Bath. Tesla Charger

Portland

7% off
AU$1,691
for 7 nights, 1 home
AU$242 per night
includes taxes & fees
Charming and minimal with private Backyard ADU 1-bedroom, 1-Bath. Tesla Charger
Fully stocked Chef's kitchen.
Picture yourself enjoying a glass of wine surrounded by modern chic.
A lovely cozy room to wake up in.
Oversize custom Italian tiled shower.
Exceptional
(169 reviews)

★ CLEAN ★ NEAR DOWNTOWN + PRIVATE PATIO ★ WALKABLE

Portland

7% off
AU$2,175
for 7 nights, 1 apartment
AU$311 per night
includes taxes & fees
★ CLEAN ★ NEAR DOWNTOWN + PRIVATE PATIO ★ WALKABLE
Living room looking at front door
Our home on a snowy day in winter
Living Room from entry way looking to French doors to deck.
Garden room private deck looking to Council Crest. Deck seats two.
Exceptional
(175 reviews)

Sunny 1400 SQFT Dutch Colonial in Portland Heights - 5 min to downtown, NW 23rd

Portland

7% off
AU$2,342
for 7 nights, 1 home
AU$335 per night
includes taxes & fees
Sunny 1400 SQFT Dutch Colonial in Portland Heights - 5 min to downtown, NW 23rd
Living room
Property grounds
Property grounds
Exterior detail
Exceptional
(340 reviews)

A garden view hideaway in the Irvington neighborhood

Portland

7% off
AU$1,545
for 7 nights, 1 apartment
AU$221 per night
includes taxes & fees
A garden view hideaway in the Irvington neighborhood
Property grounds
Outdoor dining
Property grounds
Living area
Exceptional
(47 reviews)

Tranquil Forest Escape-Extended Stays Welcome

Oregon City

9% off
AU$1,465
for 7 nights, 1 home
AU$209 per night
includes taxes & fees
Tranquil Forest Escape-Extended Stays Welcome
Interior
Dining
Property grounds
Exterior detail
Exceptional
(15 reviews)

Charming 1-bedroom apt; cleaned with non-toxic, plant based cleaning products

Milwaukie

9% off
AU$1,455
for 7 nights, 1 apartment
AU$208 per night
includes taxes & fees
Charming 1-bedroom apt; cleaned with non-toxic, plant based cleaning products
Bathroom
Living area
Private kitchen
Living area
Exceptional
(5 reviews)

Cozy ADU with AC in charming Oregon City

Oregon City

9% off
AU$1,929
for 7 nights, 1 apartment
AU$276 per night
includes taxes & fees
Cozy ADU with AC in charming Oregon City
Outdoor dining
Interior
Interior
Private kitchen
Exceptional
(58 reviews)

Cozy Modern Farmhouse, King bed, great yard, pets!

Milwaukie

17% off
AU$3,448
for 7 nights, 1 home
AU$493 per night
includes taxes & fees
Cozy Modern Farmhouse, King bed, great yard, pets!
Approach to guesthouse
Living area
nice details, fun lighting.
clean and fully stocked professional kitchen
Exceptional
(47 reviews)

Cottage in Historic Irvington neighborhood near Convention Center and shops!

Portland

7% off
AU$1,617
for 7 nights, 1 room
AU$231 per night
includes taxes & fees
Cottage in Historic Irvington neighborhood near Convention Center and shops!
Interior
Exterior
Property grounds
Interior
Exceptional
(89 reviews)

Charming, Private, Detached Studio!

Portland

7% off
AU$892
for 7 nights, 1 apartment
AU$127 per night
includes taxes & fees
Charming, Private, Detached Studio!
Downtown Milwaukie OR
Private kitchen
Interior
Exterior
Exceptional
(127 reviews)

Gem in Milwaukie 2 bedroom - 2 Bathroom - Huge yard

Milwaukie

8% off
AU$1,520
for 7 nights, 1 home
AU$217 per night
includes taxes & fees
Gem in Milwaukie 2 bedroom - 2 Bathroom - Huge yard
Interior
Living area
Room
Interior
Exceptional
(15 reviews)

Cozy Newly Remodeled Duplex

Milwaukie

8% off
AU$1,014
for 7 nights, 1 home
AU$145 per night
includes taxes & fees
Cozy Newly Remodeled Duplex
Exterior
Outdoor dining
Living area
Dining
Exceptional
(5 reviews)

1BR Apartment w/ Hot tub, walk to shops & food!

West Linn

7% off
AU$2,597
for 7 nights, 1 apartment
AU$371 per night
includes taxes & fees
1BR Apartment w/ Hot tub, walk to shops & food!
Dining
Front of main house
Outdoor dining
Room
Exceptional
(102 reviews)

Welcome to our Luxury Memory Lane Hideaway

Portland

7% off
AU$1,509
for 7 nights, 1 apartment
AU$216 per night
includes taxes & fees
Welcome to our Luxury Memory Lane Hideaway
Living area
Exterior
Room
Outdoor dining
Exceptional
(9 reviews)

Charming, close-in 2-bedroom modern apartment in Hip Portland Neighborhood.

Portland

7% off
AU$1,783
for 7 nights, 1 apartment
AU$255 per night
includes taxes & fees
Charming, close-in 2-bedroom modern apartment in Hip Portland Neighborhood.
Kellogg creek park milwaukie
Dining
Exterior
Interior
Exceptional
(117 reviews)

Cozy apartment in a lovely and quiet neighborhood

Milwaukie

8% off
AU$1,075
for 7 nights, 1 apartment
AU$154 per night
includes taxes & fees
Cozy apartment in a lovely and quiet neighborhood
Terrace/patio
Exterior detail
Dining
Room
Exceptional
(8 reviews)

Cozy caravan in Mississippi area of Portland with WiFi, AC

Portland

9% off
AU$1,248
for 7 nights, 1 home
AU$178 per night
includes taxes & fees
Cozy caravan in Mississippi area of Portland with WiFi, AC

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Explore the lakeside setting in Milwaukie

The lake and other outdoor surroundings create an inviting atmosphere in Milwaukie. This city's sporting events, shopping and cafes draw many visitors. Oregon Convention Center and Moda Center are just a couple of the must-see attractions in the area. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in Milwaukie

Do you want to find things to do during your stay? Venture out of your cosy holiday rental and experience everything that makes Milwaukie a fun place to get away to. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Oaks Amusement Park (2.1 mi / 3.4 km)
  • Eagle Landing Golf Course (4 mi / 6.4 km)
  • Oswego Hills Vineyard and Winery (4.4 mi / 7.1 km)
  • Oregon Zoo (5.6 mi / 9.1 km)
  • The Grotto (8 mi / 12.8 km)
  • Glendoveer Golf Course (8.1 mi / 13 km)

Exploring the natural landscape of Milwaukie

Whether you're looking for adventure or just want to spend some time taking in the scenery, Milwaukie is a great place to get out in nature. These are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Westmoreland Park (1.4 mi / 2.3 km)
  • Sellwood Riverfront Park (1.9 mi / 3.1 km)
  • Crystal Springs Rhododendron Garden (2.3 mi / 3.6 km)
  • Willamette River (4 mi / 6.4 km)
  • Gabriel Park (4.3 mi / 7 km)
  • South Waterfront City Park (4.5 mi / 7.2 km)

Transport to and around Milwaukie

The nearest airport is in Portland International Airport (PDX), located 10.1 mi (16.3 km) from the city centre.

Frequently asked questions

What is the best area to stay in Milwaukie when booking a holiday rental?
When considering a holiday rental in Milwaukie, Oregon, a popular area to stay is the charming downtown district. This neighbourhood offers a delightful mix of local shops, cafes, and restaurants, making it a vibrant place to experience the local culture. The proximity to the scenic Willamette River enhances its appeal, with lovely parks and walking trails ideal for leisurely strolls or picnics.Another popular area is the historic Milwaukie neighbourhood, which is known for its quaint character and tree-lined streets. Visitors can explore the Milwaukie Museum, which showcases the region's rich history. Additionally, the nearby Oak Grove area provides easy access to beautiful natural spaces, including parks with recreational facilities.While the number of properties can vary, downtown Milwaukie typically offers a range of options, from cosy flats to charming houses, suiting different preferences and budgets.
What is the most popular type of holiday rental accomodation in Milwaukie?
In Milwaukie, holiday houses are the most popular type of holiday rental, with approximately 72 available throughout the area. These homes often provide spacious living arrangements, featuring multiple bedrooms, fully equipped kitchens, and outdoor spaces where guests can relax. Many are situated in residential neighbourhoods, allowing visitors to experience the local community. Additionally, there are around 18 cottages and 18 apartments for those seeking a cozier stay. Some condominiums are also available, offering a blend of comfort and convenience, typically with amenities such as swimming pools and fitness centres.
Are there any family house rentals in Milwaukie?
In Milwaukie, Oregon, there are several family-friendly homes available—around 28 to choose from. This charming suburb, located just a short distance from Portland, offers a friendly space for families. Many of these properties feature spacious living areas, fully equipped kitchens superb for preparing family meals, and outdoor spaces ideal for children to play. Amenities such as Wi-Fi and laundry facilities are commonly included, ensuring a comfortable stay.Visitors can enjoy nearby attractions including the scenic Willamette River, where walking and biking paths abound, as well as the quaint shops and eateries in downtown Milwaukie. The area also boasts parks like Milwaukie Riverfront Park, which features playgrounds and picnic areas, making it an excellent spot for family outings.
Can I rent a holiday home with a pool or hot tub in Milwaukie?
In Milwaukie, there are several holiday homes available for rent that feature pools and hot tubs. This charming city, located just south of Portland, offers a blend of suburban tranquility and access to urban amenities. Many of the rentals you can find here often come with private pools, hot tubs, and outdoor spaces great for barbecues and relaxation. Expect amenities such as fully equipped kitchens, spacious living areas, and sometimes even game rooms, making them suitable for family gatherings or group getaways. The properties are often situated near parks and local attractions, providing both leisure and convenience for your stay.
Are there pet-friendly house rentals in Milwaukie?
In Milwaukie, there are a variety of pet-friendly house rentals available, with around 23 options for travellers seeking accommodations that welcome furry companions. Many of these properties boast modern amenities such as well-equipped kitchens, spacious living areas, and private outdoor spaces, which are superb for relaxing after a day of exploring.The neighbourhood itself is charming, with access to several parks where pets can enjoy the outdoors. For instance, the nearby Milwaukie Riverfront Park offers walking trails along the Willamette River, providing a scenic backdrop for leisurely strolls with pets. Additionally, the area features local pet-friendly cafes and shops, ideal for those travelling with animals.
Are there any remote work holiday rentals in Milwaukie?
In Milwaukie, Oregon, there are numerous holiday rentals suitable for remote work, with around 100 options available. This charming city, located just a short drive from Portland, offers a variety of properties that cater to the needs of remote workers. Many rentals come equipped with reliable Wi-Fi, ensuring you can stay connected during your work hours. You can expect amenities such as designated workspaces, including desks and comfortable chairs, which are ideal for productivity.Accommodations may also feature a mix of modern conveniences like fully equipped kitchens, spacious living areas, and outdoor spaces to unwind after a day of work. The proximity to local parks, cafes, and the scenic Willamette River enhances the appeal for those seeking a balance of work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Milwaukie?
In Milwaukie, popular rental amenities cater to a variety of needs, with many properties offering features such as fully equipped kitchens, allowing guests to prepare their own meals. Outdoor spaces are also prominent, with many rentals including patios or decks where visitors can relax and enjoy the fresh air. Onsite parking is commonly available, making it convenient for those travelling with vehicles. Additionally, many accommodations provide coffee and tea makers, ensuring that guests can enjoy a warm beverage at their leisure.
When is the best time to visit Milwaukie for a holiday rental?
The peak season for visiting Milwaukie runs from June to August, with July being the most popular month among travellers seeking a vibrant holiday experience. During this time, the warm, sunny weather creates a great backdrop for outdoor activities, including exploring the beautiful parks and enjoying scenic walks along the Willamette River.In the summer, temperatures typically range from the low 20s to mid-30s Celsius, making it an ideal time for al fresco dining, local festivals, and community events. The lively option is complemented by the chance to connect with fellow visitors and locals, enhancing your overall experience in this charming town.For those seeking a more cost-effective option, consider visiting in December. While this month is considered the low season, it offers a unique opportunity to enjoy the festive spirit of Milwaukie with fewer crowds and a more relaxed pace. You can take in the local holiday lights and enjoy the warmth of the community during this special time of year.
What are the top attractions in Milwaukie?
In Milwaukie, visitors can enjoy a variety of attractions that highlight both the natural beauty and local culture of the area. The historic downtown district features charming shops and eateries, providing a pleasant atmosphere for leisurely strolls. One popular spot is the Milwaukie Museum, where guests can learn about the city's rich history and heritage.Outdoor enthusiasts will appreciate the scenic views and recreational opportunities at the nearby Tualatin River, which offers walking and biking trails. The waterfront area is great for picnics and enjoying wildlife. Additionally, the nearby Oaks Park is a family-friendly destination, featuring amusement rides and a lovely park for outdoor activities.For those interested in local produce, the Milwaukie Farmers Market, held regularly, showcases fresh fruits, vegetables, and artisan goods from the region, making it a delightful stop for food lovers.
Are all fees included in the Milwaukie holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Milwaukie holiday homes with parking?
Stayz offers a wide selection of holiday homes in Milwaukie with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Milwaukie holiday homes?
You can find great discounts on holiday homes in Milwaukie on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Milwaukie holiday home booking on Stayz?
To find Milwaukie holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Milwaukie?
A long-stay holiday home in Milwaukie is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Milwaukie holiday home?
Book your Milwaukie holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Milwaukie?
Prices for holiday homes in Milwaukie vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Milwaukie to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.