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Milwaukie Luxury Rentals

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Milwaukie Pet Friendly Vacation Rentals

7.0 (937 Reviews)
Hotel
Comfort Suites Clackamas
  • Air Conditioner
  • Parking
  • Pet Friendly
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Why Choose Rent By Owner for your Milwaukie Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Milwaukie Vacation Rentals

Where are the best neighborhoods to stay in Milwaukie?

When exploring neighborhoods to stay in Milwaukie, Oregon, you will find a variety of options that suit different preferences and travel goals. Whether you're seeking a peaceful retreat or easy access to local amenities, the area offers neighborhoods with convenient locations and charming atmospheres. Staying in these well-connected communities allows you to experience the authentic charm of Milwaukie while enjoying comfortable and reliable vacation rentals. With a focus on providing a seamless booking experience, these neighborhoods ensure your visit to Milwaukie is both enjoyable and hassle-free.

Sellwood-Moreland

This vibrant neighborhood offers a charming blend of historic character and modern amenities, making it an ideal area to find a comfortable holiday home while exploring the surrounding region. Its picturesque streets and local shops create a welcoming atmosphere for visitors seeking an authentic experience.

View 36+ Rentals in Sellwood-Moreland

Southgate

Located within easy reach of local parks and community spaces, this neighborhood provides a peaceful setting perfect for relaxing stays. It’s an excellent choice for those wanting to enjoy a quiet retreat close to the region’s attractions and conveniences.

View 225+ Rentals in Southgate

Forest Highlands

Surrounded by lush greenery and scenic views, Forest Highlands is perfect for travelers looking to immerse themselves in nature during their visit. The tranquil environment makes it a favorable spot for renting a cozy getaway near outdoor recreational spots.

View 296+ Rentals in Forest Highlands

Historic Milwaukie

This district is rich in local history and charm, offering unique surroundings for your stay while exploring the area's cultural heritage. Its classic architecture and inviting streets provide an authentic backdrop for any vacation.

View 306+ Rentals in Historic Milwaukie

Ardenwald

Known for its well-maintained homes and friendly neighborhood vibe, Ardenwald offers a welcoming environment ideal for families and travelers seeking a comfortable base here. Its convenient location puts you close to regional attractions and outdoor spaces.

View 373+ Rentals in Ardenwald

Island Station

Situated near transportation hubs and scenic waterfront areas, Island Station combines accessibility with scenic beauty for an enjoyable stay. It’s an excellent option for visitors who value both convenience and picturesque surroundings.

View 242+ Rentals in Island Station

Robinwood

Nestled in a friendly community setting, Robinwood offers a peaceful escape just moments from the region’s main attractions. Its quiet streets and local parks make it a great neighborhood to relax and unwind during your visit.

View 166+ Rentals in Robinwood

Best Times to Visit Milwaukie

When should you plan your Vacation Rentals stay?

Choosing the right time to visit here can enhance your experience, as the region offers different attractions and weather patterns throughout the year, making it essential to plan your stay accordingly for an unforgettable getaway.

Peak Season Highlights

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Summer (June to August)

This is the most popular time for visiting, with warm weather perfect for outdoor activities and exploring the local region.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
autumn
Fall (September to November)

During this season, the area experiences vibrant foliage and mild temperatures, making it ideal for enjoying nature and outdoor pursuits.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F

Off-Season Highlights

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Winter (December to February)

This quieter period offers cooler weather and fewer visitors, providing a peaceful experience for those seeking relaxation or lower rates on vacation rentals.

Average Temperature Daytime: 45°F to 55°F - Nighttime: 35°F to 45°F
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Early Spring (March to May)

As the region transitions into spring, crowds diminish and you can enjoy the area's natural beauty with moderate temperatures and less hustle.

Average Temperature Daytime: 55°F to 65°F - Nighttime: 40°F to 50°F

Weekly Weather Forecast for Milwaukie

How to Book Your Milwaukie Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Milwaukie

More Top-Rated Vacation Rentals in Milwaukie Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy outdoor dining on a private patio or deck, perfect for relaxing evenings during your stay.
  • Take advantage of landscaped gardens or lawns to unwind or host outdoor gatherings.
  • Benefit from convenient access to nearby parks and green spaces for outdoor activities and picnics.
  • Make use of outdoor seating areas designed for enjoying the region’s fresh air and scenic views.
  • Explore available outdoor grills or barbecues for preparing meals in the open air.
  • Utilize shared amenities such as community pools or outdoor recreation areas if included with the property.
  • Take advantage of walking paths or trails located within or near the property for exercising or leisurely strolls.

Top Attractions Around Milwaukie

What attractions are nearby?

Enjoy a variety of outdoor activities, local parks, and scenic trails just moments from your stay here in the region, making it easy to explore and experience the natural beauty that surrounds you during your visit.

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Family Activities

  • Milwaukie Riverfront Park: Enjoy a family picnic or a leisurely walk along the Willamette River at this scenic park situated close to the area.
  • Milwaukie Historic District: Discover the local history through charming shops and family-friendly events that showcase the region’s unique heritage.
  • Ledding Library of Milwaukie: Engage with interactive programs and storytime sessions designed for children, making it a perfect spot for a family outing.
  • Clackamas County Fairgrounds: Experience seasonal events and community festivities here, offering fun activities suitable for all ages in the region.
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Adult Activities

  • Waverley Country Club: Experience a round of golf at this renowned private course known for its scenic fairways and historic clubhouse, perfect for adult enthusiasts seeking leisure in the area.
  • Milwaukie Ale House: Savor craft beers and enjoy the local brewing scene with friends at this popular spot that captures the essence of the region’s vibrant culinary culture.
  • Oregon City Downtown Historic District: Explore boutique shops, dine at local eateries, and immerse yourself in the historic charm of the nearby city just a short drive from here.
  • Clackamas County Fairgrounds: Attend seasonal events, concerts, or exhibitions that showcase the lively community spirit of this destination’s surrounding region.

Other Places to Stay in Milwaukie, OR

Ardenwald
Ardenwald Vacation Rentals
Waverley Country Club
Waverley Country Club Vacation Rentals
Providence Milwaukie Hospital
Providence Milwaukie Hospital Vacation Rentals
Historic Milwaukie
Historic Milwaukie Vacation Rentals
Milwaukie Farmers Market
Milwaukie Farmers Market Vacation Rentals
Milwaukie Museum
Milwaukie Museum Vacation Rentals
Island Station
Island Station Vacation Rentals
Southgate
Southgate Vacation Rentals
Concord
Concord Vacation Rentals
Jennings Lodge
Jennings Lodge Vacation Rentals
Oak Grove
Oak Grove Vacation Rentals
Oatfield
Oatfield Vacation Rentals
More Places to Stay Near Milwaukie

Milwaukie Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Transit Options: Take advantage of the area's public transportation or bike-friendly paths to easily access nearby attractions and enjoy a stress-free stay.
  • Visit Nearby Natural Spots: Make time to experience the region's scenic parks and outdoor spaces to truly immerse yourself in the local scenery.
  • Plan Your Meals Wisely: Discover local eateries or grocery options close to your rental to make your dining experience both convenient and authentic.
  • Connect with the Community: Engage with local events or markets to gain insight into the area's culture and enhance your overall visit.

Transportation Options

  • Portland International Airport (PDX): This major airport offers convenient domestic and international flights, making your arrival in the region straightforward and accessible.
  • Public Transit - TriMet Light Rail and Buses: The area's public transportation options provide an affordable and efficient way to explore here without needing a vehicle.
  • Car Rental Services: Several car rental companies operate nearby, offering flexibility for discovering the surrounding attractions at your own pace.
  • Taxi and Rideshare Services: Reliable taxi and rideshare options are readily available, providing quick and comfortable transportation within the region.

Local Customs Options

  • Local Coffee Culture: Embrace the area's vibrant coffee scene by visiting local cafes that serve as community gathering spots, reflecting the region’s appreciation for artisanal brews.
  • Farmers' Market Traditions: Experience the community-oriented farmers’ markets where residents share fresh produce and handcrafted goods, showcasing the region's agricultural roots.
  • Festival Celebrations: Participate in seasonal festivals that highlight regional arts, music, and food, offering an authentic taste of local culture during your stay.
  • Respect for Nature: Observe local customs that emphasize environmental stewardship, with residents often engaging in outdoor activities and conservation efforts in the area’s natural surroundings.

Frequently Asked Questions About Milwaukie?

1. What are the top vacation rentals in Milwaukie?

There are a lot of options in Milwaukie. If you plan on staying in the Milwaukie area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Milwaukie:

2. Which vacation homes in Milwaukie are best for families?

If you are looking for a family-friendly vacation home in Milwaukie, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Milwaukie:

3. How many Rentbyowner vacation rentals are available in Milwaukie?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 139 in the Milwaukie area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Milwaukie. 

4. What is the cancellation policy for vacation rentals in this area?

Cancellation policies vary depending on the individual property listing. It is important to review the specific cancellation terms outlined in the listing details or contact the property owner directly before booking.

5. How do I find the most suitable vacation rental in the region?

You can filter options based on your preferences such as amenities, price range, and location within the area. Reading detailed descriptions and reviews will also help ensure you select a property that meets your needs.

6. Are there any additional fees I should be aware of when booking a vacation rental here?

Additional fees like cleaning charges, service fees, or security deposits may apply. Always review the fee section of each listing carefully or reach out to the property owner for clarification.

7. What are the check-in and check-out procedures for vacation rentals in this destination?

Check-in and check-out times are specified in each listing. Some properties offer flexible options, but it’s best to confirm these details with the owner before your arrival to ensure a smooth stay.

8. Is it possible to communicate directly with the property owner during my booking process?

Yes, most listings provide a messaging platform to contact owners directly. Use this feature to ask questions, clarify details, or request special arrangements for your stay.