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.

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Top guest favorite
A serene entrance features a wooden archway draped with greenery, leading to a tranquil lake. The lush yard is complemented by a carved bear statue, and mature trees provide shade. The calm water reflects the surrounding greenery, creating a peaceful atmosphere.
Guest suite in Oak Grove
4.95 out of 5 average rating, 438 reviews

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.

Top guest favorite
A detached guest house is highlighted, featuring a blue exterior with large windows and a front door. A small patio area with a wooden table is visible, surrounded by lush greenery and decorative plants. A wooden fence provides additional privacy.
Home in Lewelling
4.95 out of 5 average rating, 102 reviews

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.

Top guest favorite
The cozy front porch features a welcoming entry with two woven chairs and decorative cushions, inviting guests to relax. The blue exterior is complemented by a white picket fence and a small garden area with greenery, enhancing the cottage home's charm.
Cottage in Ardenwald
4.99 out of 5 average rating, 135 reviews

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.

Top guest favorite
The kitchen features a retro blue fridge and dark cabinetry, providing a blend of modern and vintage aesthetics. Natural light enters through a window above the sink, illuminating the space. Indoor plants are placed around the room, enhancing the overall atmosphere.
Guesthouse in Ardenwald
4.93 out of 5 average rating, 166 reviews

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!

Top guest favorite
A serene garden scene captures early morning fog enveloping vibrant fall foliage. Lush greenery is interspersed with colorful autumn leaves, providing a peaceful backdrop. The landscape features a variety of shrubs and trees, adding depth and texture to the tranquil environment.
Guest suite in Milwaukie
4.96 out of 5 average rating, 184 reviews

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.

Top guest favorite
A cozy kitchen is highlighted by warm wood cabinetry and a decorative countertop. A binder titled 'Crossroads Country Cottage' is prominently displayed, accompanied by a flower vase filled with vibrant blooms. Colorful stained glass pieces allow natural light to filter in, adding charm to the space.
Home in Milwaukie
4.97 out of 5 average rating, 173 reviews

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.

Top guest favorite
A bright, modern room features a Queen Murphy bed with crisp white linens and yellow accent pillows. Two windows allow natural light, with views of a fenced outdoor space, enhancing the airy atmosphere. A small built-in sofa is positioned beside the bed, offering additional seating.
Guest suite in Oak Grove
4.99 out of 5 average rating, 318 reviews

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.

Guest favorite
A warm dining area is showcased with a wooden table at its center, surrounded by decorative plants. An archway leads into a cozy living room featuring a gas fireplace, comfortable seating, and large windows that invite natural light into the space.
Home in Oak Grove
4.97 out of 5 average rating, 119 reviews

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!

Top guest favorite
An open-space studio features high ceilings with wooden beams, enhancing the airy feel. A queen-sized bed is set against the wall with soft linens. A small kitchenette and dining area are visible, with a full bathroom enclosed in glass. Natural light brightens the interior.
Guesthouse in Woodstock
4.96 out of 5 average rating, 479 reviews

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

Top guest favorite
The exterior of a garden studio is illuminated by string lights, creating a warm ambiance at night. An inviting patio features two wooden chairs and floral greenery, while blooming white flowers add a touch of natural beauty to the space.
Guest suite in Milwaukie
4.99 out of 5 average rating, 468 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.

Superhost
The cabin, nestled among towering cedar trees, features a rustic exterior with warm lighting from the windows. A serene creek flows nearby, with smooth stones and mossy patches lining the water's edge. A wooden bridge connects to the surrounding natural landscape.
Cabin in Oak Grove
4.89 out of 5 average rating, 738 reviews

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.

Top guest favorite
A comfortably appointed studio features a queen bed with decorative pillows and a soft blanket. A seating area includes a modern chair beside a sleek storage unit, with a coffee setup and a mini refrigerator. Natural light filters through sheer curtains, enhancing a relaxed atmosphere.
Guest suite in Hector Campbell
4.96 out of 5 average rating, 278 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.

Popular amenities for Milwaukie vacation rentals

When is the best time to visit Milwaukie?

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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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