Vacation rentals in Milwaukie

A cozy living area features a large area rug with a floral design in shades of blue and gray. Two elegant armchairs are positioned beside a wooden console, which has a flat-screen TV mounted above it. Natural light filters in through large windows.

4.93 out of 5 average rating, 206 reviews

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.

The living room features a cozy layout with a large window providing natural light. A 55" UHD Roku TV is mounted on the wall, alongside a comfortable chair and a rustic coffee table. A portable air conditioner is positioned nearby, enhancing the space's functionality.

4.84 out of 5 average rating, 157 reviews

Springwater Retreat: Relax in quiet comfort

In a tucked-away corner of Portland’s closest suburb, you will find our private duplex on a large, private park-like lot. We are located 8 blocks from the Springwater Corridor, a popular biking/walking trail on the Portland border. It is a lovingly furnished home: queen bedroom, twin-over-full bunk bedroom, bonus room that has a very comfortable queen sofa bed and foozball table, fully equipped kitchen for real cooking, dining area, and huge private yard. Only the off-street parking is shared.

4.92 out of 5 average rating, 132 reviews

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 Milwaukie

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 spacious living room area is highlighted by a comfortable sectional sofa, positioned near large windows that allow ample natural light. A small dining chair and decorative pillows add a welcoming touch, with a television placed on a side table for entertainment.

4.85 out of 5 average rating, 188 reviews

SE Portland View Basement Apartment

Comfortable view basement apartment in the Southeast Portland Ardenwald neighborhood, 0.3 mile to Springwater corridor bike/running trail 0.5 miles from light rail station to downtown. 1 mile from downtown Milwaukie shops. 1.5 miles to Sellwood/Westmoreland. Close and convenient to freeways. Lots of natural light. Dead end street. Large separate bedroom Full bathroom with shower/tub Large living room area with adjacent breakfast nook. (Low ceiling beams about 6'2" in case you are tall).

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.

4.96 out of 5 average rating, 160 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.

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.

4.99 out of 5 average rating, 293 reviews

The 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.

4.94 out of 5 average rating, 306 reviews

A vibrant area features a comfortable gray couch paired with a glass coffee table. A colorful rug with bold patterns adds warmth to the space, while a potted plant and wall art enhance the cheerful atmosphere.

Apartment in Milwaukie

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.

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.

4.99 out of 5 average rating, 400 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.

4.88 out of 5 average rating, 701 reviews

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 Milwaukie

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.

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.

4.96 out of 5 average rating, 263 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.

The exterior showcases a red house featuring a bright yellow door. Two colorful chairs are placed beside a small table adorned with potted flowers. Lush greenery surrounds the area, with a stone walkway leading up to the entrance.

4.97 out of 5 average rating, 257 reviews

Lovely Art Filled Home 15 min to Downtown

This comfortable and newly remodeled home sits on a quiet residential street in the Ardenwald neighborhood a few blocks from the Portland border in Milwaukie. It's thoughtfully decorated throughout with local original artwork that's been curated by us, also artists! The trendy Sellwood and Woodstock neighborhoods are a little over a mile away filled with locally owned shops, bars, and restaurants.

4.97 out of 5 average rating, 187 reviews

An open living area is highlighted by a cozy sofa with patterned cushions and a spacious bed dressed in soft linens. A wooden dining table with chairs is set near a window, enhancing the light, airy feel of the space. An inviting side cabinet adds functionality.

Apartment in Milwaukie

Milwaukie Retreat in the Woods

Your private apartment is located on a wood filled lot with a private outdoor area, shade and even deer on occasion. We are 12 miles from the airport, near freeways with easy access to downtown, and to make your way to the coast or the Columbia Gorge, Mt Hood and the Willamette Valley for wine tasting. We have added extra cleaning procedures to help fight against Covid 19.

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Popular amenities for Milwaukie vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Milwaukie

A cozy living area features a white-brick fireplace, complemented by a wooden mantel and decorative plants. A modern bookshelf displays a variety of books and personal items. A soft area rug lies underneath a circular side table, creating a welcoming space for relaxation.

4.85 out of 5 average rating, 13 reviews

“The Redwood House 2.0” Safe Area, Pet friendly

4.96 out of 5 average rating, 76 reviews

A modern living area features a gray sectional sofa, positioned near large windows that invite natural light. A cozy, black gas fireplace adds warmth to the space, complemented by a round, textured pouf on the floor.

Guest suite in Gladstone

Top of the World - Apartment near PDX w/ AC

A transitional style living room is presented, featuring a spacious sectional sofa and a barrel lounge chair. Natural light filters through the windows, illuminating a corner bookshelf and a smart 55” 4K TV mounted above the fireplace. The warm tones add to the inviting atmosphere.

5 out of 5 average rating, 9 reviews

Central Stay w/Treehouse! Near Downtown & Nature

4.9 out of 5 average rating, 98 reviews

A compact kitchenette features green cabinetry, a wooden countertop, and open shelving. A white refrigerator stands beside the counter, which includes a sink and a kettle. Decorative bowls are arranged on the shelves, all set against a leaf-patterned wallpaper.

Guest suite in Portland

Cozy Sellwood District Studio

A spacious studio suite features a queen bed with a patterned blanket and soft lighting. A cozy seating area includes a gray couch and round coffee table. A small dining table for two is positioned near the window, enhancing the inviting atmosphere.

4.8 out of 5 average rating, 345 reviews

Clean & Cozy "Private" Studio Suite

5 out of 5 average rating, 6 reviews

The living area features a comfortable gray sofa with a cozy throw blanket draped over one arm. Two light-toned armchairs complement a round wooden coffee table, while textured wall art and decorative baskets adorn the bright walls. Natural light flows through a nearby window.

Home in Oak Grove

Newly Built Modern Escape | EV, Gym, Pets

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.

4.99 out of 5 average rating, 95 reviews

Oak Grove Easy-Centrally located w/King Bed