House vacation rentals in Milwaukie

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.

4.95 out of 5 average rating, 121 reviews

Secluded Studio

This a fully private and detached guest house is quiet and relaxing. Walk down your a private pathway to a completely fenced, 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 Commute Train, Reed College, Woodstock, Sellwood, & East Moreland & Milwaukie Providence Hospital. Ride, walk, run or ride along Springwater Corridor.

LocationFamilyOutdoor spaces

A spacious bed is framed by a wooden headboard, complemented by crisp white linens and fluffy pillows. A light beige quilt covers the bed, providing a soft texture. Next to the bed, a simple nightstand with a glass lamp adds a functional touch to the design.

4.95 out of 5 average rating, 184 reviews

Milwaukie Easy-Centrally located, Close to PDX

Our home is a spacious cozy contemporary home, complete with an outdoor deck, and a beautifully decorated interior with contemporary pieces that complete the design of our home. Windows in living & dining space are across from each other bringing in ample light. Our space is furnished with various mid-century, modern and contemporary pieces that complete the home. Shared Spaces •Parking area •On site laundry shared with other tenant, tenant has a separate living area with no other shared spaces

ValueFamilyCheckout

4.92 out of 5 average rating, 166 reviews

The open living space features a sectional couch with cushions, a wooden dining table, and chairs in a well-lit area. A television is mounted on the wall, with kitchen and dining areas visible in the background, illuminated by natural light from large windows.

Home in Gladstone

Forested Hygge House Getaway

Relax in a Gladstone oasis overlooking an untouched trail and forested area. A cozy, bright, and private spot. I hope you connect with my affinity for vintage art and clean lines! You’ll have the entire house and 1/3 acre to yourself. Less than 30 mins from most anywhere in Portland Metro, 10 mins to Oregon City, and 1 hr to Mt. Hood. This is a dog friendly (no cats), non-smoking house. The large yard is on a dead-end street, though not fenced. *Some uneven paths and slip hazards are present

LocationFamilyTV

A single-level home is presented, featuring a light blue and gray exterior with a combination of brick and siding. The front yard is manicured with greenery, and a driveway leads to a two-car garage. A clear blue sky serves as the backdrop.

5.0 out of 5 average rating, 171 reviews

Peaceful Spacious Single Level Home

Look no further if you are looking for a clean & spacious home with all the amenities for a comfortable stay. Single level with a walk in ADA shower in the primary bathroom. Dedicated office/den with excellent wifi. Remote work & family friendly. 5 minutes away from the Clackamas mall, Costco warehouse/gas, Target, REI, restaurants, Kaiser hospital. Clackamas is a suburb of Portland, only 25 min. drive of downtown and airport. *Co-hosts conveniently live nearby to assist whenever needed

ValueFamilyParking

4.91 out of 5 average rating, 152 reviews

A fire pit is illuminated in the foreground, casting warm light on the surrounding stones. In the background, a colorful sunset paints the sky with shades of orange and pink, while trees and distant hills create a serene landscape.

Home in Happy Valley

RoofTop FirePit, HotTub & Outdoor Theater

Our large (1,500sq ft) space (private access), has a bedroom, bathroom, living room w/ a fireplace, hot tub, full gym as well as a kitchenette w/ full sized fridge, keurig, microwave, air fryer, toaster oven, single burner, and laundry facility. Smart tvs, hammocks and a rooftop firepit are in the outdoor entertainment area. LGBT & BIPOC friendly. Gym, hot tub and laundry are shared with owners but guests have priority access. Close to Mt Hood Wilderness (45mins) & Downtown Portland (15mins).

LocationFamilyAccess

4.95 out of 5 average rating, 134 reviews

The modern two-story home features a light exterior with vertical siding and a covered porch. Two chairs are positioned near the entrance, while vibrant pumpkins and landscaped flowers enhance the welcoming atmosphere. A garage is visible to the right.

Home in Oak Grove

Cozy, Modern Farmhouse, King Bed, Great Yard, Pets

Enjoy your stay in the quaint, Oak Grove neighborhood of Portland a block from the old historic trolly trail. Minutes to the river, close to downtown, ample dog parks make this spot perfect for your getaway. Our family poured our hearts into designing a modern and cozy space that our family loves to visit. We're so very excited that we get to share that with you! We've got a yard that the whole family will love and I know you'll make some priceless memories here, just as we have. Welcome!

FamilyLocationWalkability

4.97 out of 5 average rating, 179 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.

FamilyLocationIndoor spaces

Home in Southwest Portland

Rock N Roll House + Hot Tub

Featured in The Destination Channel’s TV show “Staycation- Sports Edition” in the fall of 2025 and found on YouTube. Contemporary-style music-themed home. Jam out with instruments, classic albums and record player by the pool table. Stunning gourmet kitchen. Big lawn and deck with teak dining table and bbq. Hot tub plus gas and real fire pits. Garage is packed! Ping pong table, pinball, foosball, Pop-a-Shot basketball, Treadmill, Peloton bike, dumbbells, and four mountain bikes+helmets.

LocationFamilyDecor

4.97 out of 5 average rating, 313 reviews

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.

4.97 out of 5 average rating, 134 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!

ValueFamilyNearby

Home in Southwest Portland

A charming outdoor area is visible, featuring a stone pathway leading to a cozy seating arrangement with two black chairs. The bungalow is framed by lush greenery, with warm light emanating from the windows, inviting a peaceful ambiance.

Multnomah Village Hideout

Explore our new, artist-built bungalow in Multnomah Village, Portland. This cozy space sleeps four with a queen bed upstairs and a pullout couch downstairs. Steps away are charming cafes, shops, and a park with hiking trails and dog parks. Enjoy local activities like bingo and dining on pet-friendly patios. Complete with essentials including laundry and a breakfast nook, this bungalow is perfect for both short and extended stays, offering a unique Portland experience.

ValueFamilyGetting around

4.97 out of 5 average rating, 176 reviews

4.95 out of 5 average rating, 536 reviews

The exterior of the home features a well-maintained gray facade, accented by a wooden deck. Surrounding greenery includes grass and a few trees, creating a serene outdoor space. The driveway is visible beside the house, leading to additional structures in the background.

Home in Oak Grove

Oak Grove Getaway Retreat

Welcome to our remodeled 2,350 sqft home in a peaceful, friendly neighborhood! This cozy, modern retreat is perfect for families or groups. A short walk or drive to grocery stores, restaurants, and an 8-screen cinema. Downtown Portland is near for a fun day trip. Enjoy local trails and events. With an updated, inviting interior, it’s your ideal base for Portland’s charm. Book now for a relaxing stay with exciting discoveries!

ValueFamilyGrill

Superhost

Home in Happy Valley

Mid Century Villa w/Mountain View & Movie Theater

3400 sq ft hillside retreat decked out with rare furnishings. Take in the Cascade Mountains from the wraparound deck and lounge under giant maple trees. You'll love the 125” Hi-Def movie theater (w/ 200+ movies)! Two large primary suites with king bed and large showers. One additional queen bedroom and one large office. Close to urban and nature, 20min to the airport, with daytrip opportunities to all the PNW must-see spots.

LocationFamilySolo travel

4.88 out of 5 average rating, 390 reviews

Popular amenities for Milwaukie house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A spacious living area is highlighted by a warm brown leather seating arrangement, including two armchairs and a three-seat sofa. Natural light filters through the dual windows with rolled shades, complemented by two potted plants and a contemporary area rug.

4.99 out of 5 average rating, 116 reviews

Corner of Heaven

FamilyLocationTV

4.96 out of 5 average rating, 176 reviews

Home in Vancouver

The Starburst Inn: Enclosed Heated Pool, Theater

FamilyLocationTV

4.97 out of 5 average rating, 177 reviews

An airy kitchen features sloped ceilings with wooden beams and warm wood cabinetry. A vintage-style aqua refrigerator complements stainless steel appliances. Natural light filters through three windows, while a vibrant rug adds a pop of color to the space.

Home in North Portland

Rose City Hideaway

ValueFamilyGetting around

Superhost

4.73 out of 5 average rating, 94 reviews

Private Pool & Hot Tub Oasis | Cowboy Retreat

LocationFamilyBackyard

A charming Craftsman home is set against a vibrant blue sky, featuring a well-maintained garden filled with colorful flowers. The entrance is framed by lush greenery and a small set of steps leads to the welcoming front porch.

4.94 out of 5 average rating, 67 reviews

Frankie's Place; Walkable Craftsman luxury!

LocationFamilyLayout

5.0 out of 5 average rating, 38 reviews

A heated in-ground pool is surrounded by a concrete patio, featuring a slide on one end. Lush greenery and vibrant flowers are visible nearby, creating an inviting outdoor space. A covered deck area with seating is seen in the background, providing shade and relaxation options.

Home in Vancouver

5bdrm,Heated Pool, Hot Tub, Sauna.

ValueLocationCleanliness

4.92 out of 5 average rating, 39 reviews

A modern single-story house features a wide front porch with wooden railings, flanked by large windows. A spacious driveway leads to a two-car garage, while a lush green lawn and trees surround the property, providing a natural and quiet ambiance.

Home in Troutdale

The Art Farm

LocationFamilyAccuracy

4.95 out of 5 average rating, 39 reviews

A spacious outdoor area surrounds a private pool, featuring a gentle blue hue. A smooth decking is present, accompanied by a wooden privacy fence. Colorful pool floats are visible, and a waterslide can be seen at one end, enhancing the recreational space.

Home in Vancouver

One level Entertainers Dream *Heated Pool*

ValueLocationHot tub

Weekly house rentals

A charming tiny house is visible, framed by tall trees and lush greenery. The exterior features a sloped roof, with large windows offering natural light. Stone steps lead to the entrance, which is surrounded by vibrant foliage and a serene path, emphasizing the privacy of the retreat.

4.92 out of 5 average rating, 114 reviews

Charming Tiny Forest Home, PDX next to Lake Oswego

FamilyValueTV

The entrance features a covered porch with a wooden frame and decorative pillars. Colorful flower baskets and potted plants adorn the space, while a bench rests on the wooden deck. Large windows provide visibility into the home, enhancing the welcoming appearance.

4.85 out of 5 average rating, 267 reviews

Miranda's Lodge- cozy place with hot tub

ValueFamilyBackyard

4.96 out of 5 average rating, 157 reviews

A welcoming front porch is presented, featuring warm wood siding and a secure wooden door. A comfortable chair and small table are positioned on the polished wooden floor, surrounded by lush greenery visible in the background.

Home in Gladstone

Gladstone Garden Retreat

ValueLocationOutdoor spaces

4.96 out of 5 average rating, 265 reviews

Holiday Home

ValueLocationAccess

A spacious living area features a light-colored leather sofa paired with a glass coffee table, complemented by an area rug. Natural light filters through large windows, illuminating the open layout that connects to the dining area and staircase in the background.

4.99 out of 5 average rating, 100 reviews

Home in Clackamas

ValueLocationCondition

Home in Southwest Portland

A mid-century living space features high vaulted wood ceilings and large windows that invite natural light. A leather sofa and patterned rug provide comfort, while a kitchen island with bar stools enhances functionality. Artwork adorns the wall, adding a touch of character to the room.

Portland Modern

FamilyValueHospitality

4.96 out of 5 average rating, 165 reviews

4.8 out of 5 average rating, 319 reviews

Darling house,Great location!!

ValueLocationKitchen

4.97 out of 5 average rating, 281 reviews

A fully mirrored room creates an immersive experience with soft blue mood lighting. A thick mat covered with clean linens and pillows is laid out for sleeping. The reflections on the mirrored walls enhance the unique ambiance, inviting guests to rest and explore.

Home in Lake Oswego

Signal House – Light Up The Portal

LocationValueCondition

Private house rentals

5.0 out of 5 average rating, 27 reviews

Blanton House

FamilyLocationBathroom

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.

4.96 out of 5 average rating, 54 reviews

The Redwood House 2.0 Safe Cozy 2BR Pet Friendly

LocationFamilyBathroom

The exterior of the home is shown, featuring a blue-gray facade with a white front door. A spacious lawn extends in front, bordered by tasteful landscaping. The driveway leads up to the entrance, while trees and shrubs frame the property, adding a sense of privacy.

4.91 out of 5 average rating, 43 reviews

Comfortable spacious home!

ValueLocationLaundry

4.91 out of 5 average rating, 22 reviews

Beautiful Newly Remodeled Duplex

LocationFamilyAccuracy

A modern kitchen features sleek stainless steel appliances and white subway tile backsplash. A central island with a light wood countertop is accompanied by two black stools. Natural light filters through the window, illuminating potted plants and organized open shelving.

4.95 out of 5 average rating, 93 reviews

Beautifully Renovated 1920 Home | EV, Pets

LocationValueOutdoor spaces

5.0 out of 5 average rating, 11 reviews

3/2 in Milwaukie - Quiet location, Free Parking!

FamilyValueCleanliness

4.88 out of 5 average rating, 24 reviews

Lady Carmello

FamilyLocationHiking