Vacation rentals in Milwaukie

The Portland Villa on Alberta St

In the heart of NE Portland's vibrant and bustling Alberta Arts district. Endless options for dining, drinking, shopping and entertainment within walking distance. The main home is 2800 sqft plus an additional 1200 sqft on a private rooftop deck (that we built ourselves!). There is natural light (and plants) galore. Prepare meals in our chef’s kitchen. We don’t skimp on linens, supplies, cozy mattresses or bedding. A legally permitted rental by the City of Portland. 1% for The Planet member.

Heron Cottage, Urban Retreat-King Bed

The Heron Cottage was built in 1914 and was part of a network of small farms that existed in what was then the hinderlands of Portland. Now it's an urban vest pocket neighborhood with easy access to a regional hospital, light rail, bus routes and freeways. This is a pedestrian neighborhood with very narrow streets. We know our neighbors and enjoy the cultural diversity of this little enclave. The cottage's front porch beckons you to slow down, relax and maybe even make some new friends.

Old Town Retreat - Best place in Old Town Sherwood

At the gateway to wine country, our peaceful Old Town 1916 craftsman home brings historical charm with many amenities right in the heart of Old Town Sherwood. Sleeps 9 with 6 new beds, 2.5 remodeled baths and an open kitchen with gas range, everything you need for a few or many. Owner occupies the basement and rear separated dwelling on property. However, both the basement and rear dwelling are completely locked off and have entirely separate entrances. The best place in town.

Sustainable Dream Container Getaway with a View

A private green-luxury container home inside a bamboo grove and lavender field overlooking a serene valley. This brand-new, single-level home features picture windows leading out to a quiet deck with sunset views every night. Situated in the heart of the Pacific Northwest between the mountain, lakes and coast - exploration, wine tasting and the best nature spots are just a short drive away. This private home can comfortably host couples or up to 3 people including the couch.

Cozy Cooper Mtn Cottage

Uniquely cozy with all the amenities of home but in a cottage up on Cooper Mt. Where you are surrounded by trees , feel the breezes, sunrise and sunset in the same day, and sometimes the wonderful wildlife around us. Birds in the sky , rabbits and sometimes deer, and yes our two friendly goats. Oh yes and the expansive midnight sky with the bright stars twinkling above or the big round moon shining down on you as you sit on the patio in the evening enjoying the night air.

Richmond Cottage in St Johns, Portland

This light, bright cottage is located in the heart of the St Johns neighborhood in Portland. Full of charm it features loads of reclaimed wood with an industrial farmhouse vibe. Complete with a private deck, keyless entry, full kitchen with eat-in island and a sleeping loft with a queen sized bed. It is a close walk to restaurants, coffee shops, bars and shopping. Easy access to downtown Portland, University of Portland, the airport and the rest that Portland has to offer.

Style Meets Comfort in Beautiful Design

Discover unparalleled comfort and style in this beautifully designed Vancouver retreat, perfect for families and groups seeking a memorable getaway. This spacious home hosts two living rooms, king-sized beds in every bedroom, and a fully equipped kitchen, this is where comfort meets convenience. Nestled in a peaceful neighborhood with easy access to local attractions, dining, and shopping, making it the ideal home base for your Pacific Northwest exploration.

The White House in Mississippi ~ 95 WalkScore

Welcome to our charming three-bedroom retreat in the heart of Mississippi Street! Step outside and dive into the vibrant local scene, with endless dining, shopping, and entertainment options just steps away. After a fun-filled day exploring, return to unwind in style with a massive 4K HDTV, a fully equipped kitchen, and comfortable memory foam mattresses in all three bedrooms. Discover the best of Mississippi Street from our perfectly situated apartment!

Villa Fontana: Modern, Wine-Country Comfort

Welcome! Enjoy a fresh, clean, retreat while you sip your way through Oregon's Wine Country. A modern home nestled amid local historic landmarks, you will be 6 blocks from the downtown Newberg strip and within a 5 mile radius of the closest wineries, making this home the perfect choice for accessibility. Enjoy complimentary Prosecco to toast your arrival and plan to cook meals that pair with your local wine purchases using our high-end appliances!