Holiday rentals in Milwaukie

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.

Huge Home with King Beds in Prime Spot with Views!

Architectural masterpiece on a safe, quiet street just blocks from Williams and Mississippi Ave, home to some of Portland’s best dining, drinking, shopping and more. Spread out across three spacious levels with multiple living areas, a large open kitchen with two eating bars, four king bedrooms and a bunk room (each with its own TV!), and 3.5 bathrooms. Relax and dine alfresco on the beautiful back patio, then watch sunrises and sunsets from the east and west facing roof decks!

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.

❤️ CLEAN ★ LUXURY OASIS ★ NEAR DOWNTOWN

☀ 10 Mins to downtown + Airport ☀ Free Private on-site parking ☀ Luxury queen bed • premium bedding ☀ Queen sleeper sofa in living room ☀ Fully stocked cook’s kitchen ☀ Large private patio ☀ Fire Pit + Gas BBQ ☀ Super Fast Wifi • USB charging outlets ☀ 65” 4K Smart TV ☀ Smart Home • Alexa equipped ☀ Nebia Spa shower ☀ Heated floors ☀ Steps from public transit ☀ Safe walkable neighborhood ☀ Bikes to explore Portland ★☆Learn More Below & Experience Portland With Us!★☆

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!

LoftHousePDX w/ Sauna & Hot Tub

Debuted during Portland's Accessory Dwelling Tour, “Loft House PDX” is centrally located just off beautiful Alameda Ridge. Business and leisure travelers alike will find a peaceful retreat awaiting them in this tastefully-appointed, open and airy, modern loft house with all the accoutrements one might wish for—including a Finlandia Sauna, and STIL hot tub to enjoy after a long day of work or play, and a custom gas firepit for evening lounging...

The Cedar House at Riverbend Orchard

Escape to nature’s beauty at this serene retreat on 23 wooded acres overlooking the Sandy River. Sip coffee on the heated wraparound deck, curl up by the stone fireplace, or soak in the hot tub under the stars. Hike the private trails, discover the pond, and unwind in the sauna. Thoughtfully designed for relaxation, with cozy nooks, books, and breathtaking views. Well-trained dogs welcome! No cats or other pets due to severe owner allergy.