Vacation rentals in Portland Downtown

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Top-rated vacation rentals in Portland Downtown

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Guest favorite

A charming yellow cottage with a white picket fence is showcased. A stylish mailboxes stands prominently, featuring a heart-shaped accent. The entrance is marked by a white door and steps leading up to the porch, surrounded by neatly arranged rose bushes.

Cottage in Newberg

4.95 out of 5 average rating, 150 reviews

The Valley Wine Cottage - Walk to Tasting Rooms

A cozy cottage in the heart of wine country. Walk to restaurants and tasting rooms and then relax on your own front porch or private back deck. The cottage has two bedrooms, both with Christopher Knight (tm) queen-sized beds for a great night's sleep and you can rent it as a one or two bedroom. Although we're walkable to many attractions, our street is tranquil and you'll enjoy sitting in a porch rocker with a glass of wine (in our varietal-correct Riedel glasses), or relaxing in the hammock.

Guest favorite

The exterior of a three-story home is showcased, featuring warm-colored walls with contrasting trim. A spacious front steps area is made of stone, leading to a wooden door with decorative hinges. Hanging flower baskets add a touch of greenery to the entrance.

Home in Northeast Portland

4.95 out of 5 average rating, 313 reviews

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.

Top guest favorite

A private patio area is featured, showcasing a wooden structure with clear roofing, surrounded by lush greenery. Two chairs with cushions are positioned near a small table, creating an inviting space for relaxation amidst flowering plants.

Home in Central Northeast Portland

4.98 out of 5 average rating, 106 reviews

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.

Top guest favorite

A well-lit upper hallway leads to a cozy bedroom, featuring sloped ceilings. Artwork hangs on the wall, while a wooden chair and bedside table accompany a spacious bed adorned with light bedding. Natural light enters through an adjacent window.

Home in Sherwood

4.99 out of 5 average rating, 144 reviews

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.

Guest favorite

An outdoor patio features a long wooden dining table set with dishes and glasses, inviting shared meals. Comfortable seating arrangements include plush chairs and a sofa, surrounded by greenery. Sliding glass doors provide access to the interior, while string lights add a charming ambiance.

Home in Northeast Portland

4.9 out of 5 average rating, 334 reviews

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!

Top guest favorite

A modern container home is nestled among trees, featuring a deck with railing and large windows. Soft outdoor lighting highlights the structure against a colorful twilight sky, while the surrounding bamboo adds a lush green contrast.

Shipping container in Oregon City

4.97 out of 5 average rating, 125 reviews

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.

Guest favorite

An illuminated patio area features a covered wooden structure with string lights providing a warm glow. Comfortable seating is arranged around a central table, and a large umbrella adds color to the outdoor space. Lush plants are visible along the perimeter, enhancing the tranquil atmosphere.

Cottage in Beaverton

4.93 out of 5 average rating, 106 reviews

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.

Top guest favorite

A modern kitchen showcases stainless steel appliances and a farmhouse-style island with seating. Reclaimed wood accents include a bench along the wall. The space is filled with natural light, illuminated by large windows and exposed wooden beams overhead.

Guesthouse in North Portland

5 out of 5 average rating, 222 reviews

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.

Superhost

A bright living room features a cozy gray sectional sofa with blue accent pillows and two dark armchairs. Natural light flows through large windows, with lush greenery visible outside. A coffee table sits centrally on a plush area rug, complementing the fireplace and wall-mounted TV.

Home in Vancouver

4.76 out of 5 average rating, 189 reviews

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.

Guest favorite

An open living space showcases stylish furnishings and a modern kitchen. A light blue sofa pairs with a round coffee table on a patterned rug. Natural light floods the area, highlighting the dining table with black chairs and a kitchen featuring sleek appliances and decorative shelving.

Apartment in Northeast Portland

4.92 out of 5 average rating, 136 reviews

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!

Top guest favorite

A modern kitchen and dining area features wooden cabinetry and stainless steel appliances. A large island with a sink and bar seating is prominently displayed. A wooden dining table with round chairs is complemented by neutral decor on the table, creating a functional and inviting space.

Home in Newberg

4.98 out of 5 average rating, 176 reviews

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!

Top guest favorite

A modern kitchen space features sleek cabinetry and stainless steel appliances. A wooden dining table is surrounded by white chairs, with simple place settings visible. Open shelving displays dinnerware, adding a touch of warmth to the contemporary design.

Guesthouse in Central Northeast Portland

4.99 out of 5 average rating, 471 reviews

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...