Holiday rentals with outdoor seating in Milwaukie

Open garden studio in the heart of the SE Portland

This spacious and open floor plan garden studio is in the heart of SE Portland. Within steps of the Belmont District, a few blocks from Hawthorne Blvd, Division St, Stark St, 28th & Burnside, and so much more. You can easily walk, bike, or bus to awesome places to see, drink, eat, visit, etc. An excellent launching point for all of the Rose City, we are a short bike ride or bus to Downtown, museums, and concert venues. Enjoy all that Portland has to offer at this centrally-located neighborhood.

Cozy vintage camper in the woods of Portland.

Warm & cozy vintage trailer nestled next to Forest Park. Enjoy a fire pit, covered patio, uninterrupted forest vista, and hot, dreamy outdoor bath. Minutes to the center of PDX by car, rideshare, or bus. Comfortable, easy, & whimsical camping experience. Forest Park trail is steps away, Sauvie Island and the historic Cathedral Bridge are 5 minutes by car, and 10 minutes to Slab Town and Alphabet District. The beauty and privacy of this spot may make it hard to venture out. IG: @lilpoppypdx

Pinot Paradise in Dundee Hills

Beautiful wine country guest suite and property in a stunning setting. 2 bedroom / 1 bath, sleeps 5. Located in the heart of Dundee Hills on 3 acres of picturesque farmland, offering a peaceful getaway and quick access to local wineries and restaurants. Private entrance, parking, wifi, fire pit (wood and smores kit provided!) , goats, creek, and much more to enjoy. Great for a couple's getaway, girls/guys weekend, family vacation, or personal retreat. A slice of heaven in wine country!

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.

@TheShireAirbnbPDX nature retreat

Enjoy the sounds of nature when you stay in this unique Shire themed 1 bd RV with both sunrise field views & sunset forest views. Snuggle up on the patio for evening relaxation, or drink coffee while you spot the native birds. Far enough away from town, but close enough to drive 5min for delicious choices in local restaurants, wineries and taprooms. Also close by 10/15mins are activities like golf, horseback riding, hiking, waterfalls, swimming, festivals, & escape rooms.

Henriette House - Cozy, Artsy, Walkable & AC!

Step into this charming 1907 craftsman, nestled in the heart of Portland’s trendiest neighborhood. Just steps from breweries, shops, and top restaurants, it’s the ultimate spot to soak up local culture—or unwind in style. Relax in the sunny backyard with a game of cornhole, whip up meals in the fully stocked kitchen, or venture out to explore Portland and the stunning PNW wilderness nearby. We have cold AC and a warm, inclusive vibe—LGBTQ+ friendly!

Patio Cottage for 1-2 w/kitchen & gas firepit

With its private entrance at the end of a secluded patio, this eco-friendly cottage is the ideal retreat for solo travelers or couples. In its super-quiet, colorfully decorated, chemical-free interior, you're just steps from the happening Alberta Arts District, Killingsworth Street, and Williams and Mississippi Avenues, all chock full of locally-owned shops, restaurants, pubs, and food cart pods of all kinds.

La Petite- BRAND NEW!

ELEGANT URBAN OASIS IN PORTLAND'S DIVISION NEIGHBORHOOD. Step into an enclave of opulence and comfort in our newly designed Accessory Dwelling Unit (ADU). This private haven, sculpted with attention to every detail, stands as a testament to luxury and comfort, offering you Portland's finest in an intimate, and sleek setting. You'll cherish our ADU's tranquil ambiance and our foodie forward neighborhood.

Free Parking/Gym/Rooftop/Pearl District/Downtown

Tahitian, one of the four types of Pearls in the world. Welcome to Pearl District in PDX! Simple yet elegant, the Tahitian Stay combines convenience and style. Location is extremely walkable and offers quick access to Whole Foods and the MAX Light Rail. Simply step out of the building and get lost in the brewery blocks, fine dining, entertainment & premier retail shopping.