Villa holiday rentals in Oregon

On Sale Now! Cute Downtown Gem! Walk to the Hult!

Priced perfect for one, but cute & cozy for a couple! Possible, but snug for up to 4 with living room air mattress set. Private one bedroom with natural light & adorable furnishings includes coveted on-site parking! Galley kitchen stocked w/basic appliances. Shopping, galleries, & night life, Whiteaker/downtown adjacent. Great spot to get your feet planted & checking out town! Cool, arty vibe with open space makes it feel like your own home. Ground floor with outside courtyard patio terrace.

Wine Country Villa w/ Pool, Sauna, Hot Tub- 5 BD

Hex Odyssey is a newly expanded 5 Bedroom, 3 Bath six sided villa in Dundee Oregon, the epicenter of Oregon Wine. Here you'll find a spacious, modern, and serene retreat with expansive views. The home has 3 living rooms, 2 kitchens, an exercise room with hot sauna, a swimming pool and a hot tub. A perfect place to reflect + rejuvenate. Our sauna and hot tub are open year round, the pool is open May to Sept. We offer this property as either a 5 bedroom or 3 bedroom rental to fit your needs.

New Riverfront Luxury with acreage and great views

Trask River Fishing Lodge is a brand new Riverfront modern luxury custom home completed in spring ‘22 on 13 acres. The state has 1300 ft of accessible RIVER 💦 frontage. It is located only 5 minutes from Tillamook and 15 minutes from the beach. The property is a paradise for the wildlife and fishing lover. Enjoy beautiful sunsets, cows roaming, direct river access, multiple trails, evening bonfires and world class fishing. A perfect place to gather with family and friends or a romantic getaway!

Hello, GORGEOUS! Amazing Vintage King Stunner!

Enjoy an over the top, one of a kind, lavishly stylish, retro experience at this high end vintage, spacious & fully furnished LUX DELUXE get-away!! Centrally located with private parking lot, you're just minutes away (and walking distance) from all of the best attractions Eugene has to offer! Downtown adjacent in the fun filled historic Jefferson-Westside neighborhood, you're also a short stroll from the 5th Street Market District, Amtrak Train Depot, and arty night life of a Whiteaker party!

Gated Wine Country Estate w/ Valley Views and Spa!

Welcome to your private wine country escape! This handcrafted 4BR/3BA home sits on 11 quiet acres in a gated community, surrounded by hillside and vineyard views. Enjoy a soak in the jacuzzi under the stars after a day exploring 40+ nearby wineries. Built with love by artist and craftsman owners, this 2,500 sf. retreat offers warmth, privacy, and a truly unforgettable stay in the heart of wine country. - 2min. to Bravuro Cellars - 10min. to Brooks Winery - 15min. to The Bramble Wine Tasting

Sleeps 14: Villa with Hot Tub, Pool & Sauna

Sleeps 14 – Hot Tub, Pool (seasonal), Sauna, Gym, Pool Table & Entertainment Room. You are renting the top unit with full access to all the amenities. Both units are available to be rented together under another listing. Experience the perfect group getaway in this luxurious 5-bedroom retreat designed for comfort, fun, and relaxation. Ideal for family reunions, corporate retreats, or friend gatherings. Relax and recharge with a private outdoor pool (seasonal), hot tub, sauna, and gym.

Cascade Lookout

This newly built, high desert getaway stunner has four suites. With a vaulted ceiling, wooded accents, and floor to ceiling windows, the open concept living area features a stunning stone fireplace, a flat screen TV and a modern, fully equipped kitchen. Relax on the large deck with ample seating and vista views. The downstairs includes a pool table, large TV area and a tatami room for the young kids. Enjoy a soak in the hot tub under the starry skies, or gather around the fire pit.

Hendricks Park Sanctuary 1: Elegance & Harmony

Beautiful home in a fully-fenced one acre park like setting. You will be surrounded by nature with lots of wildlife coming to greet you. The house is located at a walking distance of Hendricks Park and its famous Rhododendron Garden. Being in proximity of giant ancient trees is a delight for the eyes as well as the Soul. The bottom floor, ‘The Fawn Lilies Studio’, is reserved to other Airbnb guests. The two spaces are totally independent, having their own access, their own patio…

The Gem & Cottage, Pool, Hot tub, Views

Magnificent Hilltop Getaway with Incredible Views (sleeps 14.) Come enjoy this oasis on the outskirts of the magical town of Ashland. This gorgeous home is perched above town on 3 acres offering some of the most epic mountain views and best sunsets in the valley. This special place pampers you with 5 bedrooms, 4 bathrooms, gas fireplace, hot tub, copper cold plunge, outdoor pool and multiple decks to take in the breathtaking views. Located 7 minutes from downtown Ashland.

La Casita at Castillo de Feliciana - Winery on site

If privacy is what you're looking for, this cute little casita is tucked away in the vineyards of Castillo de Feliciana! Enjoy the peace and quiet of the Walla Walla countryside inside this large 1 bed, 2 bath oasis! Features include a full kitchen, with a gas stove and dining area, large Smart TV, a gas fireplace, a large step-in shower, a beautiful soaking tub, and a gorgeous patio/outdoor eating area, to name a few.

Views • Pickleball • 85” TV • Relax & Play

Welcome to Villa Solé—your high desert retreat with panoramic views of 7 Cascade peaks. Perfect for family getaways, couples retreats, or stargazing escapes. With tons of space for everyone, it’s your new base for Central Oregon adventures. Pickleball, lawn games, air hockey, 85" tv, 2 living rooms, library, wine cellar, gardens & views—oh my! Peaceful. Exciting. Unforgettable. Come experience the beauty of Solé.

Heart of Yachats Condo, Park & walk to everything!

Welcome to Sunset Villa. Once you arrive you may park and walk to everything! The Villa has 2 bedrooms and two baths, one with a jett tub. Cape Perpetua is the highest viewpoint on the Oregon Coast and is located just 2 miles south. There are many hiking trails and lighthouses to explore. Located directly below the condo is a lovely wine bar which offers live music several day per week.