Villa vacation rentals in Southern 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.

Riverside Vineyard Estate

On over 800 ft of year-round flowing Applegate River frontage for trout, fishing, swimming, rafting, stand-up paddleboarding, kayaking, or just relaxing. Enjoy amazing mountain & river views from the expansive deck to chill by the fabulous river. Large club-style great room with plenty of natural light from large windows. Big screen cable TV, pool table, and yoga area. Entertainer's kitchen delight with large dining table for large gatherings. Proven venue for wedding events up to 150 guests!

Luxury Ashland Mountain Escape: Pool, Hot Tub

Live the Southern Oregon paradise life at the Jefferson Estate — a fabulously appointed home on 8 acres, perfect for group getaways or small gatherings. Take in views of Grizzly Peak while fishing in the small stocked pond, or soak in the seasonal outdoor pool or hot tub while enjoying the quiet of nature. Play games on the lawn, read by the living room fireplace, or try your hand at the billiards table. The kitchen is fully equipped to live out all your entertaining dreams, and a screened sun

Leaburg Lakeside Villa

We welcome you to enjoy this spacious and unique home, nestled at the upper end of Leaburg Lake. The house is stunning inside and out. It's surrounded by forest and gardens. The house is beautifully decorated and fully equipped with all your needs. Enjoy the beautiful deck with a view of Mckenzie River as it flows in to Leaburg Lake. There is a private dock down on the water where you can swim, kayak, fish or even dock your own boat. This house provides a unique, wonderful experience for all!

Family Friendly Home! HotTub, Game Room, MiniGolf!

Welcome to our family friendly little home with all the fun add ons you could dream of. A Tiny home with tons to offer for the kids!! There's mini golf, a hot tub, a full arcade room, a playground, a jungle gym, and half court basketball court... Located on a pleasant street in a great part of town with a market just blocks away. just 3 minutes off the freeway. Two Bed room with queen size beds, and a sleeping loft for two kids. Come sit by the fire, watch the kids play in the yard, and relax.

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!

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.

Luxury Mansion near Crater Lake!

Newly listed on AirBNB, be one of the first to enjoy this incredible 7500 sqft home! Beautiful hardwood finishes throughout the home, new luxury wood furniture to go with it. Views of Agency lake and the Cascade mountains throughout the house. Game room with pool table, foosball. Movie theater with 150" screen/4K projector. Sirius XM audio/speakers in all rooms! Starlink 200Mbps internet. Nearby Airplane Hangar also available if you are flying in to Chiloquin in your private airplane!

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.

Near UO, 2 KING suites Zen Spa Retreat, views

Welcome to Zen Haus Suite A, a serene mid-century modern retreat with breathtaking west-facing views. Designed for one-level living, it’s senior and disabled accessible. Embrace the minimalist design and "hygge" ambiance, surrounded by nature’s tranquility. Whether you’re working remotely or unwinding on vacation, you’ll find all the comforts of home. Recharge at Zen Haus, where style, comfort, and relaxation come together flawlessly.

The Gem Estate by AvantStay | Modern Farmhouse

- Beautiful estate consisting of a main house, detached barn with bedrooms - Perfect layout for large groups of multiple families or friends - Large patio with a hot tub, al fresco dining area, and grill - Sauna and cold plunge - Firepit with comfortable Adirondack seating - Large, private lot for plenty of space and privacy - 25 minutes north of central Bend - Game room and garage with workout equipment