Vacation rentals with a pool in Jackson County

Riverfront Retreat w/Pool, Hot Tub, Mountain Views

Soak in riverfront & mountain views from the hot tub or private balconies at this luxury 10-acre retreat! 3BR/4BA with 2 master suites, plus a separate pool house with its own bath — sleeps up to 12. Enjoy the pool, gravel paths to the river, and total privacy on the property. Ideal for extended stays (30+ nights) — perfect for relocations, remote work, or seasonal getaways. Interested in a shorter stay or your desired dates aren’t available? Message us directly to check availability and rates.

Value · Family · Parking

The Green Arrow Loft

Situated right on the state line this studio apartment is nestled in its own little corner of the gorgeous Colestine Valley. We're located on 80 acres that adjoin the Cascade-Siskiyou National Monument to the north, perfect for a scenic hike or a casual stroll. Nature and wildlife abound, and though quiet and private the Loft is just five minutes off I-5 and 25 minutes from unique downtown Ashland. We're pet friendly and have an outdoor pool! See the House Rules for details on pet and pool fees.

Value · Location · Kitchen

Tiny Groove with plunge pool and soaking tubs

A unique off grid experience awaits you at our eco-friendly solar powered tiny home on 6 secluded acres. The home site is perfectly cut into a groove in the hillside 200 feet above the valley below allowing for beautiful Mountain views and amazing privacy with no visible neighbors other than the variety of local wildlife. Enjoy the outdoor soaking tubs, wood fired sauna and a seasonal plunge pool. Just a short 5 minute drive to the lovely town of Rogue River and access to I-5. Pet friendly too!

Location · River · Kitchen

Beautiful Country Home next to Jacksonville!

The whole group will enjoy easy access to everything from this centrally located home! Enjoy a pool day with the family next to the serine pool. Or a fun day of wine tasting with Relik winery less than one mile away and Hummingbird less than 2 miles away! Or have a blast at a concert this summer at the Britt festival less than 2 miles away! Downtown Jacksonville is only a 3 minute drive! All queen beds have been upgraded to NEW Tempurpedic beds! King size bed is a Jennings (Very High Quality!)

Family · Location · Walkability

Treehouse at Rancho de la Paz

Reconnect with nature. Just 19 miles from Rogue Valley international airport, and smack dab in the middle of the Upper Rogue Valley wine loop. Here you can relax in the treehouse observing all that nature has to offer here. Many Deer call Rancho de la Paz home, as do other wildlife. Perhaps sitting by the pool or soaking in the hot tub will make this a memorable stay. Just 63 Miles from Crater Lake National Park. 5 miles from the Rogue River. For safety reasons this is an adult only treehouse.

Value · Family · Hot tub

Work Crews! Swimming Pool, Great Room, Big Space

Perfect for Work Teams or Families to build lasting memories. Private home in Beautiful Scenic Medford Foothills! Close to everything, but out of town. Nearby dining and groceries. Quick drive to Ski Ashland, Crater Lake, Water Ski Lakes, Fishing Lakes, and Roxy Ann Winery. Hiking at Roxy Ann and Table Rocks. Vaulted Great Room, huge modular couch, 65" and 75" TVs, Redzone, Pool Table, Ping Pong, Coffee & Wine Bar, Golden Tee. Year-Round Hot Tub, Seasonal Swimming Pool (mid May-End of Sept.)

Location · Value · Layout

Mexico Apartment at Wood Hamlet, by Downtown

The Wood Hamlet Mexico Apartment is a delightful space filled with color and culture. A short walk to town, 72-acre park & the theaters. Feel the welcoming warmth of the hand-crafted Mexican decor. Basement unit but with lots of windows and light. (4 beams at 6'1") Kitchen, with top of the line induction burner, fridge, microwave..., full bath, W/Dryer, work area... Wi-fi. Beautiful, garden with sitting areas & swimming pond. Parking. (Ashland City Permit# 17-080) NO SMOKING ON PREMISES

Family · Location · Hospitality

The Aloha House - Hot Tub - Pool

The Aloha House is located just above the University and only 1.5 miles from downtown Ashland. Nestled up a hill in the forest, you'll be transported to your own little private resort-like getaway with stunning views, architectural design that brings the outdoors in, and ample space for dining and entertaining poolside. The property consists of two separate studios (both included) connected by a unique outdoor living space with a seasonal pool, spa, outdoor shower, bar & BBQ, and more!

Location · Value · Outdoor spaces

Entertainment Home on Golf Course - Hot Tub /Pool

Fantastic single-level home with stunning golf course views. The resort-style backyard features a heated pool, hot tub, ping-pong, cornhole, and a patio with a barbecue. This beautiful three-bedroom house also includes a studio guest house, a large chef's kitchen, a pool table, multiple TVs, and spacious living areas. Centrally located in East Medford, it's close to shopping, restaurants, the airport, and medical centers. Fully stocked with everything you need to feel at home!

Location · Family · Kitchen

Farm Cottage 1/2 Mile Outside Jacksonville

Private cottage with fenced yard. 1/2 mile to historic Jacksonville and the famous Britt Festival. Noted local winery Rellik is one property away and we are in the heart of the Rogue Valley wine country. Pool available in the summer and meeting our farm animals is available with advanced notice. Our place is designed to help you create lasting memories! We look forward to your visit!

Location · Family · River

Dream House at Paschal Winery

Discover your dream retreat in this stunning 3-bedroom, 3.5-bath home nestled on the picturesque Paschal Winery in Talent, Oregon. Surrounded by 360 degree views of mountains, vineyards and orchards with the most romantic view of city lights from the patio. Plus we do have a two foot outdoor not heated wading pool!

Family · Location · View

Jacksonville Cottage, Hot tub+wildlife+boutique

Cozy suite in the heart of wine country just down the Road to historical Jacksonville. Enjoy the private acreage , enveloped in an Oak Savannah The Farm house and jacuzzi are very private. Fireplace with wood! . Great views of the Table Rocks! Bbq griddle patio. Easy access to 5 freeway Pond!

Location · Outdoor spaces · Hospitality