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.

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.

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!

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!)

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.

Swimming Pool, Hot Tub Huge Great Room Big TVs Fun

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.)

Magnificent Hilltop - Luxury Views, Beauty & Peace

Enjoy top of the world views of the beautiful Rogue Valley and Table Rock, from this amazing home. Situated on over 80 acres with private walking trails, view deck, terraced hillsides and magnificent sunsets, this is a perfect place to gather with special people or immerse yourself in a peaceful retreat. The spacious home has an open floor plan with quality craftsmanship throughout. Enjoy a chef's kitchen (granite & stainless steel), walnut floors and magnificent views from every window.

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!

Rellik Wine Suite near Jacksonville Hot Tub/Pool

The Wine Suite at Rellik House includes one bedroom with a king-size bed and one bathroom. A sleeper sofa in the living room can accommodate two additional guests. The kitchenette is outfitted with microwave, refrigerator, coffee maker, washer and dryer, plus cable TV. The Wine Suite shares 15-acres with Rellik Winery and Vineyard as well as a lovable herd of alpacas and donkeys. Enjoy a fire pit with outdoor seating, plus a swimming pool and hot tub that are shared by all guests.

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!

Pool, Hot Tub & Sauna 2 Mi to Jacksonville

The moment the gate closes behind you, the pace changes. Cool off in the pool, soak in the hot tub, and relax the day away in the cedar sauna — mountain views by day, star-filled skies at night. ● Large pool area with plenty of lounge chairs ● BBQ & outdoor dining ● Ping pong, board games & movie nights ● Living room + family room to spread out ● Large dining table seats the whole crew ● Gated, private & serene ● Wave to the two resident goats in the fields

The Siskiyou House

Welcome to Medford Oregon! This updated two story home has 5 bedrooms with brand new memory foam mattresses and smart tv’s, two and a half bathrooms and a layout that works well for families & friends. The large dining table sits six comfortably and the glass sliding door opens up to the backyard. Enjoy the in ground pool and hot tub or sit next to the fire pit and play yard games. I live in Medford and am quick to respond if needed. Enjoy your stay!