Holiday rentals with a pool in Jackson County

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!

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.

Work Crews, build family memories, swimming/ pool!

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.)

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!

Scenic and relaxing roadtrip stop-over!

This is a scenic stop between PDX and SF and its own destination. One guest says " Her home has a magic of its own." Simple, elegant, and a great base for wine-tasters, paraglider, or roadtrippers. If a house surrounded by nature, vineyards, paraglider pilots, creativity and occasional other travelers sounds interesting, you'll love it here. As a local tourism coordinator, I can direct you to the top attractions. Note: this is a self-contained unit but attached to the main house!

Octagon Studio / Beautiful Rogue River property

Park-like setting; Rogue River premier property. Use the Octagon Studio to enjoy the luxuries of the property or as a home base for the many amenities in the Rogue Valley. Relax by the pool or soak in the hot tub, lounge on the rivers beach, watch the river go by from the floating dock(seasonal) swing between two large pine trees, have an evening fire in the fire pit, catch trout for a morning breakfast, watch the abundant wildlife. Relaxing, romantic, fun, resort quality....enjoy

The Fairway Townhouse | Minutes from Golf Course

Brand-new 3BR, 2.5BA modern townhouse. Steps to Eagle Point Golf Club. Sleeps up to 7. Enjoy mountain and golf course views, high-end appliances, and fire pit feature on outdoor private patio. Perfect for golf getaways or a relaxing extended stay in Southern Oregon. .5 Mile to Eagle Point Golf Course 15 minutes from Medford, OR 1.5 hours to Crater Lake National Park Easy access to Eagle Point shops, restaurants & activities Access to pool & clubhouse!

Broken Chair Ranch

Welcome to the beautiful Griffin Creek area just outside of Medford, Jacksonville, and Ashland. Our home is at the top of a hill with stunning views of the city lights as well as upper and lower Table Rock. Enjoy the hot tub and watch the sunset with the fire pit on the front porch. The house is on 40 acres and has a gorgeous view at the top with a stunning echo off the mountain Private setting one mile up a gravel road, 2wd friendly

Red Hawk Hideaway

This single-story home nestled in the foothills of RoxyAnn is the perfect hideaway for a weekend of entertainment or extended family stay. A charming and contemporary home offering a spacious interior with modern furnishings, a fully equipped patio and home gym. All within a quick and easy drive to wineries, restaurants, Oregon Shakespeare Festival, Britt Festival, the Rogue River and so much more!

Oregon Riverfront Oasis •Pool •Hot Tub •Sleeps 10+

✨ Soak in riverfront & mountain views from the hot tub ♨️ or private balconies 🌄 at this luxury retreat! This 3BR 🛏️, 4BA 🛁 getaway features 2 master suites, a pool house with private bath 🏠, and sleeps up to 12. Enjoy the pool 🏊‍♂️, sauna 🧖‍♀️, theater 🎬, gym 🏋️, pool table 🎱, Traeger grill 🍖 & more — all behind a gated entry for total privacy 🔐.

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!