Holiday rentals with a pool in Ashland

1940s Vintage apartment steps from the Rogue River

Welcome one and all to DunMovin'. At Riverside on the Rogue you will go to sleep with views of the stars through the skylights and wake up to the Wild and Scenic Rogue just outside your French Doors. Throw a line in and fish from the yard if you like. Lounge by the heated saline pool, feed the geese, go shopping, or head to any of our amazing local restaurants. I'm in the city limits. It's my slice of heaven and I'm sharing it with you. My other unit can be found at: 'The Cottage at DunMovin'

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!)

Forest Cottage | Hot Tub, Outdoor Baths & Alpacas

Tiny Cottage Retreat w/Alpacas –Triple Nickel Pines🌲 Escape to the Pine Tree Tiny Cottage, a romantic & peaceful getaway in the heart of Southern Oregon. Tucked between Grants Pass & Merlin (8 mins from Merlin & 15mins from Grants Pass). This cozy cabin offers the perfect blend of comfort, nature, & uniqueness—right next door to our non-profit alpaca rescue. After exploring the area; stargaze from your outdoor tubs, soak in the hot tub, or roast s’mores by the fire. PERFECT COUPLES GETAWAY!

Work Crews & Family Huge great room Relax and play

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.)

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

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!

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!

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

Currently unavailable - Pending county Review

This property is temporarily unavailable while we complete a county review process. We are not accepting reservations at this time. If you would like to be notified when this property is available, feel free to send a message. ✨ 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.

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