Holiday rentals with a pool in Ashland

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!

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'

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!)

Chef's Kitchen | Pool | Bright, Spacious | 4 Bed

Bright & open 2-story, designed for comfort, gathering, & entertaining—perfect for families, professionals, and groups seeking space, tranquility, and elevated amenities. Chef’s kitchen, features double ovens, generous prep space on a large island, that flows into the family room. Perfect for families, professionals, and groups seeking space, tranquility, and elevated amenities. Located in a peaceful cul-de-sac in the highly desirable East Hills. SEASONAL Pool, gazebos, seating areas, BBQ.

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

Cool Blue Waters-Guest Suite

Enjoy our guest suite, perfect for short stays of 26 nights max. We are a comfortable space for 3 guests. Cool Blue Waters is perfect for traveling professionals, families and dog lovers. We are centrally located in the heart of historic Grants Pass. The guest suite is attached to your Host's home and includes: Queen bed, office area, Wi-fi, TV, futon couch/folding bed, walk-in closet, kitchenette with coffee and breakfast items, Private Bathroom, toiletries, Pool and Private patio area.

The Green Arrow Loft

Situated right on the state line this studio apartment with EV charger access is nestled in its own nook of the gorgeous Colestine Valley. We're 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 5 minutes off I-5 and 20 from downtown Ashland. We're pet friendly and have an outdoor pool! See the House Rules for details on EV, pet, and pool fees.

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!

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!

Peace on the Rogue river Studio

Beautiful park like setting on the Rogue river with a jacuzzi, swim spa two decks, fishing, yard games, hammock, barbecues, kitchenette has Keurig With pods,a toaster oven, crock pot, small George Forman a portable two burner cook top , small skillet, one pot and most utensils to provide a meal. Minutes from Grants Pass, shopping, restaurants, and winery's.

Sunflower

Nestled within the serene 20-acre expanse of Wagner Creek Sanctuary, the Sunflower Cabin offers a distinctive retreat that harmoniously blends sustainable living with natural beauty. This unique straw bale structure stands as a testament to eco-conscious design, providing guests with a cozy and authentic living experience.

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!