Holiday rentals with a pool in Jackson County

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Top-rated rentals with a pool in Jackson County

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite

Tiny home in Rogue River

4.88 out of 5 average rating, 100 reviews

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!

Superhost

Loft in Hornbrook

4.93 out of 5 average rating, 385 reviews

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.

Top guest favourite

Home in Central Point

4.96 out of 5 average rating, 112 reviews

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!)

Guest favourite

Treehouse in White City

4.95 out of 5 average rating, 20 reviews

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.

Top guest favourite

Home in Eagle Point

4.79 out of 5 average rating, 58 reviews

Historic Rushing Water Lodge on the rogue river

This historic lodge & 4 cabins were built in 1910 on the best fishing area on the Rogue River, the cabins are now vacation homes, rarely occupied, (one has been upgraded to a modern home). There is nothing like this lodge, it has been modernized with insulation, new windows and HVAC system, it is surrounded by undeveloped land, there is total quiet privacy: the only sounds are from the river, Canada Geese & a pair of Great Horned Owls that nest in the woods. It's 1 mile from the paved road.

Top guest favourite

Home in Ashland

4.95 out of 5 average rating, 107 reviews

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!

Superhost

Home in Medford

4.86 out of 5 average rating, 214 reviews

Swimming Pool! Large TVs, Spa, for Family or Crew

Perfect for 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 with a double-sided fireplace, 65" and 75" TVs, Redzone, Pool Table, Ping Pong, Coffee & Wine Bar, Golden Tee. Year-Round Hot Tub, Seasonal Swimming Pool (mid May-mid October.

Superhost

Home in Eagle Point

4.88 out of 5 average rating, 49 reviews

Cascade Sunset Home+HOT TUB - Crater Lake Vacation

This beautiful country home offers stunning sunsets over Sam’s Valley and the Cascades, best enjoyed from the open living, kitchen, and dining area, as well as from the spacious decks and outdoor areas. Sip local wine, wake to birdsong, then jump in the pool or unwind in the hot tub beneath a covered deck. You’ll also have access to the private basement suite, known as Shadow Bear Lodge. Crater Lake is 55 minutes away. Planning an event or long-term stay? Just ask—we’re happy to help!

Guest favourite

Guest suite in Jacksonville

4.84 out of 5 average rating, 246 reviews

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!

Guest favourite

Guest suite in Gold Hill

4.92 out of 5 average rating, 214 reviews

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

Top guest favourite

Guest house in Ashland

4.97 out of 5 average rating, 197 reviews

Wood Hamlet - Picasso Cottage by Downtown, kitchen

Our 'Picasso Cottage' sleeps up to 2 adults and is perfect for those who wish to enjoy artful living close to downtown Ashland! The space is the entire bottom floor of Carriage House, with full bathroom, bedroom (queen bed) with sitting area, washer/dryer, living room and full kitchen. Between shows relax on patio or by the swimming pond in garden. Private parking behind Carriage House. Walk to theater! (Ashland City Permit# 17-080) NO SMOKING ON PREMISES

Guest favourite

Townhouse in Eagle Point

4.91 out of 5 average rating, 11 reviews

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!