Vacation rentals with a pool in Ashland

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Ashland

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

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Guest favorite

A cozy cottage exterior is framed by well-maintained grass and landscaping. A wooden bench is positioned on the porch, while a circular patio features a small table and blue chairs, inviting relaxation in the outdoor space.

Guesthouse in Grants Pass

4.94 out of 5 average rating, 458 reviews

Sweet Vintage Cottage steps from Rogue River

Welcome one and all to DunMovin'. The Cottage you will be staying in may make you feel like you have stepped back in time. Don't forget your fishing pole, this property is on the banks of the Wild and Scenic Rogue River. Lounge by the pool, feed the geese, go shopping, or head to any of the amazing restaurants that are just around the corner. I'm in the city limits, so everything is a minute or two away. It's my slice of heaven. I also have a larger unit, search for 'Riverside on the Rogue'

Superhost

Loft in Hornbrook

4.93 out of 5 average rating, 388 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.

Superhost

The tiny home is nestled among lush trees, showcasing a wooden deck with a railing. Large windows offer views of the surrounding greenery. The exterior features vibrant colors, contrasting with the natural landscape under a clear blue sky.

Tiny home in Rogue River

4.87 out of 5 average rating, 103 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!

Top guest favorite

Home in Central Point

4.97 out of 5 average rating, 116 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 favorite

A serene swimming pool is framed by lounge chairs and umbrellas, providing shaded seating areas for relaxation. A beach ball floats on the crystal-clear water, inviting enjoyment. Surrounding greenery and a wooden fence add to the peaceful outdoor atmosphere.

Home in Medford

4.86 out of 5 average rating, 221 reviews

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.)

Top guest favorite

The image showcases a serene outdoor space featuring a solar-heated pool with clear blue water. Surrounding the pool are landscaped areas with vibrant flowers and a wooden pavilion. Large glass doors of the house reflect natural light, enhancing the connection to the outdoor environment.

Home in Ashland

4.95 out of 5 average rating, 111 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

Four orange Adirondack chairs are arranged on a grassy area, facing a wide, open view of a distant mountain landscape. A clear blue sky scattered with white clouds creates a serene backdrop, while leafy branches frame the scene.

Guest suite in Jacksonville

4.84 out of 5 average rating, 247 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 favorite

An inviting bedroom features a spacious bed with light-colored bedding, positioned beneath a sloped wooden ceiling. Large windows provide natural light and a view of the surrounding greenery. A decorative wooden dresser and a small table add functional charm to the room.

Guest suite in Gold Hill

4.92 out of 5 average rating, 218 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

Superhost

A compact travel trailer is positioned under a wooden structure, providing shade and support. Two bright blue chairs sit on a white wooden deck, inviting relaxation. Soft lighting fixtures accentuate the area, and a pathway lined with landscaping is visible in the background.

Camper/RV in Medford

4.68 out of 5 average rating, 31 reviews

La Caravane on a Country Estate

Reconnect with nature at this unforgettable escape. La Caravane ("travel trailer" in English) is a homey, comfy, compact space. The home overlooks Pebblestone vineyard and the beautiful foothills of the Klamath Mountains. It sits on a landscaped acre that is Le Jardin Familial, home to our extended family and other Airbnbs. Le Jardin boasts a Koi pond and stream, gardens, labyrinth, and amenities such as hot tub, steam room, and swim spa. This is glamping at its best!

Guest favorite

An inviting swimming pool is set in a landscaped area, surrounded by palm trees and a wooden fence. The pool features a unique shape with a brick border and a small, rounded seating area nearby. Sun loungers are positioned adjacent to the water.

Guest suite in Grants Pass

4.91 out of 5 average rating, 46 reviews

Cool Blue Waters-Guest Suite

Enjoy our newly renovated guest suite, perfect for short stays of 26 nights max. 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.

Guest favorite

A clear blue swimming pool is framed by a wooden deck and green trees, offering a refreshing ambiance. Lounge chairs are positioned along the poolside, and a covered seating area is visible in the background, providing shade and comfort.

Apartment in Medford

4.92 out of 5 average rating, 185 reviews

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

Top guest favorite

The exterior of the yurt is highlighted by warm light emanating from the windows, creating a welcoming ambiance in the evening. A wooden deck leads to the entrance, while a nearby chair rests under a small tree. Soft landscaping and a hammock are visible in the background.

Yurt in Grants Pass

4.98 out of 5 average rating, 771 reviews

Sunset View Yurt of Applegate Valley with HOT TUB!

NO CLEANING FEE! Large 24 ft yurt located on our 5 acre property. Gorgeous views to the west. Includes a king size bed, and queen sofa bed. Located in Applegate Valley. Many fabulous wineries nearby. We're 6 miles south of downtown Grants Pass, and 2 miles north of Murphy. Enjoy the hot tub under the stars, or catch a spectacular sunset. It's all good! Please note: Well behaved, non destructive children are welcome.