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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Superhost

Home in Medford

4.75 out of 5 average rating, 156 reviews

Cute 3 king with 85" 4k TV, near huge park POOL

Cute and quiet older house with 3 king beds. Just added Huge above ground pool, but no safety fence or deck yet. Working on that but do not rent if that is a concern. Huge 85" top end Samsung 4k tv, brand new tech! Like having a movie theater in the living room!!!!! pool closed oct-mid may Comfortable memory foam mattresses. New listing, forgot to take picture of kitchen. Ice maker and water are not hooked up yet. washer and dryer are in garage. garage is not cleaned between every guest.

Guest favorite

Rental unit in Grants Pass

4.95 out of 5 average rating, 211 reviews

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'

Superhost

Loft in Hornbrook

4.94 out of 5 average rating, 374 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

Home in Medford

4.85 out of 5 average rating, 185 reviews

Relax in Large Space Hot Tub Big TVs Crews and Fam

Perfect for work teams with privacy or socialization. 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.

Guest favorite

Guest suite in Jacksonville

4.84 out of 5 average rating, 232 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!

Superhost

Guest suite in Gold Hill

4.84 out of 5 average rating, 104 reviews

Amazing Rogue River frontage/1-BR guest house/pool

ROGUE RIVER ESTATE Park-like setting on a 5 acre premier property. Use the 740 square foot guest house to enjoy the luxuries of the property or as a home base for the many amenities in the Rogue Valley from Grants Pass to Ashland. Relax by the pool or on the floating river dock, swing between two large pine trees, lounge on the river's beach, an evening fire in the fire pit, trout for a morning breakfast, watch the abundant wildlife: deer, eagles, osprey, hawks, ducks and geese .

Guest favorite

Yurt in Grants Pass

4.97 out of 5 average rating, 708 reviews

Sunset View Yurt of Applegate Valley with HOT TUB!

NO CLEANING FEE! Large 24 ft yurt located on our 5 acre horse 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: ONLY well-behaved children are welcome. If your kids are destructive or abusive, you will be asked to leave.

Guest favorite

Guesthouse in Grants Pass

4.99 out of 5 average rating, 103 reviews

Serene Upstairs Studio with Bath & Kitchenette

This upstairs studio is surrounded by beautiful trees that gives you the impression of staying in a treehouse. Located in a panoramic rural area just 5 miles from downtown Grants Pass and 5 miles from downtown Rogue River. Perfect place to be away from the hectic city lifestyle, yet close enough to restaurants, local shops, wineries, jet boat rides, hiking trails and much more... In addition, this pictured-postcard location is 8 mins walking from Pierce Riffle County Park.

Superhost

Home in Medford

4.76 out of 5 average rating, 34 reviews

Medford home with a Pool and Hot tub

Escape to paradise with our exquisite 4-bedroom, 2.5-bathroom vacation rental home, where your dream getaway becomes a reality. This stunning retreat is tucked away in a tranquil oasis, promising an unforgettable experience for you and your fellow travelers. Want to book directly with us? Visit our website. Shared amenities include the backyard, hot tub, firepit, BBQ, and seasonal pool (tentative opening April-September depending on weather

Guest favorite

Rental unit in Medford

4.92 out of 5 average rating, 171 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

Guest favorite

Rental unit in Grants Pass

4.95 out of 5 average rating, 841 reviews

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, bicycles, 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.

Guest favorite

Cottage in Central Point

4.9 out of 5 average rating, 161 reviews

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!