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Vacation rentals with a pool in Jackson County

Find and book unique homes with a pool on Airbnb

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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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.

Tiny home in Rogue River

4.9 out of 5 average rating, 49 reviews

Tiny Groove with sauna 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!

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.

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.

Home in Ashland

4.97 out of 5 average rating, 67 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!

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!

Guest suite in Gold Hill

4.92 out of 5 average rating, 199 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

Home in Eagle Point

4.93 out of 5 average rating, 15 reviews

Cascade Sunset Home+HOT TUB - Crater Lake Vacation

Entire Home. Never miss a sunset setting over Sam's Valley and the Cascade Mountains. Enjoy local wine as the sun sets or wake up to a peaceful morning to watch the birds. Open floor plan allows for you and your guests to enjoy each others company. Cool off at the pool or relax in the hot tub! We are 55 minutes away from Crater Lake! Making it a perfect day trip. Dont forget to check out the waterfalls along the way. If you would like to host an event please message us.

Home in Central Point

4.97 out of 5 average rating, 71 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 winery 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 with adorable restaurants and wonderful boutique stores!

Home in Medford

4.78 out of 5 average rating, 18 reviews

Luxury Home in East Medford

East Medford luxury home with a HEATED POOL! If you are looking for a wonderfully located, well cared-for custom-built home loaded with character, quality finishes, high ceilings, large windows, hand scraped wood floors + travertine stone floors, gorgeous tiles, incredible kitchen, newly updated bathrooms, covered patio, and a beautiful Master Suite that includes a balcony overlooking the private back yard with a pool, then this is it!

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

Home in Medford

4.94 out of 5 average rating, 33 reviews

Red Hawk Hideaway

This single-story home nestled in the foothills of RoxyAnn is the perfect hideaway for a weekend of entertainment or extended family stay. A charming and contemporary home offering a spacious interior with modern furnishings, a fully equipped patio and home gym. All within a quick and easy drive to wineries, restaurants, Oregon Shakespeare Festival, Britt Festival, the Rogue River and so much more!

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Popular amenities for Jackson County rentals with a pool

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House rentals with a pool

Home in Medford

4.95 out of 5 average rating, 22 reviews

Capital House - Private getaway with POOL!

Home in Medford

4.93 out of 5 average rating, 14 reviews

3BR House with pool, Near Hospital

Home in Ashland

4.89 out of 5 average rating, 36 reviews

Serenity Awaits: Pool, Hot Tub, Sauna, Gym

Home in Rogue River

5 out of 5 average rating, 13 reviews

In Town of Rogue River. Home with Pool and Hot tub

Home in Medford

4.86 out of 5 average rating, 28 reviews

I love this house!

Home in Medford

5 out of 5 average rating, 3 reviews

Fantastic Bright 4 Bedroom- Deck - Fireplaces

Home in Ashland

5 out of 5 average rating, 11 reviews

Siskiyou Chateau

Home in Central Point

4.85 out of 5 average rating, 20 reviews

Poolside Retreat W/ Sauna Heart of Wine Country

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