
Holiday rentals with a pool in Southern Oregon
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Southern Oregon
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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'

Riverfront Retreat w/Pool, Hot Tub, Mountain Views
Soak in riverfront & mountain views from the hot tub or private balconies at this luxury 10-acre retreat! 3BR/4BA with 2 master suites, plus a separate pool house with its own bath — sleeps up to 12. Enjoy the pool, gravel paths to the river, and total privacy on the property. Ideal for extended stays (30+ nights) — perfect for relocations, remote work, or seasonal getaways. Interested in a shorter stay or your desired dates aren’t available? Message us directly to check availability and rates.

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.

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!

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!)

Studio between Bend and Crater Lake on the water
Make some memories at this unique and family-friendly place. In the summer this 12 acre compound has numerous activities to keep you busy. Heated swimming pool, hot tub, tennis and basketball courts, badminton, volleyball bicycles, and lots of water toys…paddle boards, pedal boat, kayaks, and pontoon boats. Winter heated pool and hot tub, large fire pit and seasonal snow. Willamette pass 20 min. Wildlife very abundant, and a working lumber mill across the water. Sunsets are usually gorgeous!

Forest Cottage | Hot Tub, Outdoor Baths & Alpacas
Tiny Cottage Retreat w/Alpacas –Triple Nickel Pines🌲 Escape to the Pine Tree Tiny Cottage, a romantic & peaceful getaway in the heart of Southern Oregon. Tucked between Grants Pass & Merlin (8 mins from Merlin & 15mins from Grants Pass). This cozy cabin offers the perfect blend of comfort, nature, & uniqueness—right next door to our non-profit alpaca rescue. After exploring the area; stargaze from your outdoor tubs, soak in the hot tub, or roast s’mores by the fire. PERFECT COUPLES GETAWAY!

4BR W/ View, Crater Lake, Running Y Resort House
Take in the views at our "Dark Sky" Crater Lake Resort House. This family friendly home features 4 bedrooms and 2.5 bathrooms modernly designed and decorated to create a calm peaceful stay. This is not a condo or tiny chalet located at the Running Y Resort, it is a full on private custom home equipped with everything you will need to make you feel at home. With full access to all amenities at the Running Y Resort, a very short commute to Crater Lake National Park, you simply cant go wrong!

Hot Tub +Bikes +8SHARC Passes +PingPong +Fireplace
Stylish luxury family home w/8 SHARC passes (pool & lazy river), 6 Cruiser bikes, Hot Tub, 3 New Smart TV's for streaming, Ping Pong table, board games. Short walk to the river & Cardinal Landing Bridge. Fast 1GB WiFi, propane BBQ, Air Conditioning, cozy wood burning fireplace. Fully stocked kitchen for cooking, laundry inside. Quiet + Private w/large deck backing up to natural common space w/wildlife walking by. Bike everywhere w/easy access. Minutes to Mt Bachelor for skiing & sledding.

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!

Modern home - Billiards, Pingpong, Sauna & Views!
Enjoy panoramic sunset views over Eugene when you stay at this modern Skyline property. This luxurious newly-remodeled 3-bedroom house has a private sauna, game room, and is centrally located, 5 minutes from the University of Oregon and Matthew Knigh Arena and 10 minutes from Autzen Stadium. It is 5 minute walk to Hendricks Park and steps away from the famous Pre's Rock! This home is ideal for travelers, reunions, bridal groups, graduations, office retreats and romantic staycations!

Delightful Cottage, Spa/Pool, Crater Lake
Enjoy the lovely setting of this romantic spot in nature, perfect for two guests and approved pet(s) in the heart of Chiloquin. Private use of spa/pool. Simply message host to reserve. Parking included. If your dates are not available check out our by sister sites. https://airbnb.com/h/muledeer-lookingdeerlodge OR https://airbnb.com/h/whitetaildeer-lookingdeerlodge OR https://airbnb.com/h/reddeer-lookingdeerlodge OR. https://airbnb.com/h/reinddeer-lookingdeerlodge
Popular amenities for Southern Oregon rentals with a pool
House rentals with a pool

Sunriver by AvantStay | Modern Home w/ Indoor Pool

Sunriver Luxury Family Home at Caldera Springs

Updated Sunriver-Hot Tub, Walk to SHARC & Village

Single level, pet friendly, downtown, cute cottage

A Little Peace of Paradise, A/C, & 8 SHARC Passes

Indoor Pool, Game Room, EV Charger, Pets Welcome!

3K ft² | SHARC Pass | Hot Tub | Arcade | Ping Pong

Stunning mtn Views, sleeps 14, Hot tub, rec passes
Apartment rentals with a pool

Renovated Sisters Condo; perfect getaway!

Spacious 2 bedroom Sunriver condo + 6 SHARC passes

Pool, AC, close to Amphitheater & Old Mill

Beautiful Condo in SR Village

Sunriver Getaway

Oasis right in the Sunriver village 6 sharc pass

Klubhouse in Sunriver AC/Hot Tub/Heated Pool/BBQ

Short walk to SR Village and SHARC, includes bikes
Other holiday rentals with a pool

Serene Escape Studio (with w/d, a/c, kitchen)

Fun & Relaxing Getaway!

Capital House - Private getaway with POOL!

Cozy Retreat/ 6 Express Pool Passes

Rellik Winery - The Alpaca Suite

HOT TUB, Dog Friendly, Steps from pickleball/pool!

Kestrel House At The Running Y

Sunriver Cabin | SHARC, Hot Tub, Sleeps 4
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