Holiday rentals with a pool in Bend

Popular BBR A-Frame | 2 golf courses | 5 pools

Welcome to Your Modern A-Frame Cabin at Black Butte Ranch! - Accommodations: Sleeps 8 in 2 queen bedrooms and a 2 twin loft, and trundle downstairs - Amenities: Relax in the living area with a Roku TV; the chef's kitchen makes meal prep easy, and self check-in ensures a smooth arrival - Sunny Recreation: Access to 6 pools, including the nearby Paulina pool, plus golf, pickleball, horseback riding, and hiking - Winter Fun: 20m drive to HooDoo Ski Resort Book your unforgettable getaway today!

Romantic Guest House w/Hot Tub, Pool, Tennis Court

Sweetums Guest House is a private, beautifully appointed 2 bedroom, 2 bath guest house located on 20-acre Sweetums Ranch. Amazing views of Three Sisters and Broken Top mountains from the property, horses,& abundant wildlife viewing. 8 mi to downtown Bend & 12 mi to Sisters. 45 min to Mt Bachelor and mountain trailheads. Large private yard & partially covered patio w/private hot tub. Amazing swimming pool and tennis court. On the Oregon scenic bike route. A perfect location for your getaway!

Mt. Bachelor Village Condo - Near Town & River

This newly remodeled condo is fully furnished with a gas fireplace, granite counter tops, jetted tub, three flat screen TV's, surround sound and gas barbecue on private deck. Heating and cooling is provided through a ductless heat pump system. The beds are super comfortable! The kitchen is fully equipped and comes complete with refrigerator, microwave, dishwasher and stove top oven. It has everything you need for a relaxed get away with private forested view. Super clean and comfortable.

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.

Gorgeous Condo With River View - Pool and Hot Tub

Condo 309/310 is a stunningly remodeled condo here at Bend Riverside Rentals, which we have named 'Deschutes Trail Mix." This condo went through an extensive head to toe remodel and is now ready to host travelers! It can sleep up to six guests, has a full kitchen, two full bathrooms, a washer and dryer, a private patio and comes with access to our indoor heated pool and hot tub! This condo is also pet friendly! Bring up to two pets for an additional fee.

Cozy 3 bdrm + loft Eagle Crest Chalet w/ Hot Tub!

Welcome to our Chalet in the Eagle Crest Resort! You are guaranteed to feel like you are on vacation the minute you walk in. This 3 bedroom + loft can sleep 8 guests and comes with washer/dryer, WiFi, and desks in the loft. Relax in the space indoors or out, with the outdoor patio, hot tub, BBQ, and golf course views. There is so much to see and do on the resort property or you can grab a blanket, sit by the fire and do absolutely nothing at all!

Sunriver Studio with Pool and Hot Tub

-Year Round Hot Tub and Seasonal Pool- -Walking distance to Food Truck Lot and Beer Garden- -25 Minutes to downtown Bend- -25 minutes to Mt Bachelor- -No Chores (no trash takeout, bed stripping, laundry, etc.)- -Super Clean -Owner Cleaned, Managed, and Maintained- -Free Parking Steps from Your Door- -Easy Self Check-In with Digital Locks (unique code for every guest)- -King Sized Bed- -50” Samsung TV Logged into Netflix, Hulu, HBO and more-

Luxury in the Forest

Dog Friendly at the Inn at the Seventh Mountain The Inn has been delighting visitors for 30+ years. It is the closest lodging to Mt Bachelor, and is just 7 miles from all that downtown Bend has to offer. There are amazing restaurants, great shops, and more. The condo has just been completely remodeled. Winter or summer, the Inn at the Seventh Mountain resort offers something for everybody in the family. Welcome! DCCA#720734

Mt Bachelor Village Resort- Room in River Ridge II

Hotel style room with private entry in forested Mt Bachelor Village Resort on the westside of Bend. Quick access to hiking, biking, the river trail, Old Mill district, Mt Bachelor, and many restaurants and breweries. It's a nice walk or bike ride to the Old Mill district and 2.5 miles from downtown Bend. The beautiful Deschutes River Trail is just down the hill from our unit-great for that morning walk or jog!

Deschutes River Getaway-near Bachelor & Sunriver

Our charming family home is the perfect place to relax and enjoy the outdoors. Just a short walk from the Deschutes River, you'll find miles of walking and biking trails, a pool, tennis and pickleball courts, and docks to launch your raft or kayak. And, with its convenient location, you're just 10 minutes from Sunriver Village, 25 minutes from downtown Bend, and 30 minutes from Mt. Bachelor.

Pool, AC, close to Amphitheater & Old Mill

Easy access to the heart of Bend from this perfectly located home base. A short walk takes you to the Deschutes River Trailhead for scenic hiking. You can leisurely stroll the mile trek to the Old Mill shopping center or meander a little further to the Amphitheater to enjoy summer’s many concerts. Enjoy a picnic on the lawn and enjoy watching the wildlife.

3BR 2.5BA—Deschutes dock, near Bachelor & Sunriver

The RiverBend House is the restorative escape you’ve been looking for. This 3-bedroom, 2.5-bath home sleeps 6 adults (8 total guests if there are young kids) and is located in a tranquil, wooded residential community on the Deschutes River, just 5 miles south of all the amenities of Sunriver, 20 miles SW of Bend, and 20 miles SE of Mt. Bachelor.