Holiday rentals with a pool in Bend

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

Alpenview Retreat | Perfect Gathering Home for Friends and Family Designed for unforgettable group stays, this spacious modern home combines luxury, entertainment, and location- just minutes from Downtown Bend and close to Mt. Bachelor. Spend your days skiing, hiking, or exploring, then come home to soak in the private, indoor heated pool and hot tub, sip your favorite beverage in the courtyard, or compete in your private game room. Perfect for families, friend groups, and multi-family trips.

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!

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.

Wine Down and Play

Our condo is part of the Powder Village Condominiums, B building, second floor #2. The condo has vaulted ceilings with a lofted area for relaxing. It includes a full kitchen and bathroom with a shower. There is also a balcony with seating and an electric grill. The property includes a seasonal outdoor pool and a hot tub that is open year round and laundry facility on property. There are paved walking/biking trails nearby and a short walk to bars, restaurants and convenience stores.

King Bed, Private Pool, Riverfront, Theater & Spa

Welcome to the Lazy River Lodge! This home is perfect for large families, reunions, retreats, or any fun group looking to have an amazing vacation! If you’re a homebody that likes to stay in, you can enjoy your time in the hot tub, watching movies at the in-home theater, taking a stroll by the river, or even enjoying a dip in our private indoor pool! If you like exploring, there are plenty of hikes, beautiful mountains, hot springs, with food & shops also nearby to spend your days at.

Seventh Mountain Resort Getaway

This newly remodeled one bedroom condo sits right above the Deschutes river. Seventh Mountain Resort is your winter and summer outdoor adventure destination in sunny Central Oregon. The premier location for recreational activities, from biking, hiking, and whitewater rafting in summer, to ice skating and skiing in the winter. Your stay here will have you encircled by peaks, lakes, meadows, culture, adventure, breweries, festivals, family fun, shopping and more.

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.

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.