Holiday rentals with a pool in Bend

Private Indoor Pool + Hot Tub | Game Room

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.

Sunriver-Pool/HotTub Walkable to Food Trucks/Shops

- This unique and friendly spot boasts a convenient location to Central Oregon's famous outdoor activities. The space is only a 26-minute drive to Mt. Bachelor, the beginning of the scenic Cascade Lakes Highway, and a short walk to The Village at Sunriver. Community pool, hot tub, and laundry are on site and accessible. Wifi and Netflix logins are provided to all guests. The hot tub is open year-round. The pool typically opens on Memorial Day weekend and typically closes sometime in September.

European-Inspired Retreat + SHARC & EV Charger

Enjoy our Euro inspired 3 bdrm/2.5 bath home with bonus room. Ideal S. Sunriver location on a quiet cul-de-sac close to the Lodge, Village and River. We offer a completely remodeled home with a new kitchen, flooring, and bathrooms and a well-stocked kitchen, A/C throughout, SHARC passes, hot tub, bicycles, and an EV charger port. Our bonus room over detached garage has a TV, yoga space, 1/2 bath and A/C. ONE dog welcome and must be added at time of reservation. Must be 25 yrs. old to book.

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.

Serenity Retreat | Pool, Spa, Trails & Mt Bachelor

Situated in the serene Mt Bachelor Village, our home is a harmonious blend of seclusion & natural charm. Encircled by a lush landscape & towering trees, it serves as a tranquil retreat, perfect for relaxation. The property is just a short distance from Bend's lively amenities, offering access to both outdoor adventures & urban pleasures. This residence is an ideal choice for those wishing to enjoy the tranquility of nature while being conveniently close to the city's attractions.

A-Frame Cabin on 4.5 Acres - HOT TUB, Dog Friendly

This 2 bedroom Northwest themed A-Frame is the perfect destination for your couples retreat or small family vacation! It is situated on a super peaceful 4.5 acre lot and is only a 7 minute drive to Downtown Sisters. Our cabin sleeps 4 people comfortably in the 2 upstairs bedrooms, has 2 full bathrooms, a stocked kitchen, and a private back patio featuring our brand new hot tub. This is a dog friendly home so you are more than welcome to let your furry friend tag along!

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

The House on the River

From the moment you enter the neighborhood, you will enjoy a private road that is peaceful and tranquil. The neighborhood is full of beautiful trees, birds, and an abundance of deer that roam the area frequently laying in and enjoying the large front yard. Bring the bikes for the kids to enjoy riding in the big circular driveway or through the neighborhood. You can take in the surrounding nature with a walk along the river trail.

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!