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!

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.

Cozy Studio Cottage on the River!

The studio condo is a charming accommodation nestled along the banks of the Deschutes River. Up to four guests can vacation here and sleep on a queen sized bed, as well as a pullout couch. This cottage has a kitchen, full bathroom and a large closet for those wishing to stay a little longer! A desk is nestled up to the window, providing the perfect backdrop while you to get a little work done or even just enjoy a meal! A pet fee is required for those bringing their four-legged friends.

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.

*Sunriver* HotTub/Pool In Room Sauna Popcorn Cart

Calm, quiet and friendly condo with loft in Powder Village, Sunriver. Located walking distance from the Main Village at Sunriver. 26 minutes to Mt. Bachelor. The condo has it’s way of leaving a good impression as the natural sunlight, high ceilings and overall comfort level tend to leave people feeling uplifted, welcome and at ease. Private, in room infrared sauna for two and adventure kit included. Community laundry room is available and Netflix login is provided to all guests.

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.

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-

Adorable Studio at Seventh Mountain Resort

What an incredible getaway with all of the amenities of Seventh Mountain Resort and just 12 miles to Mt. Bachelor. Very welcoming, bright and comfortable. Queen size bed, love seat and a patio with a nice view. Enjoy all resort amenities which include mini-golf, gym, disc-golf, two pools, three spas, the Outfitter Bar and more. Access to hiking and biking trails. Seasonal rafting trips. 24-hour guest check-in at the main lodge.

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!

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.