Family-friendly vacation rentals in Prineville

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Prineville

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite

A well-organized playroom shelf displays a variety of colorful children's toys, including blocks, stacking rings, and a wooden crown. A blue storage bin is seen on the lower shelf, while a high chair is positioned in the corner of the room.

Home in Bend

4.91 out of 5 average rating, 204 reviews

Light-Filled 5BR, Great location!

Our corner home sits on a tree-lined block within a family neighborhood with two private parks and walking paths. While snow-capped peaks can be enjoyed from our windows, the home is conveniently located in town on the desirable Westside. Our spacious 3300 sf home is central to Bend's many amenities. Phil's Trail, a mountain biking Mecca, is just seven minutes away past Mount Washington and Skyliners Drive, the main cross streets of our neighborhood. Broken Top Country Club and golf course is adjacent to the neighborhood off of Mount Washington Drive. The Bend Athletic Club is six minutes away on Mount Washington. Cascade Lakes Scenic Byway, the gateway to Mount Bachelor, is also off of Mount Washington Drive. Skiing and recreational areas at Mount Bachelor can be reached in less than 30 minutes. Historic Downtown Bend is just over five minutes away by car and within easy walking or biking distance. The Old Mill District, which has a spectrum of dining, entertainment and shopping opportunities is also only minutes away by car. The Southern Crossing bridge which links us to Old Mill also leads to the Deschutes River. Within two minutes (1/2 mile away) are neighborhood conveniences at Northwest Crossing, as well grocery stores, pharmacies, restaurants, and bike and ski shops off of Century Drive and Galveston. For rock climbers, Smith Rock State Park in Terrebonne is just 45 minutes away. Sleeping arrangements: comfortably sleeps 10 (on beds, not sofas) Bedroom 1: King bed with sofa/futon and master bath Bedroom 2: King bed with window sitting area Bedroom 3: Queen bed Bedroom 4: Queen bed Bedroom 5: 2 twin beds total (no mattresses in trundles) Dining areas: Rectangular dining table with seating for 10-12 Oval dining table with seating for 6 Island bar with seating for 3 Great room living area: 2 large sofas 2 large arm chairs 2 leather chairs 2 upholstered benches/ottomans Seats 10-12 with additional seating nearby Amenities: Free Wifi High definition cable and 4 TVs Hot tub Game room with board games, books and Wii Air hockey table Table tennis (ping pong table) Foosball table Consumables provided: shampoo, conditioner, body gel, hand soap, dish soap, sponge, aluminum foil, plastic wrap, laundry detergent Parking: Garage parking for one large vehicle or plenty of bike storage Parking for two cars in driveway Corner home with plenty of street parking Thank you for your interest! **No pets. No smoking. No parties. No exceptions. ***Maximum occupancy of 10 for rates listed. 11th and 12th person possible with owner agreement and $25/per person per night. *****One week minimum booking during the Holiday period in December through New Year's. 3-night minimum booking during High Season in the months of June through August. If there is a gap in between bookings, a shorter reservation is definitely possible.

Guest favorite

A modern retreat is nestled among tall pine trees, showcasing large windows that allow for natural light. A spacious deck features a dining table under an orange umbrella, with two hammocks hanging nearby. The surrounding area is dotted with vibrant greenery and soil covered with pine cones.

Home in Black Butte Ranch

4.89 out of 5 average rating, 152 reviews

Family retreat on Black Butte Ranch

Perfect space for a family vacation to enjoy the beautiful outdoors. Lots of space to relax and feel at home. Two double bedrooms and kids bunk room with three bathrooms. Two living spaces with entertainment options. A home office area with a wi-fi booster. Very close to Glaze Meadow pool complex, tennis courts, golf course and the games area. We welcome a dog but ask you are confident they are well behaved. There are carpets upstairs and we appreciate those dogs who pee and poop outside!

Guest favorite

A variety of bicycles and watercraft are arranged in front of a garage. Four bicycles in different colors are positioned alongside two red kayaks, two green kayaks, a blue paddleboard, and a canoe, all set against a backdrop of greenery.

Cabin in Sunriver

4.88 out of 5 average rating, 226 reviews

The Sunriver Hive

My home is close to family-friendly activities. You’ll love the house because of the views, the location, the ambiance, and the outdoor space. The deck is expansive and perfect for enjoying the sun, or take a dip in the hot tub! The house is good for couples, families (with kids), and groups of 9 or less. Take advantage of the water toys we include for use for free, or go for a bicycle ride! The world is yours! Check in is 4 PM (Inquire about early check in availability). Checkout 11AM.

Guest favorite

A spacious living area features a high, wooden ceiling with natural light streaming through large windows. A stone fireplace serves as a focal point, complemented by comfortable seating. A coffee table is centrally positioned, creating a welcoming space for relaxation.

Home in Sunriver

4.96 out of 5 average rating, 117 reviews

Pet friendly, upscale home, AC, sleeps 8

Our beautiful 1900 sq. ft. Home, is the perfect spot for your vacation. Our kitchen has every gadget, and upscale appliances to create gourmet meals. King master upstairs, and 2 queen bedrooms down, share a bathroom. We have bikes and ping pong and TV in the garage. A Weber BBQ on the deck, with a sparkling, bubbling hot tub. Decks face both east and west, so morning sun, and evening sunsets. Dog friendly! (2 dog limit). Warm up by our big fireplace after a fun day skiing at Mt. Bachelor.

Guest favorite

Home in Sunriver

4.86 out of 5 average rating, 279 reviews

Private & fenced, hot tub, river near by, pets

DCCA#628494 If you are looking for a quiet & peaceful home, close to the mountains & the river, surrounded by beautiful forest & wildlife vs tourists, you found it ! Just on the edge of Sunriver, but close enough to all the activities. Here you will find privacy & zen you needed! Imagine sitting by the warm fire in a fully fenced in backyard, looking at the million stars and the moon, or perhaps enjoying it from the hot tub, while sipping on some of the best beer in Oregon. 2 pets allowed.

Guest favorite

A welcoming living area features two comfortable sofas arranged around a central coffee table. A large area rug adds color beneath the seating. Natural light enters through nearby windows, and a decorative wall clock and artwork enhance the space's ambiance.

Home in Bend

4.94 out of 5 average rating, 176 reviews

5 Minute Drive to Downtown Bend, Dog Friendly

Centrally located in Bend, we're just minutes away from shopping, restaurants, downtown, Old Mill, and Mt Bachelor. We're thoughtfully stocked with cooking supplies (pots, pans, utensils, seasoning), Smart TVs with cable, coffee, and tea. All rooms have top-rated memory foam mattresses. Washer/Dryer in home. Towels, linens, shampoo, soap all provided. Fire pit and Gas Grill in fenced in back yard. Cleaned by a professional cleaning service after each stay. Parking limited to 5 cars.

Guest favorite

A comfortable living area features a bright red sofa and an additional lounge chair. Natural light filters through large windows, highlighting the neutral wall colors and carpeting. A television is positioned on a sturdy stand, while a small dining table is visible in a corner.

Apartment in Sisters

4.94 out of 5 average rating, 162 reviews

Contemporary apartment in Sisters, OR. USA

A contemporary 2 bedroom apartment in a quiet neighborhood just 4 blocks from Sisters main street. Minutes from music venues, festival locations, trails, and popular biking routes. Sisters has art, music, movie theater, good coffee, beer, restaurants, and boutique shopping. Village Green is close by. Superb biking, hiking, skiing, fly fishing, and outdoor opportunities abound year round. The apartment is perfect for couples, solo adventurers, business travelers, and families.

Top guest favorite

A welcoming living area features a comfortable sectional sofa and a textured area rug, positioned around a central coffee table. Natural light enters through large windows, complementing the neutral wall tones, while a decorative piece adds subtle interest to the space.

Home in Bend

4.97 out of 5 average rating, 161 reviews

Old Mill Charm

Great Location in Old Mill District – Walk to Summer Concerts! ♥ Fenced Backyard ♥ Pet Friendly Nestled in the heart of Bend, Old Mill Charm offers the perfect blend of comfort and convenience. Thoughtfully designed with many amenities to ensure a seamless stay, this charming rental is ideal for relaxing or exploring all that Bend has to offer. There is a tenant in the apartment above the detached garage who does not use the driveway or backyard, ensuring your privacy.

Superhost

A bathroom features a beige tiled floor and walls. A white sink with an elegant basin is positioned beside a mirror. A shower curtain with a blue and white geometric pattern provides privacy for the bathtub. Natural light enters through a nearby window with partial blinds.

Home in Bend

4.77 out of 5 average rating, 115 reviews

1 Mile to Downtown from the Orchard District

Welcome to Bend! Whether you're biking, hiking, skiing, fishing, enjoying the water, or sipping on great beer, you're sure to have an unforgettable time from our centrally located home. After completing a renovation in June 2018, we've created a warm, modern ambiance that's less than 1 mile from the heart of Bend. This space is perfect for a family retreat, a group of friends, or a family seeking the comfort of a home while away. Now, get out and play!

Guest favorite

A quaint cottage exterior is surrounded by greenery, featuring a covered porch with steps leading to the front door. Vibrant landscaping includes flowering plants, bushes, and trees, enhancing the inviting atmosphere of the home.

Home in Bend

4.95 out of 5 average rating, 407 reviews

Cozy, Pet Friendly, Hot Tub. Garage.

Our cozy, pet-friendly cottage is located on the very popular westside of Bend and conveniently located to numerous pubs, restaurants, Hayden Homes Amphitheater, the Pavilion, shopping, parks and sightseeing! Beautiful, private, secure, fenced back yard with hot tub and BBQ in the covered patio area and a portable fire pit to sit around and roast marshmallows or hot dogs. Park in the garage and securely store your bikes, skies, snowboards and more.

Superhost

Home in Bend

4.95 out of 5 average rating, 105 reviews

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.

Guest favorite

A well-appointed bathroom features sleek cabinetry and a modern sink. A walk-in shower is visible beside a glass door, with neatly hung towels displayed on a rack. A framed artwork adds a touch of design, complementing the calming green walls.

Apartment in Bend

4.98 out of 5 average rating, 107 reviews

Amazing West Side* Walk Everywhere * Dog Friendly

The location of this home is just exceptional for visiting Bend. You will be in the heart of the wonderful and popular West Side. We built the home specifically to be used as a vacation rental. We would love to make sure you have a great experience visiting Bend and staying in our home so please let us know what we can do to make sure you have a 5 star experience.

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What guests are saying

Bluebird Day - Riverside Cottage

4.79 out of 5 average rating, 126 reviews4 days ago

What a fantastic stay! We absolutely loved this place. The location was excellent, right on the edge of the park, less than 10 minutes to walk to the town with lots of great bars and places to eat just 5 minutes around the corner. A very easy drive to Mr Batchelor. The house has parking for 1 car on the drive, a lovely porch to sit and watch the world go by, a spacious living area and kitchen diner with well stocked cupboards. Comfy beds with blackout curtains, lots of towels, toiletries and towels for the hot tub. A perfect retreat and home from home. Thank you!

Home in Old Bend

What guests are saying

Family Fun - ping pong, foosball, hot tub, A/C

4.95 out of 5 average rating, 148 reviews1 month ago

Fantastic house. Great location for a ski trip base (why we booked) and convenient for everything in Sunriver. Well-appointed kitchen, which is always a plus. Kids loved the garage play area. Hosts were super-responsive and the house is great. Will definitely be coming back.

Home in Sunriver

What guests are saying

It's Ski Time!-Spend it in a charming cozy cabin!

4.98 out of 5 average rating, 61 reviews3 months ago

We enjoyed our stay at Linda's place! It's tucked away in the woods which made it feel private and you're surrounded by nature, which we liked. We enjoyed the fireplace, and the open kitchen / dinning room / living room is great for socializing with family. I would recommend this place if you're coming to Black Butte.

Cabin in Black Butte Ranch

What guests are saying

Large Group Comfort - 7 Separated Sleeping Areas!

4.95 out of 5 average rating, 155 reviews1 month ago

We absolutely loved our weekend at this home, with our large group of adults and kids. We came here for my daughter’s state basketball tournament and this home did not disappoint. There was more beds and space than we could even utilize and the home was as described. Home was fully stocked with absolutely anything you could possibly need. The kids spent all their time outside shooting hoops and loved riding provided bikes around the very family friendly, and safe neighborhood! The host was extremely proactive, helpful and responsive. I have nothing but wonderful things to say about this lovely home and the host! We will be back for sure.

Home in Redmond

What guests are saying

Private Riverfront Log Cabin Retreat on 1.5 Acres

4.97 out of 5 average rating, 131 reviews1 month ago

This place was Beautiful, and perfect for a winter giveaway!! The house has absolutely everything we needed, the most well supplied Airbnb I have been to. The beds were comfortable, and enough space for hanging out and enjoying the space! The house was clean and beautiful, and would love to stay here agin!

Cabin in Bend