Family-friendly holiday rentals in Bend

4.99 out of 5 average rating, 223 reviews

The modern exterior of the ADU features wooden accents and large windows, surrounded by lush greenery. A small outdoor seating area with two chairs and a fire pit is visible. The entrance is framed by a wooden fence, providing privacy and inviting atmosphere.

Home in River West

Modern retreat in central Bend

Enjoy our new custom-built ADU located a block away from the Deschutes River in a quiet residential neighborhood, just a 10-minute walk from downtown along the River Trail. In this modern, bright, and private space, you'll enjoy the luxuries of hardwood floors, waterfall countertops, a built-in workspace, heated tile bathroom floors, a 55" Smart TV, BBQ and fire pit, and endless hot water—plus off-street parking and EV charger. One king bed, one daybed with a trundle, and one queen sleeper sofa.

4.89 out of 5 average rating, 388 reviews

A modern kitchen area features a stainless steel stove, refrigerator, and wooden dining table with two stylish chairs. Decorative plants and light wooden accents add warmth to the space, while patterned wallpaper enhances the design, creating a cozy atmosphere.

Tiny home in Bend

The Oasis Airstream

Reconnect with nature at this unforgettable escape, surrounded by gorgeous desert views. Beautifully designed and fully equipped for your comfort. Pet friendly and located just 15 min from downtown Bend. The Oasis Airstream is on a quiet 10 acres. I live here with my family and have a small farming business. There is an ample yard with outdoor table and chairs, outdoor couch, and fire place. There's also a hammock for swinging in the shade on those long summer evenings. Please read all info.

The exterior of a modern home is framed by blooming trees and shrubs, showcasing a gray exterior with large windows. A decorative pathway leads to the entrance, which features a covered porch. The driveway is spacious, providing easy access.

4.98 out of 5 average rating, 589 reviews

Home in Lodges at Bachelor View - Book Now!

Enjoy Bend’s newest west-side neighborhood nestled beside Century Drive, the gateway to Mt. Bachelor and the Cascade Lakes. Our unique location puts you right on the connector trails to the popular Phil's Trail System for mountain biking or casually strolling along the Deschutes river trail. With access to the National Forest in just steps and breweries mere minutes down the road, Pinehaven is as 'Bend' as it gets. Thank you for considering Pinehaven for your stay. We think you’ll love it here!

4.98 out of 5 average rating, 109 reviews

The spacious living room features a modern fireplace and large windows allowing natural light to fill the space. A soft area rug lies beneath a round coffee table, surrounded by comfortable seating, offering a cozy environment. Sliding glass doors lead to an outdoor patio surrounded by greenery.

Townhouse in Bend

Minutes to Bachelor! Spa. Fire pit. Ski!

Welcome to Hummingbird House, your Bend home away from home! This beautiful three bedroom plus den home is sure to become a vacation favorite for you and your family! Located within the Deschutes National Forest, these are the closest homes to Mt. Bachelor and just ten minutes to town. An outdoor patio area features a hot tub, fire table and dining table perfect for hanging out after a long day exploring Bend. The Deschutes River Trailhead is only a few steps from the back door. Book today!

The cozy bedroom features a rustic wooden bed frame with soft linens, complemented by natural light from a nearby window. A stylish soaking tub is presented with a wooden shelf nearby. The kitchen showcases modern appliances with a striking blue cabinetry, while a snowy mountain landscape is displayed outdoors.

4.96 out of 5 average rating, 268 reviews

Romantic Farmhouse near Mt. Bachelor

Relax at a peaceful farmhouse for a romantic weekend, or take your time exploring Bend with friends. Baltzor Farm and Guesthouse is fewer than 2 miles from some of Bend's amazing breweries and restaurants. Smith Rock and Mt. Bachelor are both within 30 minutes of the guesthouse. Catch a concert, float the Deschutes, or go on a bike ride. Our relaxing farmhouse has rustic, old-world charm with all of the modern amenities, including a soaking tub, waterfall showerhead, soft linens, and Starlink.

4.96 out of 5 average rating, 128 reviews

The A-frame cabin is framed by tall pine trees, showcasing a modern black exterior. Large windows reflect the surrounding forest, while a wooden deck serves as an entry point, inviting guests to explore the natural setting.

Cabin in La Pine

Discover tranquility in our A-frame cabin nestled among the pines. A rustic haven where the scent of pine fills the air, inviting you to unwind on the porch. Inside, a cozy living space & quaint kitchen offer comfort. Retreat to the loft bedroom, where the soft glow of morning light through pine branches awaits. Whether a romantic escape or family adventure, this cabin is a sanctuary, a respite from the daily rush. Embrace simplicity, enjoy the peace & quiet, and enjoy all the nearby beauty.

4.9 out of 5 average rating, 353 reviews

The exterior of the cottage is shown with a charming deck and two white chairs positioned under string lights. A well-maintained path leads through lush greenery and stone steps to the entrance, highlighting the inviting atmosphere of the cottage.

Cottage in Bend

The Blackberry Cottage

This adorable 1950's cottage is located in the heart of Midtown Bend, within walking distance to local coffee shops, restaurants, parks and Pilot Butte State Park, and less than a mile away from downtown Bend. Two light-filled bedrooms both have double French doors leading out to a large back deck and a fenced, private backyard. A cozy living room, and eat in kitchen make this home the perfect place for a small family or a few friends to share. Serene fenced back yard space with hot tub.

5 out of 5 average rating, 135 reviews

An inviting hot tub is positioned alongside a sauna grotto, both nestled within a natural setting. The hot tub features clear water with soft illumination, while the sauna's wooden exterior is accentuated by warm light. Surrounding trees and rocks enhance the tranquil atmosphere.

Bungalow in Bend

River Run Bend Bungalow & Romantic Spa Grotto

**NEWLY INSTALLED! ** Spa & sauna grotto is all ready for your romantic Bend getaway! This quiet, wooded, centrally located, standalone bungalow is steps from the Deschutes River trail, easy walking distance to Mill Dist. and Hayden Amphitheater. It boasts a comfy king bed w/premium down bedding & pillows, dedicated free parking (+ extra cars or small RVs), outdoor dining and patio area, washer/dryer, and a kitchen fully stocked with everything you need for fun and relaxation for all seasons!

4.97 out of 5 average rating, 359 reviews

A spacious deck offers unobstructed views of the canyon and distant mountains during sunset. Comfortable outdoor seating is arranged around a central table, inviting relaxation while taking in the serene landscape. Warm hues light up the sky, creating a tranquil atmosphere.

Home in Terrebonne

Pointe of Blessing with hot tub and canyon views

Prepare to be blown away by the astounding sunrises , sunsets and awesome moonrises you will enjoy at the Pointe of Blessing. We feel our canyon perch is a gift from God too good to keep to ourselves. Our cozy home sits atop an outcropping of rock which juts out from the canyon rim affording us unobstructed views up and down the length of the Crooked River Canyon. We overlook several holes of the Crooked River Ranch golf course and Smith Rock is visible in the distance to the South.

4.94 out of 5 average rating, 532 reviews

Dome in Bend

Welcome to Dome Sweet Dome

Your chance to stay in a true-to-name Geodesic Dome! This one-of-a-kind retreat blends comfort with architectural charm. Guests call it cozy, inspiring, and unforgettable — a stay that feels like an experience, not just a place to sleep. Nestled in the First-on-the-Hill neighborhood off Century Drive, the Dome is perfectly positioned for everything Bend has to offer. Whether you’re here for skiing, biking, hiking, or just relaxing, you’ll love how close you are to Bend’s best adventures.

4.96 out of 5 average rating, 394 reviews

The exterior of a red brick apartment building features multiple entrances, framed by green awnings and surrounding trees. Warm light emanates from the windows, highlighting the architectural details of the structure against an evening sky.

Flat in Bend

The Heart Of Bend. Brownstone Apartment.

LOCATION CAN'T BE BEAT Meticulously Clean Modern Space Private apartment STEPS AWAY FROM THE DESCHUTES RIVER AND A 5 MINUTE WALK TO THE SUMMER SHOWS AT THE AMPHITHEATER A PERFECT BASE FOR WINTER AT MT. BACHELOR NO-CONTACT EASY CHECK-IN OLD MILL LOCATION IN THE MOST DESIRED NEIGHBORHOOD IN BEND Perfect setting in the heart of Bend between downtown & The Old Mill District Walk to fine dining, boutiques, galleries, theaters, coffee and the Deschutes River Trail steps away

A spacious living room features a light-colored sectional sofa positioned around a glass coffee table. Large windows invite natural light, revealing a view of the outdoors. A stone fireplace provides a warm focal point, complemented by a cozy armchair and decorative elements throughout.

4.99 out of 5 average rating, 199 reviews

Airy Bend Oasis - Two Ensuites

Cheers to your stay at Bent Pine Oasis, located in the picturesque west side of Bend! This home provides the ideal location for any outdoor enthusiast: Mt Bachelor's slopes are just a 20 minute drive & the Deschutes River Trail is mere steps from the front door- your avenue to biking, running and exploring Bend. Looking for a more relaxing day? You can make the 5 minute drive into the Old Mill District to enjoy food trucks, a river float, or fresh hops at a local brewery.

Popular amenities for Bend family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.93 out of 5 average rating, 121 reviews

Two blue Adirondack chairs are positioned on a lush green lawn, overlooking the calm Little Deschutes River. In the background, the river reflects the surrounding trees and grassy areas under a clear sky, creating a serene outdoor space for relaxation.

Home in La Pine

Riverfront/Hot Tub/Dock/Pet Friendly/Game Room

A spacious outdoor patio features a built-in BBQ station, surrounded by loungers and an outdoor dining table. A natural gas firepit sits at the center, with seating around it, offering a relaxing atmosphere amid landscaped greenery and trees.

4.99 out of 5 average rating, 105 reviews

Tall Pine Tuckaway! Hot tub, EV charge, RV hookup

The front exterior of the newly constructed home features a welcoming entrance with large glass doors framed by warm lighting. A landscaped pathway of stones leads to the entrance, surrounded by gravel and desert flora, under a colorful twilight sky.

4.95 out of 5 average rating, 136 reviews

SAGE HAVEN* Hot tub* Mountain Views* Sleeps 8

Camper van/Motorhome in Bend

The exterior features a wooden fence and walkway leading to Miss Clementine, the Airstream, with surrounding shrubs and trees providing a natural setting. A welcoming entryway is visible, framed by the rustic wood structure, emphasizing a blend of comfort and nature.

4.88 out of 5 average rating, 549 reviews

Meet Miss Clementine-1973 Airstream w/Cozy Hot Tub

4.99 out of 5 average rating, 134 reviews

An outdoor seating area is set up near a pool, featuring various tables and a gas fire pit surrounded by comfortable couches. Umbrellas provide shade, and string lights offer a warm glow above. The backdrop consists of tall trees and a well-maintained lawn.

Apartment in Bend

Pool, AC, close to Amphitheater & Old Mill

A northwest style house is nestled among tall ponderosa pine trees. The front features welcoming wooden accents, a large stacked firewood pile, and an attached garage. Natural grasses are scattered across the landscaped area, providing a rustic charm to the peaceful setting.

4.93 out of 5 average rating, 245 reviews

☆ Quiet Forest Retreat | 10min from Old Mill ☆

4.98 out of 5 average rating, 239 reviews

A hot tub is positioned on a wooden deck, surrounded by tall greenery for privacy. The house features large sliding doors leading to an open space, with outdoor seating visible nearby, creating a relaxed outdoor retreat.

Bungalow in Bend

Ski, Bike, and Golf from a Spacious Family Bungalow

4.89 out of 5 average rating, 388 reviews

Adventure Retreat - Sunriver/Bachelor/Waterfront

Family- and pet-friendly home rentals

4.94 out of 5 average rating, 580 reviews

A rustic log cabin is nestled among tall pine trees, featuring a welcoming porch with wooden railing. Sunlight filters through the branches, illuminating the surrounding forest floor and creating a serene atmosphere in the natural setting.

Cabin in Bend

Log Cabin on Tumalo Creek

4.89 out of 5 average rating, 513 reviews

A wooden deck provides seating with two Adirondack chairs facing the tranquil river. Potted flowers add a touch of color to the space, while lush greenery lines the riverbank. Kayakers can be seen leisurely paddling on the water under a bright blue sky.

Cabin in Old Bend

Mill Cabin at Deschutes Dunes River/ beach access

4.98 out of 5 average rating, 321 reviews

Have a Patio Barbecue at a Pet-Friendly House in Midtown

4.94 out of 5 average rating, 147 reviews

Close to Bachelor! Hot Tub, Dog Okay! Luxury. Ski

4.99 out of 5 average rating, 164 reviews

A bright living room features large windows allowing ample natural light. Neutral-toned sofas are arranged around a wooden coffee table atop a patterned area rug. Soft drapes frame the windows, while a cozy chair and dining area are visible in the background.

Home in River West

West House: 2 blocks to River-walk/bike everywhere

4.95 out of 5 average rating, 305 reviews

A modern kitchen features sleek cabinetry and quartz countertops, complemented by stainless steel appliances. Two wooden stools sit at the kitchen island, with a spacious layout that encourages cooking and socializing.

Cottage in Old Bend

Contemporary Chic, Walk Downtown, Gourmet Kitchen

A spacious living area is highlighted by a modern entertainment center and a comfortable seating arrangement, including a large ottoman. Light-colored walls complement the wooden floors, while natural light filters through windows, enhancing the room's inviting appearance.

4.97 out of 5 average rating, 191 reviews

Old Mill Charm

The kitchen features modern white cabinetry and a large central island with a wooden cutting board. Stainless steel appliances, including an oven and refrigerator, are present. Shelving holds various kitchen items, while a window offers natural light and views of the outdoor greenery.

4.96 out of 5 average rating, 159 reviews

Downtown with hot tub and fenced-in yard

Family-friendly home rentals with a pool

4.86 out of 5 average rating, 259 reviews

The room features a queen bed with a light-colored bedspread, accompanied by bedside tables with lamps. A cozy seating area with cushions is beside a large window, allowing natural light to illuminate the space. Artworks are displayed on the walls, enhancing the serene atmosphere.

Guest suite in Bend

Mt Bachelor Village Resort- Room in River Ridge II

Superhost

An indoor lap pool is highlighted by large floor-to-ceiling windows, allowing natural light to illuminate the wooden walls and ceiling. The calm water reflects the serene outdoor surroundings, enhancing the peaceful atmosphere of the space.

Home in Sunriver

4.88 out of 5 average rating, 105 reviews

Sunriver by AvantStay | Modern Home w/ Indoor Pool

The exterior of a charming two-story home is surrounded by tall trees, featuring a welcoming porch with seating. A neatly arranged driveway provides access to a garage, and flower pots line the entrance. Sunlight filters through the branches, creating a serene atmosphere.

4.95 out of 5 average rating, 111 reviews

Deschutes River Getaway-near Bachelor & Sunriver

4.92 out of 5 average rating, 203 reviews

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

A private patio features a bubbling hot tub and an umbrella table with chairs. Nearby, a gas grill is positioned for outdoor cooking. Soft lighting enhances the space, while large windows offer views into the cozy interior.

4.98 out of 5 average rating, 244 reviews

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

4.85 out of 5 average rating, 119 reviews

A spacious living area features a comfortable L-shaped sofa adorned with a light throw. Natural wood beams accentuate the ceiling, while a gas fireplace adds warmth. A flat-screen TV is visible, and a dining table with bar stools is situated nearby against neutral-toned walls.

Home in Sunriver

Updated Sunriver-Hot Tub, Walk to SHARC & Village

4.88 out of 5 average rating, 298 reviews

The living area showcases a modern design with leather seating arranged around a natural wood coffee table. A television is mounted above a stone fireplace, and a dining table is situated nearby. The kitchen features stainless steel appliances and light wood cabinetry.

Townhouse in Bend

Charming Mt. Bachelor Village Condo