Family-friendly rentals near Old Mill District

5.0 out of 5 average rating, 181 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

Relaxing, private spa & sauna grotto is ready for your romantic Bend getaway! This quiet, wooded, centrally located standalone bungalow is steps from the Deschutes River trail and within easy walking distance of 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!

4.95 out of 5 average rating, 152 reviews

The exterior of the townhome is showcased, featuring a blend of stone and wood materials. A spacious deck with a railing is visible on the upper level, while a pathway leads through well-maintained landscaping and manicured grass, enhancing the inviting look of the residence.

Townhouse in Bend

Salmon Lodge Luxury 3BR Bend OR Old Mill District

The Salmon Lodge is a West Bend luxury 3 BR 3 Bath townhome in the Old Mill District. It has served as a premier vacation rental for the last decade. Under new ownership since 2022, we are excited to honor the legacy of the thoughtfully built Salmon Lodge. We will continue to offer the quintessential Bend experience. Walk or bike everywhere! Close to Old Mill shopping, downtown, Mt Bachelor, Deschutes & concert venue. Mountain view from upstairs deck with attached bar. Sleeps 8 to 9

4.96 out of 5 average rating, 184 reviews

Best for Old Mill:River Trail, Views & Town

Enjoy an unbeatable location within walking distance of the Hayden Homes Amphitheater, Old Mill and the scenic Deschutes River Trail. Experience all the best of Bend right outside your door! Whether you’re here for a concert, outdoor adventure, or a relaxing weekend, you’ll be close to everything that makes Bend special—riverfront trails, restaurants, breweries, nightlife, cycling, kayaking, paddleboarding, and hiking. Mt. Bachelor is just a short drive away—approx. 25 minutes.

A historic two-story building is showcased in a monochrome setting. It features a large entrance with broad steps flanked by neatly trimmed hedges. The exterior has a simplistic design, with a gabled roof and multiple windows, contributing to its classic architectural style.

5.0 out of 5 average rating, 101 reviews

The Church In Bend

The Alliance Tabernacle Church, built in 1923, is reported to be the first house of worship west of the Mississippi to be built entirely by volunteers from the congregation. By the 1970s the building had fallen into disrepair. Beginning in October 2014 the current owners began the process of restoring the building to it's original condition under the supervision of the Historic Landmark Commission. This special place is close to everything, making it easy to plan your visit.

Superhost

Bungalow in Bend

Sunny Getaway: fenced | Near trails, dining, music

This inviting, relaxing, cottage is just minutes from great dining, shopping & trails in SE Bend’s Larkspur neighborhood. Enjoy the deck, fire pit, BBQ, fenced yard, fast WiFi and washer/dryer. Stroll the Deschutes River, explore bike trails, and enjoy quick access to downtown and shops at the Old Mill District! Visit Bend’s brunch scene or stay in and cook up waffles in the stocked kitchen. Book the Stadium Bungalow as your perfect basecamp for exploring Bend year-round!

4.88 out of 5 average rating, 265 reviews

The exterior of Tokyo Starfish displays a welcoming façade with dark wood siding and vibrant red accents. Potted plants line the entrance, and a white flag featuring a green cross signals cannabis offerings. A bicycle leans against the building, adding to the inviting atmosphere.

4.96 out of 5 average rating, 255 reviews

Westside "Bud-And- Breakfast"

The first and only "Bud-And-Breakfast" in Bend, Or, located in the heart of Bend's Westside. Situated above Tokyo Starfish, the unparalleled cannabis dispensary in Central Oregon, this fantastic 2-bedroom apartment isn't just in a great location, but is also cannabis friendly. Just head downstairs to Tokyo Starfish with your complimentary gift card and experience the freshest selection of flower, edibles, drinks and other top cannabis products the dispensary has on hand.

4.95 out of 5 average rating, 338 reviews

Townhouse in Bend

Drake @ The DUPE - blocks from Old Mill District -

Drake: Located blocks from the Old Mill District, this beautifully updated 2-bed, 2-bath townhouse blends privacy with an unbeatable location. Walk or bike to the Old Mill, Deschutes River, dining, and the Hayden Homes Amphitheater. Tucked in a serene, tree-lined setting, the private home features a bright kitchen with updated appliances, a primary suite with a walk-in tile shower, and a separate porch with a BBQ grill. The perfect mix of modern comfort and convenience.

4.94 out of 5 average rating, 461 reviews

A modern three-story apartment building features a striking combination of wood and contemporary architectural elements. Large windows provide ample natural light, while a wide staircase leads to the entrance. Trees are visible in the background, contributing to a serene outdoor setting.

Loft in Bend

Cozy River Front "NEST" | Old Mill | Dog | Bikes

Enjoy this Luxury 2nd level apartment directly on the Deschutes River. Easy trail access is steps away where you can run/hike the 3 1/2 mile loop or paddle up and down the river. Back at home sit on your deck and listen to the sounds of the river going by. The Old Mill, Box Factory, Food Carts and more are a peaceful 3/4 mile stroll along the river trail ....yet you are a world away in your "Nest" within the Ponderosa Pines along the river. ** Enjoy! **

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.

4.98 out of 5 average rating, 205 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 ensuring your privacy.

A light-filled living area features a black leather sofa and a wooden armchair facing a large window. A patterned area rug adds warmth to the hardwood floor. Barstools are placed at the kitchen counter, and artwork is displayed on the white wall.

5.0 out of 5 average rating, 214 reviews

Central Modern Guesthouse with EV Charger

We built this home out of a passion for creating welcoming spaces. Years ago, we renovated a motel on the coast - an experience that sparked our love of hospitality and shapes how we host today. We live around the corner with our kids, a golden retriever, and a few cats. Mike’s a local realtor, and Betsy manages business ops for the local fire department. We love books, music, and helping you discover the best of Bend - trails, eats, and community.

An exterior view of a single-story home is shown, surrounded by landscaped gardens with rocks and greenery. A cozy patio area features blue and white striped lounge chairs, an umbrella, and string lights overhead, creating a welcoming outdoor space.

4.97 out of 5 average rating, 205 reviews

Close, Cute & Clean! *Hot Tub* Bend Adventure Base

Welcome to your Central Oregon adventure base! Book now to enjoy the convenience and comfort of this centrally located Bend home!! Quick access to all of the activities and events that make this area so special! Conveniently located for walking and biking to the Old Mill, Deschutes River, concerts, parks, restaurants, breweries, and grocery stores. Come settle in for exploration and recreation!!

4.99 out of 5 average rating, 146 reviews

Cottage in Old Bend

Riverfront Cottage | Miller's Landing

Truly one of the best riverfront homes in Bend! This luxury 2 bed, 2 bath cottage sits directly on the Deschutes River with a fenced yard, deck, gazebo, fire pit, kayaks, paddleboards, bikes, and more. Walk to downtown, Old Mill, and Galveston Ave breweries. Pet-friendly, fully updated, and made for cozy, upscale stays. Relax, explore, and enjoy Bend like a local — right on the river.

Popular amenities for family-friendly rentals near Old Mill District

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A combined dining and living area features a wooden dining table with multiple chairs alongside a comfortable sectional sofa adorned with decorative pillows. Pendant lighting hangs above the kitchen island, highlighting the modern appliances in the kitchen, while large windows allow natural light to brighten the space.

4.89 out of 5 average rating, 474 reviews

Location! 4-Bedroom, 3-bath Downtown w/Hottub

A bright living area features a cozy gas fireplace and a flatscreen TV mounted on the wall. Two blue armchairs and a round dining table create a comfortable seating arrangement. The fully equipped kitchen, visible in the background, includes stainless steel appliances and wooden cabinetry.

4.98 out of 5 average rating, 185 reviews

Cozy Mt. Bachelor Village Condo near Downtown Bend

A historic craftsman bungalow is framed by vibrant autumn foliage. A concrete path leads to the covered front porch, surrounded by tall grasses and fallen red leaves, evoking a welcoming outdoor space in the fenced front yard.

4.99 out of 5 average rating, 262 reviews

Lucinder - Modern historic home, views, Downtown

4.91 out of 5 average rating, 379 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

4.95 out of 5 average rating, 317 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 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.

4.95 out of 5 average rating, 459 reviews

Cozy, Pet Friendly, Hot Tub. Garage.

A living area features large windows allowing natural light to illuminate the space. A cozy seating arrangement includes a dark leather sofa and a wooden chair. A blue coffee table contrasts with a warm wood floor, while a rustic brick fireplace adds a touch of charm.

4.92 out of 5 average rating, 478 reviews

Five minutes from old mill with hot tub.

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.

4.97 out of 5 average rating, 154 reviews

Pool, AC, close to Amphitheater & Old Mill

Family- and pet-friendly home rentals

4.95 out of 5 average rating, 302 reviews

The bungalow's exterior features a warm brown facade with vibrant red accents. Large windows with white frames allow natural light to enter. A small seating area with a round table and two chairs is positioned on the front porch, surrounded by minimal landscaping.

Bungalow in Old Bend

Wren's Nest Updated Home in the Heart of Bend

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.

4.99 out of 5 average rating, 179 reviews

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

A single-story house with a welcoming porch is framed by a gravel driveway. Lush greenery surrounds the entrance, complemented by blooming pink flowers. The cloudy sky adds depth to the scene, while large windows provide ample natural light. The structure features a simple, rustic design.

4.96 out of 5 average rating, 193 reviews

Bend 3BR Home Near River Trail | Dog-Friendly

Superhost

A cozy living area is highlighted by a modern fireplace and a large television built into a white cabinetry. Soft seating is provided by a sectional sofa and accent chairs. Natural light flows through the large windows, illuminating the room's neutral decor.

4.82 out of 5 average rating, 115 reviews

Cozy 3-BR house w/ EV charger & trailer parking

4.96 out of 5 average rating, 158 reviews

Bungalow in Bend

Kid & Dog Friendly Bungalow In The Heart Of Bend

4.93 out of 5 average rating, 116 reviews

A modern living area showcases a comfortable dark sofa alongside a bright orange armchair. A wooden coffee table is positioned in front, with a small plant and speaker on top. A dining table with four chairs is visible in the background, and a fireplace adds warmth to the space.

Apartment in Bend

Modern Condo~Fireplace~Walk to Old Mill & River

4.98 out of 5 average rating, 178 reviews

Game Room | Hot Tub | Easy 2 Bachelor | Old Mill

4.98 out of 5 average rating, 147 reviews

Old Mill Spa Lodge • Sauna + Hot Tub • Walkable

Family-friendly home rentals with a pool

4.96 out of 5 average rating, 121 reviews

Serenity Retreat | Pool, Spa, Trails & Mt Bachelor

4.97 out of 5 average rating, 194 reviews

Private Indoor Pool + Hot Tub | Game Room

4.97 out of 5 average rating, 252 reviews

A comfortable guest suite is designed with a spacious bed covered in a white quilt. An accent wall of exposed brick enhances the warm ambiance. A wooden desk and two brown armchairs complement the space, with light filtering through a window dressed with blinds.

Guest suite in Bend

River Ridge Getaway - River Trail & Hot Tub

4.88 out of 5 average rating, 319 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

A spacious living area is highlighted by large windows that allow ample natural light. A cozy seating arrangement featuring a patterned chair faces a TV on a wooden stand. A dining table accommodates several guests, while wooden accents enhance the room's warmth.

4.91 out of 5 average rating, 454 reviews

Luxury in the Forest

4.95 out of 5 average rating, 147 reviews

Home in Sunriver

Hot Tub +Bikes +8SHARC Passes +PingPong +Fireplace

The fully equipped kitchen features granite countertops and wooden cabinetry. Large windows allow natural light to fill the space, providing views of the surrounding forest. The kitchen area includes modern appliances, a kitchen island with seating, and overhead lighting for an inviting cooking environment.

4.86 out of 5 average rating, 309 reviews

Mt. Bachelor Village Condo - Near Town & River

4.94 out of 5 average rating, 283 reviews

The open living space features a high beamed ceiling and natural wood accents. Two leather sofas are arranged around a light-colored coffee table. A dining area with a wooden table sits adjacent to the kitchen, which displays modern appliances and bar seating.

Home in Sunriver

A Little Peace of Paradise, A/C, & 8 SHARC Passes

Family-friendly home rentals with Wi-Fi

A comfortable living area features a grey sofa and two wooden armchairs, arranged around a rectangular coffee table. A brick fireplace with decorative items rests on the wall. Natural light enters from a nearby window, and a door leads outside.

4.97 out of 5 average rating, 214 reviews

Franklin Flat - House @ Downtown & Historic Dist

4.84 out of 5 average rating, 409 reviews

Guest suite in Bend

Haven’s Nest | Walk to Old Mill / Deschutes River

4.98 out of 5 average rating, 756 reviews

The entrance to the basement apartment is framed by a decorative iron railing and features a set of steps leading down. Surrounding greenery enhances the natural setting, with a nearby window indicating the light and airy atmosphere indoors.

Apartment in Old Bend

Historic Drake Park Neighborhood .

4.92 out of 5 average rating, 391 reviews

A red, single-story house features a sloped roof and white trim. Two white columns support the covered porch, leading to a front door with a large window. Surrounding greenery includes trees and shrubs, enhancing the home’s inviting exterior.

Bungalow in Old Bend

Georgia Avenue Getaway

4.98 out of 5 average rating, 158 reviews

A charming exterior view of the rustic cabin showcases a covered porch with comfortable seating. Surrounding landscaping features a variety of plants and rocks, complemented by a small fire pit area. The home's muted color palette blends harmoniously with the natural setting.

Cottage in Bend

River Camp House

4.94 out of 5 average rating, 553 reviews

Dome in Bend

Welcome to Dome Sweet Dome

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, 222 reviews

Airy Bend Oasis - Two Ensuites

The charming exterior of the Craftsman home features a yellow façade with white shutters and a bold red front door. A symmetrical front porch is flanked by two large windows, and colorful landscaping enhances the welcoming curb appeal.