Family-friendly holiday rentals in Bend

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.

4.99 out of 5 average rating, 249 reviews

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.

FamilyKitchenNearby

4.98 out of 5 average rating, 980 reviews

The lookout tower is framed by green trees, featuring multiple wooden decks and a spacious entryway. Steps lead up to the main entrance, and large windows provide glimpses of the interior overlooking the natural landscape.

Home in Terrebonne

Cozy Three Story Lookout Tower

Thank you for your interest in The Cozy Lookout Tower! Our unique vacation home is really a destination location rather than just a place to stay while you explore the area. Many of our guests are repeat guests that use our home as a place to recharge, relax, cook, read, talk, play games and connect with that special someone. There are some lovely hikes in the area, we encourage you to bring your dog and enjoy the beautiful surroundings by taking some hikes then returning for a soak in the tub!

FamilyIndoor spacesWi-Fi

4.97 out of 5 average rating, 237 reviews

Butler Corner - New, Clean & Minutes From Downtown

Relax and enjoy all that Central Oregon has to offer in this nice, clean and newer 2019 built home. Butler Corner is located in Midtown and sits on a corner lot in a nice quiet and charming neighborhood just minutes from Downtown. We invite you to stay a while in this comfortable space and think of it as your home away from home. ***Please keep an eye out for posted road signs, I recommend using Google or Apple Maps to help navigate the temporary one-way directions. Completion late Fall 2026

KitchenFamilyDecor

4.97 out of 5 average rating, 194 reviews

The bedroom features a spacious bed with white linens, complemented by two bedside tables with lamps. A green bench sits at the foot of the bed, while a landscape painting hangs above the headboard. Soft curtains frame a window, allowing natural light to fill the space.

Guesthouse in Bend

NEW Tranquil Retreat On Canal

Charming, clean, comfortable, fully renovated guest house on 3 acres, nestled by a canal. A quiet escape near Pine Nursery Park, just 5 miles from downtown and less than 20 minutes from the airport. Enjoy beautiful natural light, vaulted ceilings, large bathtub, and balcony with outdoor seating and a beautiful view. Fully stocked kitchen, washer & dryer, heat & AC, blackout shades, board games, books, amenities for kids, smart TV, and a Blu-ray player for rentals from The Last Blockbuster.

KitchenFamilyWalkability

4.9 out of 5 average rating, 393 reviews

Bungalow in Old Bend

FLOAT THE RIVER! River, Beach Access Downtown Bend

Welcome to our 1918 Bungalow on Riverfront Street. This simple, no frills one bedroom, one bath sleeps two to three. Enjoy a fully equipped kitchen, floor to ceiling river rock gas fireplace, inviting front porch, back deck with propane BBQ, table/ chairs. The Bungalow has a peek of the river, as it is considered the "guest house" to the larger "main house" it shares the lot with. Enjoy low bank river access to launch your kayak. Park the car and experience the best Bend has to offer.

KitchenFamilyBeach

4.94 out of 5 average rating, 265 reviews

An A-frame cabin is set against a colorful sunset, showcasing warm lights illuminating the exterior. The front entrance features a door with a welcoming window, while two rustic chairs sit on the porch, accompanied by potted plants and neatly stacked firewood.

Cabin in Bend

Black Duck Cabin

Cozy A frame cabin set in a quiet neighborhood among the pine trees just a short walk from the Deschutes River. The Black Duck Cabin is a perfect destination for all of Central Oregon's amazing activities. 10 minute drive to Sunriver Village, 30 minute drive to Mt. Bachelor, 30 minutes to Downtown Bend, 10 minute walk to the Deschutes River, golfing, fishing, hiking, shopping, mountain biking, all a short drive. If you're looking for a rustic, cabin experience this is the place for you!

KitchenIndoor spacesCondition

4.98 out of 5 average rating, 165 reviews

An outdoor living space features four wooden Adirondack chairs arranged around a smokeless firepit. A hot tub and sauna are visible within a nearby structure, with steam rising gently from the hot tub. The area is surrounded by a wooden fence and trees.

Cottage in Old Bend

Historic Old Bend Cottage & Carriage House Spa

This historic Old Town Bend cottage boasts a relaxing setting for unwinding with a lovely cedar hot tub & sauna in its restored carriage house. Walk to the attractions: 0.2 mi. to the best shops and restaurants, and 0.4 mi. to Mirror Pond & Drake Park! Split heating in each room, snow gear storage, boot warmer, grill, and new washer/dryer. Driveway and extra street parking (free). Fast WiFi and a smart TV. The kitchen is fully stocked, and we look forward to hosting you!

KitchenIndoor spacesHiking

A modern kitchen space features a large island with three stools, complemented by sleek cabinetry and stainless steel appliances. Natural light floods in through nearby windows, illuminating the stylish fixtures and inviting design. The adjoining living area, visible in the background, enhances the open layout.

4.95 out of 5 average rating, 129 reviews

Zen w/ Hot Tub, Office, Yard, Dog Friendly, Park

Welcome to your peaceful Bend basecamp, thoughtfully managed by The Home Co.—a local small business focused on clean, well-functioning homes with easy checkouts. This stylish 2-bedroom, 2-bath home is centrally located near Ponderosa Park and Pilot Butte, with easy access to Downtown, the Old Mill, and the Deschutes River. With a fully fenced yard, dedicated office, hot tub, and flexible living space, it’s perfect for families, remote workers, and pet lovers.

KitchenFamilyCondition

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, 213 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.

Indoor spacesKitchenView

4.98 out of 5 average rating, 221 reviews

An outdoor seating area is featured under a canopy, equipped with comfortable gray couches and a fire pit at the center. Soft lighting is provided by strand lights along the structure. A hot tub is visible in the corner, contributing to a relaxing atmosphere.

Cottage in Sunriver

Cozy Home w/River Access, Hot Tub, 7min to Village

Welcome to our Backcountry Basecamp Cottage! Nestled in the heart of the Deschutes National Forest. Our home is a short walk from the crystal-clear waters of the Deschutes River, which you can access through a private neighborhood marina. You can enjoy hiking, floating, kayaking, or skiing and snowshoeing nearby. It is the perfect base camp for exploring all that the area has to offer.

FamilyIndoor spacesBackyard

4.97 out of 5 average rating, 150 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.

Condo in Bend

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.

FamilyIndoor spacesHospitality

4.98 out of 5 average rating, 155 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

The perfect getaway for the outdoor enthusiast and for local entertainment in this ultra clean Bend home. Hop on the trails from the doorstep of this riverside home. Rustic tables, wooden floors, and a central fire place lend to the warm, cabin ambiance. Relax on the patio by the fire pit perfect for roasting marshmallows after a full day on the slopes.

KitchenFamilyCheckout

Popular amenities for Bend family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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, 120 reviews

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

KitchenFamilyComfort

4.95 out of 5 average rating, 191 reviews

Aerial view of a beautiful riverside home surrounded by lush trees and vibrant foliage. The property features a large private backyard that leads directly to the water, showcasing a peaceful escape into nature. The nearby river reflects the sky and trees, enhancing the tranquil scenery.

Home in Old Bend

Bend Waterfront Home: Hot Tub, Walk to Town

KitchenFamilyBackyard

4.96 out of 5 average rating, 198 reviews

A spacious bed is adorned with various blue and plaid decorative pillows. A wall-mounted television is visible, along with a black storage cabinet. Natural light enters through a small window, framed by light curtains. A rustic wall decoration adds character to the space.

Guesthouse in Bend

Charming studio in the heart of town

FamilyIndoor spacesHiking

4.98 out of 5 average rating, 117 reviews

A spacious living area is highlighted by large windows that allow natural light to fill the room. A cozy seating arrangement surrounds a central coffee table, with a modern fireplace adding warmth. A television mounted on the wall provides entertainment options.

Townhouse in Bend

Minutes to Bachelor! Spa. Fire pit. Ski!

KitchenFamilyHeating

A modern kitchen features stainless steel appliances, including a refrigerator and microwave, framed by white cabinetry. A spacious granite countertop provides seating for three on dark wood stools, enhancing functionality. Natural light enters through a nearby door, contributing to the welcoming atmosphere.

4.92 out of 5 average rating, 165 reviews

Trendy West Side by 10 Barrel, Hot Tub, Fence Yard

KitchenIndoor spacesCleanliness

A spacious living area features a large sectional sofa with plush cushions, complemented by a wooden coffee table. A flat-screen TV is mounted above a modern fireplace, with decorative shelves showcasing plants and accessories. Natural light flows in through multiple windows.

4.97 out of 5 average rating, 140 reviews

Hot Tub~King Bed~Dog Friendly-New Construction

KitchenFamilyValue

4.98 out of 5 average rating, 173 reviews

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

FamilyKitchenPets

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, 155 reviews

SAGE HAVEN* Hot tub* Mountain Views* Sleeps 8

Indoor spacesKitchenLocation

Family- and pet-friendly home rentals

A wooden deck overlooks a serene river, flanked by lush greenery. Two comfortable armchairs with bright cushions are arranged around a small table, inviting relaxation and enjoyment of the peaceful environment.

4.84 out of 5 average rating, 474 reviews

THE TROUT HOUSE a cabin on the River

Indoor spacesFamilyBathroom

4.94 out of 5 average rating, 395 reviews

A welcoming front porch features two white folding chairs and a small table. Potted flowers add color to the space. The green door complements the light exterior, while overhead lights enhance visibility. Natural light filters through the surrounding trees.

Cottage in Bend

Adorable West Side Cottage, Pet Friendly!

FamilyKitchenBiking

4.9 out of 5 average rating, 419 reviews

A spacious sleeping area features a large bed adorned with a patterned comforter and decorative pillows. Dark curtains frame a window that allows natural light to fill the room. Two nightstands with lamps are positioned on either side of the bed.

Guest suite in Bend

Cozy Studio! Walk to NW Crossing and Shevlin Park

Indoor spacesKitchenHeating

4.97 out of 5 average rating, 154 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

FamilyIndoor spacesHospitality

4.97 out of 5 average rating, 433 reviews

An open living and dining area features large windows, allowing natural light to fill the space. Comfortable seating, including a leather armchair and a sectional sofa, is complemented by a kitchen with bar stools. The rustic decor includes a mountain wall hanging and a soft area rug.

Guesthouse in Bend

Old Mill and River Walk Retreat

FamilyKitchenBiking

A spacious backyard features a circle of comfortable outdoor seating surrounding a fire pit. The cozy home is visible in the background, with warm lights illuminating large windows. Lush green grass and well-maintained landscaping create a welcoming outdoor space.

4.98 out of 5 average rating, 341 reviews

Spacious Pet-Friendly Home • Fire Pit • Fenced Yd

Indoor spacesFamilyDecor

4.9 out of 5 average rating, 372 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

Indoor spacesFamilyCheckout

4.94 out of 5 average rating, 457 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

Indoor spacesFamilyComfort

Family-friendly home rentals with a pool

4.96 out of 5 average rating, 118 reviews

Serenity Retreat | Pool, Spa, Trails & Mt Bachelor

FamilyKitchenLaundry

4.98 out of 5 average rating, 183 reviews

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.

Condo in Bend

Cozy Mt. Bachelor Village Condo near Downtown Bend

KitchenIndoor spacesAmenities

4.97 out of 5 average rating, 246 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

FamilyKitchenCleanliness

4.85 out of 5 average rating, 540 reviews

The open living space features high ceilings with natural light flooding in through large windows. A comfortable sofa and coffee table are present, while a dining area with four chairs is visible. A spiral staircase leads to a loft area, enhancing the room's spacious feel.

Condo in Sunriver

*Sunriver* HotTub/Pool In Room Sauna Popcorn Cart

KitchenIndoor spacesCheck-in

4.96 out of 5 average rating, 134 reviews

Townhouse in Sunriver

Newly Remodeled 3 bdrm-Hot Tub-SHARC passes-Bikes

KitchenIndoor spacesPets

4.98 out of 5 average rating, 284 reviews

The exterior of the chalet is showcased, featuring a peaked roof and large windows that allow ample natural light. A spacious wooden deck is present, accompanied by outdoor seating and a barbecue. The surrounding grassy area enhances the outdoor setting.

Chalet in Redmond

Cozy 3 bdrm + loft Eagle Crest Chalet w/ Hot Tub!

FamilyIndoor spacesWalkability

The exterior of a large two-story house is displayed, featuring a covered porch supported by columns. Lush green grass surrounds the structure, complemented by neatly arranged shrubs. A clear blue sky with soft clouds is visible above, enhancing the overall setting.

4.93 out of 5 average rating, 282 reviews

Updated Game Room! Hot Tub, SHARC (8), 2,800sq/ft

FamilyKitchenRiver