Family-friendly holiday rentals in Redmond

A cozy living area features a grey sofa adorned with decorative pillows, positioned on a textured area rug. A flat-screen television is mounted on the wall, while a stylish black stove adds warmth. Natural light enters through a nearby window, enhancing the space.

4.92 out of 5 average rating, 129 reviews

Cozy Downtown Redmond Cottage

Welcome to our cozy Redmond cottage, located in the heart of downtown! Enjoy walking to local breweries, restaurants, and shops, all just steps away. This inviting space offers a perfect blend of comfort and convenience, ideal for couples or solo travelers. Unwind in the cozy living area after a day exploring Central Oregon. Experience the best of Redmond right outside your door! Conveniently close to: 15 minutes to Smith Rock 25 minutes to Bend 8 minutes to Deschutes County Fair & Expo Center

KitchenFamilySleep quality

4.92 out of 5 average rating, 156 reviews

Townhouse in Redmond

HOT TUB, Eagle Crest Condo on Golf Course, DOGS OK

This beautiful condo is located in the desirable resort community of Eagle Crest which is home to three 18-hole golf courses, an 18-hole putting course, and miles of trails. There is a private hot tub on the back deck that backs up to the golf course, as well as a BBQ. There are 2 spacious upstairs bedrooms each with their own private attached bathroom and walk-in closets. Downstairs is a fully stocked kitchen, propane fireplace, and dining area/table. Come enjoy all Eagle Crest has to offer!

FamilyIndoor spacesRiver

4.84 out of 5 average rating, 709 reviews

Immaculate, Cozy Home in the Heart of Downtown

This gorgeous, welcoming, solar-powered house offers self check-in, speedy WiFi, and complimentary craft beer and coffee. It's located just a couple blocks from downtown, 5 minutes from the airport, 10 minutes from Crooked River Canyon, 15 minutes from Smith Rock, and 20 minutes from Bend. 4 breweries & 3 taprooms are located less than 6 blocks away, and tons of restaurants & shops are close by. Amazing nearby hiking options abound. This space is half of a duplex. No pets or parties allowed.

KitchenIndoor spacesRiver

4.93 out of 5 average rating, 321 reviews

Guest suite in Redmond

Spacious and Private Suite in Central Oregon!

Want a spacious, private, comfortable, and clean place to stay for the weekend or business trip with great discounts for week + stays? This might be the place for you! The space is a sports themed, super clean, private living room, bedroom and bathroom near great Central Oregon attractions such as Smith Rock (12mi), Bend (14mi), and Sisters (18mi)! Deschutes County Expo Center and Redmond/Bend airport are within 4 miles. Guests enjoy a private entrance/exit and contactless check in/out!

Indoor spacesFamilyQuiet

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.

4.97 out of 5 average rating, 392 reviews

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.

KitchenIndoor spacesBreakfast

4.98 out of 5 average rating, 439 reviews

A spacious living area features two comfortable sofas adorned with colorful decorative pillows. A coffee table sits in the center, and a large bed is positioned in the background, draped in a bright quilt. Natural light floods through large windows, illuminating the open space.

Guesthouse in Bend

Bend Ranch Guesthouse on 20 acres

Enjoy our private/detached guesthouse and wake up surrounded by nature on a 20 acre property bordered by farms and views of the Sisters Mountains. Excellent WIFI. Featuring wedding venue, Sage & Honey Spa, tube/lifejacket rentals. On the 2nd floor, 1 king bed, 1 queen bed, queen sofa bed, Full kitchen, refrigerator, dishwasher, microwave, hot plate, toaster oven, Keuirg. 17min to downtown Bend, 12min to downtown Redmond/Airport, 35min to Mt. Bachelor, 30mins to Sisters, 10mins to Tumalo.

Indoor spacesFamilySkiing

4.99 out of 5 average rating, 293 reviews

A bright living area is filled with natural light from large windows. The cozy sofa offers a relaxed seating option, complemented by a stylish ottoman. A well-equipped kitchen features modern fixtures, and exposed wood details enhance the warm and inviting ambiance.

Tiny home in Redmond

Close to Smith Rock, Mountain View, Country Charm

The Tiny House at Aspen View Farm is just what you need! Great location for exploring beautiful Central Oregon - Smith Rock is only 15 min away. On a unique 14 acre farm, relax and retreat with tranquil Cascade Mountain and country views, say hi to Roo the farm dog, and watch cute grazing sheep. The Tiny is cozy and comfy with quality amenities to make you feel right at home - stocked kitchen, a/c, heated floors & more! Please read full listing before booking so there are no surprises :)

Indoor spacesKitchenAccuracy

4.92 out of 5 average rating, 652 reviews

The living room features a combination of modern and rustic decor, including a brown leather sofa, a wooden coffee table, and a cozy area rug. A flat-screen TV is mounted on the wall, with large windows allowing natural light to brighten the space.

Bungalow in Redmond

1918 Bungalow | Modern Renovation•Walk to Downtown

Beautifully restored 1918 bungalow in the heart of Downtown Redmond. Walk to local brewpubs, coffee shops, and food carts. Just 17 miles to Bend. Enjoy luxe linens, plush towels, a soaking tub, and a fully equipped kitchen. Immaculate, cozy, and full of character—this historic gem blends comfort, style, and walkable charm for a memorable stay. Steps from local favorites—food, drinks, and downtown vibes! Perfect base for exploring Smith Rock, and Central Oregon beauty!

FamilyIndoor spacesCleanliness

Campervan/RV in Terrebonne

A vintage camper is seen under a clear night sky, adorned with string lights that create a soft glow. A campfire ring is positioned in the foreground, surrounded by natural stones. Nearby, a shower house can be seen, also illuminated, with outdoor seating available.

4.97 out of 5 average rating, 172 reviews

Tin Can Ranch

Welcome to Tin Can Ranch! Kick your legs up and enjoy the sunset at Tin Can Ranch where your worries drop away like the leaves in Autumn! Our cozy Vintage Yellowstone "Tin Can" camper is nestled in it's own corner of our 5 acre property located in Terrebonne, OR just a 10 minute drive from Smith Rock State Park and within an hour of the very best outdoor adventures in Central Oregon! Next to the camper is the shower house/bathroom with an outdoor washing sink.

Indoor spacesFamilySleep quality

The living area features vaulted wooden ceilings and large windows that allow ample natural light. A stone fireplace is situated beside two dark leather sofas, facing a wooden coffee table. A dining table with chairs is visible in the background, creating a welcoming space.

4.92 out of 5 average rating, 178 reviews

3bdrm Chalet + Hot Tub in Eagle Crest

Welcome! Come enjoy and relax in our rustic chalet. Unwind on the back deck while barbecuing, drinking a cup of coffee, or enjoying our private hot tub. Our chalet offers sports passes to all three sports complexes that include indoor/outdoor pools and tennis courts, spas and saunas, play grounds, BBQ areas, horse shoes, volley ball courts and much more. Enjoy golf, mini golf, enjoy nearby hikes and rivers. The perfect place for a family get away!

Indoor spacesFamilyCheck-in

4.97 out of 5 average rating, 355 reviews

Wow Holy Cow Chalet

Wow Holy Cow! will be your first thought when you set foot into this knotty pine walled, sunlit filled chalet. Furnished with everything you need for a fun, family getaway. Channel Maria von Trapp while taking in the beautiful mountain views from the loft space. Have a drink on the deck while your kids search for frogs in the rock feature and shallow creek below. Grill a steak on the bbq and admire the deer who often pass by. DCCA# 1453

KitchenFamilyTV

4.98 out of 5 average rating, 317 reviews

A modern living space features a light-filled open layout, showcasing a comfortable gray sofa with coordinating pillows. A stylish wooden coffee table complements the area. The kitchen, equipped with sleek cabinetry and appliances, is visible in the background, promoting a functional and inviting atmosphere.

Guesthouse in Redmond

Modern Downtown Cottage near Outdoor Adventure

Nestled in the heart of Downtown Redmond, this beautifully designed cottage offers the perfect blend of convenience and comfort. You'll find yourself within walking distance of charming coffee shops and restaurants, and just 14 minutes away from the breathtaking Smith Rock. The Redmond Airport is less than 10 minutes away, and if you're planning a visit to Bend, you can be downtown or floating on the Deschutes River in under 20 minutes.

KitchenIndoor spacesAir conditioning

Popular amenities for Redmond family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

The exterior of a charming home is showcased, featuring a warm-toned siding with multiple windows. The front porch is covered, providing a welcoming entrance. Lush green shrubs and trees surround the property, enhancing the serene outdoor setting.

4.95 out of 5 average rating, 119 reviews

Eagle Crest Resort - 3 bdrm home in Central Oregon

FamilyIndoor spacesBathroom

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.

4.98 out of 5 average rating, 284 reviews

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

Indoor spacesKitchenAccuracy

4.96 out of 5 average rating, 138 reviews

An open living area is displayed, featuring a dark leather sofa and a wooden coffee table. A dining area with wooden chairs is seen in the background, along with a well-equipped kitchen that is partially visible. Natural light brightens the space, highlighting the warm wood flooring.

Townhouse in Redmond

Eagle Crest townhome Dog friendly-sleeps up to 6

KitchenIndoor spacesWalkability

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.

4.98 out of 5 average rating, 980 reviews

Cozy Three Story Lookout Tower

Indoor spacesKitchenHospitality

4.88 out of 5 average rating, 266 reviews

Place to stay in Redmond

Cozy 2BR Townhome in Eagle Crest w/ Hot Tub!

FamilyKitchenCleanliness

4.85 out of 5 average rating, 235 reviews

Guest suite in Redmond

Cozy, Light & Bright Private Guest Suite + Hot Tub

Indoor spacesFamilyDecor

4.93 out of 5 average rating, 184 reviews

Smith Rock Oasis w/ Hot Tub Steps to the Park

FamilyKitchenDecor

An expansive deck overlooks the Deschutes River canyon, featuring a hot tub and several outdoor seating areas. The rugged landscape is characterized by rocky cliffs and sparse vegetation, leading to a serene view of the river winding through the canyon.

4.97 out of 5 average rating, 518 reviews

Canyon House, Crooked River Ranch

FamilyKitchenAmenities

Family- and pet-friendly home rentals

4.9 out of 5 average rating, 294 reviews

A studio cabin is positioned on a deck overlooking a canyon, surrounded by native plants. Two wooden chairs are placed on the deck, providing a space to absorb the expansive mountain views in the distance. The structure features a large window reflecting the evening light.

Cabin in Culver

Cabin on The Rim

KitchenFamilyBarbecue

A cozy living area features a leather couch facing a propane stove, with a warm fire flickering. Two wooden stools are positioned at a small table, and a stack of magazines is displayed on a wooden coffee table. Natural light filters through the window.

4.96 out of 5 average rating, 736 reviews

"Little Pine Cabin" attached to my home.

KitchenFamilyOutdoor spaces

The living area features a brick fireplace as a focal point, surrounded by comfortable seating options. A coffee table sits in front of a couch with a soft throw. Natural light enters through large windows, and a door leads to the exterior.

4.87 out of 5 average rating, 507 reviews

The Little Red Chimney House - 3 BR 2 BA

FamilyKitchenPets

4.97 out of 5 average rating, 242 reviews

A small balcony is visible, featuring two woven chairs and a round blue table. Panoramic views of the surrounding landscape and distant trees can be seen, with clouds casting soft shadows over the scene and sunlight filtering through the open space.

Apartment in Redmond

Cascade View Suite · Balcony · Smith Rock

FamilyKitchenAccuracy

4.92 out of 5 average rating, 177 reviews

A cozy seating area is presented with a gray armchair beside a small white dining table. A decorative mirror and greenery adorn the wall, while sunlight filters through a nearby window, illuminating the space. A rug adds warmth to the wooden floor.

Cottage in Redmond

Blossom Cottage Studio

FamilyKitchenCheckout

A spacious living room features a comfortable sectional sofa with an ottoman, a decorative rug, and a large mirror. Natural light filters through the windows, which have blue curtains. An air conditioning unit and a small side table are visible, enhancing the room's functionality.

4.92 out of 5 average rating, 257 reviews

Spacious downtown pad - billiards/ping pong/sauna

KitchenFamilyBarbecue

A modern kitchen is showcased with a wooden countertop and several metal stools arranged in front. Open shelving holds dishware and kitchen essentials, while stainless steel appliances provide functionality. Large glass doors allow natural light to illuminate the space and offer views of the yard.

4.96 out of 5 average rating, 142 reviews

Dog friendly Home near parks and Dry Canyon

KitchenIndoor spacesAccess

4.94 out of 5 average rating, 183 reviews

A cozy living area features a gray sofa with colorful cushions, accompanied by a wooden table and a lamp. A large window allows natural light, partially covered by a light shade. A landscape painting adds a touch of color to the blue accent wall.

Guest suite in Redmond

Adams Corner, WiFi, courtyd w/games Sewist access

FamilyKitchenTV

Family-friendly home rentals with a pool

The exterior of the home displays a combination of dark blue siding and natural stone accents. A spacious front porch is featured, along with two garage doors and a wide paved driveway. The sloped roof adds to the home's structural interest.

4.84 out of 5 average rating, 129 reviews

Stunning mtn Views, sleeps 14, Hot tub, rec passes

Indoor spacesFamilyAccuracy

An outdoor deck features a long wooden bar top with counter stools, providing seating for guests. A spacious sectional sofa offers a comfortable area to relax. The landscape includes grassy areas and trees, with golf course views extending into the distance.

4.97 out of 5 average rating, 197 reviews

Knotty Pine Oasis on Eagle Crest Ridge Golf Course

FamilyIndoor spacesQuiet

4.99 out of 5 average rating, 139 reviews

A modern living room is highlighted by a large flat-screen TV and a stylish fireplace. Expansive windows provide views of the outdoors, allowing natural light to fill the space. Comfortable seating arrangements create an inviting area for relaxation.

Home in Sisters

Cozy Mountain Escape: Amazing Views! Hot tub!

FamilyKitchenLayout

The living area features leather sofas arranged around a stone fireplace, providing a cozy gathering space. An entertainment unit houses a flat-screen TV, while warm lighting enhances the wood accents. A decorative area rug adds texture to the carpeted floor.

4.9 out of 5 average rating, 191 reviews

Eagle Crest Luxury Chalet w/Private Hot Tub&Garage

FamilyIndoor spacesQuiet

4.93 out of 5 average rating, 112 reviews

Eagle Crest:9th Hole/Priv Hot Tub/Resort Amenities

KitchenFamilyRiver

4.95 out of 5 average rating, 78 reviews

The front entrance of a two-story townhome features a covered porch with a pitched roof, supported by wooden beams. Large windows invite natural light, while potted plants and shrubs enhance the landscape. The door is adorned with a modern design, emphasizing a welcoming entry.

Townhouse in Redmond

Kid friendly Eagle Crest townhome w/ Hottub

FamilyKitchenCleanliness

4.77 out of 5 average rating, 62 reviews

A well-appointed bedroom is furnished with a spacious bed, dressed in crisp white linens and a decorative blanket. Two framed floral artworks adorn the wall, and a soft bedside lamp provides gentle lighting, enhancing the room's serene ambiance.

Apartment in Redmond

Scenic Two-Bedroom Suite Near Redmond

Indoor spacesFamilyAir conditioning

The exterior of the chalet is showcased at dusk, featuring large triangular windows illuminated from within. A spacious deck is visible, surrounded by a metal railing and equipped with a seating area. Soft colors of twilight fill the sky, enhancing the welcoming atmosphere.