Family-friendly vacation rentals in Redmond

4.98 out of 5 average rating, 979 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 spacesWalkability

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

Book your stay today and experience all the comforts of home, with the added bonus of a fantastic location within walking distance to local parks. Located in a quiet neighborhood, it provides a peaceful and tranquil atmosphere. Enjoy a large fenced yard with mature trees, perfect for barbecues and outdoor activities or star gazing in the hammock. The beginning of Dry Canyon trail is only a mile away for walking, running or taking the family for a bike ride. Close to local businesses and dining.

KitchenFamilyParking

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

KitchenIndoor spacesDecor

4.84 out of 5 average rating, 707 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.

Indoor spacesKitchenValue

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!

FamilyKitchenCondition

4.97 out of 5 average rating, 390 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.

FamilyKitchenBiking

4.98 out of 5 average rating, 438 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.

KitchenFamilyCheck-in

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

Take it easy at this unique and private getaway. This off the grid studio cabin is located just 10 minutes from Smith Rock and 10 minutes from Lake Billy Chinook. It is positioned on the edge of the Crooked River Gorge with breathtaking views of the canyon. Near the cabin is a trail head to a private hiking trail that takes the adventurer down into the canyon where the scenery is otherworldly. Enjoy a sunset with full cascade Mountain View’s, green pastures, and grazing horses.

KitchenFamilyComfort

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, 735 reviews

"Little Pine Cabin" attached to my home.

MASTER SUITE Go hiking, fishing, sight seeing and enjoy upscale steak houses, Sushi Bars, food carts, all within a couple of miles. Then come back to your Little Pine Cabin. Enter into a comfortable living area with a vaulted knotty pine ceiling, propane stove, a dual reclining leather couch. Relax in front of the 42 inch flat screen, a well stocked coffee bar, microwave and a mini-fridge. Similar to a studio apartment. You will enjoy the space and quiet neighborhood.

FamilyIndoor spacesCheckout

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!

FamilyKitchenComfort

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!

Welcome to our Chalet in the Eagle Crest Resort! You are guaranteed to feel like you are on vacation the minute you walk in. This 3 bedroom + loft can sleep 8 guests and comes with washer/dryer, WiFi, and desks in the loft. Relax in the space indoors or out, with the outdoor patio, hot tub, BBQ, and golf course views. There is so much to see and do on the resort property or you can grab a blanket, sit by the fire and do absolutely nothing at all!

Indoor spacesFamilyLocation

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 spacesLong stay

Popular amenities for Redmond family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.85 out of 5 average rating, 234 reviews

Guest suite in Redmond

Cozy, Light & Bright Private Guest Suite + Hot Tub

FamilyKitchenAir conditioning

Superhost

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, 176 reviews

3bdrm Chalet + Hot Tub in Eagle Crest

Indoor spacesFamilyAmenities

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

KitchenFamilyRiver

A cozy living area features large windows with sheer curtains allowing natural light. A stack stone gas fireplace serves as a focal point beside a TV unit. Comfortable seating options include a pair of sofas and a rustic dining table adorned with greenery.

4.94 out of 5 average rating, 119 reviews

Creekside Escape at Eagle Crest Golf Resort

FamilyIndoor spacesSleep quality

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.

4.96 out of 5 average rating, 137 reviews

Eagle Crest townhome Dog friendly-sleeps up to 6

KitchenIndoor spacesView

A shaded deck area features a striped umbrella over a black dining table with four chairs. A private hot tub is positioned to one side, and expansive views of green fairways and tall trees are visible in the background.

4.88 out of 5 average rating, 303 reviews

Eagle Crest-w/private hot tub/Resort passes!

FamilyIndoor spacesValue

4.97 out of 5 average rating, 355 reviews

Wow Holy Cow Chalet

FamilyKitchenGrill

4.93 out of 5 average rating, 183 reviews

Home in Terrebonne

Smith Rock Oasis w/ Hot Tub Steps to the Park

Indoor spacesFamilyHiking

Family- and pet-friendly home rentals

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, 255 reviews

Spacious downtown pad - billiards/ping pong/sauna

FamilyIndoor spacesParking

4.97 out of 5 average rating, 241 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

Indoor spacesKitchenCondition

4.91 out of 5 average rating, 175 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

FamilyIndoor spacesAccess

4.97 out of 5 average rating, 237 reviews

Home in Bend

Butler Corner - New, Clean & Minutes From Downtown

Indoor spacesFamilySleep quality

4.85 out of 5 average rating, 378 reviews

A modern living area features a spacious gray couch and a dining table with white chairs. A vibrant abstract painting adds color to the wall, while a fully equipped kitchenette is visible in the background with blue cabinetry and natural light streaming through large windows.

Tiny home in Bend

The Big Tiny

Indoor spacesFamilyCleanliness

4.8 out of 5 average rating, 237 reviews

Luxurious 5 bedroom w pool table

Indoor spacesKitchenNearby

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

Indoor spacesFamilyWalkability

4.85 out of 5 average rating, 289 reviews

A colorful hammock is suspended from a snow-covered tree, inviting relaxation. The quaint WeeHouse, featuring large windows and a bright yellow door, is partly obscured by the snow. A serene winter landscape surrounds the property, showcasing the tranquility of the setting.

Tiny home in Bend

IT'S A WEE HOUSE

KitchenFamilyCheck-in

Family-friendly home rentals with a pool

4.92 out of 5 average rating, 25 reviews

An open concept living area features a striking stone fireplace and a grand piano. Large floor-to-ceiling windows provide expansive views of the outdoors. Wood accents and vaulted ceilings enhance the space, while a cozy leather sofa and area rug invite relaxation.

Villa in Redmond

Cascade Lookout

KitchenIndoor spacesWalkability

A spacious living area is enhanced by large windows allowing natural light to fill the room. A comfortable sectional sofa is complemented by accent pillows. A dining table for six stands nearby, while the cozy fireplace and wall-mounted TV add a modern touch.

4.89 out of 5 average rating, 106 reviews

3 Kings on the 12th Green! Large resort home

FamilyKitchenHiking

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

KitchenFamilyCleanliness

An indoor pool area is featured, featuring a modern curved pool with clear water. Natural stone walls create a warm ambiance, while soft lighting from hanging globes enhances the space. A waterslide adds a playful element, making it an inviting area for family enjoyment.

4.88 out of 5 average rating, 68 reviews

Timber & Springs Retreat: Indoor Pool and Hot Tub

KitchenFamilyCheck-in

A modern two-story home is nestled among trees, showcasing a blend of textures in its exterior design. Soft evening light casts a warm glow on the entrance, while a colorful sunset enhances the tranquil setting. A paved driveway leads to the garage.

5 out of 5 average rating, 66 reviews

Luxury Home- On the Golf Course w/ Private Hot Tub

KitchenIndoor spacesLayout

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

Indoor spacesKitchenTV

The exterior of a spacious townhome is presented, featuring well-maintained landscaping with vibrant green grass and mature trees. A welcoming front porch is visible, framed by lush foliage, and a curved pathway leads to the entrance, enhancing the overall inviting appearance.

5 out of 5 average rating, 24 reviews

Central Oregon Escape

KitchenIndoor spacesCleanliness

Superhost

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.