Family-friendly holiday rentals in Redmond

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

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!

FamilyKitchenBarbecue

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

FamilyKitchenBackyard

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.

KitchenFamilyAccuracy

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

West Ridge Eagle Crest Creekside Townhome near Lakeside sports center (sport court, pickleball courts, gym, pool, hot tub and kids splash park). Kid and Dog friendly. Fully furnished and stocked - includes coffee. Sleeps up to 6 (master -queen, 2nd bedroom queen and sofa bed queen) Equipped with A/C for hot summer days, fireplace and digital thermostat for cold days. Lockable storage for bikes-skis-snowboards etc. Easy access to Bend, Sisters, Smith Rock, Hoodoo, Mt. Bachelor and more.

KitchenIndoor spacesOutdoor spaces

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 spacesKitchenNearby

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.

Indoor spacesKitchenCheckout

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.

KitchenIndoor spacesBathroom

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

Wake up to a wide Cascade Mountain view from this quiet upstairs studio on the rimrock, minutes from town. Step onto your private balcony, then head out to Smith Rock. Keypad self check-in, then settle into a space with recliners, fast Wi-Fi for remote work, and a smart TV. A mini split keeps it cool in summer and warm in winter. Big windows and a large closet. Sleeps two, with a roll-away for a third on request, small extra fee. Well-behaved, house-trained dogs are welcome.

FamilyIndoor spacesBiking

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.

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.

FamilyKitchenHeating

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!

FamilyKitchenAccess

A fully stocked kitchen features a large island with two wooden stools. The cabinetry displays a blend of soft lavender and dark tones. Essential appliances, including a stove, microwave, and refrigerator, are neatly arranged. Bright light floods the space through a nearby window.

4.99 out of 5 average rating, 99 reviews

Canyon Cottage Downtown Redmond

Cozy 2-bedroom, 1-bath home in downtown Redmond, just steps from Dry Canyon and its parks and trails. The home features a fully stocked kitchen, perfect for cooking meals during your stay. Relax in the private backyard after a day of outdoor adventures. A short walk to downtown shops and restaurants, and a quick drive to the airport. Centrally located for all of Central Oregon’s outdoor activities, making it an ideal base for your adventure-filled getaway.

Indoor spacesFamilyWalkability

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 spacesFamilyAir 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

4.85 out of 5 average rating, 235 reviews

Guest suite in Redmond

Cozy, Light & Bright Private Guest Suite + Hot Tub

Indoor spacesKitchenPets

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, 177 reviews

3bdrm Chalet + Hot Tub in Eagle Crest

FamilyIndoor spacesCleanliness

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, 120 reviews

Creekside Escape at Eagle Crest Golf Resort

FamilyIndoor spacesSkiing

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, 304 reviews

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

Indoor spacesFamilyBathroom

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 spacesKitchenBathroom

4.97 out of 5 average rating, 355 reviews

Wow Holy Cow Chalet

KitchenFamilyBackyard

4.93 out of 5 average rating, 184 reviews

Smith Rock Oasis w/ Hot Tub Steps to the Park

FamilyIndoor spacesCheck-in

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, 517 reviews

Canyon House, Crooked River Ranch

Indoor spacesKitchenBreakfast

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, 256 reviews

Spacious downtown pad - billiards/ping pong/sauna

FamilyKitchenBackyard

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

KitchenIndoor spacesLaundry

4.85 out of 5 average rating, 379 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

FamilyKitchenAccuracy

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

KitchenFamilyHiking

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

FamilyKitchenAccuracy

4.85 out of 5 average rating, 290 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

FamilyKitchenBathroom

Superhost

4.77 out of 5 average rating, 158 reviews

Lovely county-fair getaway

Indoor spacesKitchenCondition

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

FamilyIndoor spacesBarbecue

Family-friendly home rentals with a pool

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

Indoor spacesKitchenView

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

Indoor spacesKitchenCheckout

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

Indoor spacesKitchenTV

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!

Indoor spacesKitchenCleanliness

4.97 out of 5 average rating, 192 reviews

An indoor pool room features a heated dipping pool, surrounded by vibrant red lounge chairs. A seating area is present with a couch and decorative pillows, while bright artwork adorns the walls. Sliding glass doors allow natural light and lead to the outside.

Home in Bend

Indoor Pool, Spa, Game Room, Pets Welcome!

FamilyKitchenLong stay

4.71 out of 5 average rating, 7 reviews

Sagewood at Eagle Crest | Hot Tub | Golf

Indoor spacesFamilySleep quality

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

FamilyIndoor spacesSleep quality

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.