Family-friendly vacation rentals in Sisters

4.98 out of 5 average rating, 188 reviews

A charming cottage exterior is depicted, featuring a white picket fence and a welcoming covered porch. Lush green grass surrounds the house, complemented by tall trees in the background. A hanging plant basket adds a touch of greenery, enhancing the inviting entrance.

Cottage in Sisters

Minutes walk Downtown/Cozy Cottage Retreat/Sauna.

Imagine yourself surrounded by majestic old-growth ponderosa pine and juniper trees, where the gentle murmur of Whychus Creek is in the distance, all while being just a short stroll from the vibrant heart of downtown Sisters. Embrace the tranquility as you explore an array of delightful restaurants, local festivals, and enjoy nearby parks, as well as endless hiking and biking trailheads, the Creekside campground, all within moments’ reach. Minutes’ drive to Hoodoo Mountain, Blackbutte, Aspen

4.99 out of 5 average rating, 137 reviews

A spacious living area features a sectional sofa in neutral tones, accompanied by a soft area rug. A stone fireplace adds warmth, while large glass doors open to a private balcony with outdoor seating. Natural light fills the room, enhancing the inviting ambiance.

Condo in Sisters

Beautiful Sisters Condo - Great location

Great location! Remodeled 2 bedroom and 2 bath condo is a spacious retreat set within the pine trees. The complex includes a seasonal pool. The hot tub/sauna are open year round. The club house includes ping pong, foosball and a pool table. You just need to walk through the city park and across the creek to get into town. We are also located a block or two from the MovieHouse and Three Creeks Brewing. Enjoy bike paths close by and lots of hiking in the area. Easy self check-in and out.

The cabin is nestled among tall trees, featuring a green exterior with a welcoming entrance. The front yard showcases natural grass and scattered pine needles, leading to a spacious driveway with a two-car garage on the right. Large windows provide an inviting view into the cabin.

4.94 out of 5 average rating, 122 reviews

Cozy family cabin in the tall pines of Tollgate.

Relax with the family at this peaceful well appointed sapcious cabin. 'Your Sisters Cabin' is located 3 miles from Downtown Sisters, 20 minutes to Hoodoo ski area and 10 minutes from Black Butte Ranch. We've geared the spaces towards fun and relaxation for the whole family! Well curated amenities will help your family enjoy all that the Sisters area has to offer. From an easy to use propane fireplace to a beautiful fenced backyard, fully stocked kitchen, comfy beds and kid friendly amenities!

4.99 out of 5 average rating, 539 reviews

A charming tiny log cabin is nestled amidst tall evergreen trees, gently blanketed in snow. The cabin's sloped roof is thick with snow, creating a cozy appearance. A path through the white snow leads toward the cabin's entrance, inviting exploration in a serene winter landscape.

Cabin in Bend

Skyliners Getaway

Our tiny log cabin is a cozy getaway, close to hiking, mountain biking, and cross country skiing but only 10 miles from the amenities of Bend Oregon. It is a rustic place, with modern touches, like a gas range, refrigerator, and a gas fireplace. The bathroom is detached from the cabin - steps from the door. It is fully equipped with plumbing and a shower. Our place is perfect for people who love the outdoors with the comforts of home. No children under the age of 12 -- And alas, No Pets.

4.97 out of 5 average rating, 342 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.

An open-plan living space features a wooden dining table surrounded by white chairs, complemented by a decorative plant in a pot. Natural light filters through a skylight and windows, enhancing the wooden beams and soft color palette of the room.

5 out of 5 average rating, 154 reviews

Modern Mountain Cabin Close to Town (HOT TUB!)

Come enjoy this beautiful home filled with tons of natural light, skylights, a cozy fireplace and a highly functional open floor plan. The backyard features a newly built deck and outdoor dining, BBQ, patio loungers, fire pit and HOT TUB! All the benefits of a quiet neighborhood while being just a 5 - 10 minute walk from the heart of downtown Sisters and a short drive to endless hikes and running trails, beautiful lakes and rivers, skiing, rock climbing, mountain biking and so much more.

The cabin features a welcoming entrance with a wood deck and rustic details. Framed by green trees, the two-story structure showcases a steep gabled roof and large windows, providing a warm and inviting sight. A path leads to the entrance, surrounded by low shrubs.

4.96 out of 5 average rating, 151 reviews

Pet + kid friendly w/ private hot tub!

Relax with the whole family at this peaceful cabin in Sisters! Take a short drive into downtown Sisters or ride bikes into town via neighborhood trails to do some shopping or explore the nearby lakes, rivers and mountains. Or stay in! Enjoy happy hour on the roof top deck, unwind in the steamy hot tub, cook dinner in the fully equipped kitchen, or have a BBQ on the outdoor patio! This is the perfect place to experience all Sisters has to offer! Just the getaway you've been waiting for!

4.93 out of 5 average rating, 129 reviews

Home in Sisters

Modern Tollgate Home - HOT TUB | Half Acre Lot

This newly renovated 3 bedroom/2 bathroom home sits on more than a half acre lot in the quaint town of Sisters. When you stay at this Tollgate home you get all of the community amenities with it: community pool, pickle-ball/tennis courts, walking trails, basketball courts, etc. Bring the whole family as we comfortably sleep 6 people and enjoy the hot tub! This is an incredibly well-done high-end modern home that is virtually brand new. We are also a dog friendly home ($100/stay fee).

Superhost

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

4.84 out of 5 average rating, 249 reviews

IT'S A WEE HOUSE

Quiet, serene, warm and cozy. Relax in this cute little pet friendly WeeHouse with a wee loft. Located in the heart of Central Oregon just minutes from downtown Bend and the Redmond airport. You'll enjoy countryside views of Smith Rock and the valley below. Bask under 1000 year old Juniper trees. High Speed wifi, private bathroom and kitchenette. If this doesn't feel like a fit or is unavailable please check out our other options: "The Sunset Bungalow" and "The Sunrise Studio"

4.92 out of 5 average rating, 140 reviews

The exterior of the condo features a welcoming entrance, framed by vibrant landscaping. A covered porch with seating is visible, alongside manicured shrubs and decorative plants. Bright sunlight highlights the facade, creating an inviting atmosphere.

Condo in Sisters

Views! 1 Blk to Town,New+Spotless, pets ok- South

Prime safe Sister's upscale neighborhood! Newly built condo offers EVERYTHING you expect without sacrificing a thing! Perfect INTERNET/WI-Fi and ONLY 1 BLOCK to downtown, restaurants, shopping. Leave your car at the unit and walk! Nice kitchen, king size bed in master, new queen size sofa/sleeper in living room! Relax on sofa or recliner w/ EXCELLENT Wi-FI, internet, cable, Netflix. Washer and dryer too! $35.00 pet fee PER pet under 40 lbs for the stay, Limit 2 pets.

4.98 out of 5 average rating, 283 reviews

A modern studio features a spacious bed with crisp white linens, a wooden accent wall, and an electric fireplace below a wall-mounted television. A unique wood table sits atop an area rug, with plants adding a touch of greenery to the warm atmosphere.

Condo in Bend

Sunriver Studio with Pool and Hot Tub

This stylish studio in the heart of Sunriver is newly remodeled with a King bed. Seasonal pool and year round Hot Tub! Just a short walk to a brand new food truck lot with 7 trucks, indoor and outdoor seating and a bar. Fast WiFi, a new Samsung 50” tv signed into Netflix, Hulu, HBO Max and more. 25 minutes to Mt. Bachelor. 25 minutes to downtown Bend. Parking is just a few feet from your door. This super clean condo is perfect for all of your central Oregon adventures.

4.96 out of 5 average rating, 154 reviews

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.

Chalet in Redmond

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!

Popular amenities for Sisters family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 316 reviews

A cozy living area features a comfortable gray sofa with colorful cushions and a wooden coffee table. Natural light fills the space through large windows, highlighting warm wooden accents. A flat-screen TV and bookshelf are positioned against the wall, offering convenience for relaxation and entertainment.

Guest suite in Bend

Private Apartment, Separate Entrance, Spacious

4.98 out of 5 average rating, 945 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

4.95 out of 5 average rating, 112 reviews

An illuminated hot tub with turquoise water sits in the foreground, surrounded by trees. Warm string lights hang above, casting a soft glow over the outdoor seating area, which includes two chairs and a table, creating a cozy atmosphere for relaxation.

Home in Sisters

XL Hot Tub, Dog Friendly, EV Charger, Fenced Yard

4.93 out of 5 average rating, 221 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

4.97 out of 5 average rating, 337 reviews

Chalet in Redmond

Wow Holy Cow Chalet

Guest suite in Powell Butte

Two Adirondack chairs are positioned on a patio, facing a stunning sunset over distant mountains. A small table is located between the chairs, accompanied by a flower pot. The sky is painted with hues of pink, orange, and purple, creating a serene atmosphere.

4.96 out of 5 average rating, 239 reviews

Panoramic Mountain View Oasis

4.85 out of 5 average rating, 117 reviews

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.

Home in Redmond

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

The living area features a spacious layout with a cozy seating arrangement, including a large armchair and a round ottoman. A wood-burning stove is positioned for warmth. The kitchen is visible, showcasing modern appliances and stylish wooden cabinetry, fostering a homey ambiance.

4.99 out of 5 average rating, 145 reviews

Ranch Cabin-2pm Check-In & no resort fees-Sleeps 4

Family- and pet-friendly home rentals

4.98 out of 5 average rating, 213 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

Mountain View Suite near Smith Rock + Airport

4.92 out of 5 average rating, 130 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

4.94 out of 5 average rating, 160 reviews

A spacious living area is presented, featuring a large sectional couch and a leather ottoman. A wall-mounted television displays a scenic view. The dining area is visible in the background, showcasing a round light fixture above a table with four chairs. Light-colored walls enhance the bright atmosphere.

Townhouse in Larkspur

Bend Base-camp! Near river, mts, shops, fun stuff!

Superhost

A spacious living area features a wooden ceiling and tiled flooring. Comfortable seating options include a couch and armchair. A patterned rug adds color, and a coffee table sits centrally. The dining area and kitchen are visible in the background, with a staircase leading to the upper level.

Farm stay in Sisters

4.82 out of 5 average rating, 155 reviews

The Casa at the Red Barn Farm

4.97 out of 5 average rating, 115 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

5 out of 5 average rating, 118 reviews

A cozy bedroom features a spacious bed with a colorful blanket, complemented by wooden accent walls. A wall-mounted flat-screen TV is above a modern electric fireplace. A small table with two chairs is positioned nearby, with a mirror framed in green accentuating the space.

Guest suite in Bend

Sixties Suite Spot

4.94 out of 5 average rating, 375 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 River West

Adorable West Side Cottage, Pet Friendly!

4.9 out of 5 average rating, 295 reviews

An A-frame interior features warm wooden paneling, with a cozy seating area highlighted by a stylish armchair and a television unit. The open door reveals a view of the outdoor pathway, surrounded by greenery, bringing natural light into the space.

Tiny home in Bend

Rajneesh Aframe/Hot Tub, 10 min from downtown Bend

Family-friendly home rentals with a pool

4.86 out of 5 average rating, 257 reviews

The room features a queen bed with a light-colored bedspread, accompanied by bedside tables with lamps. A cozy seating area with cushions is beside a large window, allowing natural light to illuminate the space. Artworks are displayed on the walls, enhancing the serene atmosphere.

Guest suite in Bend

Mt Bachelor Village Resort- Room in River Ridge II

The exterior of the Cozy Hideaway features a red cabin with a covered deck supported by wooden beams. A hammock is seen on the deck beside a hot tub, surrounded by a natural landscape of pines and grassy areas.

4.93 out of 5 average rating, 158 reviews

Cozy Hideaway w/outdoor living and hot tub!

4.9 out of 5 average rating, 145 reviews

A comfortable living area showcases a cozy sofa and a well-lit dining space with a light-colored table surrounded by colorful chairs. Natural light filters through the windows, illuminating the modern vinyl flooring and the stylish decor elements, including a wall-mounted TV above a decorative fireplace.

Condo in Bend

Adorable Studio at Seventh Mountain Resort

4.98 out of 5 average rating, 106 reviews

A spacious kitchen features modern appliances and a large island with seating. Sleek cabinetry complements the countertops, while pendant lighting adds subtle illumination. Natural light flows in through nearby windows, with views of the surrounding greenery visible outside. A dining area is located adjacent to the kitchen.

Home in Sunriver

On Golf Course, Walk to Park, Hot tub, SHARC

4.94 out of 5 average rating, 264 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

4.98 out of 5 average rating, 127 reviews

A spacious living area is furnished with a gray sectional sofa and a decorative coffee table, enhancing comfort and relaxation. A television is mounted on the stone fireplace wall, while an adjacent dining area features a round table with seating for four. Natural light floods through large windows.

Condo in Sunriver

Beautiful Condo in SR Village

4.92 out of 5 average rating, 132 reviews

A modern home is surrounded by snow-covered trees, showcasing large windows that reflect natural light. The wooden exterior complements the winter landscape, while steps lead from the porch to the yard blanketed in fresh snow.

Home in Sisters

Black Butte Ranch Home with THE View