Holiday rentals with outdoor seating 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, 218 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.

A charming cottage is featured with a sandy pathway leading to the front porch. Lush green trees and manicured shrubs surround the home, while natural stone accents are visible in the landscaping. The inviting exterior showcases a well-maintained facade under a clear blue sky.

4.87 out of 5 average rating, 157 reviews

Cottage in Bend: Walk Everywhere

COTTAGE IN BEND: Cozy 1920’s, one bedroom, one bathroom cottage with a large private yard-blocks from the river and downtown Bend. Enjoy your own space on a large lot-not an ADU. Walk to the market for groceries and coffee on Newport Ave. During your stay walk 3 blocks to the pedestrian footbridge crossing the Deschutes River and into Drake Park and downtown Bend, The Union house is just a block away from Newport Avenue and Newport Market. It is also 3-4 blocks from many restaurants and coffee

A welcoming living area features a stone fireplace with a wooden mantel and decorative antlers mounted above. The textured ceiling adds warmth, while large windows allow natural light. A plush gray sofa and armchair are arranged around a coffee table, creating a cozy space for relaxation.

4.88 out of 5 average rating, 368 reviews

House on the Hill in Bends River West Sleeps 8!

Private Westside Location! Dog friendly! Bends Best location! Available for monthly and long-term stays, just ask! Gorgeous private four bedrooms, three full baths!Private Hot Tub. Luxury open floor plan and deck. A minute to Newport Market and restaurants. A spacious gourmet open kitchen, a wrap-around bar that opens to the living room, fireplace, and dining room, perfect for entertaining your guests. Extra family room with ping pong table. Comfy beds and pillows! Close Mt.Bachelor Ski Resort.

4.92 out of 5 average rating, 405 reviews

A welcoming green house with a sloped roof is surrounded by tall pine trees. A front porch with wooden steps leads to the entrance. A gravel path and a seating area can be seen in the front yard, enhancing the outdoor space.

Bungalow in Bend

Westside Bend Adventure Cottage-Walk Bike Hike Ski

This comfortable 3 Bedroom/2 Bath home in the Heart of Bend`s trendy Westside is centrally located and yet on a quiet street. Just blocks from restaurants and breweries and a quick walk to downtown. Enjoy a gourmet kitchen, large master suite, and washer and dryer. Newer whole house air conditioning and heating system. The kitchen will have new granite countertops and the two bathrooms are being remodeled in March and April 2026. New photos will be updated in April 2026. It's going to be nice!

5 out of 5 average rating, 127 reviews

An inviting hot tub is positioned alongside a sauna grotto, both nestled within a natural setting. The hot tub features clear water with soft illumination, while the sauna's wooden exterior is accentuated by warm light. Surrounding trees and rocks enhance the tranquil atmosphere.

Bungalow in Bend

River Run Bend Bungalow & Romantic Spa Grotto

**NEWLY INSTALLED! ** Spa & sauna grotto is all ready for your romantic Bend getaway! This quiet, wooded, centrally located, standalone bungalow is steps from the Deschutes River trail, easy walking distance to Mill Dist. and Hayden Amphitheater. It boasts a comfy king bed w/premium down bedding & pillows, dedicated free parking (+ extra cars or small RVs), outdoor dining and patio area, washer/dryer, and a kitchen fully stocked with everything you need for fun and relaxation for all seasons!

4.94 out of 5 average rating, 527 reviews

Dome in Tetherow

Welcome to Dome Sweet Dome

Your chance to stay in a true-to-name Geodesic Dome! This one-of-a-kind retreat blends comfort with architectural charm. Guests call it cozy, inspiring, and unforgettable — a stay that feels like an experience, not just a place to sleep. Nestled in the First-on-the-Hill neighborhood off Century Drive, the Dome is perfectly positioned for everything Bend has to offer. Whether you’re here for skiing, biking, hiking, or just relaxing, you’ll love how close you are to Bend’s best adventures.

The exterior of the two-story cabin features a charming combination of wood and siding. A welcoming porch with seating is visible, framed by manicured landscaping. Above, a private balcony invites relaxation, showcasing the property’s connection to the surrounding natural beauty.

5 out of 5 average rating, 288 reviews

Mountain Bliss: Gateway to Mt. Bachelor and More

When the mountains are calling, Bend is like nothing on earth. Savor the charms of Base Camp throughout the year in this luxurious and spacious cabin (1200 square feet). Celebrate the great outdoors – best experienced through unparalleled adventures at Mt. Bachelor (18 miles), Phil’s trailhead (15 minutes), the Deschutes River (5 minutes) as well as the endless access to hiking, biking, running trails, skiing, golf, breweries, restaurants, coffee shops, and the Hayden Homes Amphitheater.

4.98 out of 5 average rating, 238 reviews

A hot tub is positioned on a wooden deck, surrounded by tall greenery for privacy. The house features large sliding doors leading to an open space, with outdoor seating visible nearby, creating a relaxed outdoor retreat.

Bungalow in Bend

Ski, Bike, and Golf from a Spacious Family Bungalow

Mountain Bird Bungalow offers something for everyone with an open kitchen-dining area, intimate living spaces, and a cozy fireplace. Mountain Bird Bungalow is the perfect location to enjoy the beautiful nature of Bend, or within a short distance from the downtown area, with its shopping and dining. Garage parking is provided. If your trip involves remote work, you are covered with a dedicated work space and very fast Wi-Fi. Two bedrooms and two full bathrooms make for a comfortable stay.

4.85 out of 5 average rating, 361 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

Reset and rejuvenate at the Big Tiny. Our thoughtfully designed, unique tiny house is fully equipped for your comfort and is surrounded with gorgeous desert views, and is also pet friendly. Conveniently located just 15 mins from downtown Bend. Enjoy all that Central Oregon has to offer. Start your days sipping coffee in the front yard while drinking in the fresh air. Relax after a day of adventure under the starry sky with a local beer or glass of wine next to the propane fire pit.

4.98 out of 5 average rating, 241 reviews

A bright living area features a light-colored sofa draped with yellow and gray cushions. Two stylish chairs provide additional seating, while a central wooden table holds decorative items. Natural light filters through sheer white curtains, illuminating plants and a patterned rug on the hardwood floor.

Apartment in Larkspur

Villa77: Renovated Stay Near Downtown & Old Mill

Newly renovated and thoughtfully designed, our airy apartment in Bend’s Midtown offers a 5-star experience. Enjoy crisp linens, plush towels, and fresh-ground local coffee brewed just the way you like it. Perfectly located near Downtown, the Old Mill District, and Bend’s best shops and eateries, our apartment is a cozy and stylish retreat. After a day of adventure, unwind in comfort at this charming home base! Owned by locals, this is the perfect launch pad for your Bend adventures!

A modern living room features large windows that provide views of the outdoors. A gray sectional sofa and a bright orange chair are arranged around a light area rug. A wooden coffee table is positioned nearby, and a TV is mounted on the wall. A stove adds a touch of warmth to the space.

4.99 out of 5 average rating, 194 reviews

Modern high-end home, walk downtown

This fantastic modern home is in the sweet spot of Bend...just next door to the Deschutes River, Downtown Bend, parks, restaurants and dining, nightlife, and family-friendly activities. You'll love our home because of the amazing location, the mid-century inspired ambiance, the high ceilings, the people, and the local views. We are the perfect centrally located home for any Bend adventure. Our place is great for couples and solo adventurers. This is not a party house. Sorry no pets.

Cottage in Orchard District

A modern kitchen is equipped with wooden cabinetry, stainless steel appliances, and a decorative counter space. The kitchen features a gas oven and microwave, alongside a coffee maker. Natural light enters through a nearby window with wooden blinds, and a vase of colorful flowers adds a cheerful touch.

4.99 out of 5 average rating, 141 reviews

Blue Spruce Cottage, 2/1, Modern, & Clean.

This cottage is located in the heart of Midtown - 20 mIn walk downtown & walking minutes from great food/beer/coffee. You will enjoy a very quiet, newer home, with air conditioning & 2 KING tempurpedic beds, tucked under mature Spruce trees. For active guests a hose is available to wash bikes, washer/drier and indoor racks to dry your clothing. A full kitchen and BBQ for meal prep. Garage is secure and available UPON REQUEST. Lastly, wireless internet is super fast, 300mbs.

Popular amenities for Bend outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

4.97 out of 5 average rating, 267 reviews

Home in Orchard District

Cozy 2Bd Duplex Family, Dog Fenced yard, fire pit

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, 130 reviews

SAGE HAVEN* Hot tub* Mountain Views* Sleeps 8

The kitchen features a spacious island with seating for six and modern appliances. Ample cabinetry is present, complemented by glass shelves displaying colorful dishware. Natural light streams in through large windows, highlighting the warm tones of the wood and the polished concrete floors.

4.91 out of 5 average rating, 136 reviews

Luxury Modern on Newport | Walk | Dog Friendly

4.98 out of 5 average rating, 952 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

4.98 out of 5 average rating, 313 reviews

Home in Orchard District

Have a Patio Barbecue at a Pet-Friendly House in Midtown

A deer stands gracefully in a lush green lawn, surrounded by mature trees and colorful foliage. The animal is captured mid-stride, with its antlers prominently displayed, showcasing the serene natural environment that enhances the outdoor experience of the property.

4.96 out of 5 average rating, 167 reviews

Theater Room w/Movies, Netflix, Amazon Prime

The exterior of a modern home is framed by blooming trees and shrubs, showcasing a gray exterior with large windows. A decorative pathway leads to the entrance, which features a covered porch. The driveway is spacious, providing easy access.

4.98 out of 5 average rating, 583 reviews

Home in Lodges at Bachelor View - Book Now!

The exterior of the home features a two-story structure with warm wooden siding, surrounded by lush greenery and mature trees. A balcony extends from the upper level, and a vibrant red-leafed tree adds color to the landscape. A stone wall borders the property.

4.99 out of 5 average rating, 117 reviews

Drake Park Walk Everywhere Ski Wk Nt Special 250!

Apartment rentals with outdoor seating

4.98 out of 5 average rating, 214 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

Apartment in Orchard District

A spacious living room is featured with a gas fireplace and a large-screen TV, complemented by a pull-out sofa. Large windows allow natural light to fill the room, while bar seating is available at the open kitchen, creating an inviting atmosphere for relaxation or gatherings.

4.96 out of 5 average rating, 317 reviews

Midtown Gem With Cozy Fire and Park Views

4.97 out of 5 average rating, 551 reviews

A spacious outdoor deck is furnished with two Adirondack chairs facing a circular fire pit. A panoramic view of distant mountains and valleys is framed by a railing, showcasing the landscape under clear blue skies.

Apartment in Redmond

Smith Rock Contemporary

A modern living area showcases a comfortable dark sofa alongside a bright orange armchair. A wooden coffee table is positioned in front, with a small plant and speaker on top. A dining table with four chairs is visible in the background, and a fireplace adds warmth to the space.

4.93 out of 5 average rating, 105 reviews

Modern Condo~Fireplace~Walk to Old Mill & River

An inviting living area showcases a gray sofa paired with a patterned area rug. A wooden dining table with two chairs occupies one corner. Natural light is offered through two windows, enhancing the warm color scheme of the walls.

4.96 out of 5 average rating, 535 reviews

Riverside loft closest to amphitheater, rapids

A cozy living area is furnished with a leather couch and wooden chairs, accented by a glass coffee table. Natural light fills the space through the large window with blinds, highlighting potted plants and decor on the side table.

4.93 out of 5 average rating, 460 reviews

Private Spacious Studio Apartment

4.94 out of 5 average rating, 181 reviews

A comfortable living area features a bright red sofa and an additional lounge chair. Natural light filters through large windows, highlighting the neutral wall colors and carpeting. A television is positioned on a sturdy stand, while a small dining table is visible in a corner.

Apartment in Sisters

Apartment in Sisters, OR. USA

The living room area features a red leather sofa and a small wooden coffee table, situated on a richly patterned area rug. A staircase with wooden railings leads to the upper loft. Natural light enters through windows positioned above, illuminating the space.

4.95 out of 5 average rating, 934 reviews

The Garden Apt-Hot Tub Fireplace AC 250+ Mbps

Condo rentals with outdoor seating

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.

4.98 out of 5 average rating, 291 reviews

Sunriver Studio with Pool and Hot Tub

4.91 out of 5 average rating, 115 reviews

An open living area is depicted with a large gray sectional sofa facing a wooden coffee table. Natural light enters through skylights and windows, illuminating the dining area equipped with a wooden table and chairs. The warm wood accents enhance the cozy feel of the space.

Condo in Sunriver

Spacious 2 bedroom Sunriver condo + 6 SHARC passes

The fully equipped kitchen features granite countertops and wooden cabinetry. Large windows allow natural light to fill the space, providing views of the surrounding forest. The kitchen area includes modern appliances, a kitchen island with seating, and overhead lighting for an inviting cooking environment.

4.86 out of 5 average rating, 297 reviews

Mt. Bachelor Village Condo - Near Town & River

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.

4.98 out of 5 average rating, 130 reviews

Pool, AC, close to Amphitheater & Old Mill

4.94 out of 5 average rating, 119 reviews

Adventure Awaits! Walk to downtown and river!

Condo in Seventh Mountain

A spacious living area features a comfortable grey sectional sofa and a wooden coffee table. Large windows provide natural light and showcase views of surrounding trees and mountains. A circular mirror is mounted on the wall, enhancing the sense of openness in the room.

4.95 out of 5 average rating, 101 reviews

Modern 3-bedroom Seventh Mountain Resort Condo

4.91 out of 5 average rating, 151 reviews

The living area features high vaulted ceilings with wooden beams and large windows allowing natural light to fill the space. A stone fireplace is the focal point, surrounded by comfortable leather seating and a centerpiece table. Colorful accents offer a pop of vibrancy to the neutral decor.

Condo in Sunriver

Short walk to SR Village and SHARC, includes bikes

A modern living space is presented with a comfortable gray sofa and a matching armchair. A circular table with decorative elements is set nearby. Natural light enters through large sliding glass doors, offering views of trees outside. A dining area with black folding chairs is visible in the background.