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, 230 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.

4.9 out of 5 average rating, 356 reviews

The exterior of the cottage is shown with a charming deck and two white chairs positioned under string lights. A well-maintained path leads through lush greenery and stone steps to the entrance, highlighting the inviting atmosphere of the cottage.

Cottage in Bend

The Blackberry Cottage

This adorable 1950's cottage is located in the heart of Midtown Bend, within walking distance to local coffee shops, restaurants, parks and Pilot Butte State Park, and less than a mile away from downtown Bend. Two light-filled bedrooms both have double French doors leading out to a large back deck and a fenced, private backyard. A cozy living room, and eat in kitchen make this home the perfect place for a small family or a few friends to share. Serene fenced back yard space with hot tub.

5 out of 5 average rating, 146 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!

4.98 out of 5 average rating, 179 reviews

The bedroom features a spacious bed with white linens, complemented by two bedside tables with lamps. A green bench sits at the foot of the bed, while a landscape painting hangs above the headboard. Soft curtains frame a window, allowing natural light to fill the space.

Guest house in Bend

NEW Tranquil Retreat On Canal

Charming, clean, comfortable, fully renovated guest house on 3 acres, nestled by a canal. A quiet escape near Pine Nursery Park, just 5 miles from downtown and less than 20 minutes from the airport. Enjoy beautiful natural light, vaulted ceilings, large bathtub, and balcony with outdoor seating and a beautiful view. Fully stocked kitchen, washer & dryer, heat & AC, blackout shades, board games, books, amenities for kids, smart TV, and a Blu-ray player for rentals from The Last Blockbuster.

4.98 out of 5 average rating, 242 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.

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, 203 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.

A spacious living room features a light-colored sectional sofa positioned around a glass coffee table. Large windows invite natural light, revealing a view of the outdoors. A stone fireplace provides a warm focal point, complemented by a cozy armchair and decorative elements throughout.

4.99 out of 5 average rating, 205 reviews

Airy Bend Oasis - Two Ensuites

Cheers to your stay at Bent Pine Oasis, located in the picturesque west side of Bend! This home provides the ideal location for any outdoor enthusiast: Mt Bachelor's slopes are just a 20 minute drive & the Deschutes River Trail is mere steps from the front door- your avenue to biking, running and exploring Bend. Looking for a more relaxing day? You can make the 5 minute drive into the Old Mill District to enjoy food trucks, a river float, or fresh hops at a local brewery.

A modern mid-century ranch home is showcased from the exterior, featuring a combination of large windows and contemporary architectural elements. Surrounding landscaping includes trees and shrubs, creating a natural buffer. A clear driveway leads to a two-car garage, adding convenient access to the property.

4.98 out of 5 average rating, 137 reviews

Mid Century West side home-walk everywhere

Newly built mid century ranch has 2 bedrooms/2 bathrooms with a king sized hide-a-bed in the large living area. Home is 4 blocks from Newport Market and a 10-15 minute walk into downtown Bend. Just walk a couple of blocks down the hill and you'll be on Newport Ave, where you can enjoy many of Bend's west side favorite restaurants and coffee shops. This architectural home features an open floor plan with high ceilings, towering windows and quality finishes throughout.

A modern kitchen space features a large island with three stools, complemented by sleek cabinetry and stainless steel appliances. Natural light floods in through nearby windows, illuminating the stylish fixtures and inviting design. The adjoining living area, visible in the background, enhances the open layout.

4.95 out of 5 average rating, 125 reviews

Zen w/ Hot Tub, Office, Yard, Dog Friendly, Park

Welcome to your peaceful Bend basecamp, thoughtfully managed by The Home Co.—a local small business focused on clean, well-functioning homes with easy checkouts. This stylish 2-bedroom, 2-bath home is centrally located near Ponderosa Park and Pilot Butte, with easy access to Downtown, the Old Mill, and the Deschutes River. With a fully fenced yard, dedicated office, hot tub, and flexible living space, it’s perfect for families, remote workers, and pet lovers.

A light-filled living area features a black leather sofa and a wooden armchair facing a large window. A patterned area rug adds warmth to the hardwood floor. Barstools are placed at the kitchen counter, and artwork is displayed on the white wall.

5 out of 5 average rating, 204 reviews

Central Modern Guesthouse with EV Charger

We built this home out of a passion for creating welcoming spaces. Years ago, we renovated a motel on the coast - an experience that sparked our love of hospitality and shapes how we host today. We live around the corner with our kids, a golden retriever, and a few cats. Mike’s a local realtor, and Betsy manages business ops for the local fire department. We love books, music, and helping you discover the best of Bend - trails, eats, and community.

An inviting entryway is featured, with a green door framed by a porch. A wicker chair sits beside a white planter, adding a touch of greenery. Brick columns complement the wooden deck and ceiling, creating a warm and accessible entrance.

5 out of 5 average rating, 435 reviews

Downtown - Super Walkable - King - Local Hosts

Stay in a rare home in the heart of downtown—a beautifully restored 1922 craftsman with warm wood, plants, vaulted ceilings, and natural light. Enjoy charming architecture and local artwork. Walk to dozens of restaurants, breweries, coffee shops, and stores. Cross the alley to food trucks and live music, or relax in your private walled courtyard with native plants. We keep a clean, low-allergen home with no pets and no scented products.

4.93 out of 5 average rating, 209 reviews

A comfortable living area features a green sectional sofa and a gray accent chair. A large coffee table sits in the center, with a light-colored rug beneath. Exposed wooden beams adorn the ceiling, while a staircase leads to an upper level. A television is mounted on the wall.

Home in Old Bend

Drake Park Cottage in the Heart of Bend

This location can’t be beat! The cottage is steps away from Drake Park and the river as well as walking distance to downtown. Enjoy summer festivals in the park, floating or stand up paddleboard on the river. Located in the historic parks district, this property is quiet and comfortable yet close to all the action. Guests have been coming back year after year to enjoy this unique vacation spot. It’s a gem! SORRY NO PETS and NO SMOKING.

Popular amenities for outdoor seating rentals in Bend

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.99 out of 5 average rating, 104 reviews

The front of the home features a welcoming porch with two large adirondack chairs. A garden surrounds the entrance, which has a vibrant orange door. The house is framed by tall trees and has well-maintained landscaping, creating an inviting atmosphere.

Home in Old Bend

Downtown Bend Historic Bungalow *HOT TUB*

An exterior view of a single-story home is shown, surrounded by landscaped gardens with rocks and greenery. A cozy patio area features blue and white striped lounge chairs, an umbrella, and string lights overhead, creating a welcoming outdoor space.

4.97 out of 5 average rating, 189 reviews

Close, Cute & Clean! *Hot Tub* Bend Adventure Base

4.99 out of 5 average rating, 215 reviews

Butler Corner - New, Clean & Minutes From Downtown

4.98 out of 5 average rating, 965 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

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, 171 reviews

Theater Room w/Movies, Netflix, Amazon Prime

The living area features engineered hardwood floors and a cozy leather sofa positioned near a wall-mounted smart HDTV. A rustic wooden coffee table is set with snacks, while the open kitchen showcases modern stainless appliances and quartz countertops. Natural light fills the space through multiple windows.

4.97 out of 5 average rating, 111 reviews

Walk to Amphitheater & Old Mill I Beach Cruisers

4.95 out of 5 average rating, 265 reviews

Home in Old Bend

Park Place - Walk to Downtown & Old Mill

The kitchen features modern white cabinetry and a large central island with a wooden cutting board. Stainless steel appliances, including an oven and refrigerator, are present. Shelving holds various kitchen items, while a window offers natural light and views of the outdoor greenery.

4.96 out of 5 average rating, 161 reviews

Downtown with hot tub and fenced-in yard

Apartment rentals with outdoor seating

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, 323 reviews

Midtown Gem With Cozy Fire and Park Views

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

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

4.92 out of 5 average rating, 106 reviews

Sunriver Studio with Pool & Hot Tub

A cozy living area features a gray sofa facing a wooden television stand. A colorful rug adds warmth to the hardwood floor. Natural light streams through two large windows, with vintage ski equipment displayed on the ledge. A comfortable armchair is positioned nearby.

4.96 out of 5 average rating, 507 reviews

Riverside loft closest to amphitheater, rapids

A cozy living area features a blue sofa and a matching armchair, set on a patterned area rug. A round wooden coffee table occupies the center, while natural light streams through a small window. The walls are adorned with artwork and decor, creating a welcoming ambiance.

4.96 out of 5 average rating, 1,055 reviews

Urban Studio Loft-Hot Tub AC 250+Mbps Views

An open room features vaulted ceilings and large windows, allowing natural light to fill the space. Two surfboards are artfully displayed on the wall, while a circular dining table and four chairs are positioned in the center. A black office chair is visible at a desk, enhancing the work-friendly atmosphere.

4.94 out of 5 average rating, 104 reviews

Wine Down and Play

A cozy living area features a green sofa against a mural of a vibrant forest. Indoor plants are arranged around the space, complemented by natural light filtering through sheer curtains. A round dining table with two chairs sits adjacent to the seating area, enhancing the inviting atmosphere.

4.96 out of 5 average rating, 166 reviews

The Grove at Midtown Manor - King Beds & Hot Tub!

Apartment rentals with outdoor seating

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.

4.9 out of 5 average rating, 147 reviews

Adorable Studio at Seventh Mountain Resort

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, 301 reviews

Mt. Bachelor Village Condo - Near Town & River

A spacious living area features a round dining table surrounded by six light-colored chairs, complemented by a textured area rug. Large windows offer views of the outdoors, while a cozy seating arrangement sits nearby. A modern kitchen area is visible in the background.

4.94 out of 5 average rating, 219 reviews

Luxury View Condo - Mt Bachelor, Amphitheater

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.

4.99 out of 5 average rating, 138 reviews

Pool, AC, close to Amphitheater & Old Mill

4.94 out of 5 average rating, 130 reviews

Adventure Awaits! Walk to downtown and river!

A modern living space features a gray sofa with decorative cushions and a round coffee table. Four sleek bar stools are positioned around a kitchen island with a white countertop, while natural light fills the area from the windows, enhancing the warm tones of the decor.

4.91 out of 5 average rating, 160 reviews

Riverfront Condo, Walk to Downtown Bend

4.93 out of 5 average rating, 168 reviews

Apartment in Sunriver

Room With a View Condo, Sharc passes included.

Superhost

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.