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, 223 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.

4.98 out of 5 average rating, 956 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!

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, 587 reviews

Home in Lodges at Bachelor View - Book Now!

Enjoy Bend’s newest west-side neighborhood nestled beside Century Drive, the gateway to Mt. Bachelor and the Cascade Lakes. Our unique location puts you right on the connector trails to the popular Phil's Trail System for mountain biking or casually strolling along the Deschutes river trail. With access to the National Forest in just steps and breweries mere minutes down the road, Pinehaven is as 'Bend' as it gets. Thank you for considering Pinehaven for your stay. We think you’ll love it here!

4.96 out of 5 average rating, 127 reviews

The A-frame cabin is framed by tall pine trees, showcasing a modern black exterior. Large windows reflect the surrounding forest, while a wooden deck serves as an entry point, inviting guests to explore the natural setting.

Cabin in La Pine

Discover tranquility in our A-frame cabin nestled among the pines. A rustic haven where the scent of pine fills the air, inviting you to unwind on the porch. Inside, a cozy living space & quaint kitchen offer comfort. Retreat to the loft bedroom, where the soft glow of morning light through pine branches awaits. Whether a romantic escape or family adventure, this cabin is a sanctuary, a respite from the daily rush. Embrace simplicity, enjoy the peace & quiet, and enjoy all the nearby beauty.

5 out of 5 average rating, 133 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!

4.97 out of 5 average rating, 355 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.

4.94 out of 5 average rating, 529 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.

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, 195 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.

4.89 out of 5 average rating, 251 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.

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, 197 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.

5 out of 5 average rating, 196 reviews

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.

Home in Larkspur

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.

4.98 out of 5 average rating, 228 reviews

Natural light filters through large windows, illuminating a cozy seating area with a dark sofa adorned with decorative cushions. A wooden coffee table sits centered on a textured rug, while a potted plant adds a touch of greenery to the space.

Guest suite in Bend

The Sawmill — Designer Cabin Vibes Glow In Natural Light

This Scandinavian-inspired abode has minimal, designer decor and crafted details. Set in the heart of Bend’s popular Westside, vaulted ceilings and wood paneled finishes bathe this tranquil space in natural light. Everything you need is right outside the doorstep, within blocks away from Bend's best restaurants, breweries, coffee shops and boutiques. You won’t find a better spot for couples and solo adventurers. Family friendly too!

Popular amenities for Bend outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

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, 134 reviews

Mid Century West side home-walk everywhere

An inviting outdoor seating area features a modern fire pit surrounded by cushioned chairs, offering a cozy spot for gathering. A dining table is set for outdoor meals, and thoughtful lighting enhances the space under the covered patio, framed by lush trees.

5 out of 5 average rating, 116 reviews

Family/Remote Work Friendly House in Bend OR

4.93 out of 5 average rating, 201 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

4.99 out of 5 average rating, 204 reviews

Home in Orchard District

Butler Corner - New, Clean & Minutes From Downtown

An open living space is displayed, featuring sliding barn doors that lead to a bedroom. A large wall artwork of a bridge over a misty landscape adds depth, while a cozy armchair and a small ornate table create inviting seating options.

4.88 out of 5 average rating, 429 reviews

Charming east side house, with hot tub.

An outdoor deck features a hot tub and a shaded seating area, surrounded by potted greenery. A table with an umbrella is positioned nearby, alongside comfortable chairs, creating a space for relaxation or dining. The deck's two levels are connected by stairs.

4.96 out of 5 average rating, 158 reviews

Modern home in NW Bend (w/HOT TUB!) Walk to Shops!

A spacious living area is highlighted by a modern entertainment center and a comfortable seating arrangement, including a large ottoman. Light-colored walls complement the wooden floors, while natural light filters through windows, enhancing the room's inviting appearance.

4.97 out of 5 average rating, 190 reviews

Old Mill Charm

A private hot tub bubbles invitingly on a deck surrounded by natural landscaping. Wooden railings frame the area, with two Adirondack chairs positioned nearby, offering views of the Deschutes River and lush trees in the background.

4.98 out of 5 average rating, 405 reviews

<SALE> River Front | Hot Tub | Old Mill | Dogs

Apartment rentals with outdoor seating

4.98 out of 5 average rating, 215 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, 320 reviews

Midtown Gem With Cozy Fire and Park Views

4.97 out of 5 average rating, 557 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

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

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, 504 reviews

Riverside loft closest to amphitheater, rapids

A spacious living area features warm wooden floors and large windows allowing ample natural light. Unique architectural elements, including a yellow accent wall and natural wood pillars, create a welcoming atmosphere. A cozy seating arrangement with a sectional couch and armchair is highlighted by a decorative area rug.

4.96 out of 5 average rating, 798 reviews

Tranquil & Magical-HotTub Fireplace AC 250 Mbps+

4.93 out of 5 average rating, 347 reviews

A comfortable living area features a dark gray sofa positioned in front of a stone fireplace. A simple coffee table sits on a patterned area rug, and a dining table is visible in the background. The space is complemented by a lofted sleeping area with a ladder for access.

Apartment in Old Bend

The Hub—Apartment @ Downtown & Historic Dist

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, 296 reviews

Sunriver Studio with Pool and Hot Tub

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

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, 298 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, 133 reviews

Pool, AC, close to Amphitheater & Old Mill

4.94 out of 5 average rating, 122 reviews

Adventure Awaits! Walk to downtown and river!

Superhost

A spacious living area features a comfortable sofa and a dining table with woven chairs. Large glass doors lead to a balcony, allowing natural light to fill the room. A neutral color palette is complemented by artwork on the walls and greenery scattered throughout.

4.83 out of 5 average rating, 129 reviews

Gorgeous Condo near Downtown & the Deschutes 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