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, 234 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 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, 416 reviews

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

Enjoy this Contemporary Luxury Home directly on the Deschutes River. Literally step out your back door and stroll, run or paddle up and down the river. The river trail is a 3 3/4 mile loop and one of the best hikes around. Back at home sit on your deck or in the Hot Tub and listen the the sounds of the river going by and enjoy peaceful solitude. Shop or get a bite to eat at The Old Mill, Box Factory, Food Carts and more which are a peaceful 3/4 mile stroll along the river trail. Enjoy!

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.

4.99 out of 5 average rating, 608 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!

5 out of 5 average rating, 147 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

Relaxing, private spa & sauna grotto is ready for your romantic Bend getaway! This quiet, wooded, centrally located standalone bungalow is steps from the Deschutes River trail and within easy walking distance of 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!

4.93 out of 5 average rating, 102 reviews

Modern Home Close to OLD MILL | HOT TUB! | 6 Bikes

This absolute gem is located in the heart of Bend and is less than 5 minutes from the Old Mill District. Our 3 bed/2.5 bath mountain modern home backs up to the canal and has just about every amenity you could ask for. Such amenities include a private hot tub & back patio, 2 separate living rooms, gourmet fully stocked kitchen, dedicated workspace, high end furniture/artwork, and much more. This home is light and bright with large windows and vaulted ceilings. Come enjoy all Bend has to offer!

4.9 out of 5 average rating, 455 reviews

Quiet Escape: Fireplace, 5min to Downtown & River

Relax on the private balconies overlooking the park. After your coffee take a 2 minute walk down to the Deschutes river trail. Or walk 10 minutes and you're in downtown Bend. After a day of outdoor and ski adventures, you'll love the king size bed or relaxing by the fireplace. You'll have super fast wifi with Netflix, and a Smart TV in each room. Looking to stay longer? Send us a message to talk about long term stays and remote working. Locally owned and operated. Book your stay today!

4.99 out of 5 average rating, 193 reviews

A spacious living area showcases a modern fireplace with a stone surround. The open floor plan includes a dining table, comfortable seating, and a television. Natural light pours in through nearby windows, highlighting the warm hardwood floors and contemporary decor.

Townhouse in Bend

Bend Getaway | 2BR, King Bed, Garage, Fast WiFi

Renovated 2 level townhome, fully stocked, 100% cotton 400 thread count hotel quality sheets. Lives like a house and is the perfect home base for your outdoor adventures in Bend! The primary BR has a comfy King bed & private bathroom. The 2nd BR has a bunk bed (full on the bottom, and a single up top) with private bathroom. Main level features a spacious LR, DR & Kitchen along w/ a 1/2 bath. Located in the Boyd Acres neighborhood, just minutes to downtown and everything Bend has to offer.

4.98 out of 5 average rating, 181 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.

4.85 out of 5 average rating, 373 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.

A spacious outdoor patio features a built-in BBQ station, surrounded by loungers and an outdoor dining table. A natural gas firepit sits at the center, with seating around it, offering a relaxing atmosphere amid landscaped greenery and trees.

4.99 out of 5 average rating, 110 reviews

Tall Pine Tuckaway! Hot tub, EV charge, RV hookup

Welcome to Tall Pine Tuckaway! This sprawling home sits among the peaceful wooded edge of town yet is just a 10-minute drive to Downtown Bend! Perfect for large families or groups, this home has it all - salt water hot tub, firepit patio, landscaped acreage for kids and pets to play, universal EV charger, two living rooms, dedicated office with lightning-fast 1G wifi, and full RV hookups! Bring your trailer and toys and ride directly onto China Hat Road for some excellent off-roading.

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, 209 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 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.

Popular amenities for outdoor seating rentals in Bend

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

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, 137 reviews

Mid Century West side home-walk everywhere

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.

4.96 out of 5 average rating, 193 reviews

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

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, 119 reviews

Family/Remote Work Friendly House in Bend OR

The cabin's exterior is crafted with natural wood and features large, angular windows that showcase the surrounding forest. A spacious deck with Adirondack chairs extends across the front, inviting relaxation and connection with nature.

4.98 out of 5 average rating, 177 reviews

Private Luxury w/Hot Tub on Pvt Lake Amazing Views

4.93 out of 5 average rating, 240 reviews

The Craftsman home features a welcoming front porch with two chairs positioned on either side. A traditional American flag adds a festive touch, while lush greenery surrounds the entrance. The exterior showcases a blend of wood tones and architectural details characteristic of the Craftsman style.

Home in Old Bend

Paddle House

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, 297 reviews

Mountain Bliss: Gateway to Mt. Bachelor and More

A single-story house with a welcoming porch is framed by a gravel driveway. Lush greenery surrounds the entrance, complemented by blooming pink flowers. The cloudy sky adds depth to the scene, while large windows provide ample natural light. The structure features a simple, rustic design.

4.96 out of 5 average rating, 176 reviews

Bend 3BR Home Near River Trail | Dog-Friendly

A sunlit living area features a large glass door leading to the backyard, surrounded by greenery. A comfortable sectional sofa is positioned near a gas fireplace. A dining table accommodates multiple chairs, while a wall clock and artwork add charm to the open space.

4.91 out of 5 average rating, 160 reviews

Comfy Quiet*Hot Tub* Remote-work+Family ready

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, 324 reviews

Midtown Gem With Cozy Fire and Park Views

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, 542 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, 461 reviews

Private Spacious Studio Apartment

4.93 out of 5 average rating, 110 reviews

Sunriver Studio with Pool & Hot Tub

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, 106 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, 169 reviews

The Grove - King Beds & Hot Tub - No pets

The living room features a cozy seating area with a gray sofa and a large white bean bag chair. A wood-burning fireplace is centrally located, complemented by a television mounted above. Large windows allow natural light and offer views of the surrounding trees.

4.85 out of 5 average rating, 101 reviews

Easy Access to Bend+Bachelor | Hot Tub | Pets OK

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, 945 reviews

The Garden Apt-Hot Tub Fireplace AC 250+ Mbps

Apartment rentals with outdoor seating

Superhost

A well-lit sleeping area features a spacious bed with a colorful striped blanket. Flanking the bed are two bedside tables with lamps. Above the bed, three framed botanical prints add a touch of decor, while a small plant is positioned on one table.

Apartment in Sunriver

4.78 out of 5 average rating, 257 reviews

SunriverSiesta-Near it all-Sleeps 2 adults 2 kids

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

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, 140 reviews

Pool, AC, close to Amphitheater & Old Mill

4.94 out of 5 average rating, 134 reviews

Adventure Awaits! Walk to downtown and river!

4.9 out of 5 average rating, 254 reviews

A comfortable living area features a patterned sofa adorned with red and blue pillows, paired with two recliners. A small side table is visible next to one recliner. Natural light fills the space, highlighting the hardwood flooring and a decorative area rug.

Apartment in Sunriver

Sunriver Getaway

4.96 out of 5 average rating, 229 reviews

A comfortable living area features two gray sofas adorned with plaid throws, paired with a wooden coffee table. Two framed black-and-white landscape photographs hang on the walls. Natural light enters through sliding glass doors, complementing plants placed around the room.

Apartment in Sunriver

Remodeled SunriverVillage Condo 6Free Sharc passes

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.