Holiday rentals with outdoor seating in Bend

Hygge & Harmony on Hip Galveston - Luxe with Charm, Hot Tub

Gather round the fire pit, then hop in the hot tub after a day exploring this vibrant part of town. Period features like vintage chandeliers and cozy fireplaces, and upscale appliances like a Viking range, make this single-story home a real gem. * Please note the half bath has a sink, shower and laundry...but no toilet Welcome to Hygge Harmony, a 1927 westside bungalow that delivers big on style! This light and bright home has two bedrooms (king, king) and one full bathroom and one extra shower. Queen sleeper sofa in the living room too. You'll love the large bedrooms which are so rare for bungalow homes. Snuggle up in front of either of the 2 gas fireplaces in the master bedroom and kitchen, as well as the luxury of a private hot tub! You'll arrive to comfy beds with fresh and clean linens. Each bedroom has it's own sitting area. The master bedroom also features it's own gas fireplace and french doors to the backyard deck. You won't want to miss the hot tub in the backyard either! One of the highlights of this home is the fully stocked and chef ready kitchen. Your happy and pampered chef will feel a bit spoiled when cooking on a 6 burner Viking range and marble countertops. We always supply basic oils and spices for your use too. You'll find all the expected appliances (oven, stove, fridge, dishwasher, microwave, toaster) plus more and dining space for 6. The bathroom is updated and you'll find a classic clawfoot tub and shower stocked with earth friendly soaps and shampoos. There is an additional shower in the laundry room with it's own sink and mirror (no toilet). Feel free to use the washer and dryer during your stay. Outdoors you find a firepit, outdoor lounges with umbrella and your very own hot tub. Enjoy the grill for your summer BBQs. Don't feel like cooking? Walk out your back gate and right into the food cart lot! Or a few steps more to 10 Barrel. This is a quintessential Bend location! *A Stone's Throw Bungalow homes are NOT appropriate for noisy groups. The home, garage and property is yours to enjoy. We live nearby and are happy to help if you have any questions! Otherwise, the home is yours to enjoy and you probably won't see us during your stay. Less than a block from Galveston Bridge, the home is a walkable spot for restaurants, coffee shops, and Drake Park for festivals and Mirror Pond float activities. The location has a Walk Score of 86, and offers fantastic hiking, biking, and skiing. There is a binder in the home with more details about the home and the neighborhood, including restaurant recommendations, transporation, and activites around Bend! ** This is a quiet residential neighborhood! Quiet hours are enforced after 10PM ** Grab a cruiser bike from the bike shop 1 block away or bring your own! In the summer, there is a free town shuttle to all the favorites spots around town. Look for more info in our binder when you arrive. The river float shuttle is just 1 block away if you plan on spending your time in Bend on the river! Pets are allowed with a $20/nt pet fee.

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.

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!

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.

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.

Location! Bungalow River & Beach Access

Welcome to our 1918 Bungalow on Riverfront Street. This simple, no frills one bedroom, one bath sleeps two to three. Enjoy a fully equipped kitchen, floor to ceiling river rock gas fireplace, inviting front porch, back deck with propane BBQ, table/ chairs. The Bungalow has a peek of the river, as it is considered the "guest house" to the larger "main house" it shares the lot with. Enjoy low bank river access to launch your kayak. Park the car and experience the best Bend has to offer.

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.

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.

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.

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.

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.

Mid Towns NEW modern private guesthouse

The Mid Town Majesty house is our cozy little detached guesthouse located in a quiet residential neighborhood. A brand new build thoughtfully designed with stylish mid century modern finishes throughout the house. Plenty of off street parking right in front of the home. You are a short drive to downtown, Old Mill District and grocery stores. Walking distance to Mid Town Yacht Club which has Bends finest food trucks.