Holiday rentals with a patio in Bend

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.

The Oasis Airstream

Reconnect with nature at this unforgettable escape, surrounded by gorgeous desert views. Beautifully designed and fully equipped for your comfort. Pet friendly and located just 15 min from downtown Bend. The Oasis Airstream is on a quiet 10 acres. I live here with my family and have a small farming business. There is an ample yard with outdoor table and chairs, outdoor couch, and fire place. There's also a hammock for swinging in the shade on those long summer evenings. Please read all info.

| The Chalet | 1+ acre| Remodeled | Quiet |

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.

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!

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.

Craftsman Style Retreat in Bend River West

Located in one of Bend’s most walkable neighborhoods, this studio is a couple blocks away from Columbia Park with easy walking access to Drake Park, Harmon Park, McKay Park and the Old Mill District (and amphitheater). After (or before) you’ve explored nearby shopping and food, head out and explore the endless outdoor activities such as skiing, Mt. Biking, rafting, fishing, and much more! You are short pedal to Phils Trails, a 5 min walk to Mt. Bachelor’s Park n Ride (or 25 min. drive).

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.

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.

Panoramic Mountain View Oasis

Your high desert sanctuary awaits. Enjoy breathtaking panoramic mountain views from your second floor apartment, stargaze in the hot tub, cozy up outside by the wood-burning fireplace, and so much more! Only 2 miles from Brasada Ranch, convenient for weddings and events. Close to world-famous Smith Rock, centrally located between Bend, Redmond, and Prineville for a myriad of outdoor activities. Forget your worries in this serene and peaceful place!

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 @ The DUPE - blocks from Old Mill District -

This beautiful and updated townhouse is located just blocks away from the Old Mill District. You can walk or ride down to the Hayden Homes Ampitheater, shopping, dining and of course the Deschutes River. The 2 bedroom 2 bath house itself is surrounded by trees and is very private. You will love the full tile shower in the master bathroom and the light and bright kitchen with updated appliances. This place is a perfect mix of comfort and location.

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.