Family-friendly holiday rentals in Deschutes County

Ranch Cottage: Desert, Forest, Horses, Hot Tub

Beautiful guest cottage studio, with mountain views, in the southeast Bend neighborhood of Sundance. 15 minutes to town and 45 minutes to Mt. Bachelor ski area. This special ranch property is two blocks away from endless recreation in the Deschutes National Forest. (PLEASE NOTE; national forest access has been closed as of May 1, 2025-May 2027 for fire reduction and restoration. blm trails are open) Includes one king Sleep Number bed and one queen Murphy bed. Private hot tub out the back door.

LOCATION! WALK DOWNTOWN & OLD MILL - #2

Modern one-bedroom with fully equipped kitchen, washer/dryer in unit and designer touches to make your stay feel like home. Maximum of two guests. Ductless heat/air conditioner for your comfort. Free wi-fi, smart TV with HD cable service. Plenty of off-street parking spaces. A private 5' x 9' locked storage for your kayaks, bikes, clubs, skis, boards. .... NO smoking ... and sorry, no pets. No room tax for stays of 30 days or more. City of Bend Short Term Operating License No. STR-15-0016.

A-Frame cabin • hot tub • near Bend • Crater Lake

This cozy and unique A-frame cabin sits on 1+ private acres in the Deschutes Forest. Relax here with wooded pines, hot tub jacuzzi, soaking bathtub, 80" home theater projector, modern amenities, and beautiful forest views. Close to the city of Bend and all the outdoor activities Central Oregon has to offer. Proximity to the best hiking trails, mountain bike trails, hot springs, Deschutes River, Mt Bachelor ski resort, Cascade Lakes highway, Smith Rock State Park, and Crater Lake National Park.

Romantic Farmhouse near Mt. Bachelor

Relax at a peaceful farmhouse for a romantic weekend, or take your time exploring Bend with friends. Baltzor Farm and Guesthouse is fewer than 2 miles from some of Bend's amazing breweries and restaurants. Smith Rock and Mt. Bachelor are both within 30 minutes of the guesthouse. Catch a concert, float the Deschutes, or go on a bike ride. Our relaxing farmhouse has rustic, old-world charm with all of the modern amenities, including a soaking tub, waterfall showerhead, soft linens, and Starlink.

| 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.

Skyliners Getaway

Our tiny log cabin is a cozy getaway, close to hiking, mountain biking, and cross country skiing but only 10 miles from the amenities of Bend Oregon. It is a rustic place, with modern touches, like a gas range, refrigerator, and a gas fireplace. The bathroom is detached from the cabin - steps from the door. It is fully equipped with plumbing and a shower. Our place is perfect for people who love the outdoors with the comforts of home. No children under the age of 12 -- And alas, No Pets.

Riverfront/Hot Tub/Dock/Pet Friendly/Game Room

Welcome to Lucy’s Riverfront Retreat, a peaceful getaway on the Little Deschutes River in La Pine, Oregon. This spacious home sits on 2+ acres with a private dock and stunning Paulina Peak views. Perfect for family trips, romantic escapes, or adventures with friends—offering comfort, nature, and endless relaxation! A short drive to top Central Oregon attractions: • 2 min to Quail Run Golf Course • 15 min to Sunriver Village (Dining & Shopping) • 25 min to Bend • 40 min to Mt. Bachelor

Yurt at Rainbow Ranch: Quiet, Cozy and Luxurious!

Looking for a quiet, cozy stay in a luxurious yurt? Well, then look no further than the Rainbow Ranch! We are located fifteen miles from Bend and a ten minute drive from Sisters. Whether you're seeking a place to land after an adventurous day or looking for a unique spot to unwind, you’re sure to cherish your time here. Enjoy views of the Sisters and Broken Top from the property by day. Then, snap a few photos of the glorious sunset, sit back, and watch as the stars light up the night sky.

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.

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.

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.

The Outpost Bend

The Outpost is a seperate guest home located on our 10 acre hobby farm. It offers spectacular views of the Cascades, stunning sunsets and a peaceful, private location 15 minutes east of downtown Bend. The property adjoins public land, and is on a quiet country road. Our family lives onsite with our 3 sons, dogs, hens, and sheep. The Outpost has a private driveway, use of basketball court, and a lovely private outdoor seating area. 45 min drive to Mt. Bachelor.