Bend Vacation Rentals

Our Bend Vacation Rentals in central Oregon are the perfect places to enjoy the outdoor sports and gorgeous mountain views that Bend has to offer. Bend, OR is also a thriving Central Oregon city that caters to enthusiasts of all kinds. You can enjoy exceptional dining, craft-brewed beers and Oregon wines, shopping at the Old Mill District or Bend Factory Stores, hiking along the Deschutes River or a kayak paddle through Drake Park. With over 300 days of sunshine per year and a four-season climate, Bend is your launching pad to dozens of outdoor activities including golf, boating, fishing, skiing, horseback riding and ice skating.

Planning a trip to Bend? Bend features events such as the Oregon for the Oregon High Desert ClassicsPole Pedal PaddleRush Soccer TournamentBend Elks Memorial Day TournamentThe Halloween Cyclocross Crusade of Bend, and many more! Check out our events page or Visit Bend.

Large Group? We have you covered. Many of our large Bend rental homes are designed to accommodate large groups, families, reunions and corporate rentals, and some of our Bend rentals are even pet friendly. Hot tubs, golf course views, resort settings and convenient locations to downtown Bend, the Old Mill, and Mt. Bachelor ski resort make your Bend vacations even better. 

Check out the Bend, Oregon Good Neighbor Policies

  • Mt. Bachelor Ski Resort
  • Old Mill District and Bend Factory Stores Shopping
  • High Desert Museum
  • Drake Park

Portlandia

Bend
  • Downtown
4 Bedrooms
2 Bathrooms
8 Guests

Huge Backyard with Hot Tub and Close to Downtown Bend! You and your family and friends will love exploring Bend and returning at night to dine, relax and soak under the stars!

Georgia Peach

4.666665
(4.7 Average)
Bend
  • Downtown
3 Bedrooms
2.5 Bathrooms
8 Guests

A perfect location for your ultimate Bend experience. Leave the car in the driveway and walk everywhere in central downtown Bend from this spacious home with outdoor patio and hot tub!

Landrise 10

4.583335
(4.6 Average)
Sunriver
  • SHARC Pass Included
3 Bedrooms
2 Bathrooms
9 Guests

This magnificent Sunriver vacation home, designed for your comfort and relaxation, offers unmatched vacation accommodations with everything you need.

The Osprey

5
(5.0 Average)
Bend
  • West Side
4 Bedrooms
2.5 Bathrooms
10 Guests

Panoramic Cascades Views, Fenced Yard, Hot Tub Grace this Family Home in Bend! With a near-perfect location for golfers, bikers, hikers, paddlers and skiers, Osprey will delight your active friends and family!

The Trailhead

5
(5.0 Average)
Bend
  • West Side
3 Bedrooms
2.5 Bathrooms
10 Guests

Great for a getaway that’s close to amenities. Family-friendly & spacious, located in SW Bend. This home is ideal for single or multi-family vacations, retreats, or trips with friends. Hot tub, fully equipped kitchen, and sleeps 10.

Three Pines

5
(5.0 Average)
Bend
  • Close to Mountain
4 Bedrooms
3 Bathrooms
10 Guests

Ski, golf, float and hike from this spacious home in a quiet Bend neighborhood, your perfect all-season retreat! Just 25 minutes from Mt. Bachelor and 5 minutes from Tetherow and Widgi Creek Golf Courses.

Darby Manor

Bend
  • East Side
5 Bedrooms
3 Bathrooms
10 Guests

Excellent Gathering Space for Family and Friends in this Five-Bedroom Bend Beauty with King Master Suite and Hot Tub!This beautifully appointed Northeast Bend home will give you and your guests over 3,000 sq. ft. of luxury and comfort within easy reach of

Oregon Loop 1

4.727275
(4.7 Average)
Sunriver
  • Near Sunriver Village
5 Bedrooms
5 Bathrooms
10 Guests

This stunning Sunriver home, with luxurious décor, 4 bedroom suites, and incredible entertainment options is designed for large families & lots of fun!

Meadowbrook

5
(5.0 Average)
Bend
  • West Side
3 Bedrooms
2.5 Bathrooms
10 Guests

Updated Luxury in this Gorgeous Two-Story Home in Bend’s Westside! Close to all the activities that make Bend such a great vacation destination, Meadowbrook has a beautiful outdoor space for dining and relaxing!

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