Holiday rentals with a pool in Bend

Romantic Guest House w/Hot Tub, Pool, Tennis Court

Sweetums Guest House is a private, beautifully appointed 2 bedroom, 2 bath guest house located on 20-acre Sweetums Ranch. Amazing views of Three Sisters and Broken Top mountains from the property, horses,& abundant wildlife viewing. 8 mi to downtown Bend & 12 mi to Sisters. 45 min to Mt Bachelor and mountain trailheads. Large private yard & partially covered patio w/private hot tub. Amazing swimming pool and tennis court. On the Oregon scenic bike route. A perfect location for your getaway!

House + Bonus Room | HOT TUB, Huge Yard, Dogs OK!

This modern and family friendly home is nestled among mature pine trees on a fully landscaped half acre lot with a hot tub, fire-pit, and huge backyard just minutes outside of Sisters. Our 4 bedroom home + detached bonus room sleeps 10 comfortably. You'll also have access to the community pool (during Summer months), pickle ball/tennis courts, basketball courts, and walking trails. This vacation home truly checks all the boxes for your Central Oregon getaway.

Gorgeous Condo With River View - Pool and Hot Tub

Condo 309/310 is a stunningly remodeled condo here at Bend Riverside Rentals, which we have named 'Deschutes Trail Mix." This condo went through an extensive head to toe remodel and is now ready to host travelers! It can sleep up to six guests, has a full kitchen, two full bathrooms, a washer and dryer, a private patio and comes with access to our indoor heated pool and hot tub! This condo is also pet friendly! Bring up to two pets for an additional fee.

Cozy 3 bdrm + loft Eagle Crest Chalet w/ Hot Tub!

Welcome to our Chalet in the Eagle Crest Resort! You are guaranteed to feel like you are on vacation the minute you walk in. This 3 bedroom + loft can sleep 8 guests and comes with washer/dryer, WiFi, and desks in the loft. Relax in the space indoors or out, with the outdoor patio, hot tub, BBQ, and golf course views. There is so much to see and do on the resort property or you can grab a blanket, sit by the fire and do absolutely nothing at all!

3bdrm Chalet + Hot Tub in Eagle Crest

Welcome! Come enjoy and relax in our rustic chalet. Unwind on the back deck while barbecuing, drinking a cup of coffee, or enjoying our private hot tub. Our chalet offers sports passes to all three sports complexes that include indoor/outdoor pools and tennis courts, spas and saunas, play grounds, BBQ areas, horse shoes, volley ball courts and much more. Enjoy golf, mini golf, enjoy nearby hikes and rivers. The perfect place for a family get away!

Luxury in the Forest

Dog Friendly at the Inn at the Seventh Mountain The Inn has been delighting visitors for 30+ years. It is the closest lodging to Mt Bachelor, and is just 7 miles from all that downtown Bend has to offer. There are amazing restaurants, great shops, and more. The condo has just been completely remodeled. Winter or summer, the Inn at the Seventh Mountain resort offers something for everybody in the family. Welcome! DCCA#720734

The House on the River

From the moment you enter the neighborhood, you will enjoy a private road that is peaceful and tranquil. The neighborhood is full of beautiful trees, birds, and an abundance of deer that roam the area frequently laying in and enjoying the large front yard. Bring the bikes for the kids to enjoy riding in the big circular driveway or through the neighborhood. You can take in the surrounding nature with a walk along the river trail.

Riverfront Condo, Walk to Downtown Bend

Enjoy the peaceful Deschutes River views and walk to downtown Bend in just minutes from this fully remodeled riverfront condo. Perfectly located directly on the river and only a short walk to Bend’s best restaurants, coffee shops, breweries, and boutiques, this home offers the ideal balance of relaxation, comfort, and convenience. Guests consistently love the peaceful setting, unbeatable location, and comfortable, modern space.

Bungalow at The Parks

Our Bungalow has easy access to Mt. Bachelor, Bend's famous mountain bike trails, one mile from OSU Cascades, very near Old Mill shopping and dining, and easy access to downtown Bend, also. You’ll love our place because of the coziness, the comfy bed, and private access to your space. The Bungalow is good for couples, solo adventurers, and business travelers. Our neighborhood pool is open May through August.

Knotty Pine Oasis on Eagle Crest Ridge Golf Course

This fully furnished 3 bedroom 2 bathroom chalet sits on the 15th tee box of the Eagle Crest Ridge Golf Course, which neighbors BLM land and is one of the more private settings at Eagle Crest. Enjoy the charm of the knotty pine and log accents, a primary suite with a king log bed and jetted tub, and a large deck that looks out to the golf course that has a pergola, lighting and oversized couch with bar.

Pool, AC, close to Amphitheater & Old Mill

Easy access to the heart of Bend from this perfectly located home base. A short walk takes you to the Deschutes River Trailhead for scenic hiking. You can leisurely stroll the mile trek to the Old Mill shopping center or meander a little further to the Amphitheater to enjoy summer’s many concerts. Enjoy a picnic on the lawn and enjoy watching the wildlife.

The RiverBend House—Deschutes dock, near Sunriver

The RiverBend House is the restorative escape you’ve been looking for. This 3-bedroom, 2.5-bath home sleeps 6 adults (8 total guests if there are young kids) and is located in a tranquil, wooded residential community on the Deschutes River, just 5 miles south of all the amenities of Sunriver, 20 miles SW of Bend, and 20 miles SE of Mt. Bachelor.