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Holiday Rentals with Pools in Bend

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401 rentals in Bend.
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NEW! Old Bend 2 Bdrm Duplex, walk to Box Factory, Old Mill, brew pubs, wine tast
2 bedrooms
1 bathroom
Sleeps 4
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Ponderosa Paradise with a million dollar view
2 bedrooms
3 bathrooms
Sleeps 4
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Westside Home near Mt. Bachelor
3 bedrooms
2 bathrooms
Sleeps 6
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Comfortable condo w/ private hot tub, shared pool & tennis - great location!
1 bedroom
1 bathroom
Sleeps 4
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Happiness is just Around the Bend, Caldera Springs Resort Sunriver, Bend Oregon
4 bedrooms
4 bathrooms
Sleeps 12
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Truly one of the Best Homes on the River! Safe & Open!!!
2 bedrooms
2 bathrooms
Sleeps 6
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Immaculate & Secluded downtown Bend Cottage- Extended Stays starting in the Fall
1 bedroom
1 bathroom
Sleeps 4
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RiverWild Mt. Bach Village PRIVATE HOT TUB Wi/Fi A/C
3 bedrooms
3 bathrooms
Sleeps 8
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Amazing West Side * 2 King Suites * Walk Everywhere * 8 Person Hot Tub
5 bedrooms
4 bathrooms
Sleeps 10
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Historic Belle Millhouse in Bend, OR. Walk to Downtown.vrbo
2 bedrooms
1 bathroom
Sleeps 4
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Old Mill Getaway At Deschutes Landing
3 bedrooms
3 bathrooms
Sleeps 8
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Epic Riverfront Estate. Iconic Bend home. Walk everywhere. Recreate on river. 4
6 bedrooms
4 bathrooms
Sleeps 10
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Beautiful inside, amazing outside, bikes, kayaks, SHARC
3 bedrooms
3 bathrooms
Sleeps 8
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Amazing West Side * 2 King Suites * Walk Everywhere * 8 Person Hot Tub
5 bedrooms
4 bathrooms
Sleeps 10
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Craftsman Bungalow - Walk Everywhere! Only 2 Blocks To Downtown
2 bedrooms
2 bathrooms
Sleeps 6
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Pet Friendly, luxury log cabin with hot tub near Sunriver!
2 bedrooms
2 bathrooms
Sleeps 6
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Charming Bungalow, Location, Location, Location!
4 bedrooms
3 bathrooms
Sleeps 8
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20 acres private ranch 5 miles east of bend
7 bedrooms
3 bathrooms
Sleeps 16
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River View Condo, Close To Town/Mountain, New Private Hot Tub
2 bedrooms
2 bathrooms
Sleeps 6
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Luxury Home yet Family-Friendly! It's all about creating memories!
4 bedrooms
5 bathrooms
Sleeps 10
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Downtown Bungalow, Gourmet Kitchen, 2BR/1.5BA
2 bedrooms
2 bathrooms
Sleeps 5
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Downtown by the River! Cozy, Contemporary Cottage
2 bedrooms
2 bathrooms
Sleeps 6
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This waterfront home on Mirror Pond is steps away from Downtown Bend
3 bedrooms
3 bathrooms
Sleeps 8
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River View Contemporary Vacation Townhouse
2 bedrooms
2 bathrooms
Sleeps 4
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# 4 Backwoods Lodge 6BR/6BA SHARC, by Village, LD Wknd 4th nt free
6 bedrooms
6 bathrooms
Sleeps 15
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Amazing West Side - Walk Everywhere - Dog Friendly
1 bedroom
1 bathroom
Sleeps 2
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AWESOME Unobstructed Deschutes RIVER VIEW! Downtown Bend
1 bedroom
1 bathroom
Sleeps 4
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Bend Country Cabins/ Private Setting Pet Friendly - $90/night for 2 plus nights
2 bedrooms
1 bathroom
Sleeps 6
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Amazing West Side * Walk Everywhere * Dog Friendly
1 bedroom
1 bathroom
Sleeps 2
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Family-Friendly Luxury Retreat Featured On 2015 Tour Of Homes! DCCA#1253
4 bedrooms
6 bathrooms
Sleeps 12
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Cute Westside Craftsman, Walk to Downtown, Large Garage, Cruiser Bikes!
2 bedrooms
2 bathrooms
Sleeps 4
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Bend Getaway in RiverWild-Walk to Deschutes River and Old Mill District
3 bedrooms
3 bathrooms
Sleeps 8
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Beautiful 5 bdrm! Hot tub! River! Bring the dogs! 5 minutes to Sunriver Village!
5 bedrooms
4 bathrooms
Sleeps 16
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Stay In The Heart Of Bend, Walk Everywhere! New Hot Tub!
2 bedrooms
2 bathrooms
Sleeps 6
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Awesome location! Next to river, close to downtown. Walk everywhere!
2 bedrooms
2 bathrooms
Sleeps 6
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Great River Front Vacation Home in Sunriver with Hot Tub! Pet Friendly DCCA#1432
5 bedrooms
4 bathrooms
Sleeps 12
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The Executive Lodge up in the West Hills and is 2 miles from downtown Bend.
5 bedrooms
3 bathrooms
Sleeps 10
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Beautiful Family Vacation Home. 5 Bedrooms, Wi-Fi, Westside, 5mins from Old Mill
5 bedrooms
3 bathrooms
Sleeps 10
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Location! Location! BUNGALOW at DESCHUTES DUNES River & Beach
1 bedroom
1 bathroom
Sleeps 3
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Inn Wildness - A Cozy 1924 Cottage on Bend's Westside
2 bedrooms
1 bathroom
Sleeps 4
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DOWNTOWN RIVERFRONT HOME W/ RIVER ACCESS, BEST LOCATION, 2 MASTER SUITES!
4 bedrooms
3 bathrooms
Sleeps 8
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Log Lodge is close to Bend, Mt Bachelor, & Sun River, large enough for groups
6 bedrooms
4 bathrooms
Sleeps 22
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3 King Masters! Built-in Bunks! SHARC! A/C, Hot Tub, Location! Brand New Luxury!
5 bedrooms
5 bathrooms
Sleeps 16
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Perfect Staycation! 2 Bed 2 bath + Loft Cabin: 6 SHARC Passes, Dog Friendly
2 bedrooms
2 bathrooms
Sleeps 6
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Remodeled Historic Home In The Heart Of Bend. Available Summer 2020.
2 bedrooms
1 bathroom
Sleeps 4
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Great condo w/2 decks, near the slopes - city view (3rd bedroom option)
2 bedrooms
2 bathrooms
Sleeps 6
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Spectacular Luxury Old Mill District Townhouse Walking Distance To River Walk
2 bedrooms
3 bathrooms
Sleeps 6
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Perfect Escape! 3 BR home, SHARC passes/hot tub/bikes
3 bedrooms
2 bathrooms
Sleeps 8
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Caldera Springs Luxury home! Sleeps 12
5 bedrooms
6 bathrooms
Sleeps 12
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Serene Sunriver Home, Newly Remodeled!
3 bedrooms
2 bathrooms
Sleeps 6
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