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Holiday Rentals with Pools in Bend

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    Travellers to Bend are booking January dates now. Secure your holiday rental today, and have the perfect trip.
    26 Matching Rentals in BendView all 215 rentals
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    Mt Bachelor Village -Top floor with 2 Queen beds +1 / 22
    (7)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 5 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    • Hot Tub
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Of all the Bend, Oregon rentals to vacation in, River Ridge 617, is certainly one to see all the sights. Enjoy the impressive views of the Deschutes River, as well as the amenities of Mt. Bachelor Village Resort, including a swimming pool, tennis courts and more. This three-bedroom condominium has...
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    Bend, Central Oregon 97702
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Hot Tub
    • Mountain Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you're looking for the best of Bend's luxury vacation rentals, Outcast is an ideal choice. Named for one of the owner's favorite craft beers at Crux Fermentation Project, Outcast is the perfect balance of down-to-earth attitude and elegant luxury. Located in the far-Westside neighborhood of...
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    Bend, Central Oregon 97702
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Hot Tub
    • Parking
    • Wi-Fi
    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay in style at Mt. Bachelor Village, home to some of the nicest vacation rentals in Bend, Oregon, and just a short drive or walk from Old Mill District!  This unit is great for one large family or two small families traveling together, and can be combined with our Big Eddy and Big Boulder...
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    Bend, Central Oregon 97702
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Parking
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 3 Bedroom, 3 Bath Mt Bachelor Village Condo features 3 master suites. Two Queen Master Suites are located on the first floor and a King Master Suite on the second floor. The King Master Suite has a private balcony with birds nest views of the river. Relax in the living room, which features a...
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    Bend, Central Oregon 97702
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Parking
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The living room features a gas fireplace, comfortable furniture and a TV. There is a washer and dryer in the unit and the balcony has a BBQ and patio table for your use. You can enjoy all the Mt.Bachelor Village amenities: WIFI, community pool (seasonal) and 2 hot tubs (year round). The Deschutes...
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    Bend, Central Oregon 97702
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Addie Triplett Loop is located in Bend's Southeast residential area close to Bend Golf Club area! Short drive to grocery stores, restaurants, and shopping. Easy parkway access for daily commuting and only 10 minutes to Old Mill District, 15 minutes to Downtown. If you're looking for a long term...
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    Bend, Central Oregon 97702
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    7th Mountain Resort in Bend, Or1 / 21
    (3)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Hot Tub
    • Wi-Fi
    • DVD Player
    • Children's Pool
    • Air Conditioning
    • Sauna
    • Cable/satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 June 2018
    Very comfortable lodging. The condo owner was very responsive to a small issue.The children enjoyed the pool and miniature golf.
    Reviewed 14 July 2016
    Checking in was our first Summer Time Delight. My friend loved the Iced Tea and shared one with me. And yes it was indeed the best ice tea we ever had. Made just right not too...
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    About this property
    Very clean, light and comfortable, well furnished one bedroom two full baths/shower/tub. Sleeps 4 very comfortably. Includes all utilities, wifi, basic cable, land line and use of all amenities. Fireplace ( presto log only), balcony with Deschutes Forest views and of the Paulina's. On site you...
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    Location Information
    Bend, Central Oregon 97702
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Luxury and Comfort at Mount Bachelor Village Condo, Views, Mountains and Lakes!1 / 42
    (7)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Parking
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 October 2018
    The condo was all updated and absolutely gorgeous! It came stocked with all the essentials needed during our stay. We found ourselves wanting to just stay in the condo and relax...
    Reviewed 29 June 2018
    This is a great location to relax and escape the everyday hustle. It was great to have a big enough space to enjoy the family,cooking and playing together. The grand-kids loved...
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    About this property
    Located in beautiful Mount Bachelor Village offering spectacular views of downtown Bend & Old Mill District. This Condo House is 2.0 miles from downtown Bend and 20 miles from the slopes of Mount Bachelor Ski Resort. Nearby activities include downhill & cross-country skiing, ice skating,...
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    Bend, Central Oregon 97702
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Mt.Bachelor Village Resort--Comfortable living1 / 14
    (8)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Balcony
    • Patio
    • Wi-Fi
    • DVD Player
    • Mountain Views
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 February 2018
    If you want privacy and roominess close to skiing and just outside Bend, this the place. Some variation in the units but same basic amenities. Updates must be on a rotation...
    Reviewed 13 September 2017
    If you're looking for a quiet and out of the mainstream place, this is it!The surroundings are amazing.There are trails for walking and a short distance from water sports.I...
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    About this property
    Located on Bend's westside, a short walk along the Deschutes to the Old Mill district and off the Cascade lakes road to Mt.Bachelor, this cozy, recently upgraded condo in Mount Bachelor Village is a convenient base for any recreation or vacation plans. Features a full kitchen with stainless steel...
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    Location Information
    Bend, Central Oregon 97702
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Condo at 7th Mountain Resort Enjoy proximity to Mt. Bachelor and just seven miles to Bend in this modern, ground-floor one-bedroom condo at 7th Mountain Resort. Situated along the Deschutes River and ensconced in the Deschutes National Forest with wonderful amenities, 7th Mountain gives you access...
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    Location Information
    Bend, Central Oregon 97702
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    2BR Serene Sunriver Condo w/ Pool & Hot Tub - Minutes to The Village1 / 24
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • DVD Player
    • Washer
    • Grill
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 March 2018
    This apartment provided a pleasant, low cost base for winter recreation in Sunriver. The mostly new floors, kitchen, and furnishings showed good taste and quality. The beds...
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    About this property
    This 2BR condo offers a peaceful getaway with easy access to year-round activities. The welcoming first-floor unit features hardwood floors, new furnishings, and a private patio. On-site amenities include a seasonal heated pool and hot tub. Located less than one mile from local dining and...
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    Location Information
    Bend, Central Oregon 97707
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Private loft condo - Seventh Mountain Resort1 / 2
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Grill
    • Wi-Fi
    • Parking
    • Sauna
    • Hot Tub
    • Children's Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 May 2015
    This was a great place to stay when going to a show at the amphitheater. It is an older place with a few older fixtures, but very comfortable and practical. Great value. Make...
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    About this property
    Bendgetaway is a privately owned 2 bed/2 bath loft condominium located within the Seventh Mountain Resort near the town of Bend in central Oregon. Central Oregon is known for it's nearly 300 days of sunshine per year!
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    Bend, Central Oregon 97702
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Washer
    • Wi-Fi
    • Sauna
    • Patio
    • Cable/satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This appealing 4BR/2BA home sits in a quiet Sunriver neighborhood minutes from Fort Rock Park. Enjoy complimentary passes to the Sunriver Aquatic & Recreation Center, an all-season center that offers indoor and outdoor aquatics, a disc golf course, winter tubing hill, as well as basketball and...
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    Location Information
    Bend, Central Oregon 97707
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Grill
    • Air Conditioning
    • Patio
    • Washer
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Peaceful in the Parks You’ll enjoy peace and quiet in this desirable Westside home in The Parks, an exclusive neighborhood with its own community park and pool. But you’ll also love its proximity to all the activities you want to access in your visit to Bend: rafting the Deschutes River, golf at...
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    Bend, Central Oregon 97702
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Grill
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Split across two levels, this inviting 3BR/2.5BA condo in Sunriver is located on Sunriver’s north end, putting you within close proximity to a host of local attractions. Meadows Golf Course, Sunriver Tennis, and the Deschutes River are all walking distance. Your rental will include passes to SHARC...
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    Bend, Central Oregon 97707
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Updated Mt Bachelor Village Condo for 6 Slope Lovers. 3 Couples or 1-2 Couples with Kids. Since this is a new listing, we encourage you to contact us so we can tell you everything you need to know about it, and about getting the most out of your stay here in Mt Bachelor Village resort. SLEEPING...
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    Bend, Central Oregon 97702
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Hot Tub
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Family-friendly Mt Bachelor Village Condo accommodates 6 skiers, snowboarders and swimmers. Since this is a new listing, we encourage you to contact us so we can tell you everything you need to know about it, and about getting the most out of your stay here in Mt Bachelor Village resort....
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    Bend, Central Oregon 97702
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Private Garden
    • Wi-Fi
    • Secure Parking
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape the hustle and bustle of normal life by retreating to this beautiful 3-bedroom, 3-bathroom vacation rental house that sleeps 12 in Bend. Nestled on 2 private acres, this home boasts a large deck with an in-ground pool and outdoor fireplace, perfect for relaxing outside and enjoying the...
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    Bend, Central Oregon 97701
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
    • DVD Player
    • Washer
    • Hot Tub
    • Patio
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With an ultra-spacious floor plan and crowd-pleasing perks, this 5BR/5.5BA Sunriver home is perfect for a big group getaway! The house overlooks the second fairway at Woodlands Golf Course, and boasts an array of amenities, including a pool table, ping-pong, and private hot tub. An upscale...
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    Bend, Central Oregon 97707
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Washer
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled in picturesque Sunriver, this pet-friendly 3BR/2BA is a nature lover’s dream. Highlights of this updated cabin-style home include rustic-chic decor, wood paneling, and cathedral ceilings offering loads of natural light. Take in gorgeous views from the multi-level deck or soak in the private...
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    Bend, Central Oregon 97707
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Patio
    • DVD Player
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Steps from the Deschutes River and Cardinal Landing Bridge, this exceptional 4BR/3.5BA home boasts a private hot tub, two decks, an inviting Great Room. Enjoy access to Sunriver's Aquatics Center, complete with multiple pools and a lazy river. Additional recreational activities include a disc golf...
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    Bend, Central Oregon 97707
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Mountain Views
    • Washer
    • Skiing: Property Is In A Ski Resort
    • Air Conditioning
    • DVD Player
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bring the whole family along for a trip to this 4-bedroom, 3.5-bathroom vacation rental house that sleeps 12 in Sunriver! While the home boasts 2,100 square feet of living space, the amenities featured are what truly takes the cake - including 3 outdoor decks, a billiards table, 9 bikes provided,...
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    Location Information
    Bend, Central Oregon 97707
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Wi-Fi
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Washer
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Sage Springs Cabin! Tennis Village condo in Sunriver is perfect for family looking to get lost in the beauty of Central Oregon Since this is a new listing, we encourage you to contact us so we can tell you everything you need to know about it, and about getting the most out of your...
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    Bend, Central Oregon 97707
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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