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Holiday Rentals with Pools in Sisters

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    Travellers to Sisters are booking October dates now. Secure your holiday rental today, and have the perfect trip.
    18 Matching Rentals in SistersView all 48 rentals
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Mountain Views
    • Air Conditioning
    • Hot Tub
    • Wi-Fi
    • Washer
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You can't beat this practically new home on the west side of Pine Meadow Village. A corner lot with an awesome view of Three Sisters. Relax on our large covered porch and watch the mountains, sunset, and roaming deer. Or just relax in our living room and view it all out of two sets of glass...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Patio
    • Cable/satellite TV
    • Grill
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This vacation home sits on a beautifully landscaped home site with large Ponderosas and vine maple, a perfect habitat for abundant birds and wildlife. The spacious back deck is very private, bordering forest land and there are bird houses everywhere for nesting and a wonderful hot tub to relax in...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    • Internet Access
    • Air Conditioning
    • Mountain Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This condo takes full advantage of the gorgeous views of the 10th Fairway plus the North, the South Sister Mountains as well as Broken Top. There is a large Trex deck where the views are stunning to sunbathe, enjoy the golfers, evening BBQs with family or just relax with friends. This may be the...
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    Sisters, Central Oregon 97759
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Mountain Views
    • Cable/satellite TV
    • Waterfront
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stunning rental home will help make your family's Black Butte Ranch vacation the best ever! A beautiful entry leads to a staircase that enters on the main floor. The room showcases soaring ceilings and windows and natural light from all directions. The 'grand' great room consists of a very...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Washer
    • Mountain Views
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Inviting and sunny, the wall of windows and vaulted ceilings make this condo a delight to be in, in the quaint Pine Meadow Village neighborhood. Enjoy everything Sisters has to offer, walk to everything in town, hang out at the pool (seasonal), or soak in the hot tub. There are tennis courts just a...
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    Sisters, Central Oregon 97759
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    5 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Washer
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    As you walk into this five bedroom house, you will feel as if you have come home! Charming decor and warmth will make you feel welcome and comfortable. The entry enters into the large great room, with an open concept living space of living room, dining room, and kitchen. The kitchen is updated...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 11
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Patio
    • Washer
    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Grill
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious (1,744 sq. ft) home has loads of charm and is beautifully updated. Surrounded by Ponderosa Pines and within a short walk to the popular Paulina Springs Pool area, it will be ideal for your family vacation. Paulina Springs Pool, which is as unique as Black Butte and this beautiful...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Hot Tub
    • Parking
    • Washer
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great affordable vacation home for 2 couples or a small family, 2 bedrooms, 2 bathrooms, will sleep up to 6. Free pool access at the Tollgate seasonal pool, biking paths all around the community, a tennis court, basketball court and many acres of National Forest land for miles of mountain biking or...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Mountain Views
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Park the car and walk or bike to everything in town, mountain views and A/C. Come to Sisters and take in the views of four mountains and pond w/seasonal fountain from this condo. It is on the west edge of Sisters and only a few blocks to the heart of downtown Sisters to shop, dine, browse. Year...
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    Location Information
    Sisters, Central Oregon 97759
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Wi-Fi
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful custom built condo on ground level in desirable Pine Meadow Village with exceptional outdoor space. Spacious, 1720 sq. ft. of living space, the clubhouse, with seasonal swimming pool and year round spa, is conveniently just across the street from this very spacious property. Walking...
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    Sisters, Central Oregon 97759
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Washer
    • Patio
    • Grill
    • Internet Access
    • Air Conditioning
    • Parking
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This four bedroom charmer is welcoming and close to many facilities. GM#235 is a single level 2,100 sq. ft home with four bedrooms and three baths. The bunk room is off the family room and has a nearby 1/2 bath. Down the east hallway is a queen bedroom with bathroom across the hallway and a king...
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    Sisters, Central Oregon 97759
    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
    • Washer
    • Air Conditioning
    • Waterfront
    • Mountain Views
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cozy, charming condo is in a prime location. Walk to most facilities and enjoy the stunning scenery Black Butte offers every time you look outside or venture onto the deck! Perfect for the sunbather or wildlife buff or photographer. This condo is ideal for experiencing the true ambiance of...
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    Sisters, Central Oregon 97759
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Skiing: Property Is In A Ski Resort
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Remodeled in 2015, this 5 bedroom, 2.5 bath beautiful Black Butte Ranch home sits on a double lot, has an upgraded kitchen and bathrooms, and features natural bamboo flooring.  The main level master suite with king bed and large soaking tub provides a quiet sanctuary for guests. Two additional...
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    Sisters, Central Oregon 97759
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Grill
    • Washer
    • Cable/satellite TV
    • Balcony
    • Wi-Fi
    • Patio
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 5BR/4BA home offers a private, woodsy stay at Black Butte Ranch, where you can spend your days reading on the wraparound deck, exploring the trails, or making new friends at the horse stable. The Lodge, with indoor pool and rec center, is just a few miles away. Your 3,000 square foot retreat...
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    Location Information
    Sisters, Central Oregon 97759
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Patio
    • Washer
    • Hot Tub
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Room for your whole family in this beautiful spacious home in a great location for your family vacation, just minutes from downtown Sisters. Come and make memories with your loved ones! Free pool access at the Tollgate seasonal pool, biking paths all around the community, a tennis court, basketball...
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    Location Information
    Sisters, Central Oregon 97759
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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