Property with pools

Properties in Pine Meadow Village, Tollgate and Black Butte Ranch that have a seasonal pool available. Most pools are open Memorial Day thru Labor Day.


Properties Available 12 properties available
Experience the allure of this custom-built, ground-level condo nestled in the sought-after Pine Meadow Village. Enjoy the ample outdoor space that surrounds this 1720 sq. ft. home, complete with easy access to the clubhouse, offering a seasonal swimming pool and spa, conveniently located just across the street from this expansive property. Explore
Hot HOT 32
Mountain Sage
3 Bedrooms Pet Friendly
$124 - $538 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (9)
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 a 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-round spa and seasonal pool privileges are included
Hot HOT 21
Riley`s Mountain View
2 Bedrooms Pet Friendly
$118 - $307 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (17)
Welcome to Fairway View, a distinctive residence located on the 7th hole of Big Meadow golf course, in the prestigious Black Butte Ranch community.Inside, this three story home boasts generously sized living areas, perfect for family gatherings and entertaining. On the second level you will find a well-equipped kitchen featuring modern appliances,
Hot HOT 11
Fairway View
5 Bedrooms
$144 - $776 / per night
Bedrooms 5 bedrooms
Guests 11 guests
Let us welcome you to, Magical Sisters Retreat. A calm and relaxing 2 bedroom 2 bath condo located in the Pine Meadow Village neighborhood.  With easy access to Highway 20 and a short walk to downtown; you will be positioned perfectly to enjoy all that Sisters Oregon has to offer. When you enter you will be greeted by an open, bright and inviting s
Hot HOT 13
Magical Sisters Retreat
2 Bedrooms
$94 - $288 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
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 couple of blocks too! This upstairs condo has one
Hot HOT 14
Pine Rest
2 Bedrooms Pet Friendly
$110 - $231 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (15)
The 4th Sister Lodge - Bottom floor, easy access to assigned parking. These condominiums are surrounded by Creekside park where Whychus Creek runs year round. The complex features a seasonal pool and year round sauna and hot tub. Also a club house with a pool table, ping-pong, foosball and a fitness area. It's an easy walk to the historical town o
Hot HOT 12
Fourth Sister Retreat
2 Bedrooms
$114 - $350 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Experience a Tranquil Getaway at our 2-Bedroom Condo in Pine Meadow Village, Sisters OregonWelcome to our charming 2-bedroom, 2 full bath vacation rental condo located in the peaceful Pine Meadow Village neighborhood of Sisters Oregon. This delightful vacation retreat offers a comfortable and relaxing experience for up to 6 guests.Upon entering, yo
Hot HOT 34
Big Mountain View Condo
2 Bedrooms
$122 - $371 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Welcome to our charming and dog-friendly vacation rental nestled in the beautiful Tollgate community of Sisters, Oregon. This inviting home offers a perfect getaway for your family vacation to Central Oregon. With three bedrooms, a spacious yard, access to a seasonal pool, community basketball and tennis courts, your stay here promises to be a memo
Hot HOT 25
Lariat House
3 Bedrooms Pet Friendly
$150 - $455 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Jacob’s Ladder is a charming 3-bedroom, 2 1/2-bathroom family friendly vacation home ideally located in the community of Black Butte Ranch. With so much space, it is perfect for a family vacation, or getting together with friends. Inside, the well-appointed kitchen, complete with bar stools, opens up to a dining room for more formal meals. Relax in
Hot HOT 16
Jacobs Ladder - Black Butte Ranch
3 Bedrooms
$118 - $419 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 9 guests
Welcome to our charming vacation rental in the picturesque Tollgate neighborhood of Sisters, Oregon. This delightful getaway offers a comfortable and spacious retreat for your family or group of friends, boasting four bedrooms, two bathrooms, and a variety of amenities to make your stay memorable.As you step inside, you'll be greeted by a warm and
Halter Garden Home
3 Bedrooms Pet Friendly
$128 - $353 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
Rating 5 (3)
Escape to this charming and budget-friendly vacation retreat, perfect for two couples or a small family. With two inviting bedrooms and two bathrooms, this cozy haven comfortably accommodates up to six guests.Nestled just a stone's throw away, you'll discover the Tollgate seasonal pool, a tennis court, basketball court, a delightful children's play
Hot HOT 39
The Sisters Moose
3 Bedrooms
$98 - $190 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (21)
This Beautiful home has room for the whole family, extended family, and friends.  Located in the neighborhood of Tollgate, you are surrounded by acres of National Forest, have access to the seasonal pool, biking paths, a tennis court, and a basketball court.  Making memories is easy in this spacious home.  Imagine relaxing in the hot tub with your
Hot HOT 10
Wagon Wheel Home
5 Bedrooms
$124 - $652 / per night
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 5 (2)

Tell us what you're looking for and someone will contact you with available options.

I agree