Holiday rentals with a pool in Deschutes County

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Top-rated rentals with a pool in Deschutes County

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite
Cabin in Sisters
4.94 out of 5 average rating, 123 reviews

Cozy family cabin in Sisters, Central Oregon.

Relax with the family at this peaceful well appointed spacious cabin that embodies the spirit of central Oregon. The cabin is located 3 miles from Downtown Sisters, 20 minutes to Hoodoo & 10 minutes to Black Butte Ranch. We've geared the spaces towards fun and relaxation. Well curated amenities will help your family enjoy all that the Sisters area has to offer. From an easy to use propane fireplace to a fenced backyard for your pup, fully stocked kitchen, comfy beds and kid friendly amenities!

Guest favourite
The living area features high vaulted ceilings with wooden beams and large windows allowing natural light to fill the space. A stone fireplace is the focal point, surrounded by comfortable leather seating and a centerpiece table. Colorful accents offer a pop of vibrancy to the neutral decor.
Condo in Sunriver
4.91 out of 5 average rating, 149 reviews

Short walk to SR Village and SHARC, includes bikes

Enjoy Sunriver’s most popular amenities located a short walk to The Village and SHARC including a tubing hill, pool’s and hot tub. This recently renovated, rustic modern condo is in the heart of Sunriver Village. It’s truly a retreat being an end unit, offering great views and ample privacy. Leave everything at home, this condo comes equipped with all things needed to enjoy your stay! There are 2 sleds and bikes of various sizes to go cruise the miles of paved bike paths, right outside the door.

Top Guest favourite
A spacious living area features a sectional sofa in neutral tones, accompanied by a soft area rug. A stone fireplace adds warmth, while large glass doors open to a private balcony with outdoor seating. Natural light fills the room, enhancing the inviting ambiance.
Condo in Sisters
4.99 out of 5 average rating, 137 reviews

Beautiful Sisters Condo - Great location

Great location! Remodeled 2 bedroom and 2 bath condo is a spacious retreat set within the pine trees. The complex includes a seasonal pool. The hot tub/sauna are open year round. The club house includes ping pong, foosball and a pool table. You just need to walk through the city park and across the creek to get into town. We are also located a block or two from the MovieHouse and Three Creeks Brewing. Enjoy bike paths close by and lots of hiking in the area. Easy self check-in and out.

Guest favourite
The exterior of the home displays a combination of dark blue siding and natural stone accents. A spacious front porch is featured, along with two garage doors and a wide paved driveway. The sloped roof adds to the home's structural interest.
Home in Redmond
4.86 out of 5 average rating, 119 reviews

Stunning mtn Views, sleeps 14, Hot tub, rec passes

Enter the first floor to immediate views of the Cascade Mountain range. The fully-equipped kitchen with Sub-Zero Fridge and gourmet range has direct access to the wrap-around deck, which features an outdoor dining area gas fireplace & gas grill. Upstairs you’ll find the primary suite with king bed with a private balcony boasting views of seven Oregon’s tallest peaks; the bunk room, & queen bedroom. Downstairs is another bedroom, game room, wet bar, 65” TV, & access to the hot tub. Don’t wait!

Top Guest favourite
The modern A-frame cabin is surrounded by snow-covered trees, highlighting its dark exterior. A deck extends around the cabin, accentuated by a row of small evergreen planters against the backdrop of a winter landscape, showcasing the serene setting.
Cabin in Sisters
4.92 out of 5 average rating, 131 reviews

Popular BBR A-Frame | 2 golf courses | 5 pools

Welcome to Your Modern A-Frame Cabin at Black Butte Ranch! - Accommodations: Sleeps 8 in 2 queen bedrooms and a 2 twin loft, and trundle downstairs - Amenities: Relax in the living area with a Roku TV; the chef's kitchen makes meal prep easy, and self check-in ensures a smooth arrival - Sunny Recreation: Access to 6 pools, including the nearby Paulina pool, plus golf, pickleball, horseback riding, and hiking - Winter Fun: 20m drive to HooDoo Ski Resort Book your unforgettable getaway today!

Guest favourite
Home in Sunriver
4.94 out of 5 average rating, 140 reviews

Hot Tub +Bikes +8SHARC Passes +PingPong +Fireplace

Stylish luxury family home w/8 SHARC passes (pool & lazy river), 6 Cruiser bikes, Hot Tub, 3 New Smart TV's for streaming, Ping Pong table, board games. Short walk to the river & Cardinal Landing Bridge. Fast 1GB WiFi, propane BBQ, Air Conditioning, cozy wood burning fireplace. Fully stocked kitchen for cooking, laundry inside. Quiet + Private w/large deck backing up to natural common space w/wildlife walking by. Bike everywhere w/easy access. Minutes to Mt Bachelor for skiing & sledding.

Guest favourite
A classic two-story home is presented against a vibrant sunset sky. The wrap-around porch features white columns and is surrounded by neatly trimmed shrubs. Large windows face the yard, allowing for ample natural light to enter the living space.
Home in Sisters
4.97 out of 5 average rating, 102 reviews

Downtown Pine Mountain Paradise

Classic Pine Meadow Paradise! 3 bedrooms and an additional ADU, this consists of one King bed, two Queen beds and two twin beds. You will love all of the natural light and french doors right off the living room. Fully equipped kitchen with Island. Master bedroom has mountain views, sandstone shower and soaking tub upstairs. There is also a private ADU over the garage guests are free to use. Enjoy sitting around on the wrap around porch with your favorite drink with family and friends.

Top Guest favourite
The exterior of a large two-story house is displayed, featuring a covered porch supported by columns. Lush green grass surrounds the structure, complemented by neatly arranged shrubs. A clear blue sky with soft clouds is visible above, enhancing the overall setting.
Home in Bend
4.92 out of 5 average rating, 272 reviews

Updated Game Room! Hot Tub, SHARC (8), 2,800sq/ft

Your winter getaway or ski trip. Updated Game Room!! Escape to our Sunriver house. 2,800sq/ft - Big enough to entertain with lots of room for everyone, coffee with someone or everyone together. You'll have everything you need for a fun family, couples, girls trip or guys getaway. Living Room, Game Room & 3 decks/patios are yours to enjoy when not exploring all Sunriver has to offer. Game room has foosball, darts, basketball, pool, ping pong, sound bar, & TV (Firestick with YouTubeTV.)

Top Guest favourite
Home in Sisters
4.93 out of 5 average rating, 133 reviews

Modern Tollgate Home - HOT TUB | Half Acre Lot

This newly renovated 3 bedroom/2 bathroom home sits on more than a half acre lot in the quaint town of Sisters. When you stay at this Tollgate home you get all of the community amenities with it: community pool, pickle-ball/tennis courts, walking trails, basketball courts, etc. Bring the whole family as we comfortably sleep 6 people and enjoy the hot tub! This is an incredibly well-done high-end modern home that is virtually brand new. We are also a dog friendly home ($100/stay fee).

Guest favourite
A modern home is surrounded by snow-covered trees, showcasing large windows that reflect natural light. The wooden exterior complements the winter landscape, while steps lead from the porch to the yard blanketed in fresh snow.
Home in Sisters
4.92 out of 5 average rating, 133 reviews

Black Butte Ranch Home with THE View

With a view like no other, you’ll be able to slow down, take it all in and press reset. You’ll be centrally located with an unobstructed view of the magnificent meadow. Floor to ceiling windows will have you gazing DIRECTLY at beautiful Black Butte throughout your stay. *Effective 1/1/24: All posted rental rates include your resort fee that Black Butte Ranch Resort charges for access to the resort amenities. Homeowners remit payment to the resort and do not retain any of this fee.

Top Guest favourite
A modern studio features a spacious bed with crisp white linens, a wooden accent wall, and an electric fireplace below a wall-mounted television. A unique wood table sits atop an area rug, with plants adding a touch of greenery to the warm atmosphere.
Condo in Bend
4.98 out of 5 average rating, 289 reviews

Sunriver Studio with Pool and Hot Tub

This stylish studio in the heart of Sunriver is newly remodeled with a King bed. Seasonal pool and year round Hot Tub! Just a short walk to a brand new food truck lot with 7 trucks, indoor and outdoor seating and a bar. Fast WiFi, a new Samsung 50” tv signed into Netflix, Hulu, HBO Max and more. 25 minutes to Mt. Bachelor. 25 minutes to downtown Bend. Parking is just a few feet from your door. This super clean condo is perfect for all of your central Oregon adventures.

Top Guest favourite
The exterior of the chalet is showcased, featuring a peaked roof and large windows that allow ample natural light. A spacious wooden deck is present, accompanied by outdoor seating and a barbecue. The surrounding grassy area enhances the outdoor setting.
Chalet in Eagle Crest
4.98 out of 5 average rating, 266 reviews

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!

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