Holiday rentals with a pool in Bend

An aerial view captures the expansive property featuring a lush English Country Garden filled with vibrant flowers and greenery. A serene swimming pond is visible in the foreground, while the well-maintained guest suite is framed by trees in the background.

4.99 out of 5 average rating, 201 reviews

Luxurious Private Tumalo Suite Nestled in Trees

The Treehouse Guest Suite is nestled in the trees in the beautiful community of Tumalo, Oregon! Tumalo, a short 10 minute drive west of Bend, is well known for its beauty to include easy access to hiking and biking trails. Your second floor craftsman style guest suite is surrounded by trees and includes a private entrance, garage, and deck. Our farm has scenic views of the Cascade Mountains. During the summer, guests can enjoy our English Country Garden, swimming pond, and Alpacas in the field.

A modern kitchen features green cabinetry and a large marble island with seating. Stainless steel appliances, including a refrigerator and microwave, are prominently displayed. Natural light flows in through nearby windows, enhancing the open layout adjacent to a cozy living area.

4.97 out of 5 average rating, 206 reviews

Walk to Everything! Hot tub, SHARC passes

- Hot tub water is drained and refilled with fresh water between EVERY guest stay! - Best location in Sunriver! - Just steps (2-minute walk) from Sunriver Village (Coffee, restaurants, shops, bike/ski rentals, ice cream, grocery store, ice skating, mini golf, bouncy houses, rock climbing). Fully renovated 3 bedroom (plus a loft with bunks!), 3 bath home right next to Sunriver village! - 8 reusable waterpark passes, and just a 5-minute bike ride or 10-minute walk, to the SHARC waterpark.

4.99 out of 5 average rating, 138 reviews

A modern living room is highlighted by a large flat-screen TV and a stylish fireplace. Expansive windows provide views of the outdoors, allowing natural light to fill the space. Comfortable seating arrangements create an inviting area for relaxation.

Home in Sisters

Cozy Mountain Escape: Amazing Views! Hot tub!

Relax in this calm, stylish newer home! The unobstructed mountain views are Jaw-dropping!! Walking distance to all that this amazing town has to offer. Enjoy the mountains and wildlife from the upper and lower decks after a day of exploring. Located in the desirable Pine Meadow Village neighborhood. Includes access to clubhouse, with a seasonal pool and a hot tub. You will take part of the mountain escape experience with you, wherever you go, and the memories you create will last a lifetime!

A comfortable guest suite is designed with a spacious bed covered in a white quilt. An accent wall of exposed brick enhances the warm ambiance. A wooden desk and two brown armchairs complement the space, with light filtering through a window dressed with blinds.

4.97 out of 5 average rating, 232 reviews

River Ridge Getaway - River Trail & Hot Tub

Our peaceful guest suite with private entrance & pool/hot tub access is in Mt Bachelor Village, nestled in the trees above the scenic Deschutes River trail where you can enjoy walking, jogging, floating, kayaking, SUP, surfing, rock-hounding and fishing. It is one of the best locations in town, just off Century Dr on the way up to Mt Bachelor Ski Resort and within walking distance to the The Old Mill, Hayden Homes Amphitheater and Bend's popular west side. Pool (Jun-Sep) & Hot Tub (10am-9pm)

A private patio features a bubbling hot tub and an umbrella table with chairs. Nearby, a gas grill is positioned for outdoor cooking. Soft lighting enhances the space, while large windows offer views into the cozy interior.

4.97 out of 5 average rating, 228 reviews

Romantic Guest House w/Hot Tub, Pool, Tennis Court

Sweetums Guest House is a private, beautifully appointed 2 bedroom, 2 bath guest house located on 20-acre Sweetums Ranch. Amazing views of Three Sisters and Broken Top mountains from the property, horses,& abundant wildlife viewing. 8 mi to downtown Bend & 12 mi to Sisters. 45 min to Mt Bachelor and mountain trailheads. Large private yard & partially covered patio w/private hot tub. Amazing swimming pool and tennis court. On the Oregon scenic bike route. A perfect location for your getaway!

4.81 out of 5 average rating, 161 reviews

The living area features large windows providing views of the river, with natural light enhancing the space. A comfortable blue couch and two armchairs are arranged around a wooden coffee table. The stone flooring adds texture, and patio doors offer easy outdoor access.

Apartment in River West

Riverfront Cottage - Steam Room & Pet Friendly!

Welcome to "Hot Damn", up to three guests can stay here, on the queen bed and a twin size sleeper sofa (in the living room). You’ll have everything you need to relax and take in the beauty of the Deschutes River and popular Trail through the windows or on your patio. Enjoy heated floors, a fireplace, in unit laundry, a huge walk in shower that doubles as a steam room, as well as access to an indoor pool and hot tub! Bring along 2 pets for a one-time fee ($55.95/pet), requested after booking.

The open living space features high ceilings with natural light flooding in through large windows. A comfortable sofa and coffee table are present, while a dining area with four chairs is visible. A spiral staircase leads to a loft area, enhancing the room's spacious feel.

4.84 out of 5 average rating, 490 reviews

*Sunriver* HotTub/Pool In Room Sauna Popcorn Cart

Calm, quiet and friendly condo with loft in Powder Village, Sunriver. Located walking distance from the Main Village at Sunriver. 26 minutes to Mt. Bachelor. The condo has it’s way of leaving a good impression as the natural sunlight, high ceilings and overall comfort level tend to leave people feeling uplifted, welcome and at ease. Private, in room infrared sauna for two and adventure kit included. Community laundry room is available and Netflix login is provided to all guests.

The open kitchen and dining area features high wooden ceilings and large windows, allowing ample natural light. A spacious wooden dining table with multiple chairs accommodates larger groups. A well-equipped kitchen with modern appliances and wooden cabinetry is visible, enhancing the inviting atmosphere.

4.89 out of 5 average rating, 409 reviews

The House on the River

From the moment you enter the neighborhood, you will enjoy a very private road that is peaceful and tranquil. The neighborhood is full of beautiful trees, birds, and an abundance of deer that roam the area frequently laying in and enjoying the large front yard. Bring the bikes for the kids to enjoy riding in the big circular driveway or through the neighborhood. You can take in the surrounding nature with a walk along the river trail. Licensed. Deschutes County license 1443

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.

4.97 out of 5 average rating, 265 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.

A two-story, brown wooden building is featured, with a staircase leading to the upper level. A bicycle is parked next to the structure, and a tree provides greenery against the exterior. Windows are present on both levels, allowing natural light to enter.

4.91 out of 5 average rating, 216 reviews

Comfortable Powder Village Condo in Sunriver OR

Enjoy the quiet, natural back-drop of undeveloped land out the front door of this comfortable Powder Village condo. This ground-level condo offers sleeping for 5 guests (2 bedrooms with queen beds, 1 full size sleeper sofa) and 2 full baths. Seasonal outdoor pool/year-round hot tub, Washer/Dryer, Wifi, Keurig coffee maker, Vizio & Roku Smart TVs. Walking distance to The Village at Sunriver and easy access to bike/walking trails and nearby Mt. Bachelor.

The living area features a cozy leather sofa facing a mounted television. A wooden coffee table is centered on an intricately patterned rug. Two windows allow natural light to fill the space, complemented by light-colored walls and decorative elements.

4.94 out of 5 average rating, 267 reviews

Bungalow at The Parks

Our Bungalow has easy access to Mt. Bachelor, Bend's famous mountain bike trails, one mile from OSU Cascades, very near Old Mill shopping and dining, and easy access to downtown Bend, also. You’ll love our place because of the coziness, the comfy bed, and private access to your space. The Bungalow is good for couples, solo adventurers, and business travelers. Our neighborhood pool is open May through August.

The room features a queen bed with a light-colored bedspread, accompanied by bedside tables with lamps. A cozy seating area with cushions is beside a large window, allowing natural light to illuminate the space. Artworks are displayed on the walls, enhancing the serene atmosphere.

4.86 out of 5 average rating, 255 reviews

Mt Bachelor Village Resort- Room in River Ridge II

Hotel style room with private entry in forested Mt Bachelor Village Resort on the westside of Bend. Quick access to hiking, biking, the river trail, Old Mill district, Mt Bachelor, and many restaurants and breweries. It's a nice walk or bike ride to the Old Mill district and 2.5 miles from downtown Bend. The beautiful Deschutes River Trail is just down the hill from our unit-great for that morning walk or jog!

Popular amenities for Bend rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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.

4.92 out of 5 average rating, 266 reviews

SR Escape- Hot Tub, Game Room, 8SHARC, 2,800sq/ft

A spacious living area features a high ceiling with wooden beams, enhancing the sense of openness. A modern sectional sofa is arranged around a central coffee table. Natural light floods through a large window, while a cozy seating nook with stylish decor and a fireplace adds warmth to the space.

4.96 out of 5 average rating, 112 reviews

The Birch Abode: Spacious & Serene-Sleeps 8 +SHARC

The exterior of the home displays a two-story structure nestled among tall trees. A wooden deck features a table and chairs, a barbecue grill, and an umbrella for shade, providing an inviting space for outdoor relaxation.

4.88 out of 5 average rating, 178 reviews

Sunriver home 8 SHARC passes, hot tub, wood stove

A spacious living area features a comfortable L-shaped sofa adorned with a light throw. Natural wood beams accentuate the ceiling, while a gas fireplace adds warmth. A flat-screen TV is visible, and a dining table with bar stools is situated nearby against neutral-toned walls.

4.85 out of 5 average rating, 112 reviews

Updated Sunriver-Hot Tub, Walk to SHARC & Village

4.97 out of 5 average rating, 169 reviews

An indoor pool room features a heated dipping pool, surrounded by vibrant red lounge chairs. A seating area is present with a couch and decorative pillows, while bright artwork adorns the walls. Sliding glass doors allow natural light and lead to the outside.

Home in Larkspur

Family Friendly Home | Indoor Pool | Pets Welcome

4.93 out of 5 average rating, 120 reviews

The exterior of the modern home features dark blue siding and stone accents, set against a backdrop of tall pine trees. A well-paved driveway leads up to a two-car garage. A warm glow emanates from windows, hinting at the inviting interior.

Home in Sisters

Modern Tollgate Home - HOT TUB | Half Acre Lot

The exterior of the cabin is shown, featuring a sloped roof and welcoming front porch. Surrounded by trees, the landscaped front yard includes green grass and shrubs, creating a serene atmosphere. A gravel pathway leads up to the entrance, emphasizing the cabin's inviting presence.

4.94 out of 5 average rating, 144 reviews

3BR/3BA | Hot Tub +SHARC +AC +Pool Table+Ping Pong

4.96 out of 5 average rating, 484 reviews

An expansive deck overlooks the Deschutes River canyon, featuring a hot tub and several outdoor seating areas. The rugged landscape is characterized by rocky cliffs and sparse vegetation, leading to a serene view of the river winding through the canyon.

Home in Terrebonne

Canyon House, Crooked River Ranch

Apartment rentals with a pool

A cozy living area is highlighted by a modern fireplace and a mounted TV. Comfortable seating is arranged around a wooden coffee table. The room features a blend of textured stone and wood paneling, complemented by a blue accent wall.

4.82 out of 5 average rating, 341 reviews

Updated Condo steps to SR Village, 8 SHARC passes!

A comfortable living area showcases a cozy sofa and a well-lit dining space with a light-colored table surrounded by colorful chairs. Natural light filters through the windows, illuminating the modern vinyl flooring and the stylish decor elements, including a wall-mounted TV above a decorative fireplace.

4.9 out of 5 average rating, 145 reviews

Adorable Studio at Seventh Mountain Resort

An open living area features a modern design with a cozy seating arrangement, including a comfortable couch and accent chairs. A fireplace is positioned against a neutral wall, while large windows offer a view of the balcony and surrounding forest.

4.92 out of 5 average rating, 73 reviews

Sunrise view! Pool HotTub Sauna IceSkate Disc-Golf

4.96 out of 5 average rating, 127 reviews

The open living area features two brown leather couches and a large coffee table set on a patterned rug. A flat-screen TV sits on a white media console. Bright natural light enters through multiple windows, creating a welcoming atmosphere that connects to the dining area.

Apartment in Sisters

Renovated Sisters Condo; perfect getaway!

4.99 out of 5 average rating, 126 reviews

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.

Apartment in Sisters

Beautiful Sisters Condo - Great location

A shared pool area features a spacious swimming pool and a separate hot tub, surrounded by tall trees. Lounge chairs are arranged around the pool, alongside a patio table with chairs set on a paved surface, providing a tranquil outdoor space.

4.97 out of 5 average rating, 242 reviews

*A/C* Family Friendly/Forest view/Hot Tub/Pool*

The fully equipped kitchen features granite countertops and wooden cabinetry. Large windows allow natural light to fill the space, providing views of the surrounding forest. The kitchen area includes modern appliances, a kitchen island with seating, and overhead lighting for an inviting cooking environment.

4.86 out of 5 average rating, 292 reviews

Mt. Bachelor Village Condo - Near Town & River

A spacious living area features a comfortable grey sectional sofa and a wooden coffee table. Large windows provide natural light and showcase views of surrounding trees and mountains. A circular mirror is mounted on the wall, enhancing the sense of openness in the room.

4.95 out of 5 average rating, 101 reviews

Modern 3-bedroom Seventh Mountain Resort Condo

Other holiday rentals with a pool

4.98 out of 5 average rating, 45 reviews

The living area features wood-paneled walls and a vaulted ceiling, with a stone fireplace as the focal point. Two green armchairs complement a dark sofa, and a coffee table sits atop a vibrant area rug. Large windows frame forest views, providing natural light.

Cabin in Bend

Cozy Cabin in the Pines- 2bd/2br at Seventh Mtn

4.97 out of 5 average rating, 35 reviews

An open kitchen and living area is showcased, featuring a large island with two wooden barstools. The space is accented by wooden beams and a warm color palette. A well-equipped kitchen with stainless steel appliances is visible next to a cozy seating area with a leather couch.

Cabin in Sunriver

New! Modern Cabin w/ Primary Suite, Hot Tub, SHARC

A spacious bed is positioned against a large mural depicting rolling mountain landscapes. Two decorative pillows are placed against a textured throw, with a knitted blanket draping over the end of the bed. Soft lighting is provided by glass pendant lamps on either side.

4.92 out of 5 average rating, 87 reviews

Two Sisters

4.95 out of 5 average rating, 99 reviews

A cozy living area features large windows with sheer curtains allowing natural light. A stack stone gas fireplace serves as a focal point beside a TV unit. Comfortable seating options include a pair of sofas and a rustic dining table adorned with greenery.

Townhouse in Redmond

Creekside Luxury @ Eaglecrest-Dog Friendly Escape!

A comfortable living area features a cozy sectional sofa with decorative pillows, a wooden coffee table, and a recliner chair. A large TV is positioned above a wooden console, and natural light filters through the blinds of the window, creating a welcoming ambiance.

4.93 out of 5 average rating, 56 reviews

Newly remodeled. Tastefully set for your getaway!

4.89 out of 5 average rating, 37 reviews

A couple is seated on a cozy balcony, wrapped in a blanket, overlooking the tranquil river at sunset. Warm colors fill the sky, reflecting on the water. A fire pit offers warmth and light, enhancing the serene setting, complemented by glasses of wine held in their hands.

Flat in River West

Relax by the Rapids Riverfront Gem Downtown Bend

4.92 out of 5 average rating, 63 reviews

The living area features light-colored walls and a plush carpet. Two armchairs and a sectional sofa surround a wooden coffee table. A fireplace is integrated into the wall, with a mounted television nearby. Natural light enters through large windows, enhancing the spacious ambiance.

Townhouse in Bend

Spacious two story 2 bed 2 bath west side condo