Holiday rentals with a pool in Bend

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.

Indoor Pool, Spa, Game Room, Pets Welcome!

Alpenview Retreat | Perfect Gathering Home for Friends and Family Designed for unforgettable group stays, this spacious modern home combines luxury, entertainment, and location- just minutes from Downtown Bend and close to Mt. Bachelor. Spend your days skiing, hiking, or exploring, then come home to soak in the private, indoor heated pool and hot tub, sip your favorite beverage in the courtyard, or compete in your private game room. Perfect for families, friend groups, and multi-family trips.

Klubhouse in Sunriver AC/Hot Tub/Heated Pool/BBQ

Spoil yourself by visiting this cozy condo in Sunriver. The embellished accent walls, vaulted ceilings, and a plethora of high-end decor will leave you speechless. Step onto the porch to enjoy stunning forest views, relax by the heated pool & spa, or drive to the Sunriver Village and SHARC just minutes away. ✔ High-Speed Wi-Fi ✔ 2 Comfortable Bedrooms (1 King and 1 Queen) ✔ Loft w/ Queen Floor Mattress ✔ Fully Equipped Kitchen ✔ 55' Smart Tv ✔ 2 Full Bathrooms w/ spare towels See more below!

Sunriver-Pool/HotTub Walkable to Food Trucks/Shops

- This unique and friendly spot boasts a convenient location to Central Oregon's famous outdoor activities. The space is only a 26 minute drive to Mt. Bachelor, the beginning of the scenic Cascade Lakes Highway, and a short walk to The Village at Sunriver. Community pool, hot tub, and laundry are on site and accessible. Wifi and Netflix logins are provided to all guests. The hot tub is open year round. The pool typically opens on Memorial Day weekend snd typically closes sometime in September.

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)

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!

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!

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.

Serenity Retreat | Pool, Spa, Trails & Mt Bachelor

Situated in the serene Mt Bachelor Village, our home is a harmonious blend of seclusion & natural charm. Encircled by a lush landscape & towering trees, it serves as a tranquil retreat, perfect for relaxation. The property is just a short distance from Bend's lively amenities, offering access to both outdoor adventures & urban pleasures. This residence is an ideal choice for those wishing to enjoy the tranquility of nature while being conveniently close to the city's attractions.

Sunriver Studio with Pool and Hot Tub

THE POOL IS OPEN! -Year Round Hot Tub and Seasonal Pool- -Walking distance to Food Truck Lot and Beer Garden- -25 Minutes to downtown Bend- -25 minutes to Mt Bachelor- -No Chores (no trash takeout, bed stripping, laundry, etc.)- -Super Clean -Owner Cleaned, Managed, and Maintained- -Free Parking Steps from Your Door- -Easy Self Check-In with Digital Locks (unique code for every guest)- -King Sized Bed- -50” Samsung TV Logged into Netflix, Hulu, HBO and more-

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!

Wow Holy Cow Chalet

Wow Holy Cow! will be your first thought when you set foot into this knotty pine walled, sunlit filled chalet. Furnished with everything you need for a fun, family getaway. Channel Maria von Trapp while taking in the beautiful mountain views from the loft space. Have a drink on the deck while your kids search for frogs in the rock feature and shallow creek below. Grill a steak on the bbq and admire the deer who often pass by. DCCA# 1453