Bend, Oregon, is nestled on the edge of the Cascade Mountain range. The snow peaks of the Cascades provide a gleaming background to this exciting town. Travelers from all over the world visit this city to indulge in outdoor fun and adventure. Some of the city’s tourist attractions are family-friendly where even children can have so much fun. It provides the best river attractions, hiking, and biking trails with wonderful views of the forest. Visit High Desert Museum and learn about the regions’ natural environment, art, culture, and wildlife from its interesting exhibits. Know that the city has several accommodations waiting for you in your futures vacation here. Read on to see our list of the top five vacation rentals with private pool in Bend, Oregon.
We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to private pool. The image galleries get refreshed with the latest updates regularly. They were last updated on April 21, 2025.
1. Farm guesthouse with charming mountain views (from USD 286)
This beautiful guesthouse is located on a working farm where you can see horses grazing and chicken laying fresh eggs. The home has two bedrooms and can accommodate five guests with lots of space to move around. The main room has a lounge, a dining area, and a huge kitchen with cooking basics. The huge deck has a picnic table, a seating area, a barbecue grill, and a wonderful hot tub to soak in. Feel free to stay in shape by stepping onto the tennis court that comes with a deck. Sitting next to it is a refreshing pool with magnificent views of the mountains.
Top guest reviews
Host:
the host is graciousthe hosts were very welcomingthe owners were very kind and communicativeour host tracy was delightful and so accommodatingawesome place tracy and bill are great hostsLocation:
lovely setting and a very comfortable house close to both bend and sisters will come back againif you want to relax this is the place to goCleanliness:
hot tub was clean and easy to useRead more reviewsAmenities & Room:
property is awesome pool hot tub grill etctracy brought us some breakfast for the first morning which was very welcomingexcellent location with all the amenities: tennis court hot tub cable television and most importantly peace and quietoverall this was a comfortable stay in a well-equipped propertythe saltwater pool is truly unique and quite amazing
2. Beautiful vacation home at the foot of Cascade Mountains (from USD 1138)
The Cascade Mountains serve as the perfect background for this astoundingly beautiful cabin that can accommodate a large group of 12. The stunning home has an engaging indoor lap pool where everyone can gather and have a splash in the refreshing water. At the end of the pool is a calming hot tub where you can soak in while having a glass of wine. On the deck, there’s a fire pit with chairs perfect for a tete-a-tete with family or friends. Nearby are two sun loungers where you can sunbathe all day. With three bathrooms, four bedrooms, and the main area with a kitchen, dining room, a lounge, and a family room, this home is perfect for a family getaway.
Top guest reviews
Cleanliness:
other than that the house was clean and well appointedRead more reviewsAmenities & Room:
the pool was super fun but cold the only difficult thing was heating the pool
3. Vibrant vacation home with two scenic decks (from USD 960)
Imagine yourself walking into a vacation home while feeling complete and contented. This is what you are going to feel once you step inside this amazing home built to accommodate 10 guests. It has four lovely bedrooms, two bathrooms, and two powder rooms, all for your personal needs. The open layout of the kitchen, dining room, and lounge makes it easy for everyone to move around from one spot to another. The family lounge has a flat-screen television and direct access to the favorite part of the home—the indoor lap pool with a hot tub. The lower deck has a couple of seating areas, while the upper deck has a grill and open dining area.
Top guest reviews
Host:
rating details:the property manager was very helpfulrating details:the property manager was very helpfulrating details:the property manager was very helpfulrating details:the property manager was very helpfulrating details:the property manager was very helpfulLocation:
i was very happy with the locationi was very happy with the locationi was very happy with the locationi was very happy with the locationi was more than happy with the locationRead more reviewsCleanliness:
the house was clean and comfortablethe vacation rental was very cleanthe vacation rental was very cleanthe vacation rental was very cleanhouse was clean and even better in person than what the pictures showed
4. Huge vacation home for big families (from USD 1359)
A total of 18 guests can fit comfortably in this 5-bedroom home with 4 living areas and lounges. There are many spots in the home where you can gather some of your family members and share a fun time with them. Its outdoor features include a nice heated pool, a seven-person hot tub both of which are surrounded by sun loungers, and a seating area with a patio umbrella. There are five master bedrooms, six bathrooms, two family rooms, and two kitchens in this beautiful home. There are also dining rooms, one of which can be converted into a game room.
Top guest reviews
Host:
great home with many spaces and pool proper management super helpful and responsiverating details:the property manager was very helpfulLocation:
the location close to the village was super - easy walking distanceperfect location close to the village with easy access to the paved trailsreviewer comments:a great location and home for our familyi was very happy with the locationRead more reviewsCleanliness:
it was very clean well maintained and lived up to descriptionsi spent the entire first night and most of the next day cleaning so we could feel comfortable
Nearby option
5. Family home in a peaceful neighborhood (from USD 1093)
Located in a tranquil area where deer and wild birds are found and the gentle waves of Deschutes River fill the air, this home is the ideal vacation spot for a family or group of 11. It has four large bedrooms and three full bathrooms to accommodate your personal needs. The main area has high ceilings and an open floor plan that includes the living room, the dining area, and the gourmet kitchen. It has a scenic deck that lets you breathe in the fresh mountain air and take in the view of the river. The pool room has an indoor pool with a hot tub perfect for relaxing with the family. You and your family can entertain yourselves by lounging in the game room while playing ping pong or ice hockey.
Top guest reviews
Host:
brett was a great hostbrett was a fantastic hostthe host is great at communicating and the space is huge and prettybrett was so helpful and fast to respondbrett was very helpful when we had issues (and there were a couple that he took care of)Location:
beautiful location on the river with a short drive to bendgorgeous location fun to walk by the riverclose to dt convenient store two miles away and the location on the river was very nicegreat place to stay nice location close to bendawesome stay in a beautiful locationCleanliness:
the house is clean and well-maintainedthe house was clean and well appointedit was very clean and spacious for our family of 10amazing property a super easy check in and clean upthe house was sparkling clean and everything was in perfect working orderRead more reviewsAmenities & Room:
pool was amazing and views are great bring your own firewood or duraflame so cozywhat a gem gorgeous views comfortable furnishings well-stocked kitchen and plenty of gamesthe pool the view the game room all amazingreally cool space with beautiful views and the hot tub/pool situation was super funthe indoor pool and hot tub space was amazing as were the views of the river
Enjoy a refreshing vacation in Bend, Oregon
Bend, Oregon, is one place where travelers love to immerse themselves in nature. The presence of the Snake River and Pilot Butte are prime examples of this. After a day of visiting these and other destinations, you might want to take a relaxing dip in your vacation homes’ private pool.
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