
Holiday rentals with a pool in Oregon
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Top-rated rentals with a pool in Oregon
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Popular amenities for Oregon rentals with a pool
House rentals with a pool

Brand New Custom Built Cottage in Downtown w/Pool!
Michael created an amazing place here. All new, modern and sparkling clean. Thank you.

Sunriver Luxury Family Home at Caldera Springs
We spent three nights (two families) and wished we could have stayed longer! We appreciated the two King en-suites for the adults and the Queen room for an adult child, as well as the kids bunk/play room over the garage. Everyone had their own space! Super comfortable and perfect for two to three families with kids. The house was just across the street from the pickleball/tennis courts and the pool/clubhouse and a 5 minute drive from the Village at Sunriver. The house had tons of “toys”and we used the canoe on the lake by the clubhouse. The kitchen had everything we needed to cook for our group as was well appointed and the open concept worked well for our group. Thanks Eric for the great stay! We will stay again!

Romantic Guest House w/Hot Tub, Pool, Tennis Court
Beautiful ranch with wonderful hosts! Felt right at home in the juniper. We loved the location for easy access to Sisters or Bend. We cooked most of our meals there on the bbq, kitchen stocked with everything we needed! Very comfortable beds, everyone slept well. Loved listening to the evening frogs and morning birds. The pool was a highlight for sure. Felt very special to have this property to ourselves! Tracy and Bill are gracious and wonderful to talk to. Our family will be planning return trips in the years to come!

Cozy Mt. Hood Cabin
WOW, nice little gem we. And across when I saw this listing. We loved it so much we stayed another extra day. The place is clean and so relaxing. We will be back for sure.

A Little Peace of Paradise, A/C & 8 SHARC Passes
We loved this property so much! My family had the best time in Sunriver and we can’t wait to stay at this property again! The house was well stocked, immaculate, comfortable, and beautiful. We really enjoyed all of the bikes and the loft above the garage was an amazing bonus! Our favorite thing to do in the evening was to sit in the hot tub and stargaze. Susan was an amazing, responsive host. We can’t wait to come back!

Family Friendly Home | Indoor Pool | Pets Welcome
We had a wonderful stay at this home—perfect for our family vacation with three of us and our dog. The house had everything we needed and was in a great location, close to fantastic restaurants and plenty of activities. We enjoyed the pool and watching movies on the large TV in the evenings. The neighborhood was peaceful and quiet, making it easy to unwind. Overall, it was a great experience, and we’re already hoping to return next year!

Rose City Hideaway
Rose City Hideaway (RCH) is an amazing little place right in the the heart of Portland. We had everything we needed (dining, groceries, bars, etc.) within a very short distance. The hosts provided everything we could have wanted or needed, including accommodation for our two Vespa scooters as we were in town for a Vespa rally. The furniture is comfortable and everything is modern and clean. Amanda and Mike were very friendly and helpful. They made themselves available should we have needed assistance, yet allowed us to enjoy the space without interruption. We would definitely stay here again on our next trip to Portland!

Pano Gorge Views Mid-Mod w/pool&Htub outdoor oasis
We had another wonderful long weekend at this place! We loved it so much the first time, we visited a second time. This space was perfect for our group to spend time together and the kids had a blast. We love the pool, the views, and all the little extras that make this place special. Can’t wait to visit again!
Apartment rentals with a pool

The Whale Pod - Watch whales here!
We added 2 extra days to our stay!! The view is beautiful and the beds are comfortable. We liked the low fully enclosed balcony and how it was higher off the ground for a ground floor unit. Possibly 2 feet high. Would work nice for those with young children for safety. We kept the windows open to allow airflow with no AC and felt safe due to the patio being enclosed as well. Some of the other ground floor units are walk out patios and I would not have liked that. Jeannine gifted a bottle of wine and left some great suggestions that we appreciated. The condo has everything you need with many extras in the pantry and front closet. I was pleasantly surprised. It took a few days to spot a whale, but the included binoculars and telescope in the condo was very helpful when we finally did. Pro tip, watch for all the tour boats to gather in one area, it means something has been spotted. Great tide pooling at Fogarty beach(2 miles up the road)during low tide even without a negative low tide

Newly Updated 1-Bedroom Condo - Amazing Location!
Gus’s place has to be a little gem located in a quite place in Bend, It’s really close to the Old Mill District, about 10mins drive and really close to get to Mt Bachelor. I had so much fun at Gus’s place it was clean and tidy, sheets were clean and towels were fine. Will definitely stay again. I love BEND, OR!

New! Views ~ Private Hot Tub ~ Fireplace
We loved Jessica’s place. So quiet and relaxing. Will definitely come back! Perfect location!

Sandcastle Condo Loft
Such an awesome spot! View of the beach from the place. Very light. Great for a family stay. Short walk to the store, coffee, the beach, Mo's

Betta’s Cove: 10 steps from the sand
This was our third time staying here and it was just as great as the first. We already booked it again for next year! The access to the beach, and the view from the sliding door are probably two of the best things about this place. It feels like home every time we visit. Great host, always quick to respond if we ever need anything(which we don'). We always have a wonderful time.

Riverfront Condo 2 Blocks to Downtown Bend
This modern one-bedroom condo exceeded every expectation we had for our Bend retreat. Perched perfectly along the Deschutes River, it offers everything you could want in a Central Oregon escape – stunning views, prime location, and thoughtful touches that made us feel instantly at home. This condo delivers on every front: comfort, location, amenities, and those special details that transform a good stay into an unforgettable one. We're already planning our return visit to Bend, and there's no question we'll be booking this same slice of riverside paradise. Highly recommended for couples, solo travelers, or anyone seeking a peaceful yet well-connected base for exploring all that Bend has to offer. Enjoy!

Oceanfront Nye Beach Retreat Newport Oregon
Lovely place with a nice view!

Whale Cove: Oceanfront Dream Condo. Whales n Waves
Great place to stay in Depoe Bay with breathtaking view of the Pacific from the living room. Very well equipped with everything needed - and much more. We loved the place. Thank you so much for having us.
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