
Kid-friendly holiday rentals in Jackson County
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Top-rated family-friendly rentals in Jackson County
Guests agree: these family-friendly rentals are highly rated for location, cleanliness and more.
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Popular amenities for Jackson County family-friendly rentals
Kid-friendly house rentals

Charming One
Our stay at Dahely's home was truly delightful. The home itself is remarkably spacious, with a comfortable and flowing layout that made it easy to relax and unwind. The neighborhood is so quiet and peaceful – we especially enjoyed watching the wild turkeys stroll by in the morning! It's a lovely setting. We also loved the pretty living room, which was just perfect for enjoying a cup of coffee. It's such a welcoming and serene space.

Chic 4 bed/2 bath house with large yard
The communication was great. That's really important if you're unsure about things. Kitchen was stocked amazingly well with things I needed for baking & cooking. Fenced yard & patio was enjoyed by everyone and there was plenty of room for 4 adult, 2 children & 2 small dogs. We will enjoy our memories made here in Medford Oregon!

1930s Queen Anne Historic Downtown Retreat
The house was so clean and beautiful! one of the best Airbnb experiences I've ever had. Stefanie responded quickly whenever I needed anything and the house was so cozy and spotless clean! would 10/10 recommend staying here!

Eagle’s Nest Cottage | 40 mins to Crater Lake
Convenient to Crater Lake. Everything was great. Enjoyed the view. My only suggestion is to get a pitcher for the kitchen. We are tea drinkers and had nothing to make tea in. We would definitely stay here again if in the area.

🌟30 DAY-25%🌟PET FRIENDLY🌟PRIVATE🌟FENCED YARD🌟W/D🌟
I'm a repeat to King of Queens. Suzanne's place is perfect for my extended stays for work. My dog loves the fenced back yard. Suzanne is an amazing host! I always hope her place is available when I need to go to Medford! Highly recommend!

New house with king beds and 3 full bathrooms
Very nice place to come back to after a hard day of work.

Clean and Cozy Farmhouse
Cynthia was very responsive. The space was great and a quick drive to downtown Ashland.

Lovely Central Point Home w/EV Charger
I, along with my 12 year old son, and another mom and her son stayed here for our boys baseball tournament. It was SUCH a great, welcoming space to spread out and have a more relaxing experience than staying at a hotel. The boys loved being able to stretch out on the sofa to watch basketball in the evenings on the big TV's , and the bonus space in the garage was such a fun addition. Thanks for a great spot!
Family-friendly apartment rentals

5 Star Luxury Southern Oregon Suite
Michael's place is perfect, we loved how the room was located upstairs. It is decorated beautifully and very clean. Location is perfect, walkable to the park and library. Hosts are responsive and friendly. Would definitely stay here again, very recommended!

Winner 2024 Best of Ashland! Our Carriage House
This is easily the best experience I’ve had using this app. This host is responsive, and the accommodations are exactly what you’re hoping for. Specifically if you’re visiting for OSF, this location is the bomb because it’s not down downtown so it feels quaint not crowded and the restaurants nearest don’t fill up as fast as they do closer to theaters. Having a Safeway across the street is a dream.

Westwood Unit D
It was just what we needed and the bed is the most comfortable I’ve been on

Suite Comice EV Charging
Jim and his son both were very helpful , and helped me in every way to make my stay the best it could be. Jim was friendly and really listened to my needs during the stay. I loved the place and I was able to park in the driveway for my entire stay. I would definitely stay again should I be back in the area. I could not ask for better people to be staying next to me, in a time of personal crisis.

Classic & Cozy W/D & Parking | close to DT
Cute little place, thank you!

Clean, Stylish Apt w/kitchen. block from Downtown
This was our second spring staying at Leslie's beautiful rental. You can't beat the location. We parked on Friday and didn't drive again til we headed home. We explored Ashland by foot with great food, live music, visual art and plays just steps away. We will 100% be returning!

Madrona Suite
Jennifer has gone above and beyond to make Suite Madrona a very comfortable place to stay. I was there for a full week and could not have asked for more. She has attended to every detail. In addition, she recommended some wineries in the area I did not know about. This lovely enclave is only 15 minutes from Ashland without charging Ashland prices, and very close to the airport. I highly recommend Suite Madrona.

Park View Large Apartment Holm Stay Hosting
Very clean and comfortable space. Well organized and easy to find what we needed. Hosts are very friendly and helpful. Would definitely stay here again!
Family-friendly apartment rentals

The Executive Suite
beautiful place just a little too much pic's on the rooms

Plaza North Suite 203 Windsor
We visit Ashland regularly to visit family. I’ve traveled a lot, and this was one of those rare good finds. The host is wonderful, and so is the place. I loved the modern, minimalist, yet natural and warm interior and it’s very convenient (the Co-Op, etc). It was very quiet, too. We’d stay here again in a heartbeat.

Black Pearl
This was one of the best Airbnb’s I’ve ever stayed at we will definitely be back again. The hosts were so flexible and accommodating thank you so much for everything.

Plaza North Penthouse
The condo penthouse was amazing in every way. Beautiful, spacious, clean, and in a great location.

Spacious Modern Condo Walk To Downtown & OSF
Awesome space. I stayed here and attended UBI which is only a 5 minute walk from the “campus”. Town is an easy walk & a huge bonus was the sauna & spa baths right across the railroad tracks.

Plaza North Suite 201 Alexander
The perfect place to stay for the Shakespeare festival. Valisatie was so helpful, even when we needed to move our reservation by a day. Walking distance to everything in town — dinner, shows, shops, Lithia Park — we were truly able to park the car and leave it there until we headed out. Thank you so much!

Plaza North Suite 202 Sonoma
This is my second stay at the condo. I love the location as everything is walkable from this spot. Didn't need my car at all during my 4 day stay. The space gets great light and there are nice views of the surrounding hills. Everything worked great and the entire condo was spotless. If one were planning on doing a lot of cooking, you would need to bring provisions as only salt/pepper and oil are provided. Not a concern for me as there are so many restaurants nearby, and the Ashland Co-op is just down the street. Nice to be so close to everything and yet also in a nice, quiet location. I will be back.

Selah House!
Each time we visit everyone is pleased with the house layout and how convenient and well equipped the unit is. The house is modern, comfortable, clean and easy to relax and work in. We enjoy walking and the location is excellent for walk/access to town and local features. We will look forward to our next visit!
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