Kid-friendly holiday rentals in Winter Park

We sincerely enjoyed our time at Matt‘s place. Our accommodations were perfect for a young family and the neighbors were wonderfully welcoming to our two kids. The entertainment spaces for the kids could not be beat - I was delighted by the ease with which my kids were away from their screens. Options for food and fun were all within reasonable distance, as was a grocery store. Even without a personal vehicle we were able to access everything that we needed with ride-share/delivery vendors and felt perfectly at home. The host’s ability to be flexible with check-in and checkout was also greatly appreciated. I recommended this listing to other prospective guests/families without hesitation.

Overall our stay was great! The only snag was the place hadn’t been cleaned when we arrived due to a booking/communication error. Greg immediately responded and had cleaners there within the hour. Once It was cleaned the place was immaculate and our stay was peaceful - exactly what we were looking for!

Solid place with great proximity to restaurants.

Luis’ place was clean and spacious for us. It’s in a good location in Orlando.

Great home, the area feels safe and the location was perfect for us;close to everything but also very quiet. The home is spacious and well laid out. This was one of my favorite Airbnbs.

Thank you Tina for the incredible location for our Girls weekend! Tina was a wonderful host - communicative and clear from start to finish and check-in was a breeze. The house was just as described and immaculate upon arrival. Perfect location if you're looking to experience what the real Downtown Orlando is like and not just Orange Ave or I Drive. Growing up in Orlando, the house has everything you could need and expect from a Florida home - the pool was perfect and the outdoor lounge area was heavily loved. All we needed to do was stock the fridge and make the playlists - Thanks again!

We couldn’t ask for a more perfect place to stay for a long weekend in Orlando with our extended family. The house is so welcoming and all the beds were clean and comfortable. We will absolutely be back because we visit family in Orlando a lot. This is a great place to stay.

We had a fantastic stay! The place was absolutely amazing—clean, stylish, and incredibly cozy and private. We especially appreciated the opportunity for early check-in's (our flights ended up being delayed so we didn't need it after all, but had asked ahead of time, and we would have been able to!). The location was perfect—just a short walk to East End Market and other local gems. The snacks and wine left for us were such a thoughtful touch and made us feel instantly welcome. The host was warm, friendly, and very responsive throughout our stay. We couldn’t have asked for a better experience and would definitely love to stay here again!

Very responsive, decent location, no complaints.

We were in town for my sons baseball tournament and this place was perfect. It was in a very convenient location, close to many things, and only 35 minutes from Disney springs. We appreciate that animals were allowed and that it was easy to walk a dog through the neighborhood.

The UCF Parents Retreat was absolutely perfect. It is just 10 minutes from campus! It’s a charming, cozy apartment that made us feel right at home. My daughter and I loved our stay, and even Lucy, our 12-year-old Cocker Spaniel, settled in immediately. The bed was especially comfortable, which was a huge plus. I would highly recommend this spot to anyone visiting UCF!

The space was exactly like the pictures. It is small but it was perfect for my husband, myself, and our dog. It is in a beautiful historic district in Orlando.

A very cozy, quaint spot, and close to everything! Milton recommended great spots, and was very quick to respond and gave clear instructions. Would definitely look into staying again if coming back into the area.

This little studio was absolutely amazing for what I needed! It was a reasonable size and price. Also right down the street from the event I was going to! Lando is also an amazing host definitely would stay here again!

Everything was lovely! My husband, daughter, and I stayed for my son’s graduation from UCF. It was so convenient and close to campus. Also, it was a peaceful retreat as described. Highly recommend!

Excellent place with the perfect host! Jinet was fantastic from start to finish! Thank you for making us feel right at home!

From the moment my family arrived, everything about Brittany's place exceeded everyone's expectations. The space was spotless, beautifully decorated, and thoughtfully stocked with everything we needed for a comfortable stay. It truly felt like a home away from home. The host was incredibly kind, responsive, and made check-in and check-out seamless. The location was ideal—quiet and peaceful, yet close to great restaurants, shops, and attractions. Every detail, from the cozy linens to the well-equipped kitchen, was just right. We would absolutely stay here again and recommend it to anyone looking for a relaxing, high-quality Airbnb experience. Thank you for such a memorable stay!

Marc’s place was truly a one of a kind! Really enjoyed my stay there and would definitely recommend to anyone to stay here. Place was perfect!

I LOVED THE EXPERIENCE!

Great Stay,Check In Was Easy You Go Right Up To Room With The Codes They Provide. Room Looks Just Like Picture, Everything Was Clean And Set Up Perfect For A Studio. Everything Is Also Close To Where You Stay.

Me and my family had a great experience with Fonti. Beautiful place and lots to do around the area. I will absolutely be staying again with my family on our next trip to Florida!

This location is wonderful. Across the street is several restaurants and some shops. It is limited distance from Disney springs that you have shopping and dining with a 10 min drive at most. Parking is plentiful and easy to walk in and get right to the room.

We absolutely loved this place and would recommand it to everyone! It was nice staying here after a hot day in the Disney parks. The childrens. Mickey room was a lovely extra!

I enjoyed Ana's condo very much. Among the many features that stood out: whisper quiet air conditioning, outdoor porch with furniture, Smart TV with internet connection, tasteful furniture, comfortable bed, garage parking, convenience store across the street, Publix grocery store within walking distance.