Family-friendly vacation rentals in Winter Park

The house was incredibly clean and very spacious. I appreciated that someone came regularly to clean the pool—especially since I’m very clean and a bit of a germophobe! The host was also very responsive, which I truly appreciated. We had a small issue with the HOA, and I’m grateful the host was on top of it and supportive throughout. I felt safe at all times in the gated community, and my kids really enjoyed the pool.

Great check in process! Would boom again when in the area! Very clean, smelled good and great space!

Maria's place was super cozy. It had everything we needed and then some. the property is beautiful. Pools were nice. and the staff at the gates were very welcoming. No problems. very relaxing.

Laura’s place was very accommodating to our week trip to Disney World! Close to all of the parks as well as all sorts of restaurants and convenience stores surrounding! Cool AC, a hot shower and a cozy bed—hard to beat after a HOT day at any of the parks! Very responsive to messages and suggested lots of great recommendations! Definitely a “bang for your buck” at Laura’s place! Looking forward to referring all of our friends and planning our next trip soon! Thanks again, Laura and staff! 🙂

Excelente ubicación. A tan solo 8 minutos en auto de Universal Studios. Un poco más lejos de los parques de Disney (unos 15 minutos en auto). La ubicación me parece excelente, se encuentra cerca de comercios, restaurantes, farmacias, supermercados. Es recomendable ir con auto porque si bien la ubicación es estratégica, las distancias son largas. El apartamento era cómodo y muy completo. El complejo cuenta con pileta la cual se puede acceder durante todo el día. Muy conforme con mi elección y volvería sin dudas. El anfitrión respondía rápidamente y estuvo atento en todo momento.

Great stay, thank you for an amazing clean comfortable vacation we had. We were staying literally just a few steps away from the pool. Jetty was quick to respond to all my questions Condo was super clean and felt like i was at home. A+ on everything this condo had to offer. Dont look anywhere else, this location is a gem. Thank you once again, We will be back in the future

This was our second time staying at Nathalie’s place! We are just as happy as before. Thank you again and we will be back soon!

We really enjoyed our stay! Beautiful home and beautiful property!

Great place to stay and certainly a great price for what you get .

Kenia was very responsive if we needed anything! The home is exactly how it looks in the pics and all that’s listed was there. Kenia provides you with all you need for your stay, the kitchen is very well equipped to whip up a 5 course meal! Definitely will be booking this home again in the future

We had a great stay at this Airbnb in Orlando! The house was very clean, and the check-in process was smooth with clear, easy-to-follow instructions. The pool was a definite highlight, perfect for relaxing after a day out, though it’s worth noting it’s not super private as it’s close to neighboring homes. The space had all the basics, but be sure to bring your own essentials, as it’s lightly stocked with just the minimum. Overall, a comfortable and convenient place to stay.

Adir’s space was in excellent condition and provided excellent communication throughout our stay! Beautiful view

We spent two weeks at Disney parks and this place was an excellent choice for our family of 3. We were close enough to take breaks during the hottest parts of the day. Andrea's place was very clean and comfortable. We appreciated all the amenities provided and clear instructions for check in/out. We would not hesitate to stay here again. Excellent host!!

I had a wonderful experience staying at Sam’s place. The house was very clean, well-maintained, and located in a quiet, safe, and family-friendly neighborhood. It truly felt like a home away from home. Sam was an exceptional host—very responsive, friendly, and helpful throughout our stay. He made sure we had everything we needed and offered great local tips that made our Disneyland trip even more enjoyable. The house was spacious, comfortable, and perfect for our family of six. The kitchen was fully equipped, and the beds were cozy. One of the highlights for us was the swimming pool—my kids absolutely loved it and spent hours enjoying themselves! We especially appreciated the smooth check-in and check-out process. I highly recommend Sam’s home to anyone visiting the area. Thank you once again, Sam, for your warm hospitality!

We loved our stay here! We were greeted by the welcoming committee of ducks and White Ibises when we walked out to the patio - they are adorable. The house was very clean and nicely decorated. The pool was nice to cool down after a day at the parks and it is conveniently located near stores and restaurants and also very close to the parks - which was awesome!! I highly recommend staying here. Judy was a great host to work with and we look forward to our next visit! Oh! And I caught a bass in the pond…added bonus!

We were helping to move our daughter to Orlando area from out of state and needed a home base for a few days while we got everything set up for her. David’s place fit the bill perfectly - clean, lots of space, quiet, quick responses to any questions. It was exactly what we needed.

The property was very clean and smells good, also had everything we needed. Not too far from major parks.thanks to the host who is very kind and responsive. One of the best places we’ve stayed at. Highly recommend for a big family . Thanks so much.

Atendimento atencioso, ficou à disposição para ligarmos a hora que chegássemos caso não conseguisse entrar no apto, mesmo sendo de madrugada. Os amenities da casa foram de grande valia. Adoramos a decoração e a limpeza. Com certeza recomendaremos. Obrigada por toda atenção e cuidado.

This place was so nice for my daughter and I. We were welcomed with open arms and the place was just as described. We met the grounds keeper CC who was a joy to meet. It was quiet and conveniently located. We will definitely stay again.

This space felt like home away from home. My family and I loved it! The location area is also nice and we felt safe and secure. Simone checked in on us after check-in which I appreciated very much.

this family is beyond accommodating. I don't typically do airbnbs with the in home post this was the first for me. They are very accommodating and welcoming. They made me feel right at home and like part of the family. Their home is clean and very well decorated. If I am ever in the area again I would stay there without hesitation. They do have dogs which for me was great. But if you are uncomfortable with them I am sure they would make sure that you do not have to interact with them. But for me the dogs made it feel more like home. I cannot say enough nice things about this family and how accommodating and friendly they are. If you're unsure about staying with an in home host I would urge you to stay with this family. You won't regret it. Just like their ad says you will be staying with friends you just haven't met yet. Cannot recommend this location enough.

My girl had a wonderful time her first time in Florida and the place was amazing and felt like home….this a great place and would rent it again…top tier

This was a perfect family vacation spot we stayed 5 nights and enjoyed the pool.

Our stay was very nice everything was there, we were there for a family reunion and the Airbnb was it was only 4 houses from where the reunion was, everything was great will use again Thank You