Family-friendly holiday rentals in Winter Park

good place to stay, close to all attractions and MCO airport.

Good location with lots of restaurants in the area. The building feels dated but the apartment is clean and good value. We cooked a couple meals and the kitchen was adequate. The host communicated throughout our stay and friendly. There was adequate parking. We did not check out the amenities.

The house was absolutely gorgeous and was exactly like in the pictures. The hosts were extremely friendly and communicative through our entire stay and even before. It was very clean, had everything one needs during a vacation, and very peaceful. We will be booking again soon!

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.

Great!!! Vacation home had all the amenities a woman like me love. Plenty of everything from dishes to sheets very clean and comfortable. To say the least just right in the day far as neighborhood activities and quite peaceful and serene at night. Everything imaginable is located right around the corner a big bonus . It Felt like home away from home. Mrs.Mary place was sunshine after the rain Thanks for saving my vacation I will be recommending you to another who wants a fabulous place to stay while on vacation

Carrie thank you so much for hosting our family! This was so much better for our family than a hotel! Our kids never said they were bored! The next time we are in the Orlando area we will book again for sure!

Great location place was very nice and kept well enjoyed the hot tub and the resort this place was well equipped with all necessities for your stay it was very welcoming! Great place to stay would Love to visit again!

We had a truly wonderful stay at this property in Orlando! The location was absolutely perfect—close to everything we needed to enjoy our vacation to the fullest. The home was spotless, well-equipped, and had all the essentials to make us feel comfortable and at ease. Lynn was incredibly responsive and always available if we needed anything, which was greatly appreciated. I highly recommend this property and would like to sincerely thank Lynn for making our stay so enjoyable!

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

Jeremy was a great host! The home came with everything we needed. The pool was a little dirty when we arrived, but I contacted Jeremy and he came right out to clean it so we could swim the next day.

We had a wonderful stay !! It was very roomy and exactly like the pictures! Definitely would recommend and stay again !

The place was clean and exactly as described, and in a very peaceful neighborhood. Items like dish soap and detergent, hand soap, and laundry detergent were available upon arriving. Instructions for how to maintain the house and carpeting were clear and simple, and made it easier to remind everyone to be respectful of the place (without having to be the bad guy- lol). The gate entry was simple once we were checked in, location was easy to get to from our local plans. All in all, if you want to keep your large family or group together and happy, this place is a great choice.

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!

Aaron is an amazing host that truly cares about what is happening with his guests. We had a little trouble with our travel and Aaron went above and beyond to accommodate us when things went out of our control. The home is very nice and exactly as described. It was clean and looked well kept. The beds are extremely comfortable and the home is spacious. I will definitely book with Aaron again if I am back in Orlando!

The space was perfect for my family. We enjoyed the pool and location was perfect for stores, and near the convention center where my daughter had a competition. Great communication with host was quick to respond.

This was by far our favorite Airbnb stay and we’ve stayed at dozens over the years. The listing was 100% accurate, and the home was *immaculately* clean…truly one of the cleanest places we've ever stayed. Not a single bug or ant in sight, which has been an issue at other homes we've rented in Orlando so we really appreciated that. We stayed with an infant, and all of the baby amenities provided were perfect and incredibly helpful and made our trip so much easier. The heated pool and grill were amazing additions and made our stay even more enjoyable. The neighborhood was peaceful and quiet, and the hosts were incredibly responsive, answering any questions almost immediately. We’d absolutely stay here again the next time we’re in Orlando. Highly recommend!

this is my second time staying here and I loved it. we had a peaceful, enjoyable week, walking the grounds and enjoying the pool. The space is so close to so many attractions and awesome restaurants. The house had everything that we need including laundry so our stay was extra relaxing.

Very peaceful and beautiful! Had an excellent trip. Will try to stay here every time I go to Orlando.

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 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

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

Gérard’s home was beautiful. It was in a such a convenient location to everything we needed- especially the Disney parks, and Walmart and Aldi for our weekly groceries. My family and I enjoyed the pool each day and even got to see gators come out of the canal. The only minor thing I wish would be if we had control of the temperature in the home. It was 95-98 degrees everyday we visited, and the home got quite warm even with the blinds closed and fans on. Otherwise, it was a great home and we surely enjoyed our stayed. Thank you!