Family-friendly holiday rentals in Winter Park

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

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.

Andrea’s place was awesome! My family and I enjoyed the space outside and how open the house was gave everyone their own spot. The pool and back patio were so nice and relaxing. Would definitely stay here again in the future!

Good location, restaurants 10 mins to walk and most of all a kind host ever and provided me useful information. Thank you.

Ronaldo’s place was amazing, everything was as described, all the main attractions are nearby and he was always responsive to all our questions since day 1, definetely a great place to stay in Orlando

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!

We had a great staycation. Location was awesome. We would definitely book again!

Our family of four stayed here for our Orlando vacation. We went to Universal, SeaWorld, and Discovery Cove. The location of the house was great. Our kids enjoyed the Minions themed bedroom and the resort pools. There were a few things that need repairs (loose curtain rod, broken oven buttons, etc) but everything worked fine and it was very clean. It was perfect for us. Recommend!

The Mickey house is fabulous… you feel right at home… John and Yvonne were quick to respond and it was a minor issue about a missing remote… John came quickly and fixed in a matter of minutes… the pool was awesome… the decor was so cute and the theater room was awesome… You felt at home and able to relax after a fun day at Disney!!!! Highly Recommend !! 100/100 We were a family of 8 and had lots of room and when we needed space to ourselves, each group had a spot!! Thank you Yvonne and John for a great place and experience… Dee, Kelly, Jaela, Marcel and Family Washington/Watson Disney trip 2025

We booked this airbnb with 5 guests. The home has plenty of space, in a very welcoming and peaceful neighborhood. The house was spotless, and check in was a breeze. Tons to do around the house with a little games room in the garage, and a beautiful backyard with a pool, netted to keep the bugs away. Great communication with the host. Will definitely be coming back.

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

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!!

Nice location, right size for family vacation and kids enjoyed bunk beds a lot.. Very nearer to Disney parks, I would highly recommend and would consider again for my future Orlando vacation.

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.

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

Johann’s place was AMAZING! It was super nice and affordable and perfect for me and my husband’s trip to Disney. The private entrance made us feel safe and the place itself was clean and so cozy. We will definitely be trying to stay here again for future trips!

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

Patsy's place was very nice. it was centrally located in the middle of Disney, universal and all the major theme parks. it was very clean , well taken care of. was easy to find. Patsy was very responsive when we had a wifi issue and she helped us fix it . we enjoyed our stay and would definitely stay with her again if we were in the Kissimmee area.

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.

Fully equipped, clean and spacious accommodation. The sector was very quiet and safe. Stephanie responded very quickly and supported us in all our inquiries. Highly recommended accommodation with a very good location for the different attractions and activities in Orlando

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