Family-friendly holiday rentals in Winter Park

The place was good.. great price, amazing location, very calm, comfortable, and we all felt like home. Only two complaints we found a few plates in the cabinets that were a little dirty probably from last guests (probably ate some sticky food that couldn’t get cleaned by the dishwasher) not a big deal for us since we washed our dishes by hand before using them either way, but worth mentioning. Also the AC system doesn’t cool enough, but to be respectful of the house rules we kept it at 70 it was still a little hot for our taste, but nothing crazy. Regardless we really enjoyed our stay and we do recommend Luis and tati’s listings, we most likely will be booking with them again.

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.

Very comfortable, in a great location - close to amenities and easy for Uber to find. Dennis was super helpful and responded in minutes.

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

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

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 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.

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.

Great and safe place to stay! Only 12-16 minutes from every park and Disney Springs!

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 enjoyed our stay at Judy’s house. We found that it was very close to the magic and a nice and comfortable escape from the parks. We didn’t have much luck seeing the full fireworks show (the trees across the way have gotten a bit tall), but enjoyed the pool and outdoor space.

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.

We had a fantastic stay at this apartment in Orlando! It had all the comforts a family of four could need—spacious, clean, and well-equipped with everything we needed. The location was perfect, just a short drive to both Disney and Universal parks, and very close to supermarkets and other conveniences. We also really appreciated the thoughtful souvenirs they left for us. The surrounding area had a beautiful view, and the pool area was lovely—especially great for kids. It truly felt like a home away from home. We would definitely stay here again!

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.

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.

We loved the condo. It was beautiful and we enjoyed it. The only complaint we had (which was out of Anthony’s control) is the neighbors above us were loud and woke us up a few times with the stomping. Other than that, it was awesome! We would stay with Anthony again.

The apartment is beautiful, large, comfortable, clean, has everything you need for holidays and more! Nicolas always responded quickly and answered everything we asked. The pool is beautiful and large! Everything was great.

We really liked staying here during our Disney vacation. It’s about 20-25 minutes from the parks. Condo was clean, well stocked, and very quiet in the area. Bed was very comfortable. We would definitely stay here again. 2 pools/hot tubs close to unit as well as splash pad.

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.

The house is actually very close to the Disney parks. The condominium is quiet, easy to get to. We didn't get to use the pool, as there wasn't enough time. There was no ceiling light in the secondary bedroom, only lamps, and the host informed me that there never was. And the shower in the guest bathroom is very bad, we couldn't shower in it, there wasn't much water and it didn't heat up. It is necessary to be careful with the noise of the children, as there is a house below.