
"Recommendations from friends are a must when it comes to a sitter for my kids. UrbanSitter has expanded our network of babysitters, and it has given us peace of mind."
Matt K., dad of two
Browse background checked babysitters near you in Winter Park. Compare local reviews, rates, and experience to find the right fit.
Looking for jobs? Apply here.
Browse background checked babysitters near you in Winter Park. Compare local reviews, rates, and experience to find the right fit.
Looking for jobs? Apply here.
Families in Winter Park use UrbanSitter for date nights, after school help, and last-minute babysitting.
128 available tonight | Avg hourly rate: $19.67/hr
All babysitters shown here are background checked every year. Learn more.
Hi there! I have been a nanny and/or involved in childcare for almost ten years. I grew up in College Park, Orlando, FL and that is where I had my first nannying jobs. I was privileged to become close with my neighbors who had just moved next door and we became quick family friends. They had just had their first child and now they have four! I took care of all children throughout their lives until they moved to Utah about four years ago. Through them I found that I had a natural ability to care for children. Through word of mouth, I started nannying other families in the Orlando area and resumed during the summers when I was home from college. After I gradutated college in 2013, I came home to study for the LSAT in preparation of law school. During that two year period that I remained in Orlando, I continued to nanny for several families. This nannying included dropping off and picking up from school, transporting to afterschool activities, night sitting, overnight sitting, etc. I also would attend to household duties including laundry, washing and/or empting of dishwasher, the feeding and walking of animals, etc. After attending law school and passing the Florida Bar, I continued to nanny for families [(throughout COVID-19 for those parents who had essential jobs (e.g., a nurse)] while also working at a large insurance company part-time. Eventually, in September 2021, I decided to make the move to Washington, D.C., a goal I had always had. Although I eventually want to resume my law career, providing care to children and being able to assist parents with those they value most important is still a passion of mine that I want to continue. Throughout my nannying career, I have cared for newborns/ infants (e.g., twins, including one with a disability), toddlers, elementary aged children, middle school aged children, and even offering after-school homework help to children in high school. In addition, I have had the privilege to travel with several families on trips on multiple occasions (e.g., Utah and Vermont). Overall, I find myself to be set apart from other nannies or child care providers because I have been able to witness children at every stage of their life, providing me with a unique set of skills for whatever a family may need or require out of a babysitter/ nanny.
I'm originally from the UK and moved to the states about 4 years ago. Over the past decade, I have gained diverse experience working with children of all ages, which has shaped me into a compassionate and versatile childcare provider. I had the privilege of being an aunt to my nieces, learning the joys and responsibilities of nurturing and guiding young minds. For two years, I worked as an au pair in a different country, which broadened my perspective and honed my ability to adapt to different cultural environments. I learned to respect their individual needs, and foster a loving, supportive environment while ensuring open communication with families. As a certified swim instructor for 8 years, I have taught children of all ages and skill levels, from toddlers to teenagers. This role has not only developed my ability to teach essential life skills but also allowed me to form strong, trusting relationships with the children I work with. Additionally, I spent two summers as a counselor, working with children ranging from 7 to 16 years old. These summers solidified my leadership and problem-solving skills, and I learned how to create a positive and safe environment where children can express themselves, build friendships, and grow.
I’m a warm, dependable, and experienced caregiver with a lifelong passion for working with children and supporting families. I grew up on Long Island, New York, with my parents and brother, and from a young age I was very active in dance, gymnastics, skiing, ice skating, and soccer, which I continued through college. Staying active and enjoying the outdoors are still a big part of my life today. For the past 24+ years, I’ve been a devoted stay-at-home mother raising three children while also volunteering at school, coaching soccer, and assisting with other youth sports. We currently have two boys in college and an 11th-grade daughter attending Bishop Moore Catholic High School. I’ve been happily married for 27 years and truly value family, health, nutrition, sports, swimming, outdoor adventures, and creating a positive home environment. My childcare experience began around age 10 as a mother’s helper, and I worked closely with several families from ages 18–30. Caring for children has always come naturally to me, and I genuinely love spending time with little ones. I’m positive, easygoing, patient, consistent, and enjoy laughing, playing, crafting, baking, reading, and making everyday moments fun and engaging for kids. I also have personal experience parenting a high-functioning autistic son, now 24, which has given me added patience, understanding, flexibility, and compassion when supporting children with different personalities and needs. While I’m not overly focused on technology, I appreciate the ways it can be useful and prefer building real, meaningful connections with children and families. My goal is always to provide a safe, nurturing, active, and dependable environment where children feel comfortable, supported, and cared for.
Hi! I go by Kennedy! I am AHA BLS certified and I’m always prepared for anything, whether it be entertainment, an ouch, or a snack break, I’ll have my sitter kit ready (mess-free art, fun stickers, basic medical, and a snack bag with hand wipes) I love the randomness and wonder with kids, if they decide they want to be a dinosaur today then more power to em’! I’ll gladly translate their homework to pterodactyl. I am a reliable, punctual commuter dedicated to providing high quality in-home care for families in Orlando.
I have always had a heart for children and teaching with lots of great ideas to keep little ones engaged. I will always bring with me age appropriate activities. We are not going to be watching tv unless that’s what they really want to do. I like to keep busy and will help around the house if there is extra time. My priority however would be to keep the little ones engaged and happy.

As of July 2026
Every babysitter's profile is individually reviewed by UrbanSitter's Trust & Safety team after clearing an annual background check. Rely on reviews from local families to help you find your best fit.
146 sitters background checked in Winter Park, FL
4.9 average star rating from total of 205 reviews in Winter Park, FL

"Recommendations from friends are a must when it comes to a sitter for my kids. UrbanSitter has expanded our network of babysitters, and it has given us peace of mind."
Matt K., dad of two

"UrbanSitter has supported my needs for reliable and joyful sitters. Whether it be for work, recreation or last-minute emergencies, we've made wonderful relationships with local sitters who have become a part of our family!"
Natalie O., mom of five

"UrbanSitter is my go-to for quality sitters! I can book weeks ahead of time or easily find a same-day sitter when in a bind. I even hired a part-time nanny during a daycare transition. Customer service is helpful and babysitters respond in a timely manner."
Laura F., mom of two
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