Dog Boarding in Winter Park
Find a loving dog sitter to watch your dog overnight at your sitter's home.
More resources
A focus on safety
Enjoy photo updates, easy messaging, and the knowledge that every sitter joining Rover needs to pass an enhanced background check. Learn more about RoverProtect
Loving dog boarding sitters in your neighborhood
Search Results
1. Deanna B.
“I’m afraid to say how wonderful Deanna was with our Tilly because then she might be booked when WE need her! 🤣 Deanna was wonderful! Tilly enjoyed vacationing with her!”
2. Osmel G.
“Osmel was amazing with my dogs, Sunny and Diva! He took such great care of them—attentive, kind, and clearly experienced. I felt totally at ease knowing they were in good hands. Sunny and Diva were happy and relaxed when I got back, which says it all. Highly recommend Osmel to anyone looking for a trustworthy and caring pet sitter!”
3. Andrew & Krista O.
“Krista and Andrew gave me peace of mind while I was away. They communicated well, and sent many pictures. Will definitely book with them again.”
4. Carla B.
“Carla is the absolute best! I never regret trusting Carla with my fur baby and Bella loves her. Bella always seems so at ease and comfortable with Carla.”
5. Michael A.
“Michael is the best and took amazing care of our dog Henry! We could tell that he and his wife love dogs as soon as we met them, and we knew our pup would be in great hands. Their house and fenced in backyard are perfect for dogs and they were flexible with drop off and pickup times. Henry loved his visit and can’t wait to stay at Michael’s house again! 10/10 would recommend ?”
6. Christina W.
“Christina was wonderful with the care of my dog QC. Our dog's are our children , which some do not understand. So I was pretty nervous due to past experiences with close friends. Christina kept me well updated & sent me pictures of him. My boy is very energetic & sometimes I need him to calm down .. lol. After coming back from Christina's he was very calm. Went straight to the bedroom & layed out on the carpet snoring loud 😂. I would Definitely recommend & definitely rebook with her.”
7. Zuleica c.
“Zuleica did such a wonderful job watching our dog, Leia. She sent plenty of photos throughout the week and always assured her safety and comfort.”
8. Kevin S.
“My dog loved her stay. Kevin sent pictures multiple times per day. Jazzy was care for very well during her stay we'll definitely board her with Kevin again!”
9. Melanie & Troy W.
“Melanie and Troy took great care of our pup while we were away for a weekend vacation. Their proactive communication allowed us to enjoy our trip. We’ll be checking with them again next time we need someone to watch her.”
10. Gabriela D.
“Gabriela did such a great job with our puppy! Chuck can be kind of picky when it comes to the people who watch him but it appears he grew very fond of gabriela and her family! We got daily updates with pictures while we were away and we will 100% be asking her to watch our dog again! She is an incredibly sweet, responsive, and responsible sitter:)”
11. Jennifer B.
“Jennifer provided excellent care for my dogs while away for a long weekend staycation. She provided pictures and updates daily, and I know the dogs enjoyed their time with her and her family. Now they need a few days to recover from the extra fun and attention!! Would recommend, and book, again without any hesitation!”
12. Debra R.
“We will happily bring our dogs to Debra again. It’s always a little scary leaving our dogs with someone else, but Debra put our minds at ease right away. She sent daily updates including pictures and/or videos. It was a bonus that she genuinely seemed to love our dogs. Plus, her dogs seemed to get along well with ours. She was flexible when I had to update care instructions for one dog due to a medical issue. Debra went above and beyond for our babies. We are very, very grateful.”
13. Sara S.
“Sara was fantastic and kept me well informed during my pet’s stay with her. She is very warm and friendly and understood my dog and her needs. Thank you Sara! I will certainly use your services again!”
14. Lauren E.
“We felt very comfortable leaving our puppy in the care of Lauren! She has great communication and sent multiple updates every day! She cared for our dog as her own and we will definitely be returning to her when we need pet sitting again!”
15. Leda B.
“My girls absolutely enjoyed their time with Leda! She took amazing care of them and even provided photos of them, which put us at ease. I would definitely recommend Leda to anyone in the area.”
16. Martha D.
“Martha & her family took great care of my little yorkie. It was our first time using Rover and her first time not staying at a family members home. We couldn’t be more happy with the care and updates we received! If we’re in the Orlando area again we would definitely feel comfortable leaving her with Martha & her sweet family!”
17. Tia W.
“It was very easy to communicate with Tia about our dogs' needs and our schedules. She is flexible, accommodating, and above all, loves pets. We felt comfortable leaving our dogs from the moment we met her and think her home is also good for pets.”
18. Heather G.
“Heather was an awesome sitter for our Lily. Her dogs mingled well with our 15lbs princess! The two night stay went well. We highly recommend Heather !”
19. Marie T.
“Marie was amazing at taking care of my 2 yrs old pit, Bella. She had a great time staying with Marie and her dog and they went for walks everyday which Bella absolutely love. Definitely recommend her for your pup stay.”
20. Bruce C.
“I'd like to thank Bruce to take care of Charlie well. Many pictures sent by the time frame make me peaceful and assure that he is doing fine. I appreciate all he did for Charlie?”
How Rover works
1. Search
Read verified reviews by dog parents like you and choose a boarder who’s a great match for you and your dogs
2. Meet & Greet
Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs while you’re away
3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
Why Choose Rover?
Cashless payments
Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your dog boarding sitter has to cancel, we’ll work with you to find a new dog boarding sitter.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Dog Boarding FAQs
Frequently asked questions about Rover
As of May 2025, the median cost of dog boarding in Winter Park is $40 per night, including service fees. Boarding your dog for one week typically costs $280. Sitters on Rover set their own rates based on their qualifications, your dog's needs, and their space's amenities. As a result, most Winter Park dog boarding rates can be found as low as $23 to as high as $54 per night.
As of May 2025, 2,418 sitters provided dog boarding in Winter Park. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, dog boarding sitters joining Rover must pass a background check for you and your dog’s safety.
Rover makes it easy to reach out to multiple sitters about your booking. Typically, 92% of Winter Park dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Winter Park have an average of 17 years of experience. Dog boarding sitters with repeat customers have an average of 11 repeat clients. Experience can vary from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when you compare sitters in Winter Park.
Rover makes it easy to find Winter Park dog boarding sitters to provide loving care from their own home. The background-checked, 5-star sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog boarding is great for:
- Dogs of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Dogs who’d love to socialize with their sitter’s pets
There are 2,418 dog boarding sitters in Winter Park on Rover, so you’re sure to find the perfect match for your dog! In Winter Park, 96% of sitters offer daily exercise, 97% offer medication administration, and 91% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog boarding sitter near you. As a reminder, sitters joining Rover must pass a background check for you and your dog’s safety.
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog boarding sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your dog boarding sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your dog boarding service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.
Connect anywhere with the Rover app
