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
Top rated Winter Park dog boarders
“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.”
“For years I kenneled my Anya during vacations and didn’t want her to be so stressed out anymore. She came home so happy from her stay with Martha and Dan’s family! Couldn’t be more thrilled, Anya will definitely be back!”
“We absolutely love Andrew & Krista! We did a little overnight practice stay before our big 10+ day trip in August and they updated us on Akiro, sent us pictures and treated him as if he was their own pup. We 100% recommend them!”
“Erika was awesome. She kept us updated with pictures and videos and I felt comfortable that Boo was in good hands. Any future trips I will look to book Erika again. Thank you.”
“This was our first time ever leaving our fur baby with someone that is not family, so imagine our nerves! However, Sarahi and Leonardo helped us by sending photos and videos along with daily check in and updates. We appreciated those updates very much. Overall it was a positive experience and our little one came back home relaxed and happy. Thank you again!”
“I was very happy with Jennifer. She took care of Luna perfectly. Jennifer sent me pictures everyday. Which help give me a piece of mind while we was out of the country. Luna was very happy with her and her dog Bella. She was excited when we dropped her off to be there. I was extremely happy with Jennifer and I would definitely use her again.”
“Brooke was amazing. I trusted her with my 5 months old kitten and she took such a great care of her. Great communication. Highly recommended.”
“Gabriella is so lovable to our little old dude Doogie. He's excited to see her and looks really happy in all the photos she sends while we are away. This is our third time with her as we travel often and she's just been spot on every time. We will definitely use her again and again!”
“Carla was great. I was happy with the updates that she sent me and things couldn't have worked out any better. Will definitely look into using Carla again in the future.”
“Linda was great! She watched our two large dogs and has an amazing backyard for them to play. She sent pictures and videos throughout the stay, and the dogs seemed to have a great time. I would highly recommend her.”
“Osmel and his gf are great dog sitters, one of my dog is kind of shy at the beginning with people and it took her nothing to get comfortable with them, Osmel and his gf always make sure I get updates during the day they are very understanding and communicating people!! I would definitely have them watching my girls again.”
“Charlene is AMAZING. She watched my puppy for 2 days and 1 night and she was more well behaved with her than she is with me!! She followed the schedule perfectly and was so attentive with my puppy. She gave great updates with pictures and I know my girl loved her time with Charlene. Highly recommend and will definitely be reaching out to her again in the future.”
“Zuleica was so good to our dog. He was very well taken care of. She shared pictures and updates everyday and I enjoyed my trip knowing that he was in good hands ❤️”
“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 ?”
“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!”
“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.”
“Richard was great. Quick to respond and was happy with the updates that he sent me. Things couldn't have worked out any better and will definitely look into using Richard again in the future.”
“Maria was amazing!! :) I would highly recommend her! My dog Charlie is a nervous Cavalier. It was clear that Maria made him feel at ease. Not an easy thing to do. She showered him with attention, took him for walks and kept up me updated with pictures and messages daily.”
“Heather and her family (including her own fur babies) are the BEST! I was nervous to leave my little one for such a long time while visiting family on the other side of the globe. But Kiwi started getting excited when we arrived in Heather's neighborhood, and ran up to her as soon as we arrived. Heather sent me updates with photos EVERY day. I could easily see Kiwi was very well cared for and having a great time. It was such a comfort and allowed me to be present with my family versus worrying about my little one. THANK YOU HEATHER ❤️”
Loving dog boarding sitters in your neighborhood
Search Results
Christina W.Star Sitter
“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.”
Martha D.Star Sitter
“For years I kenneled my Anya during vacations and didn’t want her to be so stressed out anymore. She came home so happy from her stay with Martha and Dan’s family! Couldn’t be more thrilled, Anya will definitely be back!”
Andrew & Krista O.
“We absolutely love Andrew & Krista! We did a little overnight practice stay before our big 10+ day trip in August and they updated us on Akiro, sent us pictures and treated him as if he was their own pup. We 100% recommend them!”
Erika T.Star Sitter
“Erika was awesome. She kept us updated with pictures and videos and I felt comfortable that Boo was in good hands. Any future trips I will look to book Erika again. Thank you.”
Sarahi & Leandro P.Star Sitter
“This was our first time ever leaving our fur baby with someone that is not family, so imagine our nerves! However, Sarahi and Leonardo helped us by sending photos and videos along with daily check in and updates. We appreciated those updates very much. Overall it was a positive experience and our little one came back home relaxed and happy. Thank you again!”
Jennifer B.Star Sitter
“I was very happy with Jennifer. She took care of Luna perfectly. Jennifer sent me pictures everyday. Which help give me a piece of mind while we was out of the country. Luna was very happy with her and her dog Bella. She was excited when we dropped her off to be there. I was extremely happy with Jennifer and I would definitely use her again.”
Brooke A.Star Sitter
“Brooke was amazing. I trusted her with my 5 months old kitten and she took such a great care of her. Great communication. Highly recommended.”
Gabriela D.Star Sitter
“Gabriella is so lovable to our little old dude Doogie. He's excited to see her and looks really happy in all the photos she sends while we are away. This is our third time with her as we travel often and she's just been spot on every time. We will definitely use her again and again!”
Carla B.
Star Sitter
“Carla was great. I was happy with the updates that she sent me and things couldn't have worked out any better. Will definitely look into using Carla again in the future.”
Linda L.
“Linda was great! She watched our two large dogs and has an amazing backyard for them to play. She sent pictures and videos throughout the stay, and the dogs seemed to have a great time. I would highly recommend her.”
Osmel G.Star Sitter
“Osmel and his gf are great dog sitters, one of my dog is kind of shy at the beginning with people and it took her nothing to get comfortable with them, Osmel and his gf always make sure I get updates during the day they are very understanding and communicating people!! I would definitely have them watching my girls again.”
Charlene A.Star Sitter
“Charlene is AMAZING. She watched my puppy for 2 days and 1 night and she was more well behaved with her than she is with me!! She followed the schedule perfectly and was so attentive with my puppy. She gave great updates with pictures and I know my girl loved her time with Charlene. Highly recommend and will definitely be reaching out to her again in the future.”
Zuleica c.Star Sitter
“Zuleica was so good to our dog. He was very well taken care of. She shared pictures and updates everyday and I enjoyed my trip knowing that he was in good hands ❤️”
Michael A.Star Sitter
“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 ?”
Lauren E.Star Sitter
“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!”
Ivanka P.Star Sitter
“Ivanka was a great dog sitter. It looked like Frankie had a great time and enjoyed her friendly pups. I appreciated the pics and she was quick to respond!”
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.”
Richard D.Star Sitter
“Richard was great. Quick to respond and was happy with the updates that he sent me. Things couldn't have worked out any better and will definitely look into using Richard again in the future.”
Maria C S.
“Maria was amazing!! :) I would highly recommend her! My dog Charlie is a nervous Cavalier. It was clear that Maria made him feel at ease. Not an easy thing to do. She showered him with attention, took him for walks and kept up me updated with pictures and messages daily.”
Heather G.
“Heather and her family (including her own fur babies) are the BEST! I was nervous to leave my little one for such a long time while visiting family on the other side of the globe. But Kiwi started getting excited when we arrived in Heather's neighborhood, and ran up to her as soon as we arrived. Heather sent me updates with photos EVERY day. I could easily see Kiwi was very well cared for and having a great time. It was such a comfort and allowed me to be present with my family versus worrying about my little one. THANK YOU HEATHER ❤️”
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 Aug 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 $55 per night.
As of Aug 2025, 2,398 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 2,398 dog boarding sitters in Winter Park on Rover, so you’re sure to find the perfect match for your dog! In Winter Park, 95% of sitters offer daily exercise, 96% 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
