Dog Boarding in Winter Springs
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Top rated Winter Springs dog boarders
“Bobby enjoyed his stay with Brian & Popeye. He got to play and play with Popeye. I am so greatful to have found Brian. We are definitely coming back.”
“Great communication between us, she sent me pictures and kept me informed. I highly recommend her and I would definitely trust my dog with again.”
“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.”
“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.”
“Luna had the best time with Bruce and we received so many pictures. We have 100% confidence in her safety and happiness when staying with Bruce! Thank you!”
“I had no idea I could be so comfortable leaving my pups with a stranger I found on an app but this family made the process so smooth and comforting everyday. I received daily photos of them loving on my babies and it was a great experience. I could tell my babies were loved on and well taken care of when I picked them up. I will definitely use this family every time we go out of town. Thank you, Jessica for everything.”
“Jackie took such great care of my dog! I was nervous at first but felt complete ease once I met her. Her communication was excellent. She kept us updated and sent us pictures of our dog. Thank you Jackie! We appreciate you.”
“Carmin was THE BEST! Johnny is not always easy to deal with, and she handled him so well! He was able to relax, as she made him feel comfortable, safe and loved. He came back home like nothing happened, no anxiety of any kind. Thank you!”
“Denys was available on short notice after previous sitter arrangements fell through. They were super easy to communicate with and took excellent care of my dog, Rusty. I look forward to using their services again!”
“Michelle is nothing short of fantastic-- she provided my pup with a happy, fun, and cozy retreat! Her patience is especially noticeable; I needed her on short notice with a young and spunky dog, and she rolled with it all seamlessly. We were lucky to find her on Rover!”
“If I could leave six stars I would. Kevin took amazing care of my dog (also named Kevin). After having boarded him at a kennel previously, I cannot begin to describe how at ease I felt when my dog was with Kevin. He clearly has a genuine love for dogs and takes pleasure in taking care of them. He is extremely knowledgeable and is definitely someone that can be trusted to take as good if not better care of your pup than you do. He sent me updates and great photos everyday was flexible and understanding when I needed to make changes to my schedule. When I picked up my dog you could tell that he loved Kevin and he also came home smelling amazing which was just the cherry on top of a great experience. Thank you Kevin! We will definitely be seeing you soon.”
“Thanks Cristy for taking care of Emma! I'm relieved to know that I have a safe and caring place for her to stay now! We'll see you again very soon!”
“Catherine was super responsive and kept me updated about my two pups throughout my trip. Her yard is a major plus! Both pups looked happy when I got them back and that was such a relief as this was my first time booking with her. Will try to book with her for my next trip!”
“Sara was a great fit for our Portuguese water dog Chris. We felt comfortable leaving him with her and her family. Sara has a great set up for her dogs and ours as well. We knew Chris would have fun plying with her Kids and also her dogs. Sara was prompt in contacting us. She sent us pictures of Chris having fun. We would definately send Chris to her house again when we go away again. Thank you Sara!!!”
“Maria was absolutely amazing with my dog, Chance! From the start, her communication was excellent—she kept me updated with plenty of pictures and videos, which really put me at ease while I was away. Chance went on tons of walks, got to visit the dog park, and even got spoiled with homemade bone broth pup cups! She also sent him home with treats and toys, which was such a sweet touch. It’s clear she genuinely cares for the dogs she watches. Maria was flexible, reliable, and made the whole experience stress-free. I highly recommend her and would absolutely book with her again!”
“Amazing!! Kristina very help passionate with her work. She even help me with picking up my pet. Would book again in the future if needed. Definitely recommended!!”
“Loved having Susann and her family watch over my grandpa fur baby. She is super nice and sends you pictures with updates on how your doggie is doing. I would definitely recommend her!”
“Lauren is a great communicator. She was able to make our short notice request work and it couldn't have went smoother. She is our first call for pet sitting.”
“There aren’t enough stars to rate how incredible Kim is. I was very nervous about leaving my 9.5 month old puppy Izzy while I went away. I needed someone who would only watch one dog at a time and who is home during the day. I did a search and found that people say they only do one pet at a time but after initial contact, they disclosed that they won’t. Kim, on the other hand, was VERY firm that Izzy would be her only guest. I was able to meet Kim prior and see where Izzy would be. Izzy quickly made herself at home because Kim’s home has dog toys, beds and comfy places for any size dog. I knew I made the right choice. Kim is amazing. I dropped Izzy off at our agreed upon time with personal food, favorite toys and treats and favorite bedding. and I felt really comfortable leaving. And Izzy was thrilled with this situation! She had the run of the place. The two of them bonded and Kim loved my baby while I couldn’t. And it is genuine. She really did enjoy having my girl as company. I received many updates with pictures. Izzy was sleeping in the bed, allowed on the furniture, cuddling and loving Kim just like at home. It was clear that Izzy’s vacation might have been better than my time away! When I picked Izzy up she was happy to see me but was a bit reluctant to say goodbye to Kim LOL. That’s when you know your pup is telling you they had a great time. If you need a dog sitter, I can’t recommend Kim highly enough. She will do all she can to make your pup her priority and to love your fur baby as if s/he is hers. Infinite stars if possible. 💜”
“By far it has been the best experience I’ve had with a sitter! My dogs were well taken care of and I had peace of mind the whole time was away. I will definitely book again 🙌🏼❤️”
Loving dog boarding sitters in your neighborhood
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BRIAN M.
“Bobby enjoyed his stay with Brian & Popeye. He got to play and play with Popeye. I am so greatful to have found Brian. We are definitely coming back.”
Ashley M.
“Great communication between us, she sent me pictures and kept me informed. I highly recommend her and I would definitely trust my dog with again.”
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.”
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.”
Bruce C.
Star Sitter
“Luna had the best time with Bruce and we received so many pictures. We have 100% confidence in her safety and happiness when staying with Bruce! Thank you!”
Jessica & Michael W.Star Sitter
“I had no idea I could be so comfortable leaving my pups with a stranger I found on an app but this family made the process so smooth and comforting everyday. I received daily photos of them loving on my babies and it was a great experience. I could tell my babies were loved on and well taken care of when I picked them up. I will definitely use this family every time we go out of town. Thank you, Jessica for everything.”
Jackie S.Star Sitter
“Jackie took such great care of my dog! I was nervous at first but felt complete ease once I met her. Her communication was excellent. She kept us updated and sent us pictures of our dog. Thank you Jackie! We appreciate you.”
Carmin C.Star Sitter
“Carmin was THE BEST! Johnny is not always easy to deal with, and she handled him so well! He was able to relax, as she made him feel comfortable, safe and loved. He came back home like nothing happened, no anxiety of any kind. Thank you!”
Denys H.Star Sitter
“Denys was available on short notice after previous sitter arrangements fell through. They were super easy to communicate with and took excellent care of my dog, Rusty. I look forward to using their services again!”
Michelle M.Star Sitter
“Michelle is nothing short of fantastic-- she provided my pup with a happy, fun, and cozy retreat! Her patience is especially noticeable; I needed her on short notice with a young and spunky dog, and she rolled with it all seamlessly. We were lucky to find her on Rover!”
Kevin S.Star Sitter
“If I could leave six stars I would. Kevin took amazing care of my dog (also named Kevin). After having boarded him at a kennel previously, I cannot begin to describe how at ease I felt when my dog was with Kevin. He clearly has a genuine love for dogs and takes pleasure in taking care of them. He is extremely knowledgeable and is definitely someone that can be trusted to take as good if not better care of your pup than you do. He sent me updates and great photos everyday was flexible and understanding when I needed to make changes to my schedule. When I picked up my dog you could tell that he loved Kevin and he also came home smelling amazing which was just the cherry on top of a great experience. Thank you Kevin! We will definitely be seeing you soon.”
Cristy N.Star Sitter
“Thanks Cristy for taking care of Emma! I'm relieved to know that I have a safe and caring place for her to stay now! We'll see you again very soon!”
Catherine A.Star Sitter
“Catherine was super responsive and kept me updated about my two pups throughout my trip. Her yard is a major plus! Both pups looked happy when I got them back and that was such a relief as this was my first time booking with her. Will try to book with her for my next trip!”
Sara W.
“Sara was a great fit for our Portuguese water dog Chris. We felt comfortable leaving him with her and her family. Sara has a great set up for her dogs and ours as well. We knew Chris would have fun plying with her Kids and also her dogs. Sara was prompt in contacting us. She sent us pictures of Chris having fun. We would definately send Chris to her house again when we go away again. Thank you Sara!!!”
maria C.Star Sitter
“Maria was absolutely amazing with my dog, Chance! From the start, her communication was excellent—she kept me updated with plenty of pictures and videos, which really put me at ease while I was away. Chance went on tons of walks, got to visit the dog park, and even got spoiled with homemade bone broth pup cups! She also sent him home with treats and toys, which was such a sweet touch. It’s clear she genuinely cares for the dogs she watches. Maria was flexible, reliable, and made the whole experience stress-free. I highly recommend her and would absolutely book with her again!”
Khristina M.
“Amazing!! Kristina very help passionate with her work. She even help me with picking up my pet. Would book again in the future if needed. Definitely recommended!!”
Susann M.Star Sitter
“Loved having Susann and her family watch over my grandpa fur baby. She is super nice and sends you pictures with updates on how your doggie is doing. I would definitely recommend her!”
Lauren E.Star Sitter
“Lauren is a great communicator. She was able to make our short notice request work and it couldn't have went smoother. She is our first call for pet sitting.”
Kim L.Star Sitter
“There aren’t enough stars to rate how incredible Kim is. I was very nervous about leaving my 9.5 month old puppy Izzy while I went away. I needed someone who would only watch one dog at a time and who is home during the day. I did a search and found that people say they only do one pet at a time but after initial contact, they disclosed that they won’t. Kim, on the other hand, was VERY firm that Izzy would be her only guest. I was able to meet Kim prior and see where Izzy would be. Izzy quickly made herself at home because Kim’s home has dog toys, beds and comfy places for any size dog. I knew I made the right choice. Kim is amazing. I dropped Izzy off at our agreed upon time with personal food, favorite toys and treats and favorite bedding. and I felt really comfortable leaving. And Izzy was thrilled with this situation! She had the run of the place. The two of them bonded and Kim loved my baby while I couldn’t. And it is genuine. She really did enjoy having my girl as company. I received many updates with pictures. Izzy was sleeping in the bed, allowed on the furniture, cuddling and loving Kim just like at home. It was clear that Izzy’s vacation might have been better than my time away! When I picked Izzy up she was happy to see me but was a bit reluctant to say goodbye to Kim LOL. That’s when you know your pup is telling you they had a great time. If you need a dog sitter, I can’t recommend Kim highly enough. She will do all she can to make your pup her priority and to love your fur baby as if s/he is hers. Infinite stars if possible. 💜”
Jennifer B.Star Sitter
“By far it has been the best experience I’ve had with a sitter! My dogs were well taken care of and I had peace of mind the whole time was away. I will definitely book again 🙌🏼❤️”
Over 715 pet parents in Winter Springs have booked dog boarding
Winter Springs dog parents share their Rover experiences
Michelle was great with my dog Beni who needed someone to spend time with him take make sure he ate and took his medication. He was nervous but ended up having a good time at her house
Charlene was just wonderful! My two pups were well taken care of and loved on while they were with her for an eight days stay. Her daily communication was outstanding. She updated me, sent me pictures and video every day and was so attentive and loving with my pups. Highly recommend her to care for your fur babies, and I will definitely be rebooking with her again!!!
Ashley was an absolute delight to book with. I loved that she shared photos and updates of my dog, which gave me peace of mind while I was away. She cared for my pet in a very observant way, recognizing when he needed space from the other dogs and giving it to him. Her reliability and communication were top-notch, even when I reached out last minute. I would definitely recommend Ashley to others - she's a trustworthy and caring pet sitter who truly puts the needs of your furry friend first. Thanks again, Ashley, for taking such great care of Parker!
Steve and his family are absolutely amazing with my miniature poodle, Winnie! She gets so excited when we pull up—jumping and barking with joy—which says everything about how much she loves it there. They’re incredibly reliable, communicate well, and always send the cutest photo updates throughout the day. Winnie comes home happy and completely exhausted from all the playtime, walks, and love she gets. I feel at ease knowing she’s treated like part of their family. Highly recommend!
Carmin was awesome with my brownie girl. She kept me updated daily. I would highly recommend her and will use her again for sure.
Brian was great at communicating and sending pictures! We felt very comfortable leaving our puppy with him. He came home happy and well exercised. He enjoyed playing with Popeye. Well definitely be booking with him again!
Vacation for Clyde. Leaving your pet behind when going out of town can be stressful, but not with Jessica and Michael. They welcomed Clyde into their family and home as if he were their own. I received many picture updates of the fun and attention he was receiving. Clyde was on vacation and loving all the extra attention he received from the kids. He was very well taken care of. When it came time to come home, Clyde didn’t want to leave. I would recommend Jessica and Michael to anyone who needs to board their dog in a stress free, loving home.
Erin and Steve were wonderful. Tank had so much fun playing with their golden retriever and it was nice to know Tank was well taken care of while on vacation.
Courtnie M. is very friendly and greets you on her front porch, greets you and then will get details of your doggies needs, and help you carry in their stuff. She updates with texts & pictures of your pets. They looked well taken care of and she said they fit in with her and her small pack of 1 or 2 others.
Cheryl was amazing. She took great care of my dog Snowball, and she sent lots of picture every day. She was very nice and welcoming! I was able to go on a vacation because she took care of my dog. I will definitely have Cheryl dog sit again.
Jose was an excellent dog sitter. He was responsive, provided daily updates with photographs, and was genuinely interested in my dog's well being. My dog is a senior and he took gentle care with the soft food, following my instructions. He was dependable, and after I met him at a meet and greet, I no longer had any concerns. I would recommend him!
Tyler was wonderful! She communicated clearly and promptly leading up to the boarding and kept me informed during the stay. I could tell my dog was well taken care of and in good hands with Tyler. I will definitely be booking again!
Patricia was wonderful with my German Shepherd, Kara. She really helped out watching her last minute for the day and responded quickly when checking up. Would definitely book with her again.
Destiny has watched my x-large dog many times for boarding and she is an outstanding sitter. She is patient with my dog and treats him like family. She is accommodating to my requests even if they were last minute. My dog has the absolute best time with her and gets so excited as we approach her house. I always have peace of mind when I leave him there even on extended day trips. This past stay she even helped administer medication for his allergies. I highly recommend her to anyone that needs a sitter for their fur baby!
Andrea was an amazing! She took great care of our dog Sophie! She sent us frequent updates and pics that kept us at ease. She was also so flexible, we needed to extend a day due to a mix up in our travel plans, and she was super accommodating. Sophie became friends with her dogs which was awesome and all I could have asked for! I know Sophie had a great time there and she was in great hands. I will highly recommend Andrea if you’re looking for a loving and caring home for your pup while you’re away!
Jomarie is so sweet and takes good care of our two pups. She sent us photos and videos and you can tell our dogs were happy and comfortable Our flight got delayed coming home and she was so gracious and was able to watch them a couple extra hours until we got there.
Popular requests near you
Select a filter and find qualifying Winter Springs sitters!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!
The median cost per night for dog boarding in Winter Springs is $40
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.
Sitters in Winter Springs average 12 repeat dog boarding clients
Dog Boarding FAQs
Frequently asked questions about Rover
As of Aug 2025, the median cost of dog boarding in Winter Springs 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 Springs dog boarding rates can be found as low as $21 to as high as $44 per night.
As of Aug 2025, 2,127 sitters provided dog boarding in Winter Springs. 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 Springs dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Winter Springs have an average of 17 years of experience. Dog boarding sitters with repeat customers have an average of 12 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 Springs.
Rover makes it easy to find Winter Springs 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 2,127 dog boarding sitters in Winter Springs on Rover, so you’re sure to find the perfect match for your dog! In Winter Springs, 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.
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