Dog Boarding in Winter Springs
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Every sitter passes an enhanced background check. Learn about RoverProtect
Top rated Winter Springs dog boarders
“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.”
“Special thanks to Debra and Wendy for giving our pup Milo a wonderful Christmas. Milo goes to them for daycare and stayed with them while we were traveling for the holiday. I could tell that he had a wonderful time. They really made him part of the family. I felt really comfortable that he was well-taken care of. He loves them and their pups and is always so happy when we drop him off. Here's to a wonderful new year.”
“Jack enjoyed his stay with Jessica and Michael. He got plenty of exercised and enjoyed the attention from their family. He will be back for another visit in the future.”
“Kaitlyn was so awesome with my young puppy Kiko! She consistently checked in with photos and updates, and details on the day. Her warm personality assured me my pup and his quirks would be safe with her while I’m away!! 😁”
“Kevin is awesome. You can tell he genuinely loves taking care of dogs. I was a little nervous about leaving my 4 month old puppy, but Kevin did a great job looking after him and keeping him happy. He came home fulfilled, healthy and happy.”
“We got so many updates throughout the day, keeping us assured that all is well with our dog on his first overnight stay! Michelle was so good to Jack, we will definitely be using her services again!”
“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!”
“Once again, Bruce took amazing care of Taco! Right away Taco noticed where he was and he was excited to be there. Taco was comfortable right away, remembering Bruce's pups and greeting them happily. Once again, Bruce kept me updated with great pictures that made me know Taco was very happy and enjoying himself (and some that made me laugh!) It's great to know that Taco stayed with someone who does such a terrific job of caring for him, and its good to know that Bruce is someone my dog feels comfortable and safe with. I cannot recommend Bruce enough!”
“Long overdue review, but Cristy took absolutely amazing care of our dear pet dog, Cousteau! She was very responsible and is clearly very comfortable caring for a variety of dogs. I would highly recommend her!”
“Maria did an amazing job with Archie and definitely seemed to enjoy himself. Felt at ease with the frequent updates for pictures and videos, even if couldn't respond until after getting home from Welcome to Rockville since signal isn't the best there. She sent Archie home with treats and a toy. Would definitely use her again.”
“My 2 dogs had a very good time at Gypsy's! I think they enjoyed their little Vacation/Spa. We enjoyed being updated with lots of pictures and cute videos they sent us. We will defiantly use them again! Thank you for taking very good care of our dogs.”
“Amazingly patient and kind, lina and loo were pampered while in Miss.Charlene’s care. there was excellent communication. We are thankful she was able to accommodate us on such short notice. Will book again!”
“Anne is wonderful! She is an animal lover, patient, kind, attentive to a dog's needs, and has great positive energy. She watched our fur baby last weekend, and I received text and picture updates throughout his stay. I hope to book with her the next time we need a place for the fur baby--highly recommended!”
“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!”
“We were so nervous to leave our dogs for the weekend and Jennifer made them feel so at home. She also made us feel super comfortable by sending daily updates. The dogs looked so happy. Can’t thank her enough! Will definitely be using her again.”
“Terrie is the best! She was so good at keeping me updated about my fur babies. She did so well with my two cats. They were almost instantly comfortable with her and that says a lot with cats. There’s no doubt she will take wonderful care of your babies and she has plenty of space to keep them separated from other pets if needed.”
Loving dog boarding sitters in your neighborhood
Search Results
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.”
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.”
Debra R.Star Sitter
“Special thanks to Debra and Wendy for giving our pup Milo a wonderful Christmas. Milo goes to them for daycare and stayed with them while we were traveling for the holiday. I could tell that he had a wonderful time. They really made him part of the family. I felt really comfortable that he was well-taken care of. He loves them and their pups and is always so happy when we drop him off. Here's to a wonderful new year.”
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.
“Our pups loved Andrew and Krista and were sad to leave when we picked them up! We really appreciated how they sent us daily pictures and updates.”
Jessica & Michael W.Star Sitter
“Jack enjoyed his stay with Jessica and Michael. He got plenty of exercised and enjoyed the attention from their family. He will be back for another visit in the future.”
Carmin C.Star Sitter
“Carmin is the best auntie ever!! She keeps me posted and I get cute pictures daily. Johnny loves her and always comes back happy and relaxed.”
Kaitlyn F.Star Sitter
“Kaitlyn was so awesome with my young puppy Kiko! She consistently checked in with photos and updates, and details on the day. Her warm personality assured me my pup and his quirks would be safe with her while I’m away!! 😁”
Kevin S.
Star Sitter
“Kevin is awesome. You can tell he genuinely loves taking care of dogs. I was a little nervous about leaving my 4 month old puppy, but Kevin did a great job looking after him and keeping him happy. He came home fulfilled, healthy and happy.”
Michelle M.Star Sitter
“We got so many updates throughout the day, keeping us assured that all is well with our dog on his first overnight stay! Michelle was so good to Jack, we will definitely be using her services again!”
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!”
Bruce C.Star Sitter
“Once again, Bruce took amazing care of Taco! Right away Taco noticed where he was and he was excited to be there. Taco was comfortable right away, remembering Bruce's pups and greeting them happily. Once again, Bruce kept me updated with great pictures that made me know Taco was very happy and enjoying himself (and some that made me laugh!) It's great to know that Taco stayed with someone who does such a terrific job of caring for him, and its good to know that Bruce is someone my dog feels comfortable and safe with. I cannot recommend Bruce enough!”
Cristy N.Star Sitter
“Long overdue review, but Cristy took absolutely amazing care of our dear pet dog, Cousteau! She was very responsible and is clearly very comfortable caring for a variety of dogs. I would highly recommend her!”
maria C.Star Sitter
“Maria did an amazing job with Archie and definitely seemed to enjoy himself. Felt at ease with the frequent updates for pictures and videos, even if couldn't respond until after getting home from Welcome to Rockville since signal isn't the best there. She sent Archie home with treats and a toy. Would definitely use her again.”
Gypsy R.
“My 2 dogs had a very good time at Gypsy's! I think they enjoyed their little Vacation/Spa. We enjoyed being updated with lots of pictures and cute videos they sent us. We will defiantly use them again! Thank you for taking very good care of our dogs.”
Charlene B.Star Sitter
“Amazingly patient and kind, lina and loo were pampered while in Miss.Charlene’s care. there was excellent communication. We are thankful she was able to accommodate us on such short notice. Will book again!”
Anne R.
“Anne is wonderful! She is an animal lover, patient, kind, attentive to a dog's needs, and has great positive energy. She watched our fur baby last weekend, and I received text and picture updates throughout his stay. I hope to book with her the next time we need a place for the fur baby--highly recommended!”
Jennifer B.Star Sitter
“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!”
Jennifer G.Star Sitter
“We were so nervous to leave our dogs for the weekend and Jennifer made them feel so at home. She also made us feel super comfortable by sending daily updates. The dogs looked so happy. Can’t thank her enough! Will definitely be using her again.”
Terrie S.Star Sitter
“Terrie is the best! She was so good at keeping me updated about my fur babies. She did so well with my two cats. They were almost instantly comfortable with her and that says a lot with cats. There’s no doubt she will take wonderful care of your babies and she has plenty of space to keep them separated from other pets if needed.”
Over 715 pet parents in Winter Springs have booked dog boarding
Winter Springs dog parents share their Rover experiences
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!!!
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!
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.
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.
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!
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.
Connect anywhere with the Rover app
