Dog Boarding Winter Springs
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 459 pet parents in Winter Springs have booked dog boarding
Winter Springs, Find top rated dog boarding
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Emma absolutely LOVED her time with MJ and MJ's sweetbpup Buddy. She had a great time playing with Buddy, running around the yard, and swimming in the pool. The proof is that this normally crazy, almost 1 year old puppy was exhausted for 2 whole days after pick up! MJ provided regular updates, was thorough with safety questions before drop off, and is super sweet. We felt at ease having our baby with MJ.”
“So grateful for Carla taking such care with our fur baby! She sent multiple updates and photos each day so we never had to wonder how she was. Great sitter! Would definitely use her again!”
“She was great!!! Took blu in at the last minute after someone canceled on us. Blu was in great hands. She sent us pictures everyday and was In constant communication with us. Also thank you for the gift very nice touch!”
“Kevin is amazing ! Constantly sent pictures and videos of my dog. Bean looked like he was having the time of his life. Awesome at communicating fast. Will definitely book again, thank you !”
“Overall great experience. Quick to respond and took the initiative to send pictures everyday. The home was beautiful and I felt very safe leaving my puppy for a few nights.”
“Linda was fantastic for our first pet-sitting experience. From the initial meet-and-greet to our return, their communication was top-notch— loved getting photos/videos/updates every day. Moo Moo took right to her. Thank you for taking such good care of him !”
“Thank you so much! 😊🐶This was Bono’s first time staying with her, and I couldn’t be happier with the experience. She took such great care of him and kept me updated throughout, which I really appreciated. Her communication was excellent, and it was clear that Bono was in great hands. I’m definitely planning to book with her again whenever I need someone. Highly recommend!”
About: Hello! I am the owner and founder of Rada Dog Training. I have taken care of both dogs and cats, all kinds of ages, breeds, and personalities. I have 5 years of dog training experience. My dog, Midnight, has separation anxiety. If you have a pet like mine, I understand your struggle so well. If you need a reliable sitter that will never leave your pet alone, my husband and I got you! We give all animals a lot of love and affection. We treat them with respect. We accommodate based on your pet's needs. They will feel safe and comfortable in our home. I am home full time, and I can accommodate your pet's needs. I take the dogs for daily walks, play with them, and give them enrichment. I have a house with a fenced yard. My doggy, Midnight, will keep your pets company. You can give me whatever instructions you need to fit your pet's routine.
“Alyssa and Ryan are fabulous! They took such great care of our two labradoodles while we were on vacation. They sent lots of pictures every day and gave us detailed updates! Our dogs looked so happy in all of the photos! They received lots of love and lots of exercise too! We highly recommend Alyssa and Ryan. We will definitely leave our pups with them again!”
“I’m so grateful that Anne was available to take such great care of my pup! He had the best time playing with little Oakley and I will definitely reach out to you the next time he needs a sitter/play date! Thank you for everything!!”
“Shannon and Chris were so sweet to our Mochi. They both made an effort to get to know him at meet and greet. We could tell right away that they're animal lovers and felt very comforted that our puppy has someone who actually cares for him take care of him while we're away. Mochi seemed very happy when we picked him up and Shannon and Chris also gave us a run-through of his day with them.”
“Dilly loved her week long stay with Gypsy. And I loved the frequent pics and videos Gypsy sent (confirming to me that my dog was safe and happy). Gypsy will be my 1st choice whenever we need to board Dilly again and I recommend her highly.”
“This a great sitter for my 2 boys, Carina is a caring, loving sitter and treats your pets as if they are her pets. The boys have a great time over Carina's house, with 3, 4 legged playmates and one that looks like them, but in mini form for now, also a little human that interacts with the boys as they are her puppies, all had a great time! Carina sends pictures of your pet while your away, just looking in their little faces, they are happy and comfortable staying over. I have already booked their next stay there, very pleased with her service.”
“Absolutely adored Marie and how great of care she took of my baby. Sent me tons of photos and videos and was kind enough to see if her fur baby would get along with mine before officially booking. My baby came back super relaxed and well cared for. I really appreciate how courteous and sweet Marie is! 12/10 would book again! ♥️”
“Repeat Customer!!! Words cannot express how grateful I am to have found Maria. This time, we had the option of using a friend at no charge to watch our Princess, but we decided to use Maria’s services again! Once again she treated Princess like her own and kept us updated on her stay. She is always accommodating and responds in a timely manner while caring for our Princess. Thank you Maria!”
“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!”
“Miss Tisha took great care of Fozzie. I dropped him off every morning & picked him up in the evening, Sunday to Tuesday. We were on vacation in FL & didn’t want to take him to a commercial broading chain. He was pulling me to her front door; happy to go there and hang with Lili, Tisha's fur-baby. We will use Tisha the next time we are in FL.”
“It was great having Caroline watch our fur-baby. As first time Rover users we were nervous about leaving our boy with someone new. As soon as we met her we knew he would be in good hands. She sent us regular updates and pictures, which put us at ease. I could tell he felt right at home staying with her and that she took great care of him.”
The median cost per night for dog boarding in Winter Springs is $40
Dog parents share their Rover experiences - Winter Springs
Brian is great, and takes such good care of our boy, we have rebooked multiple times, and will continue to do so so long as he is in business. Most importantly, our boy loves going to his home, and nearly jumps out the car. You can tell he is comfortable and loved from the updates Brian shares, and loves getting to hang out with his pall Popeye :). Do not hesitate to book!
Carmin was wonderful! We needed a pet sitter for a 10 day trip and we were so grateful to find her! We had a meet and greet and she listened carefully as we discussed our pet's needs. We felt good about leaving him with her. She took great care of him while we were gone and communicated often with us letting us know how he was adjusting and sending pictures. It was an excellent experience and we will book Carmin again when we have another trip.
This family is truly stellar! They are incredibly flexible, accommodating, and lead with genuine care. My pups are treated so much like their own that they’re actually reluctant to come home after a long stay! If you’re looking for a welcoming environment where your four-legged kiddos will be truly loved, you’ve found the right place. My pups are always excited to jump out of the truck and run inside to find their friends and 'second family.' Highly recommended for anyone who wants total peace of mind!
Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.
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 sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
How to book dog boarding
1. Search
Browse profiles of sitters near you who offer dog boarding.
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit.
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform.
Popular requests for dog boarding - Winter Springs
Select a filter and find qualifying sitters offering dog boarding.Sitters in Winter Springs average 13 repeat dog boarding clients
FAQs for Dog Boarding - Winter Springs
Frequently asked questions about Rover
The average cost of Dog Boarding in Winter Springs is $33 per night as of October 2026. Most bookings cost between $30 and $53 per night. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of October 2026, there are 2,491 sitters on Rover offering Dog Boarding across Winter Springs. Enter your ZIP code to see which available sitters are closest to your home.
Every sitter on Rover has their own routine. Depending on the arrangements you agree on before the stay, a sitter can follow your dog’s regular feeding schedule, provide a comfortable place to sleep, offer companionship, and support their usual exercise and play needs.
96% of sitters in Winter Springs can provide daily exercise during dog boarding stays. Depending on the sitter, their home environment, and your dog’s needs, this may include walks, outdoor play, indoor enrichment activities, or supervised play with compatible dogs. These activities are not automatically included with every booking, so ask the sitter what a typical day looks like.
During the Meet & Greet, discuss your dog’s usual exercise and play routine, whether they can safely interact with other dogs, and any activities or restrictions the sitter should follow. You can also ask the sitter to send photo and message updates during the stay so you can see how your dog is spending their time.
Preparing for drop-off is easy when you have a checklist! To help your dog settle into their Winter Springs home-away-from-home, packing:
- Health and safety essentials such as their ID tags, vaccination records, medication, and emergency vet or secondary caregiver contacts.
- Food and gear such as harnesses, collars, food (portioned by day), and an item that smells like you.
- Special instructions such as a list of training cues, medical administration needs, or favorite hang-out spots in your Winter Springs.
Tip: You can upload your dog’s routine and medical info directly onto their profile so your sitter always has the details at their fingertips.
You and your Winter Springs sitter can schedule drop-off and pick-up in a way that works best for the both of you—and your dog. Most sitters offer flexible times for drop-off and pick-up but the easiest way to confirm those times will be through in-app messaging. Confirm your arrival time the day of pick-up and drop-off can also help keep the process smooth and organized.
The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.
All bookings are backed by the , which provides up to $25,000 in eligible veterinary care reimbursement.
Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.
Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit .
While each sitter sets their own vaccine requirements, staying up-to-date on your dog’s vaccines is the best way to be "boarding ready". Vaccinations help create a safe environment for all pets under a sitter’s care.
Many sitters in FL ask that dogs be up to date on core vaccines like the Canine Parvovirus, Canine Distemper, Canine Adenovirus, Bordetella, and Rabies.
By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.
If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your dog to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your dog is showing signs of possible illness.
For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.
Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.
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