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.
“Andrea was a God send! My husband and I did and 8 day roadtrip through yellowstone and Grand Teton. She and her husband kept our maltipoo Joon. Joon made friends with their 2 dogs and had the best time playing the entire time. Andrea sent updates and pictures everyday and I felt so relieved to know she was in such good hands. We will be using her in the future. Highly recommend!”
“Once again, Paddy had a "vacation" at Adriana's while we were out of town. He loves his stays there and I am totally comfortable with leaving him in her excellent care. She is a wonderful sitter and I recommend her unconditionally!”
“This was my first time booking through Rover; although I've researched and made requests before now. I have to say that all of my uncertainties for my 10-month old puppy's care were laid to rest after the boarding stay. Debra and her sister Wendy were awesome! At drop off, they asked questions to ensure Piper's stay would be like home accommodated accordingly. Daily pictures and notes were sent, but most of all, Piper looked happy, and came home happy and not stressed! Dare I say they spoiled him more than I would (in a good way!). I think I've found my "regular" daycare and boarding service! I would definitely recommend.”
“Carmin did a wonderful job with our 11 year old dog, Poppy, over the Thanksgiving holiday. I really appreciated the extra time and care she took with our anxious doggy . She sent photos and updates to us that were very much appreciated. Thank you, Carmin, for your top notch care!”
“My fur babies had a blast at Lisa’s house. She gave me daily reports and pictures. They were well cared for and I’m excited to have found a safe place to board them when we travel.”
“First stay for my 2 pitbull mixes to stay with Linda for 5 nights and they seemed very happy. I had accidentally messed up the dates but Linda was able to accommodate me on short notice. She was quick to respond whenever I asked for updates and overall made me feel very comfortable leaving my two dogs with her. Will definitely book again.”
“Cristy is the best!! my little dog Mindy was very happy to stay with Cristy. I was especially pleased that Cristy sent me a couple of photos that showed how well Mindy was being cared for and loved. I am so thankful that I have become acquainted with the wonderful service that she provides. I know that at Mindy will be back as visitor.”
“Miranda & Curtis is the perfect family I found to watch my two German Shepherd’s! Gave me cute updates with pictures and videos and their own dog, Lucky, made our dogs feel at home. I have booked twice so far and will continue my boarding with them.”
“we absolutely loved Gypsy and Keith. My boyfriend and I went for a weekend away and we needed a place to keep our fur baby. We were so lucky to have found them on DogVacay. It was our first time using the site as well and we were both so nervous about leaving our little guy behind, but they both kept our minds at ease. Gypsy sent us photos throughout the trip of him going for long walks and playing with the other dogs, which is amazing since he is usually antisocial with other animals, but he didn't seem to have an issue at all and was able to make new friends. When we picked him up he was so behaved and they actually taught him not to jump up so much, which is a plus since we have been trying to teach him not to do that for ages. He is now home and you can tell he had such an amazing time with them. He is completely worn out from the fun. :) We will definitely be leaving our little guy there every time we take a trip.”
“I felt great about leaving my dog Buddy with Briana. She was very communicative and easy to work with. We'll be using Briana again the next time Buddy needs a place to stay for a bit.”
“Anne was an Angel. I had a last minute emergency with my 5lb Chorkie. I had to perform a wedding and I left my dog at the hotel and she went crazy. I contacted Anne the day before the wedding and she said no problem. She was pleasant and although my dog was unpleasant Anne was phenomenal. Pleasant and courteous and clean. If I’m ever in Lake Mary again she’s first on the list!!”
“Kevin and Gaby were absolutely FANTASTIC! They took amazing care of my disabled dog, and consistently kept me updated. I never left her with anyone since her accident and was feeling super nervous, but they reassured me and took great care of her. Will definitely use them again in the future!”
“Alex was amazing! Our dog is very shy and has only stayed with him once for daycare. We got daily photos of our dog and she was so happy in those photos. We are so thankful we have found Alex and we will be booking with him any time we go out of town or just need daycare services! We would 100% recommend him to anyone who needs their dog watched!”
“Marie is extremely communicative and will treat your dog the way she treats her own. They go on long walks, get lots of running time and of course snuggles. I trust Marie with my girl more than anyone!”
“Milton loved his stay with Susann! Susann and her family gave him so much love and took him on plenty of adventures! I appreciated Susann’s daily updates and photos so I knew how Milton was doing throughout his time with her and her family. I will definitely be booking again next time I leave town!”
“Karen took exceptional care of our goldendoodle, Teddi. She sent frequent updates and photos and took her on a lot of walks. She went over and above to make sure Teddi felt comfortable and cared for. I would definitely recommend Karen for anyone needing a sitter for their fur baby!”
“Carla was absolutely amazing with my dog! She went out of her way to make sure my dog was happy and sent several picture updates. Would definitely use her again and again!”
“So grateful to have found Mackenzie! We had an amazing Rover when I first moved to Florida who no longer does it. I’ve tried three others since before finding Mackenzie and none of them were a fit. Mackenzie was wonderful and communicative! She sent photos of my boys and my smallest who can be grumpy and super protective went to her with no issue (a miracle). Best part, when I picked them up they weren’t barking like crazy trying to RUN out the house. They were calm and I felt at ease from the very beginning! I will be using her for every vacation! She’s a God send!”
The median cost per night for dog boarding in Winter Springs is $40
Dog parents share their Rover experiences - Winter Springs
I honestly cannot say enough wonderful things about Jomarie! George, our black lab, is basically our child, so leaving him while we went on vacation was not easy for me. I was nervous about being away from him for so long, but she made the entire experience absolutely amazing! Every single day, she sent us pictures and videos of George, which gave me so much peace of mind. She took him on so many walks, gave him tons of attention, and genuinely made him feel loved. But I think the biggest compliment came from George himself! When we picked him up, he was so excited to see us, but he actually CRIED when it was time to leave Jomarie! I’ve also never seen him give someone so many kisses! That alone told me everything I needed to know about how well he was treated. She is such a kind, lovely person, and I truly believe George had his own little vacation while we were on ours! I’m so grateful we found someone who cared for him like he was her own. I would absolutely recommend Jomarie to anyone looking for someone they can trust with their fur baby. George might even be requesting another vacation soon! ❤️🐾
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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