Dog Boarding Winter Springs
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 438 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.
“First time with Sarah and she was great with my dogs. I was able to enjoy my vacation and saw pics of my dogs playing with others. I won't hesitate to bring them to her again!”
“MJ makes you feel so welcomed and at peace. Thank you for taking care of Neo so well, and I loved that your dog Bobby was so playful and friendly. I would leave Neo again with eyes closed. She is amazing.”
“Debra and her sister could not be nicer or more accommodating!! This was the second time my pups stayed with Debra. I really appreciate their kindness and love for the pups. Her sister was so so sweet to make them each a going-away present! Definitely would use them again!”
“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.”
“We couldn’t be happier with our experience! From the moment we dropped our dogs off, we knew they were in great hands. I was very nervous leaving my boys with anyone but me but we received updates & photos, and could tell they were well cared for and loved while we were away. The boys almost didn’t want to leave lol. We are extremely happy with the care they received and will absolutely be booking with them again. Highly recommend to anyone looking for a trustworthy and caring sitter! 🐾❤️”
“Jackie did an excellent job caring for our senior dog Rosie! Rosie is mostly deaf and blind with several medications, and Jackie made sure to take her out often, give her lots of attention, and send updates and photos everyday.”
“Julieth and her husband were wonderful hosts for our dog. They took great care of him, provided plenty of updates and photos, and were accommodating with our pick up time. We will definitely board with them again in the future!”
“Ashley and Jacob were super friendly and were easy to communicate with, they were also very flexible which was much appreciated as our trip home took a lot longer than expected. Milly had a great time!”
“We went away for 2 weeks, and Bernard had the time of his life at Bruce’s! I loved seeing all the fun Bernard was having with the other dogs while we were away. Bernard also developed some ear issues and Bruce bathed and medicated him for us. We are so thankful we found the BEST pet sitter! Thank you, Bruce, for your amazing care!”
“Carmin was wonderful. She kept in touch every day, sent pics & videos of Eddie. Carmin was very organized & Eddie was fine. I didn’t worry at all about our pup at all. Next time we go on vacation I will go back to Carmin.”
“Once again, Lisa and Rocket took exceptional care of my little Fox. They truly are a dynamic duo! I love that Lisa sends me frequent photos, texts, and videos of the antics that go on there. The greatest compliment I can give Lisa is to have her take care of Fox while I'm away. She is absolutely the BEST!”
“Christina was amazing! We used her as our first dog sitter who wasn’t family. She took amazing care of our baby and even sent us daily updates of their adventures while we were away. Highly recommend and would use her again in the future!”
“It was our first time having a dog sitter for daisy, and I couldn’t recommend Susann highly enough. Susann and her family took wonderful care of our anxious furbaby. She was understanding and calmed her anxiety as soon as we left daisy in their care. Susann went above and beyond to ensure daisy was comfortable and happy, providing daily updates with pictures. She walked daisy everyday twice along the trails and daisy had a wonderful time! Lots of cuddles and playtime. It was such a comfort knowing she was loved and taken care of. Thankyou for your incredible care and for giving us peace of mind while we were away. We are so grateful!”
“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!”
The median cost per night for dog boarding in Winter Springs is $40
Dog parents share their Rover experiences - Winter Springs
Ashley and Jacob were amazing! From the beginning, they made both me and my puppies feel completely comfortable and welcomed. Their home was very neat, clean, and a great environment for Nala and Apollo. They communicated with me throughout their stay, kept me updated, and sent the cutest pictures, which gave me so much peace of mind. You can tell they genuinely care about the dogs they watch and made my pups feel right at home. I would definitely trust them with Nala and Apollo again and highly recommend them!
Jomarie was so amazing! We had to book pretty last minute, but she was so accomodating and kept us updated throughout the trip. We even had some weather delays that changed our plans, and she was more than happy to help us out. The dogs came back healthy and happy. We will definitely be booking with Jomarie again!
This was such a positive experience for both us and our dog! He has never been left with anyone at their house before, and it was the best first experience ever. Carmin was so polite, organize, and communicated with updates. She truly loved our dog and we would recommend over and over again!
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!
Jennifer was great with our little baby keeping us updated or when it was us writing to her she would reply right away. This was our first time leaving our baby behind while going away so it was hard for us but Jennifer made me feel at ease when we did the meet and greet prior to Gracie staying with her.
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.
Meet local sitters who will treat your dogs like family
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 12 repeat dog boarding clients
FAQs for Boarding - Winter Springs
Frequently asked questions about Rover
The average cost for Dog Boarding in Winter Springs on Rover is $33.3 per night (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Dog Boarding easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Boarding. For more information on service fees, click here .
As of August 2026, there are 2,459 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 rhythm and routine, but most will follow the flow that keeps your dog happiest. Sitters can give meals on your dog's regular schedule, provide a comfortable place for sleep, and plenty of one-on-one attention.
95% of Winter Springs sitters also include daily walks in the neighborhood during dog boarding stays. You can also request photo and message updates throughout the stay so you can see which Winter Springs landmarks or neighborhoods your dog is enjoying.
If your dog is a little shy, consider booking a one-night trial stay! This practice run can boost your and your dog’s confidence before your trip.
Preparing for drop-off is easy when you have a checklist! To help your dog settle into their Winter Springs home-away-from-home, we recommend 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 Rover Guarantee , 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 Rover's Trust & Safety page .
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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