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.
“This was my first time using Rover and a pet sitter. Brian was amazing. He sent me updates and pictures several times a day, and my pups looked very happy. The best part of Brian’s service is that he works from home so my pups were with him all day. It made me feel good knowing that my pups weren’t in a kennel all day like they would be in at the pet resort I used in the past. I highly recommend Brian. He’s the best!”
“Sarah is wonderful! She has flexible times throughout the day. Which makes it easy for us to book half days or full days to watch our dog. She helped arrange a friendly introduction with her pack and ours before we started booking appointments. Very knowledgeable and helpful with all types of dog breeds and personalities. Kept us posted with several pictures throughout the day! A very great experience”
“MJ is such a a caring and wonderful person! She took great care of our sweet Mielo. She sent pics each day and made us feel at ease. I highly recommend her and will definitely use her next time we go out of town. Thank you for taking care of my baby!”
“Debra was great! We received daily updates and pictures of our boy and he looked like he was having the time of his life. Debra was responsive any time we messaged and we would definitely rebook. ?”
“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!”
“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.”
“Best dog sitter we have ever had. She went above and beyond. She was able to take our dogs last minute. Her whole family is truly so kind. We would definitely recommend booking with her.”
“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!”
“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.”
“Bruce has watched by dogs several times and has done a wonderful job every time. He is very professional and very kind to my dogs. He takes very great care of all pets and is a true pet lover. I am grateful for having Bruce to help us watch out little dogs when we go out of town. Thanks Bruce and his wonderful wife.”
“Our dogs love Jackie! They feel at home at her house! Jackie is a very kind and gentle soul. We feel very blessed to have found a sitter who feels like family! Thank you so much for loving and caring for our dogs. The Sullivan’s”
“Cristy was amazing with our pups! Our youngest is a rescue and tends to get nervous with new situations and surroundings but was right at home with Cristy. She sent pictures, videos and updates that out our minds at ease and gave us the peace of mind we needed while we were away. They were happy and well cared for. Cristy will be our number one go to for future dog sitting needs.”
“Fahriye was wonderful with Molly and even groomed her and trimmed her nails (no small feat for Molly ;)). She also updated me daily with messages and pictures. I’ll definitely use her again!”
“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!”
“My puppy absolutely enjoyed her boarding, she cried on her way home when I picked her up. Susan and her kids took great care of my puppy. She sent pictures and updates multiple times daily. I will absolutely be using her again.”
The median cost per night for dog boarding in Winter Springs is $40
Dog parents share their Rover experiences - Winter Springs
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!
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.
How Rover works
1. Search
Browse profiles of sitters near you who offer dog boarding
2. Meet & Greet
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 near you
Select a filter and find qualifying Winter Springs sitters!Sitters in Winter Springs average 12 repeat dog boarding clients
FAQs for Dog 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 July 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 July 2026, there are 2,499 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.
96% 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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