Dog Boarding Winter Springs
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 460 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 took amazing care of mars! She sent over tons of photos and was very flexible with my schedule. Mars felt very at home by the time I came to pick him up :) definitely planning on requesting Andrea in the future!”
“Sarah was truly amazing! Our family and I traveled down from PA to relax for a week and decided last minute to go to a theme park. I contacted Sarah and received a response within minutes. We had the whole thing setup 15 mins later! Sarah was super nice and genuine from the start. She was available to pick up and drop off my puppers and she was promptly on time for both. Sarah did a wonderful job giving us updates and pics while at the park which let us all just relax while we were there. My puppers left happy and came back happier…..even met some new four legged friends! If you’re ever from out of town be at ease knowing your pups is in good hands! Thank you Sarah! Fiona already misses your chair?”
“We are very blessed to find MJ for Armani. MJ truly loves and cares for dogs. Armani loves going to MJs house and misses her when back home. I couldn’t have asked for anyone better. We love MJ 🤗”
“Brian was a perfect host. House was exactly what you’d want form a sitter. Clean, quiet, and tidy. Great communicator, and he has a great dog that is very friendly and welcoming to my dog. I’ve finally found my dog his new vacation spot when I have to go out of town. Thanks for the great experience Brian.”
“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!”
“Rebecca was so kind and her family too!! I felt very at ease to have our dog be with them. She would send us daily pictures and was very responsive. Definitely consider Rebecca for your fur baby. Our dog seemed very happy with her!! Thank you ☺️”
“We really appreciate Adriana for taking such good care of our Luna. She was very attentive to detail and made sure to communicate with plenty of photos and updates throughout the stay. Adriana and her whole family showed Luna so much love, and we would love to book with her again in the future!”
“Jennifer took great care of our Ginger! Being able to have a meet and greet before we decided to book was so important and we were thankful for. She sent pictures and videos while we were gone which helped relieve our worry of how she was handling our first long trip. Jennifer will be our first choice for our next trip!”
“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.”
“Easy communication and interaction. No issues whatsoever with drop-off and pickup. Got a couple cute pictures during my dog's stay. My 1.5 year old dog has a lot of energy and that was no issue for her. He seemed very happy and healthy at pickup. Would gladly use again.”
“We are so glad that we found Cristy! This is the first time we leave our dog with someone that we don't know and we were worried that he would get drepressed or anxious. Everything went great! Since the Meet & Greet until the end, she was very kind, communicative, send us pics and updates about how he was doing. Now we know who to reach to if we need future care of our dog.”
“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.”
“Sasha was very caring for Dexter. She has so much love for animals and she’s awesome with communication and sending photos during the booking. Definitely using Sasha again she’s great!”
“Debra took care of my two dogs and she sent me pictures of them playing with her dogs. Her dogs guided them through the doggy door which is awesome! My dogs don't have problem with her and she, Debra's been awesome to them. I love that she sent me pictures of them and looked very happy which me and my husband happy. I would recommend her to anyone. Thank you Debra for taking good care of my dogs.”
“Bruce always does a wonderful job with my two babies. He updates me often with photos. I highly recommend him for your pet sitting services. You will receive phenomenal care in his hands.”
“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”
“I have a velcro dog who had never spent a night away from us, so I was worried about leaving her for two weeks. Lisa put me at ease immediately during our initial meet-and-greet; she clearly loves dogs and they all seem to love her! Maisy was shy and sometimes finicky, but Lisa had nothing but patience for her and managed to coax her out of her shell. She sent several updates and lots of photos, too, which always made my kids happy to see. :) We would definitely use Lisa again the next time we can't bring Maisy with us on our next trip!”
“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.”
“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!”
The median cost per night for dog boarding in Winter Springs is $40
Dog parents share their Rover experiences - Winter Springs
Andrea is so good with our Joon Bug! Joon always comes home happy and exhausted from playing with her to pups. We never have to worry about Joon while we are traveling because she keeps us updated with pictures of Joon's daily activities. She loves spending her time snuggling and playing.
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!
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 Dog Boarding - Winter Springs
Frequently asked questions about Rover
The average cost for Dog Boarding in Winter Springs on Rover is $34.24 per night (as of September 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 September 2026, there are 2,487 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.
Connect anywhere with the Rover app
