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.
“Cristy was so lovely and took amazing care of my senior pug! She was very welcoming and flexible to my scheduling adjustments, and sent the perfect amount of photo/video updates on my boy while I was away. He normally takes a minute to adjust to a new location, but he was totally fine and trusting with Cristy. She also has the sweetest little dog, and her cat is very calm and personable!”
“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.”
“This was the second time we used Sarah. She genuinely cares for animals and we could tell by how she followed our instructions for taking care of our dogs. She was also very accommodating to make our dogs comfortable and gave us updates on how our dogs were doing. We are very glad to have found her and will definitely use her again in the future. During our entire vacation our minds were at ease because we knew our dogs were in safe hands.”
“April was amazing! She was communicative and took great care of our pup. April was flexible when our flight was delayed. It was very helpful to know we didn't have to stress about arranging for pick-up by a certain time. We received pictures while we were away and she seemed to genuinely enjoy caring for Maui. We wouldn't hesitate to hire her again.”
“Amazing care communication. Loving environment good control of pets, daily schedules and routines strictly adhered too. Don’t waste time with other look no further than Bruce!!!! Best of the best. Can not say enough good things about this caregiver. He will no disappoint. Great location very attentive and can clearly see he loves animals.”
“So thankful for Christina and Oskar! They took great care of my baby Charley, gave us updates and sent pictures of how he was doing. They are very organized and detailed, making sure Charley had everything he needed and worked with him during his pickiness in eating.”
“Leo and Sarahi were absolutely fantastic! They took great care of our dog and kept us updated every day with photos and videos, which gave us so much peace of mind. Highly recommend!”
“Fahriye and her husband were wonderful. They took good care of our two dogs. One is older and is diabetic and they had no problems giving medicine and insulin shots. They came home happy and best of all bathed. We loved our experience!”
“Susana was very kind and loving to my 6 month old puppy. She kept me updated daily and gave him plenty of love and play time. She even gave him a bath for me. Will definitely use again in the future.”
“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!”
“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 🤗”
“Dobby’s first ever overnight stay couldn’t have gone any better! Caroline and her family are so kind and caring. She communicated throughout his stay with pictures and updates. When we went to pick up Dobby, while he was super happy to see us, he was also calm. This shows how good the staycation was!! Thank you so much for taking care of our furbaby ❤️”
“Vanessa was amazing! I was scared of leaving my Chance for the first time ever and this was a great experience. Chance was well taken care of and the communication was great! I will be contacting Vanessa again in the future. Thank you again!”
“This was my first time booking with Lili and I would highly recommend her! I needed go on a work trip out of state for the week and was in need of a new sitter for my dog Abbee. I’m new to Deltona and hadn’t found a regular sitter just yet but I was happy to come across Lili. Abbee did wonderful during her stay and I love the set up Lili has for her house. She is able to separate the dogs if needed, there is adequate backyard space (with a super cute set up), and she made sure to spend time with Abbee. Thank you so much for everything Lili! Abbee can’t wait to stay again.”
“Eric was an amazing host to our little Nova. She wasn’t feeling well on her first night there, and he made sure to update us quite often. He sent us lots of pictures throughout her 3 night stay. He’s a super friendly person and clearly loves animals. Would definitely book with him again and would absolutely recommend him to anyone!”
“Dana and Jared were absolutely wonderful! They were super kind and took the best care of Lu. All of the pictures I got of Lu were super cute and she looked like she was having the best time. She was definitely happy! Lu is hoping she can hangout with them again in the future! Thank you Dana & Jared 😊”
“Odie seems to enjoy going to Linda‘s house every time. He especially liked the special treats and his new green ball. We will definitely continue to send Odie to this sitter.”
“Ariana was incredible and I’m so glad I found her for my pup Kaia. She was overly communicative, sent tons of photos and videos and was quick to respond at all times. You can tell she loves dogs and takes pride in what she does. Kaia will absolutely be a repeat customer with her (and all her doggie friends!) thank you Ariana for making this a seamless experience and tackling my anxiety around leaving her with someone after a not so great experience previously with a different sitter, you’re the best!”
“Douglania took care of my Senior English bulldog very well. She accomodated my request even though i gave her such a short notice. She made sure that he is fed, groomed (extrabut well worth it) and took him for his walks. I will definately have her again to take care of my bulldog in the future. I would give her 10 stars if I could.”
“Ana was so great with my 7 year old Pomeranian. He came home happy and healthy. She kept me updated with pictures and texts. Would recommend Ana to any pet parent!”
The median cost per night for dog boarding in Winter Springs is $40
Dog parents share their Rover experiences - Winter Springs
Andrea was so amazing. Not only did she make me feel at home when I brought my pupper over, she also fully described to me what the visit would be like and where Maizie would be. She sent me photos every day and her pups were so friendly with my girl. As an anxiously attached pet parent, Andrea made it so I could relax on my trip and knew Maizie would be okay. Thank you so much, 10/10 will be booking again
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.
Sarah was extremely attentive and excellent with my dogs. She communicated thoroughly and impressively quickly, helping me navigate the process for the first time, and my dogs were clearly chuffed under her tutelage. Will absolutely be reaching back out to Sarah for any future needs. Highly recommended.
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 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 $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.
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