Dog Boarding in Winter Springs
Find a loving dog sitter to watch your dog overnight at your sitter's home.
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Top rated Winter Springs dog boarders
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“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.”
“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!”
“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.”
“Sara was a great fit for our Portuguese water dog Chris. We felt comfortable leaving him with her and her family. Sara has a great set up for her dogs and ours as well. We knew Chris would have fun plying with her Kids and also her dogs. Sara was prompt in contacting us. She sent us pictures of Chris having fun. We would definately send Chris to her house again when we go away again. Thank you Sara!!!”
“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.”
“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 my first rover experience. My pup seemed to have had a wonderful time and came home ready for a long nap. She was definitely a 'dirt magnet' during her stay and it took a few washes to get her bed clean again, but I can tell she had a lot of fun. Thanks again!”
“I just want to take a moment to express my appreciation for Jennifer! She was incredibly patient and understanding with my shy doodle, Lilly. Her efforts truly went above and beyond to ensure Lilly felt comfortable. It really showed in the wonderful pictures she shared in her updates. I'm so grateful for her dedication and care!”
“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.”
“Wow , Un servicio increible deje a mi bebe por 6 dias y no me arrepiento para nada lo cuidaron como un bebe la comunicacion fue increible con mensajes , fotos y videos me quede super tranquila y si en algun momento vuelvo a irme de viaje lo dejare con gusto y con la gran confianza que mi niño estara bien y super seguro de verdad gracias gracias ustedes fueron increible con Zeus .”
“Oscar absolutely loved his visit with Kevin and his pups. We would definitely book with Kevin again. Such a wonderful experience and I felt at ease the entire time I was gone. Oscar came home and slept and slept because he had so much fun!”
“My doggies stayed several days with Ashley, Jacob and E and were outstanding sitters. My dogs were well taken care of, having plenty of playtime, belly rubs & cuddles.”
“This was my first time using Rover and I love it . Denys was so nice and kind . She kept us always with and update and makes us feel secure . Thank you so much Denys for taking care of Choco . If you ever need a pet care Denys definitely is the one . ☺️☺️☺️☺️☺️”
“Jackie took such great care of my dog! I was nervous at first but felt complete ease once I met her. Her communication was excellent. She kept us updated and sent us pictures of our dog. Thank you Jackie! We appreciate you.”
“Cristy was great! We received updates throughout our pets stay and pictures. Our dog was happy and healthy when we returned to pick him up. I would definitely recommend Cristy and use her services again.”
“Couldn’t have asked for a better experience! Our two dogs were so well taken care of and came home happy and relaxed. Loved getting updates and pictures while we were away—it made everything stress-free. Definitely booking again!”
“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!!”
Over 784 pet parents in Winter Springs have booked dog boarding
Winter Springs dog parents share their Rover experiences
We had a positive experience booking with Ashley and Jacob. They were friendly, accommodating, and we felt comfortable leaving Lucy with them. They sent pictures, updates through her stay. I can tell she got lots of love and attention! Thank you so much Ashley and her family for everything.
We were leaving for a weekend cruise Friday morning and our dogsitter fell through literally Thursday evening. We submitted a request through Rover and much to our surprise Brian was more than willing to help us. Our toy poodle is only 4 months and not fully trained but not only was Brian okay with that, our puppy came back a bit more disciplined than when she left. We are first time dog owners so I am certain her time with Brian had a lot to do with that. We are so grateful for his excellent service and accommodating us on such short notice. The feedback he gave while we were away was comforting and alleviated our concerns of leaving our puppy with someone we hadn't had the time to fully vet. I highly recommend Brian and will be using him in the future.
This was my first time using Rover, and I honestly couldn’t have asked for a better experience. Amanda watched Calliope for three nights and took such good care of her. She was very responsive, sent sweet photo updates, and kept me in the loop throughout the day, which really eased my anxiety. It felt comforting knowing Calliope was in good hands. I would definitely book with her again and truly appreciate the care she gave her.
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!
I cannot say enough how impressed I am with MJ. This is the first time using rover, or any pet sitting site. I was nervous leaving my dog, a senior, but from the time I pulled up she greeted me at my car and we took Pete in and went through all the details for his stay. MJ texted me and sent pictures throughout his stay. She works from home so Pete had attention all day for eating and going out and playtime. I already scheduled another stay for next week. MJ is absolutely amazing! I felt and fell so comfortable leaving Pete there. Thank you MJ for such a great experience!
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.
Popular requests near you
Select a filter and find qualifying Winter Springs sitters!How Rover works
1. Search
Read verified reviews by dog parents like you and choose a boarder who’s a great match for you and your dogs
2. Meet & Greet
Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs while you’re away
3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
The median cost per night for dog boarding in Winter Springs is $40
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 dog boarding sitter has to cancel, we’ll work with you to find a new dog boarding sitter.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Sitters in Winter Springs average 12 repeat dog boarding clients
Dog Boarding FAQs
Frequently asked questions about Rover
As of Jun 2026, the median cost of dog boarding in Winter Springs is $40 per night, including service fees. Boarding your dog for one week typically costs $280. Sitters on Rover set their own rates based on their qualifications, your dog's needs, and their space's amenities. As a result, most Winter Springs dog boarding rates can be found as low as $21 to as high as $44 per night.
As of Jun 2026, 2,203 sitters provided dog boarding in Winter Springs. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, dog boarding sitters joining Rover must pass a background check for you and your dog’s safety.
Rover makes it easy to reach out to multiple sitters about your booking. Typically, 91% of Winter Springs dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Winter Springs have an average of 18 years of experience. Dog boarding sitters with repeat customers have an average of 12 repeat clients. Experience can vary from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when you compare sitters in Winter Springs.
Rover makes it easy to find Winter Springs dog boarding sitters to provide loving care from their own home. The background-checked, 5-star sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog boarding is great for:
- Dogs of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Dogs who’d love to socialize with their sitter’s pets
There are 2,203 dog boarding sitters in Winter Springs on Rover, so you’re sure to find the perfect match for your dog! In Winter Springs, 95% of sitters offer daily exercise, 96% offer medication administration, and 89% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog boarding sitter near you. As a reminder, sitters joining Rover must pass a background check for you and your dog’s safety.
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog boarding sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your dog boarding sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your dog boarding service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.
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