Dog Boarding in Winter Park
Find a loving dog sitter to watch your dog overnight at your sitter's home.
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Top rated Winter Park dog boarders
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Our dog Aiyla had the best time at Jennifer’s house! My dog Aiyla and their dog Bella got along so well. Jennifer sent daily updates and pictures which we loved. Our vacation was so much more relaxing knowing our baby girl was safe and happy!”
“Gandalf had an amazing time with Brooke! She kept us updated daily with pictures and videos. It was my first time leaving my fur baby with someone and she made me feel at ease. If I ever have to board my cat again, I’ll definitely be using this app with Brooke. She was just awesome through the whole experience.”
“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.”
“Carla was great. I was happy with the updates that she sent me and things couldn't have worked out any better. Will definitely look into using Carla again in the future.”
“Ivanka was a great caretaker for our fur baby Alaska, she kept us updated constantly and sent pictures of her, would definitely recommend using her services, and really appreciate her taking time to take care of our baby.”
“I have two Frenchies that are glued to me. I work from home so they never leave my side. I was going on vacation and didn’t know where to leave my fur babies since I have had bad experiences with boarding places. My husband and I were googling places where we could leave our fur babies and came across Rover. After a few clicks here and there and reading reviews, I came across Leandro and Sarahí and decided to meet with them. From the first day, they gave me a sense of relief and I felt confident that they would be able to take care of my babies. Let me just say, they did not disappoint us. I gave them specific instructions for my babies and they followed them. Everyday they would send me pics and videos and kept me up to date with my frenchies. My girl did not want to eat for three days and they were finding ways to get her to eat. They even reached out to me to see if they were able to give her an alternative food. I am so pleased with them. They were welcoming, knowledgeable, kind and took great care of my frenchies. I will definitely use them again without hesitation. Thank you Leandro and Sarahi for welcoming my babies into your home! You both did an amazing job.”
“I have never left my pitbull with anyone and was very hesitant, however Kevin made me feel very comfortable that he was in charge. I would have never thought I would allow someone to introduce my dog to another without my presence and again Kevin proved me wrong by assuring me he was the pack leader.... I will never hesitate again to leave both my dogs with Kevin I already have 2 future dates set up ?my only disappointment is I wish I would of found him sooner.”
“Bryan has watched our cat and dog a few times and is always great! He keeps us updated with pictures and lets us know if there is ever anything going on with our pets. Our pets feel at home with Bryan and we recommend him highly:)”
“Melanie and Troy took great care of our pup while we were away for a weekend vacation. Their proactive communication allowed us to enjoy our trip. We’ll be checking with them again next time we need someone to watch her.”
“I cannot tell you how thankful I am to find such a good pet sitter. She is truly amazing!!!! She watched my doggy for 11 days. She loved my dog like her own and Bingo loved her and was right at home. She sent me pics and videos and kept me up today. She treated my dog like family. If I could give more stars I would. Honestly, the best ever. Would highly recommend and will be using her again. Thank you so much for taking such wonderful care of Bingo.”
“Maria is amazing! Sweet, understanding, accommodating, responsive. She sent us regular updates about our pup with very cute photos. Her house and yard are beautiful and our dog had a wonderful time at her stay with Maria and her pups! I felt very comfortable leaving my baby with her, and at ease knowing she was in good hands. 10/10 recommend, thank you 🤍”
“We left our dog with Nathaniel for more than two weeks and he took great care of him! He sent us updates and took care of him like his own. I would absolutely use Nathaniel for any future needs.”
“For years I kenneled my Anya during vacations and didn’t want her to be so stressed out anymore. She came home so happy from her stay with Martha and Dan’s family! Couldn’t be more thrilled, Anya will definitely be back!”
“Christina was wonderful with the care of my dog QC. Our dog's are our children , which some do not understand. So I was pretty nervous due to past experiences with close friends. Christina kept me well updated & sent me pictures of him. My boy is very energetic & sometimes I need him to calm down .. lol. After coming back from Christina's he was very calm. Went straight to the bedroom & layed out on the carpet snoring loud 😂. I would Definitely recommend & definitely rebook with her.”
“Heather and her family (including her own fur babies) are the BEST! I was nervous to leave my little one for such a long time while visiting family on the other side of the globe. But Kiwi started getting excited when we arrived in Heather's neighborhood, and ran up to her as soon as we arrived. Heather sent me updates with photos EVERY day. I could easily see Kiwi was very well cared for and having a great time. It was such a comfort and allowed me to be present with my family versus worrying about my little one. THANK YOU HEATHER ❤️”
“I HIGHLY RECOMMEMD ALEXIS AS A DOG SITTER. I left my 8-month old Willow golden doodle with her for a 10-day home boarding at her home while I went out of the States for Holiday. I HAD ZERO WORRIES, she sent DAILY PICTURES, and UPDATES—Willow Loved Staying and Doodle Puppy So far she has required Velcro attention and Play——Lexus Provided that Care. If u need Care and safety for your animal, Contact Alexis. Julie Miller—-And —-Willow Brie (She also took pictures and gave us a nice Welcome Home Memory Card) :)”
“My puppy had the best time staying with Nour! From the very beginning she was kind, welcoming, and attentive. She sent me updates and photos throughout the weekend, which gave me so much peace of mind. My pup came home happy, relaxed, and clearly well cared for. It’s obvious how much she loves dogs and treats them like her own. I couldn’t have asked for a better experience and will definitely be booking with her again!”
Winter Park dog parents share their Rover experiences
Amanda was so welcoming and gentle when first meeting them! She’s a very active sitter and that was perfect for my dogs because they LOVE their walks and they love to play. She communicated multiple times throughout the day with pictures and videos and even let us keep a tennis ball! I would absolutely bring them back to her again. They loved their stay!
Karyna and Emre took excellent care of Spooky. We were nervous about leaving Spooky with someone new so we reached out to Karyna and Emre for a meet and great and after talking to them and seeing them interact with our dog we felt comfortable. They asked us a ton of questions to understand our dog and his needs. He stayed with them from Thursday to Sunday and they sent me plenty of pictures and updates daily. They walked, snuggled, set up his enrichment toys and gave him plenty of treats. It was apparent he was very comfortable there with them.
Caroline and Luis watched my Trixie for 5 days while I was traveling visiting family. They did an excellent job, sending me tons of pictures every day, regularly letting me know how Trixie was doing and they were very accommodating when I needed to add another day to my trip. I highly recommend them!
This was our first time leaving our dog Gunner with someone other than family, but Brendan made Gunner feel like his family. We received updates and photos twice a day from Brendan and that made us much more comfortable and reassured that Gunner was in great hands and well taken care of. We will definitely rebook with Brendan in the future!
She was an excellent sitter! Was very caring and sweet with my dog and made him feel comfortable in a new environment. She was very accommodating and gave me multiple updates, which I appreciate and looked forward to during my trip. I recommend her to all my pet parent friends and would recommend you to a book with her as well.
I couldn’t wait to leave a review for Jeanette because she was absolutely amazing! She accepted my last minute weekend booking for my Fluffy Frenchie, Gizmo, and made the entire experience completely stress free. From the very beginning, her communication was consistent, thoughtful, and reassuring. She kept me updated throughout the weekend with messages and photos, which gave me so much peace of mind while I was away. Jeanette went above and beyond caring for Gizmo, she played with him, took him on walks, and even brought him to the park so he could get exercise and have fun. You can truly tell she genuinely loves and cares for the dogs she watches. I’m new to Orlando, but I can confidently say I’ve found Gizmo’s forever sitter! Thank you again, Jeanette, for taking such amazing care of my little guy!
Popular requests near you
Select a filter and find qualifying Winter Park 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 Park 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 Park average 12 repeat dog boarding clients
Dog Boarding FAQs
Frequently asked questions about Rover
As of Jun 2026, 2,700 sitters provided dog boarding in Winter Park. 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, 92% of Winter Park dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Winter Park have an average of 17 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 Park.
Rover makes it easy to find Winter Park 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 2,700 dog boarding sitters in Winter Park on Rover, so you’re sure to find the perfect match for your dog! In Winter Park, 96% of sitters offer daily exercise, 97% offer medication administration, and 90% 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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