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
“Amazing, thank you!! Carla took great care of our dog Henry while we were out of town for the weekend. She sent pictures and updates and was very accommodating with drop-off and pickup times. Would love to have her watch Henry again sometime!”
“Natasha was absolutely wonderful with my dog Sebastian!! My flight was delayed coming back and Natasha was super understanding when I had to pick up later than expected. Sebastian came home happy and obviously well-cared for! I really appreciated how friendly and communicative Natasha was. I will definitely use her services again and I recommend her to anyone in the Orlando area!!”
“Lexus was an amazing dog sitter for my goldendoodle. She was so kind, accommodating and sent lots of pictures and videos which put me at ease. Pick up & drop off was easy and she was flexible with my availability. Honey was definitely well taken care of! Highly recommend & look forward to using Lexus again!”
“We had the best anniversary trip knowing that our dog Olivia was safe staying with Zuleica! Thank you Zuleica for all the pictures while we were away! Olivia is super happy!”
“Linda took care of Odie for three days when we needed a break. He loved her yard and her house and her attention. We will definitely call on her again for boarding our dog.”
“I dropped my poodles off with Kevin for the first time. I was gone for about three days. Kevin kept me up-to-date throughout my trip with pictures, videos and text messages on a daily basis. When I arrived to pick up my pups, it was obvious that they both had a good time! The videos showed my pups getting along with the bigger dogs and enjoying the outdoor space. On the way home (48 minutes) my pups were knocked out! When we arrived home, again, naps naps naps! My babies had a good time and I would recommend Kevin services for those of you with little or big dogs. My babies are 8 pounds and 12 pounds and he handled them well. Thanks again Kevin, watching your YouTube video really helped me to grasp the areas in which I can improve my training habits and take control again.”
“Brooke is truly amazing! We wholeheartedly recommend her as a pet sitter. She is incredibly reliable and a genuinely caring professional, and our cat, Jilapi, absolutely loves her. We will definitely be using her services again!”
“Great experience with our dog sitter! She sent a ton of photos and videos and were very communicative. They took wonderful care of our pups while we were away. We loved getting updates and would definitely book with them again.”
“We honestly couldn’t be happier with the care they gave our Goldendoodle. Our pup got plenty of playtime with other dogs and enjoyed going outside every day in their big yard. We highly recommend Sarahi and Leandro — and we loved getting daily photo updates of our dog!”
“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.”
“This was my first time using Rover or getting a Dog sitter for my little guy. He's kind of a dramatic dog so I was extra anxious but Richard was awesome and went out of his way to make the experience smooth and easy.”
“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.”
“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.”
“Cannot be happier with Martha’s care and communication. She’s watched Filbert a couple times and each time the communication and updates have been impeccable. The latest stay was a little over two weeks and we were worry free knowing she was taking care of him as if he were her family.”
“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!”
Over 3,614 pet parents in Winter Park have booked dog boarding
Winter Park dog parents share their Rover experiences
It was my first time leaving my dog with them, and the experience was incredible—I am very grateful. Their work and dedication were excellent and highly professional. I recommend them 100% and will definitely use their services again! Era la primera vez que dejaba a mi perro cuidándolo y la experiencia fue increíble; estoy muy agradecido. Su trabajo y dedicación fueron excelentes y muy profesionales. ¡Los recomiendo al 100 % y sin duda volveré a utilizar sus servicios!
Amber is such an amazing sitter! HIGHLY recommend. It was our first time using Rover and we were a bit nervous, but after our meet and greet, we knew we had nothing to worry about. She has a huge fenced-in backyard, lives in a great area for walks, and sends the best pics of our pup throughout his stay. He looked so happy you could tell he was loving life while at “Amber Camp”. We’ll continue to book with her in the future, no questions asked.
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, the median cost of dog boarding in Winter Park 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 Park dog boarding rates can be found as low as $23 to as high as $55 per night.
As of Jun 2026, 2,493 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, 91% 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 2,493 dog boarding sitters in Winter Park on Rover, so you’re sure to find the perfect match for your dog! In Winter Park, 95% 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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