Dog Boarding in Winter Park
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Top rated Winter Park dog boarders


“Joan was fabulous! Our pup Ace is strong, super active, and a cuddler. She was able to handle anything he did. The videos she sent were so reassuring as well. Anytime we are here in Breck, we will be reaching out to Joan because she was just that fantastic!”


“Sue was absolutely amazing! We took a ski day and our dog stayed with her and had a blast, she was very communicative, sent photos, and made sure the dogs she had get along together with ours. She had repetitive doggies there and I’m sure our dog Cash will be one of them next time we come.”



“Jan is great!! Never once worried about my pup ruby while she was there. Daily updates were provided and I know my pup Ruby had the best time!”


“Mychaela is truly the best!! Gooch was so spoiled during his time with her (10 days). He was the happiest boy and she sent many pictures to share with us throughout the week. I was so happy to see how much wonderful attention he was getting and couldn’t recommend her anymore. You won’t find a better rover option in Boulder. I hope we can stay in touch so Gooch and I can see her again. 💖”


“This was our first time using Rover and Shanik made our experience nothing short of amazing! She is so kind and considerate, truly a dog lover! Shanik sent us tons of adorable pictures and updates of our dog while we were away. We felt our dog was incredibly loved and well taken care of. Both Shanik and her husband were easy to get in touch with and made pick up/drop off a breeze. We highly recommend bringing your pet to Shanik! Thanks again! We’re so glad we found you!”


About: I used to have a cat for 12 years. I am experienced watching my friends dogs in my house for a max of 2 weeks. Your animal will get a lot of attention because I am at home all day. I work at home 8-4 so your pet should have all the attention they need. For dogs, I will give them walks 3x a day. I have a yard for well trained dogs to play in. My townhome has 1 roomate, and I have quiet neighbors so your animal shouldn’t have anxiety staying with me.

“By all accounts Maple had a great time with Fred! I enjoyed the pictures and could tell she was in a dog lovers home! Peace of mind, while out of town, is priceless.”


“Mitzi & Klifton were the first people I trusted to watch my pup, Kabotie. I was nervous about leaving him with anyone but the meet and greet we had before his stay calmed my nerves. And the daily pictures, sometimes multiple per day were so appreciated. I would highly recommend them for anyones pup, they’re a very loving couple that give a ton of individual attention to each dog. Plus they have a beautiful backyard, perfect for pups to run around!”


“Ellyn was absolutely amazing! She provided many updates with photos throughout the stay and Marlo was happy (and tired from playing with her dog Murphy!) are after her stay. Will definitely be using Ellyn for future sittings!!”


“Claudia was great with my cat who stayed in her home for 5 days. He needs regular medicine of two types and Claudia was great about specific instructions while also giving him the attention he needs. I also appreciated the regular photos she sent me. My mind was at ease knowing my cat was in good hands. I would definitely have Claudia help me out again and definitely recommend her as a sitter!”



“Robyn was great with our pup. She sent pics every day so we could be reassured all was well. Off leash time to get the crazy out is something our dog needs, so it was fantastic that there is public land across the street where the dogs could run around together. When we picked our dog up, she was having a great time and didn’t even notice us at first. I’m so glad she had a relaxing and social experience while we were gone. We will be back!”


“Tracy is awesome. She loved on our pups and even sat with our lab during a thunderstorm. Tracy sent pictures so we could see that they were happy. Our pups love her and we’ll definitely use her again!”


“This was my first time using Rover and I felt anxious about it. When I picked up my black lab Benny at the end of a three day trip, he looked happy and was affectionate towards Ben. I got pictures all weekend from Ben and his girlfriend Mel, I’ve been running on trails and getting lots of time outside. They were both extremely kind, Thoughtful, and professional. I felt at ease and I will for sure use Ben again.”



“This was my first time bringing Viola to doggy daycare so I was a bit nervous. Justin brought the worry down very quickly. He was amazing to Viola, she had a blast! Thanks again Justin!”


About: I volunteer at the Frisco animal shelter so I have experience with puppies, seniors, reactive dogs and everything in between. I’ve also owned two dogs through their whole lives and have done some dog sitting on the Trusted Housesitters website. I work as a firefighter/ paramedic, so every day I wind up in people's homes on 911 calls, and often they have dogs, and it takes every bit of my self control to stay focused on the emergency at hand, and not get down on my knees and reassure the dogs and give them love. I'm a dog person through and through. Currently I own no dogs, so I've been getting my fix through dog sitting and volunteering. My work schedule is 48 hour shifts, and then I have a block of 4 days off. I only pet-sit when I am off, so, your dog(s) won't ever be left alone. I'm a bit of a homebody so I'm happy to have the company as I putter around the house, and then hiking is my main activity I do every day, and I will take your dog with me, if they're up for it. If a mosey two houses down is all your old dog can do, I'm happy to do that too. I live in a ground floor condo at the very end of a sleepy street and there are open spaces and trails all around me. I also like to hop in the car and drive just a few minutes to lots of other trailheads nearby to get the dogs out - of course only if you're ok with that. Dogs can sleep on my bed and on my couches. I don't take on more than one dog at a time (unless they are from the same household), so your dog will have my full attention and love. Whatever their normal schedule is for food, medications, treats, bathroom, exercise etc. I will have no problem keeping them to their normal routine. I live alone in a quiet and uncluttered space where I'm sure your dog will feel right at home.

“My wife and I went overseas for our honeymoon, and we were so happy to have found Nicole and Craig!! Our dog is a bit of a diva, and can't stand other dogs or traditional boarding facilities. She almost seemed sad when we brought her home. Nicole and Craig were very responsive and attentive to our pup. We will 100% be booking with them again in the future”



“Chelsea and her dog were amazing with Rosie! She got them out on walks/hikes quite a bit, and kept us super updated with great photos. She was very flexible with checking in on my cat and drop off plans as well.”


“Taryn was great watching Scout for an evening. She sent updates which I appreciated, took him on walks, and cared about taking good care of him. Highly recommended!”

“Maggie is the best! She watched our 2 dachshunds for 5 nights and took care of them as if they were her own. When we picked them up, Maggie was ready with everything neatly packed up and the dogs looking happy, warm, and well taken care of. We couldn’t have found someone better to take care of our 2 fur babies. Dachshunds are notoriously stubborn, yet Maggie worked her magic and got them in a routine so that everyone was happy. We couldn’t recommend Maggie more for anyone who wants the peace of mind that their dog(s) are in safe, loving hands while they are gone. Choose Maggie!”


“Stephanie was very accommodating. Flexible on timing and kept us up to date with amazing photos. Rummy had a blast with his new friends. She took him on many walks, and adventure to the dog park and lots of play sessions. Highly recommend!”

Loving dog boarding sitters in your neighborhood
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1. Joan C.

“Joan was fabulous! Our pup Ace is strong, super active, and a cuddler. She was able to handle anything he did. The videos she sent were so reassuring as well. Anytime we are here in Breck, we will be reaching out to Joan because she was just that fantastic!”


2. Sue D.

“Sue was absolutely amazing! We took a ski day and our dog stayed with her and had a blast, she was very communicative, sent photos, and made sure the dogs she had get along together with ours. She had repetitive doggies there and I’m sure our dog Cash will be one of them next time we come.”




3. Jan R.

“Jan is great!! Never once worried about my pup ruby while she was there. Daily updates were provided and I know my pup Ruby had the best time!”


4. Mychaela R.

“Mychaela is truly the best!! Gooch was so spoiled during his time with her (10 days). He was the happiest boy and she sent many pictures to share with us throughout the week. I was so happy to see how much wonderful attention he was getting and couldn’t recommend her anymore. You won’t find a better rover option in Boulder. I hope we can stay in touch so Gooch and I can see her again. 💖”


5. Shanik C.

“This was our first time using Rover and Shanik made our experience nothing short of amazing! She is so kind and considerate, truly a dog lover! Shanik sent us tons of adorable pictures and updates of our dog while we were away. We felt our dog was incredibly loved and well taken care of. Both Shanik and her husband were easy to get in touch with and made pick up/drop off a breeze. We highly recommend bringing your pet to Shanik! Thanks again! We’re so glad we found you!”


6. Dan T.
“I can't say enough good things about Dan as a dog sitter! He is truly amazing with pets and has such a huge heart for both dogs and cats. I always feel at ease knowing that my Rottweiler, Whiskey, is in such great hands when I need to go out of town. Dan goes above and beyond to take care of him – he not only makes sure he's well-fed and safe but also takes him on plenty of walks to keep him entertained and active. The best part? He even snaps the cutest photos of Whiskey, which I absolutely love! Every time I mention we’re going to Dan’s house, Whiskey’s tail goes wild with excitement – it’s clear he’s thrilled to spend time there. Dan’s updates are always so consistent, and they give me so much peace of mind. It’s reassuring to know he’s not just being cared for, but also having a great time. Having a safe, loving place for my dogs when I’m away is incredibly important, and Dan’s care makes all the difference. I wholeheartedly recommend him to anyone looking for a trustworthy, loving dog sitter!”


7. Fred A.


“By all accounts Maple had a great time with Fred! I enjoyed the pictures and could tell she was in a dog lovers home! Peace of mind, while out of town, is priceless.”


8. Mitzi & Klifton K.

“Mitzi & Klifton were the first people I trusted to watch my pup, Kabotie. I was nervous about leaving him with anyone but the meet and greet we had before his stay calmed my nerves. And the daily pictures, sometimes multiple per day were so appreciated. I would highly recommend them for anyones pup, they’re a very loving couple that give a ton of individual attention to each dog. Plus they have a beautiful backyard, perfect for pups to run around!”


9. Ellyn A.

“Ellyn was absolutely amazing! She provided many updates with photos throughout the stay and Marlo was happy (and tired from playing with her dog Murphy!) are after her stay. Will definitely be using Ellyn for future sittings!!”


10. Claudia M.

“Claudia was great with my cat who stayed in her home for 5 days. He needs regular medicine of two types and Claudia was great about specific instructions while also giving him the attention he needs. I also appreciated the regular photos she sent me. My mind was at ease knowing my cat was in good hands. I would definitely have Claudia help me out again and definitely recommend her as a sitter!”




11. Robyn S.

“Robyn was great with our pup. She sent pics every day so we could be reassured all was well. Off leash time to get the crazy out is something our dog needs, so it was fantastic that there is public land across the street where the dogs could run around together. When we picked our dog up, she was having a great time and didn’t even notice us at first. I’m so glad she had a relaxing and social experience while we were gone. We will be back!”


12. Tracy B.

“Tracy is awesome. She loved on our pups and even sat with our lab during a thunderstorm. Tracy sent pictures so we could see that they were happy. Our pups love her and we’ll definitely use her again!”


13. Ben C.

“This was my first time using Rover and I felt anxious about it. When I picked up my black lab Benny at the end of a three day trip, he looked happy and was affectionate towards Ben. I got pictures all weekend from Ben and his girlfriend Mel, I’ve been running on trails and getting lots of time outside. They were both extremely kind, Thoughtful, and professional. I felt at ease and I will for sure use Ben again.”




14. Justin E.


“This was my first time bringing Viola to doggy daycare so I was a bit nervous. Justin brought the worry down very quickly. He was amazing to Viola, she had a blast! Thanks again Justin!”


15. Stuss L.
“Stuss has watched my dog, Yoshi and I can't say enough good things about him. He went above and beyond. Stuss cared for my pup like it was his own. He took Yoshi on long walks, played fetch at the park and gave her lots of cuddles. Everything my pup loves. Yoshi also got sick (from eating something she shouldn't have under MY CARE) and Stuss kept me updated and took great care until I returned. He even checked in on her after he left. Stuss was the best sitter I’ve had. I would recommend his care to anyone.”


16. Nicole & Craig K.

“My wife and I went overseas for our honeymoon, and we were so happy to have found Nicole and Craig!! Our dog is a bit of a diva, and can't stand other dogs or traditional boarding facilities. She almost seemed sad when we brought her home. Nicole and Craig were very responsive and attentive to our pup. We will 100% be booking with them again in the future”




17. Chelsea B.

“Chelsea and her dog were amazing with Rosie! She got them out on walks/hikes quite a bit, and kept us super updated with great photos. She was very flexible with checking in on my cat and drop off plans as well.”


18. Taryn P.

“Taryn was great watching Scout for an evening. She sent updates which I appreciated, took him on walks, and cared about taking good care of him. Highly recommended!”


19. Maggie G.

“Maggie is the best! She watched our 2 dachshunds for 5 nights and took care of them as if they were her own. When we picked them up, Maggie was ready with everything neatly packed up and the dogs looking happy, warm, and well taken care of. We couldn’t have found someone better to take care of our 2 fur babies. Dachshunds are notoriously stubborn, yet Maggie worked her magic and got them in a routine so that everyone was happy. We couldn’t recommend Maggie more for anyone who wants the peace of mind that their dog(s) are in safe, loving hands while they are gone. Choose Maggie!”


20. Stephanie C.

“Stephanie was very accommodating. Flexible on timing and kept us up to date with amazing photos. Rummy had a blast with his new friends. She took him on many walks, and adventure to the dog park and lots of play sessions. Highly recommend!”
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 dogs2. Meet & Greet
Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs while you’re away3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
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.
Dog Boarding FAQs
Frequently asked questions about Rover
As of May 2025, the median cost of dog boarding in Winter Park is $73 per night, including service fees. Boarding your dog for one week typically costs $511. 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 $29 to as high as $66 per night.
As of May 2025, 84 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, 90% 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 4 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 84 dog boarding sitters in Winter Park on Rover, so you’re sure to find the perfect match for your dog! In Winter Park, 100% of sitters offer daily exercise, 100% offer medication administration, and 100% 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.
