Dog Boarding Windermere
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 2,629 pet parents in Windermere have booked dog boarding
Windermere, 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.
“Jonathon & Aimee Such a beautiful experience letting our baby on your hands, we are very lucky to find you and be able to be away from him having the peace of mind of knowing he was totally fine. You guys were awesome from the day we contacted you, you were always available for us and keep us updated about Brownie the whole time, we know how comfortable he felt the whole time with you. We loved how attentive, caring, reliable and loving you were throughout this weekend! We really appreciate it. Thank you also for taking the time to send all those cute pics and send brownie home with a goody bag to keep having fun. WHOEVER IS OUT THERE LOOKING FOR A HOME AWAY FROM HOME FOR YOUR BABIES. JONATHON AND AIMEE ARE THE ONES. Thank you guys!🫶🏼🫶🏼🫶🏼”
“Monica was great with our Lola. Lola was very nervous at first, but Monica was patient and kind with her, making us all comfortable. Monica provided excellent communication and videos which were much appreciated. Lola did great and we will definitely book with Monica again in the future! Thank you again Monica!”
“This is the first time I have used a boarding for Lulu and I was so happy with Kymry’s care and daily follow through. She is clearly a wonderful person and has taken care of many dogs!! There were seven dogs when I arrived Lulu, and that was so much fun to see. They all got along and Lulu adapted. She’s older and may be a bit more quiet, but I felt so comfortable while I was away. Of course, but will no doubt be taking her back to Kymry’s house soon.!!!! Xxx Victoria Regan”
“Elliott really enjoys his time with Poliana!! He’s so well taken care of and loves being with the other dogs. I couldn’t ask for more. It’s such a great doggie environment. Highly recommend.”
“OMG WE LOVE JAMIEEEEEE!!!!! Jamie and her family were amazing in every way!! Jamie is a true dog mom so right from the start you could feel that instant connection!!.. Out little girl Pinky was happy and playing with their dog Evie and fit right in with the rest of the family. She took care of her as it f she was her own,,, It is a beauuutiful atmosphere, a beautiful family and a BEAUTIFUL mom who watched over our little girl with love. We look forward to having Pinky spend more time with Jamie and her family in the near future, Thank you JAMIE you are the BEST!!!!!!!!”
“Savannah took wonderful care of my shy pup! Daily updates and photos shared and very communicative as well! Will be rebooking for any further boarding needs!”
About: Hi! I'm Cherry, an Orlando-based dog lover offering boarding and day care. Because I work from home full-time, your pup is never left alone — there's always someone here for potty breaks, play, and company throughout the day, which makes a real difference for boarding and for dogs who get anxious or need a little extra attention. I've spent years caring for my sister's small dog — daily walks, feeding, and lots of playtime — so I'm comfortable with everyone from bouncy little dogs to calm, low-key companions. I treat every dog like my own: steady routines, plenty of exercise, and a safe, relaxed space to settle in. You'll get clear communication and regular photo updates, so you always know how your dog is doing. I'm happy to start with a free meet-and-greet to make sure it's a great fit. Looking forward to meeting your furry family member! I'm available on both weekdays and weekends with advance notice. Since I work from home, I have good flexibility throughout the day for walks, drop-ins, and check-ins, and I'm happy to arrange boarding and daycare when booked ahead. I'll always do my best to accommodate your schedule — just reach out early so we can plan the details and make sure it's a great fit. I live in a quiet, non-smoking home with no children and a small fenced backyard, which makes for a calm, low-stress environment for dogs to relax in. My neighborhood is peaceful with community parks nearby and a dog park close by, so there's plenty of opportunity for safe walks and exercise.
“I was very nervous to leave Remy for a week when I went on vacation because he gets very anxious in new places, but Liz made it such a comfortable environment for him. I expected him to not eat and probably have an upset stomach, but he had no issues at all and did great! Liz does a great job caring for the dogs and making them feel at home!”
“Connor took amazing care of Latte, treating her like his own dog. You can tell he genuinely fell in love with her, which made me feel completely at ease. I received constant updates and photos of Latte looking happy and well cared for, which I truly appreciated. Everything was perfect, and I will definitely continue booking with Connor. Highly recommend!”
“I booked Reakha very last minute. Reakha was very flexible and worked with my needs. I initially booked her for 2 nights but my dog seemed very happy and got along with her dogs so I extended the stay for 2 more nights. I definitely did not bring enough food for my dog, but Reakha took care of her like her own dog. My dog didn’t want to come home after the stay! I’m very satisfied and highly recommend her to anyone.”
“Christopher took good care of Scout for almost 2 weeks while we were out of the country. He made sure she got along with his dogs, went outside in the yard, and had time to play. We really appreciated the photos, videos and updates he provided!”
“Katie was FANTASTIC 😍. We know Hunter was well cared for, and enjoyed his time with Katie. He came home looking to jump on beds;) haha so we know he was comfortable snuggling over with them 💕. Thank you for taking care of our pup. Definitely recommend!!!”
“Rennan is always so kind and loving to our dog. He follows all instructions and is very prompt in providing any updates. He’s very patient when it comes to the emotional needs of our dog specially when it was the first time we boarded him with Rennan”
“Jerry was fantastic with our high- energy Lexy and Milo. They made new friends and had a blast at his doggy daycare/ overnight stay. He kept us updated with lots of pictures and videos :) Our pups will be back :)”
“This is our second time using Jared and what can I say except that he is exceptional. I love all the updates to what my two huskies are up to while under his care. He understands the energy of a husky and my girls love hanging out with his dogs. I would definitely hire again with full confidence that my girls are being well cared for”
“Idalis and her family took amazing care of my baby Penny. It was my first time leaving her with someone “unknown” and Idalis made everything feel so comfortable by setting up a meet up before and showing us all she has to offer to take care of our beloved girl. Her house and backyard are amazing, Penny was able to socialize with other dogs and she kept sending me pictures of everything they were doing while she had Penny. Overall, I’d recommend Idalis and her family to take care of your dog and would definitely be using her services again when needed! Thank you Idalis and Alex.”
“Sarah did an amazing job watching Lola. She sent pictures everyday and I know Lola had a good time with Sarah and her family. We will definitely go to Sarah again!!”
“Gloria went above and beyond! Sent me daily updates and took such great care of my lil pup even with his separation anxiety ! She was also super flexible and understanding with us due to an unseen flight delay. Bear was in great hands and warmed up to her so quick. Thank you Gloria for making this such an easy and comfortable time for him and for us!”
The median cost per night for dog boarding in Windermere is $40
Dog parents share their Rover experiences - Windermere
Jamie has watched our mini schnauzers, Henry and Lucy, several times now, and we can't recommend her enough. She and her dog Evie treat them like part of the family from the moment they walk in. Jamie is great about communication, sending photos and updates without us ever having to ask, which makes being away so much easier. Henry and Lucy are always excited to go back. We'll definitely keep booking with Jamie.
Jonathon & Aimee were awesome sitters for Chip. He spent the weekend with them and as we picked him up, we could tell right away that he had a great time and was really well looked after. They really cared about Chip and we’d happily recommend Jonathon & Aimee to anyone looking for dog sitting.
Every time our dog, Winnie, stays with Sol, we couldn’t be happier with the care she receives! it’s clear that she’s truly loved, and Sol treats Winnie like her own. Throughout the stay, she’s incredibly communicative—sending photos, updates, and little notes that gave us total peace of mind while we were away. Our dog can be a bit shy and standoffish around other dogs at first, but Sol is patient, gentle, and attentive to her and each of her guest's needs. When we came home, Winnie was relaxed, happy, and clearly very well cared for. If you’re looking for someone reliable, kind, and genuinely amazing with pets, look no further. We will definitely be booking with Sol again!
Taryn was absolutely amazing with Kahlua! From the moment we booked, she was attentive, communicative, and so reassuring. She gave the best updates with pictures throughout the day which meant so much to me, especially since Kahlua struggles with anxiety. It was clear that Taryn gave her so much love, patience, and attention. You can truly tell she cares about the dogs she watches. I felt completely at peace knowing Kahlua was in such good hands. I would 1000% book her again!
Dianet was absolutely amazing with our Aiden. She got lots of love, attention and exercise, and even made a new dog friend. Dianet kept us updated throughout Aiden’s stay. We felt very reassured during our trip knowing that she was in good hands with Dianet and her family. Our baby came home a very happy girl! We would 100% recommend :)
This is the second time Rio has stayed with Meredith and her family. We have been looking for a sitter for a while and have finally found an absolute gem! Consistent communication, many pictures, Rio burns so much energy and loves going to their house! We will rebook time and time again, HIGHLY recommend!!!
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
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Popular requests for dog boarding - Windermere
Select a filter and find qualifying sitters offering dog boarding.Sitters in Windermere average 12 repeat dog boarding clients
FAQs for Boarding - Windermere
Frequently asked questions about Rover
The average cost for Dog Boarding in Windermere on Rover is $49.95 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 2,656 sitters on Rover offering Dog Boarding across Windermere. 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 Windermere 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 Windermere 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 Windermere 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 Windermere.
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 Windermere 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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