Dog Sitting in Windermere
Book a Windermere dog sitter to watch your dog in your sitter’s home or yours.

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Top rated Windermere dog sitters

“Dana was beyond exceptional and her star rating should be more than what’s listed. She was gentle caring and knowledgeable, which calmed my fears about someone else watching my baby. This was the first time that I’ve used and the first time my dog was cared for by someone other than me. I can’t say Thank you enough to her. I would 200% recommend her to anyone needing a skilled, reliable and caring person for dog services.”


“We love Savannah! She was able to come through in a clutch, took plenty of pics and made sure the babies were good while I took care of an emergency”


“Victoria always goes above and beyond, she even took our pups to the park to play! She is on time, organized and always communicates with us if any questions come up. She gives our pup eye drops which is a huge help since he has some extra needs and she helps with their special food as well. We are so grateful to have found Victoria and will continue to book whenever we need some help!”


“Jennifer took great care of our guy Dexter for several drop-in visits. She spent time with him, fed him, walked him, and provided detailed reports and photos. We are so excited to have him stay with her for a week. We will definitely utilize her services in the future. Thank you Jennifer for making Dexter feel he has a new family member!”


“Taryn was GREAT! If I could leave 10 stars, I would. Taryn watched our 8 month old golden retriever puppy, Blitz. From the first time she met Blitz during our meet & greet, we could tell she had a true love for dogs. We were at total peace knowing Taryn was watching Blitz, and she sent lots of pictures and videos! We will certainly be booking with Taryn again, she was the best!”


About: Over 11 Years of Trusted Pet Care With more than a decade of experience, I’ve cared for pets of all ages—including senior pets and those needing medication like insulin for diabetes. I also offer in-home boarding in a cozy, loving environment where your pet will feel right at home. My schedule is very open and flexible, which makes it easy for me to give your pet the time and attention they need. I work a job with a lot of flexibility, so I can easily adjust my day to fit your pet’s routine—whether it’s feeding, walking, or just keeping them company. Your pup will get plenty of love, cuddles, and playtime in a calm, pet-friendly home. I offer daily walks, potty breaks, and follow your feeding/medication routines. I board dogs under 25 lbs who get along with my cat and treat every guest like family! We also have a fenced backyard.

About: I have been pet sitting and dog walking for the past 10 years. I have taken care of all types of breeds and dogs of different sizes. I have also taken care of multiple animals at once and have even cared for animals (dogs and cats) with special needs requiring medications at specific hours throughout the day. I work from home and am happy to help take care of your furry friend before work, during lunch, or after work. I have more flexibility before and after work however and have full availability on the weekends. If caring for an animal in my home, I would have a separate designated area for them apart from my own animals. This is to ensure comfort for both animals

About: Hi there! My name is Hailey, and I’m a 24-year-old lifelong dog lover with years of hands-on experience caring for high energy breeds. I’ve grown up with dogs my whole life— including a husky, husky-retriever mix, and two Australian shepherds— so I’m no stranger to the energy, intelligence, and attention these pups need. Whether it’s a long walk, a jog, or active playtime, I’m in shape and more than ready to keep up! What sets me apart is not just my experience with active dogs, but my genuine love for getting to know each pup’s unique personality. I know how important it is to trust someone with your furry family member, and I bring the same level of care and attentiveness to your dog as I do with my own. Whether your pup needs a quick potty break, structured walk, or just a little extra love while you’re away, I’m here to help! I’m currently in my last semester of grad school, which means I’ve got a flexible schedule and could definitely use a study break or two with a furry friend! I’m an early riser and tend to be up at odd hours, so I’m available for morning and weekend walks. Whether your pup needs a quick walk, some playtime, or just a little company while you’re out, I’m happy to help— and always excited to meet four-legged study buddies! Your pet’s safety and comfort are my top priorities. I know every home and every dog is different, so I’m happy to follow your specific routines, rules, and preferences to make sure your pup feels secure and cared for. Whether it’s sticking to a certain walking route, managing feeding schedules, or keeping things calm and low-key, I’m flexible and respectful of your space and your pet’s needs. You can count on me to treat your home and your dog with the same care I’d give my own.

“Alexis was a tremendous help with checking in on our kitties while we were out of town for two weeks. She was timely, shared updates and photos with me, and took great care to maintain the cats food, water, and litter during her check-ins. I would recommend Alexis to any cat parent!”



About: Although I listed my official "pet care experience" as 5 years, I have had at least 1 dog in my home my entire life. While in college, I joined a club partnered with Canine Companions which gave me the opportunity to puppy sit, and later on puppy raise, future service dogs for the organization. I currently have a 2 year old lab who I puppy raised from 2 months old for Canine Companions, but who was released from professional training and is now my pet. Being a former puppy raiser, I have experience with training and grooming. While most of my experience recently has been with puppies 2 months-2 years old, my family yorkie lived to about 18 years and I would take care of him/groom him every time I visited home. Many of my friends and family own a variety of dogs, so I have been around a variety of sizes, breeds, and ages. At the end of the day, I'm a fellow dog mom who knows leaving your baby home alone can be stressful and I would love to help you out! I am currently a Freelance Theatrical Sound Designer and Technician, so half of my active work schedule is remote. Being new to rover, I am starting out only offering weekdays, but have full availability for all 5 days! I also don't mind grooming if you can provide soap, towels, and let me know the best location to bath them in your house (please note that I am not a professional groomer, I just have experience from grooming my own dog. I will not proceed with any grooming if your dog appears very stress.) There may be times where my work schedule becomes more busy, but I would inform you in advance if it makes any changes to our schedule. I promise to follow any and all rules you have for your dog and your home. I know from personal experience that every dog parent is specific about how their dog is taken care of and I want to respect that. I also know that trusting someone in your home can be a scary thing and want to respect your privacy. While I have a dog of my own, I would not bring him to your residence or around your dog unless you brought it up/gave me permission. Even with permission though, I likely wouldn't bring my dog so that I can give yours the focus and attention you are hiring me for. That being said, I would hope for the trust and respect to work both ways. Please inform me of other people who may come to the house while I am there and of any triggers/fears your dog may have.

“Our pup was very well cared for while we were away. We will definitely be using Nicholas again in the future. He did and amazing job and I love that he washed the dogs bowls before he fed him each time.”


“Adam responded to my request for a last minute drop in sitter immediately and was able to come for a meet and greet the same day! He did a great job looking after my dog and made sure to have a good understanding of how to take care of her. Will definitely use Adam again in the future.”


About: I’ve always had at least three cats in my home since birth. I’m compassionate about their unique personalities and needs. I know to always approach them with calm and quiet energy. I also know to let them come to you and to respect their hierarchy in a multi-cat home. I have a very open daytime schedule and a strong commitment to building routines that center around care, reliability, and connection. I’m currently working part-time in the evenings, so my days are wide open for drop-in visits, walks, and quality time with pets. I truly enjoy creating calm, positive experiences for animals, and I prioritize being punctual and consistent, traits I know pets thrive on. For drop-in visits, I treat each pet like they’re my own: safe, loved, and cared for. I follow the owner’s instructions closely, whether that includes feeding, refreshing water, administering medication, cleaning up accidents or litter, or simply spending quality time playing, walking, or giving attention. I’m patient with shy or anxious pets and always make sure they feel secure before I leave. I also send photo updates and notes after each visit so owners know their pet is in good hands.

“Lena was polite and very thorough when following instructions. She was able to help us deal with a mini emergency when our cat’s automatic feeder broke, and helped me troubleshoot it on the fly and was able to get it working again.”


“Erika was amazing! She provided very thorough updates and made sure our cars received a ton of love and attention. I would definitely recommend her and book her again! Excellent service!”



About: Hi! I'm Jen. I have 2 years experience working in a pet daycare and vet setting. I have also volunteered with the SPCA in Orlando FL. I've had roles from administrative to pet care. I have raised two dogs of my own and have a new puppy addition to our family. I have experience with small and large dogs from my Pomeranian (Gracie) to my Lab mixes (Penny and Leia). They each have their own sweet personality. I am willing to try to work with any temperament as long as your pup is comfortable. I love to make your pup feel comfortable and like family. I look forward to getting to know your fur baby. Thank you! Please message with any questions you may have! I currently work part-time for Disney. I would love to care for your fur babies in between my work days. I have time to be attentive to your pets needs. I currently live in a townhome with a safe neighborhood for long scenic walks and there is a clean pet park across the street from us.
Loving dog sitters in your neighborhood
Search Results


Dana Z.
Star Sitter


“Dana was beyond exceptional and her star rating should be more than what’s listed. She was gentle caring and knowledgeable, which calmed my fears about someone else watching my baby. This was the first time that I’ve used and the first time my dog was cared for by someone other than me. I can’t say Thank you enough to her. I would 200% recommend her to anyone needing a skilled, reliable and caring person for dog services.”


Samantha Y.Star Sitter

“Sam was so amazing!!! Our pup loved her! She made sure our pup got all the love he deserved!! Provided all the pictures and feedback!”


Savannah L.Star Sitter

“We love Savannah! She was able to come through in a clutch, took plenty of pics and made sure the babies were good while I took care of an emergency”


Sarah P.Star Sitter

“Sarah was great! Super friendly and easy to work with. We look forward to booking with her regularly in the future.”


Victoria D.Star Sitter

“Victoria always goes above and beyond, she even took our pups to the park to play! She is on time, organized and always communicates with us if any questions come up. She gives our pup eye drops which is a huge help since he has some extra needs and she helps with their special food as well. We are so grateful to have found Victoria and will continue to book whenever we need some help!”


Jennifer W.Star Sitter

“Jennifer took great care of our guy Dexter for several drop-in visits. She spent time with him, fed him, walked him, and provided detailed reports and photos. We are so excited to have him stay with her for a week. We will definitely utilize her services in the future. Thank you Jennifer for making Dexter feel he has a new family member!”


Brittney C.

“Great experience! Brittany was timely, provided photos, and provided results of visit! Will book again.”


Taryn N.Star Sitter

“Taryn was GREAT! If I could leave 10 stars, I would. Taryn watched our 8 month old golden retriever puppy, Blitz. From the first time she met Blitz during our meet & greet, we could tell she had a true love for dogs. We were at total peace knowing Taryn was watching Blitz, and she sent lots of pictures and videos! We will certainly be booking with Taryn again, she was the best!”


Elizabeth R.
“Hi. My name is Jason and we have been using Elizabeth to watch our babies Gigi "cat" and Riptide "dog" for well over 10 years. She is wonderful with the pets. They look forward when she's coming and taking care of them. I would not use anyone else. I feel completely confident and comfortable when she looking after our babies and know they are in great hands. Bonus, that she has family that works in a local vet. I highly 5 plus stars recommend her.”


nina s.
“I would highly recommend Nina for pet sitting experiences. She has been extremely professional and takes the responsibility of walking Olive seriously. She is very dependable and trustworthy. She even helped trim Olive’s nails once!!”


Hailey M.Star Sitter
“Hailey truly cares about animals and takes their responsibility seriously. Hailey has stayed at my house with my dog during vacations and not only did she follow every instruction I left, but they also went above and beyond to make sure my dog felt safe and loved while I was away. I received regular updates, photos, and even a few funny stories that made me feel completely at ease. Most importantly, I could tell my dog was genuinely happy and well cared for when I returned. It's such a relief to find someone so trustworthy and honest—Hailey treats pets like family, and that kind of integrity is rare. I would recommend her over and over again.”


Alexis T.

“Alexis was a tremendous help with checking in on our kitties while we were out of town for two weeks. She was timely, shared updates and photos with me, and took great care to maintain the cats food, water, and litter during her check-ins. I would recommend Alexis to any cat parent!”




Alyssa M.
About: Although I listed my official "pet care experience" as 5 years, I have had at least 1 dog in my home my entire life. While in college, I joined a club partnered with Canine Companions which gave me the opportunity to puppy sit, and later on puppy raise, future service dogs for the organization. I currently have a 2 year old lab who I puppy raised from 2 months old for Canine Companions, but who was released from professional training and is now my pet. Being a former puppy raiser, I have experience with training and grooming. While most of my experience recently has been with puppies 2 months-2 years old, my family yorkie lived to about 18 years and I would take care of him/groom him every time I visited home. Many of my friends and family own a variety of dogs, so I have been around a variety of sizes, breeds, and ages. At the end of the day, I'm a fellow dog mom who knows leaving your baby home alone can be stressful and I would love to help you out! I am currently a Freelance Theatrical Sound Designer and Technician, so half of my active work schedule is remote. Being new to rover, I am starting out only offering weekdays, but have full availability for all 5 days! I also don't mind grooming if you can provide soap, towels, and let me know the best location to bath them in your house (please note that I am not a professional groomer, I just have experience from grooming my own dog. I will not proceed with any grooming if your dog appears very stress.) There may be times where my work schedule becomes more busy, but I would inform you in advance if it makes any changes to our schedule. I promise to follow any and all rules you have for your dog and your home. I know from personal experience that every dog parent is specific about how their dog is taken care of and I want to respect that. I also know that trusting someone in your home can be a scary thing and want to respect your privacy. While I have a dog of my own, I would not bring him to your residence or around your dog unless you brought it up/gave me permission. Even with permission though, I likely wouldn't bring my dog so that I can give yours the focus and attention you are hiring me for. That being said, I would hope for the trust and respect to work both ways. Please inform me of other people who may come to the house while I am there and of any triggers/fears your dog may have.


Nicholas G.Star Sitter

“Our pup was very well cared for while we were away. We will definitely be using Nicholas again in the future. He did and amazing job and I love that he washed the dogs bowls before he fed him each time.”


Adam C.

“Adam responded to my request for a last minute drop in sitter immediately and was able to come for a meet and greet the same day! He did a great job looking after my dog and made sure to have a good understanding of how to take care of her. Will definitely use Adam again in the future.”


Lindsay L.
“Lindsay is the best! I have a lot of cats that need separating and some have special needs and I was confident in trusting Lindsay to keep all my cats safe while I was away overseas for 3 weeks. She gave me constant updates and pictures of my cats and kept the litter boxes clean and my cats happy. It gave me relief to entrust my fur babies in her hands. Highly recommend!!”




Cami C.

“Cami is the Best! Even goes above and beyond to pick up the mess my dogs made when trying to see if there was a squeaker in the couch ?!! Thank you so much Cami!!”


Lena H.

“Lena was polite and very thorough when following instructions. She was able to help us deal with a mini emergency when our cat’s automatic feeder broke, and helped me troubleshoot it on the fly and was able to get it working again.”


Erika M.

“Erika was amazing! She provided very thorough updates and made sure our cars received a ton of love and attention. I would definitely recommend her and book her again! Excellent service!”




Jennifer D.
“I'm blessed and proud to be the Mom of Jennifer, who is a caring and loving person. Her caring heart lead her to become a mental health counselor. She's had many years of growing up with our furry family members who brought joy to her and vice versa. She also carried that love for animals to her own home. I believe she would be a wonderful addition to the Rover family to spread happiness and love. 🐾❤️ Sincerely Loretta Fowler”
How Rover works
1. Search
Read verified reviews by dog parents like you and choose a sitter who’s a great match for you and your dogs2. Meet & Greet
Meet either virtually or in-person with a sitter 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 sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Dog Sitting FAQs
Frequently asked questions about Rover
Rover makes it easy to reach out to multiple dog sitters about your booking. Typically, dog sitters on Rover respond in under an hour.
Experience can vary widely from dog sitter to dog sitter, but you can view reviews, years of experience, and number of repeat clients when comparing dog sitters available in Windermere.
Rover makes it easy to find Windermere dog sitters to provide loving care from their own home. The background-checked, 5-star dog 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 sitting is great for:
- Dogs of all ages and abilities, including puppies
- Dog parents looking for a safe, loving alternative to a kennel
- Dogs who’d love to socialize with their dog sitter’s pets
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your dog is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your dog 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 sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog sitter’s cancellation policy.
