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

Over 466 pet parents in Windermere have booked dog sitting
Windermere, Find top rated dog sitting
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
About: I have had dogs and cats my whole life and my happiest memories involve animals. I know your pets are your children, and I will treat them as such. I’ve had experience with everything from pet frogs to kittens to a 150 pound Great Pyrenees. I loved them all and I will love your pets, too. I am happy to swing by to check on your pets, or to stay the night to make sure they and your home is okay while you’re away. Please don’t hesitate to message me if you have any questions or comments, I’d be happy to answer them! I work remotely from home in Winter Garden, so I am happy to stay the day with your fur babies and work from your home or stop by throughout the day - whatever you prefer! I have three cats at home and, unfortunately, they do not love dogs as much as I do, so I will need to care for your canine friends from your home. I love animals and I would love to care for your pets as I care for my own!
About: I grew up on a farm so I’m used to all kinds of shapes and sizes. I’ve also worked in the animal care industry for the last 10 years. Between dog boarding facilities, both private and corporate, to grooming, management and vet assistant experience, I will always work with animals. They’re a staple in my life and I’d like to be able to care for any future clients, as I would my own personal pets. I’m very detailed and will communicate anything and everything! Im currently working 4 days a week and have 2 set days off. That being Wednesday and Sunday. I’d like to drop down from my day job down to 2-3 days but still enjoy spending time with pets. Anytime after 7am Wednesday (gym in the mornings), and before 7pm on Sunday I will be available. I have a senior dog, and I’ve had multiple dogs in the past that needed extra attention and patience. Some dogs I’ve had also needed a lot of exercise and mental stimulation. I’ve done raw diets, freeze dried, dry and wet food. I’m able to give supplements and medications as well.
About: I am a vet student in school and I have been caring for my 6 animals for more than 10 years. You can trust me I will be very careful, responsible, and loving towards your animals. I work a part time job as a barista and my mornings and weekends are usually free so I will have a lot of time free to do what I love most and care for your animals! I will care for your animals at your home by feeding/walking them on time and I can put them to bed in their crate if needed or if not then they’ll have a safe space to get their zoomies out and relax!
About: I’ve taken care of my own cats and dogs until their passing of old age or adoption. I’m very kind and loving towards all animals. I work full time, but I have 3 days off during the week and I would love to take care of your pet in my free time! I understand that giving access to someone else’s home and pet can be scary, but I assure you that I will take good care of your pet and your home!
About: I ve taken care of my dog and cat also my Guinea pig. I took care of friends and neighbors pets. I enjoy Walking and playing with pets. I’m staying home mom I have the time to care for my kids and pets. Feeding, walking and playing with them. My kids are my helpers. I would like to watch your pet without any problems. I have Guinea pig for now she is in her cage. Your pet will get all the attention while they are under my care.
About: I’m Brittney, married, no kids or pets of my own (apartment life). Previously worked in general practice and emergency room vet medicine. I love dogs and cats alike. Looking to love all over your fur baby and steal a few kisses! Central FL resident, Disney lover. Bed cuddles and couch snuggles are always welcome. I look forward to working with you and your fur baby. I appreciate open lines of communication and making both you and your pet feeling safe and cared for. Thanks for your time and consideration! Im working part time right now, with a lot of flexibility to care for your fur babies! I offer daily walks, home check ins, and in home boarding/house watching. I’m happy to come stay for any duration at your home with your pets to keep them feeling safe and in their routine. If you prefer I don’t spend the night, that is fine too! I have general and ER vet experience, I have an associates in annual science back when I thought I’d always work in vet med. I appreciate a good walk, just as much as any pup! Cats and fun toys are my favorite pastime.

“Laura was a life saver. We were going to be be very busy, out and about for 2 days. We forgot to plan for someone to come in the afternoon to give our dogs a break outside the house since we will be out for more than 10 hours of the day. We found Laura and she was incredible. Fast response, easy to book and update us with how our dogs did with the visits. Greatly appreciated her. I will recommend and use her services again.”
About: In our home we love all shapes and sizes of dogs, I was raised with dogs as well as my son's. We will provide a loving caring experience for your "babies" with frequent TLC belly rubs and a large fenced in backyard for fresh air and outdoor play!!! Due to working from home with the availability to move around and Care for your lovely fur babies pet care fits perfectly into my schedule and allows for me to provide the best care and attention needed! Safety is priority!! Our home consists of a screened in porch and a fenced in backyard. Your babies are safe and sound with us here!
“This was super last minute and Favianna was so pleasant to my dog. Talk about going the extra mile, she walked him, played with him, and filled his bowl with food and water like I asked. I also, found the cutest goodie bag and note for my dog when I got home. I will definitely be booking her for my future dog care. :)”
“He was very kind and thorough with my cat. He paid close attention to all the details and asked questions. I really appreciated how careful and precise he was. Great communication and very punctual. Thank you!”

About: I grew up with plenty of pets and am well experienced on what it takes to care for animals. I’ve worked as a pet sitter and dog walker on the past. I also have my own Goldendoodle named Luna, she keeps me well trained 😂 I work from home and can work anywhere with WiFi/cell reception. My schedule is very flexible, So I can easily work pet care into my schedule without issue. I have a friendly, well acclimated Goldendoodle for play dates, I am experienced with animals that are both crate trained and non crate pets, so happy to follow clients preferences.
“AMAZINGGGG!!! I cannot say enough positive things about my experience with Amanda. Not only did she follow my exact instructions completely, but I could tell that she genuinely cared about my cat. This was the first time that I returned from a trip and my cat didn’t greet me with anxiety filled crying. She was calm and relaxed, and I could tell that she was given so much attention and love while I was gone. It was such a relief. Also, I unexpectedly ended up in the hospital on the way home from my vacation, so I couldn’t return to my home to check on my fur baby. And she was quick to rush over to check on her and feed her. Such a lifesaver. I’ve truly never felt at ease leaving my little girl before. But now, thanks to Amanda, I’ll actually be able to go on a vacation without feeling anxious and guilty leaving her. I know she’ll be in great hands. Thank you sooo much, seriously!”

About: I’ve been around animals all my life from dogs, cats, gerbils, cows, pigs and horses. I'm am willing to treat your pet as part of my family. I understand your pet is the world to you and want the best for your pet. I treat your pets as my own and know that they deserve the very best! I will carry out what you except to be done or treated with your pet. I am familiar with a lot of breeds, their characteristics and how to work with them. We have our own private dog park. I offer additional obedience training (additional fees apply) if requested. I'll work on obedience training the basics with your dog and try and stop any behavioral problems; if appropriate boarding days allow. Your dog will be in good hands and will either lay by me or if they are allowed on furniture (or if not allowed 🚫 just let me know). I will follow your wishes to not be on furniture, just like if they were at home at your place. I will pamper them and give love - they will love it. Where I live we have our own private dog park to take your fur baby(s) to play and get some exercise. I have one dog (tea cup) Maltese to keep your fur baby(s) company and play. She gets along with all dog(s) and sizes. If you want your dogs crated please bring one so I can easily crate your dog if needed (I do have different size crates)... A dog’s natural behavior as a pack animal allows them to learn discipline, hierarchy and socialization. And them being with other dogs that I watch. Interacting with friendly dogs and people throughout the day aides their learning of these behaviors. Pets must be uptodate on all shots and flea/tick prevention - my dog is on Bravecto/Heartguard. I keep my pet upto date on flea/tick and require your dog to be on preventative flea/tick program (no one likes fleas/ticks and don’t want pickup those parasites and spread it - thank you for following this prevention we can stop). I’m currently not working, so I’ll have plenty of time to play with ur fur baby(s)! And be home with them. I’m available to board weekdays and weekends and offer day care. We have our own private dog park, where I’ll take them for exercise and play. I go into the park when no other dogs in the park or if another dogs comes I will leave to avoid any conflicts.

About: I have been surrounded by animals throughout my life and understand that every pet has its own personality, routine, and comfort level. I was raised with a red-nose Pit Bull, an XL Bully, and two English Bulldogs, so I am comfortable caring for strong, large-breed dogs as well as smaller pets. My family also cares for a flock of chickens, African geese, ducks, and a turkey. This experience has taught me to be patient, observant, dependable, and respectful of animals with very different needs and temperaments. I can help with feeding, fresh water, walks, playtime, litter-box or pet-area cleanup, companionship, and following your pet’s normal routine. I will carefully follow your instructions and provide photos and updates so you can feel confident that your pet is safe, comfortable, and receiving attentive care while you are away. Pet care fits well into my daily schedule. I have a flexible routine and can make time to feed, walk, play with, and care for animals consistently. I’m dependable, punctual, and able to adjust my schedule to meet the needs of the pets I’m responsible for. I care for pets by following their routine as closely as possible. I make sure they have fresh food and water, get plenty of exercise and playtime, and receive lots of attention and affection. I also keep their living area clean, watch for any signs that they may not be feeling well, and follow any instructions the owner provides, including administering medication if needed and I’m trained to do so. My goal is to make every pet feel safe, comfortable, and cared for while their owner is away.
About: 🐶 Instead of simple pet sitting, dog walking or drop-in’s, you are investing in a well-mannered companion during enriching activities with a certified professional dog trainer. 🏠 HOUSE SITTING w/ TRAINING The ultimate luxury training package: While a House Sitting stay on Rover does not include an active, full-scale training curriculum, your dog will benefit from my expert background. I offer a premium, structured alternative to standard pet sitting. I stay overnight in your home to provide 24/7 comprehensive training in your dog's natural environment! What's Included: • Daily structured training sessions covering your specific goals. • Intensive behavior modification and management (separation anxiety, house rules, manners). • Daily video progress reports and a comprehensive hand-off workshop. 💎 Every immersive stay is completely tailored to your behavior goals and includes a complimentary hand-off training lesson at conclusion of stay. Having this expertise assures optimal experience in real world proofing. *Select "House Sitting" on my profile to book a premium board & train! 🏡 IN-HOME PRIVATE TRAINING LESSONS Get professional behavior coaching right where the issues happen! Perfect for backyard recall, doorbell barking, or crate training. What's Included: • 30 or 60 minutes of intensive one-on-one behavior work with brain breaks & rest. • Real-world coaching in your home or immediate neighborhood. • Clear homework steps to keep your progress on track. *Select "Drop-In Visits" on my profile to book your private lesson! 🐾 STRUCTURED LEASH MANNERS WALKS No more pulling! Turn your dog's daily walk into a professional training session focused on calm outdoor focus. What's Included: • 30 or 60 minutes of active loose-leash training. • Real-world practice with distractions (dogs, cars, squirrels). • Immediate feedback & simple handling tips for owners. *Select "Dog Walking" on my profile to book a training walk! 🐾 DAY TRAINING CAMP 🐾 Skip standard daycare. Drop off your dog for a structured day of professional behavior training! What's Included: • 3 Focused One-on-One Training Sessions (30 mins each) • Real-World Practice (Leash manners, distraction proofing, impulse control) • Behavioral Targets: Loose-leash walking, jumping, basic obedience, focus, recall & socialization. • Video Updates & End-of-Day Hand-off Consultation *Select "Doggy Daycare" on my profile to book your day training camp! 🙋♀️ A NOTE ABOUT ME: Aside from being a dog trainer, I am an active volunteer with Pet Alliance as a in-shelter bark buddy, and a foster dog parent. I participate in local events, fundraising and Hound Around Town monthly. I have since expanded my efforts with Husky Haven of Florida as a transport for rescues. I’ve worked at Disney’s pet resort & dog daycare in downtown Orlando. 💯 My base rate listed on my profile covers standard, high-quality care (feeding, potty breaks, and companionship). Since I am a certified dog trainer, the context described above is offered as an active Training Add-On Package for an extra $15 per day. Just be sure to brief me in your contact message and we can discuss together further in detail. With dog training as my core, and having an Executive Assistant professional background of over 20 years, calendar maintenance comes natural and my availability is easily workable around varying schedules. If I’m not at the dog park or training, I can be available for services as necessary. I focus on science-backed methods that are mindful and effective, while integrating enrichment, affection, stimulation (both mentally and physically), rest breaks, sniffy walks, play time and cuddles. I prioritize the pet parents requests and instructions, aligned with fulfillment that meets the dog’s foundational needs.

About: I’ve taken care of dogs my entire life. Everything from rat terriers and Shitzus to Great Danes, labs. I have experience administering medications topical, pills and injections! Our home includes lots of games and mental simulation and puzzles! Currently working part time I am available in the afternoons after 12 Thursday- Monday! I can do times outside of that if needed ur just depends on my availability at that time! My complex has a dog park nearby and I have my own puppy who is very friendly and able to play with your puppy all day. I am also able to crate your or my baby if needed. I’m available for long walks and runs couch cuddles in your home if needed!
About: Apart from caring for dogs of friends and family, I’ve also worked in a veterinary clinic and have volunteered at the animal shelter in my hometown! Animals are a huge part of my life and I hope they always will be. I do work full time, but my schedule changes every week. Some weeks I have more free time than others. I’m looking to fill that time with lots of animal love! I have no pets at home since my dog passed away in September of 2023. I live in a two bedroom apartment with two dog parks that are mostly empty during the day. I am a non smoker and I’m very active. I also have reliable transportation.
About: I am a fun and trustworthy pet caregiver and would love to help you with all of your pet care needs. I am comfortable walking dogs, feeding, bathing, and playing. Is this your first time using Rover? Ask me about how to get $20 off your first stay! For cat care I offer drop in visits to your home and do not currently board cats. But in your home I am happy to care for them and will meet them were their at! If they need distance I'll be respectful of that, if they want cuddles, I'm all about it. I am comfortable feeding and changing litter. I bathe dogs by request. Let me know if you would like this service. I am home all day. There will always be someone with them. I have experience with older pups, pups with separation anxiety, and health issues. Please reach out for questions about your dogs unique needs. I have a medium/large sized fenced in yard and no other pets of my own. In my home I will provide loving care including playing, walking, feeding, and bathing as needed. I will take your dog on two walks a day as a minimum, and take them out for potty breaks several times per day in the back yard where they are able to also run and play. During the day dogs in my care tend to like to sit by me at my desk, or on the couch near my desk. I live in the subdivision of Bay Lakes, which is right by "restaurant row" on Sand Lake rd. I am 10 minutes from Universal/Islands of Adventure, 15 minutes from Sea World, 15 minutes from Disney Springs, and 20 minutes from Magic Kingdom. I'm home all day so I'll have plenty of time to care for your loved ones! We'll go on walks and play in the yard. I have a medium sized fenced in backyard with plenty of room to run around and play in. Dogs are permitted to go outside any time they like, and I take them out every 2 hours for potty breaks. When we're inside and I'm on my computer they often like to lay next to me. :D When caring for dogs at my home, I maintain a structured schedule to ensure their well-being and happiness. Each day typically includes designated times for feeding, walks, playtime, and rest. Additionally, I adhere to consistent meal times to regulate their digestion and provide ample opportunities for exercise and mental stimulation. Furthermore, I establish a bedtime routine to promote relaxation and ensure they get enough rest. This structured approach helps maintain their routine and provides a sense of security during their stay. In both my home and my client's home, prioritizing safety, trust, and a comfortable environment for pets is paramount. Here's how I ensure optimal care: 1. Safety Measures: I conduct a thorough pet-proofing of the space, removing any potential hazards such as toxic plants, small objects, or electrical cords. Secure gates and barriers are utilized to prevent access to off-limits areas. Additionally, I keep cleaning supplies and medications stored securely out of reach. 2. Trust Building: I establish a bond with the pets through positive reinforcement, patience, and consistency. Spending quality time with them, engaging in play, and offering treats help foster trust and a sense of security. Following the owner's instructions and routines also reinforces trust between all parties involved. 3. Comfortable Environment: I create a cozy and familiar setting for the pets by providing comfortable bedding, favorite toys, and maintaining a consistent daily routine. I ensure they have access to fresh water, proper ventilation, and suitable temperature conditions. Additionally, I offer plenty of opportunities for exercise, mental stimulation, and relaxation to keep them content and happy. By prioritizing safety, trust, and a comfortable environment, I aim to provide the best possible care for pets in both my home and my client's home.
The median cost per visit for dog sitting in Windermere is $20
Dog parents share their Rover experiences - Windermere
I was panicking about my fur-babies because there's usually always someone home with them but I had to be at work for over 10 hours a day over a course of several days. Lillian did drop in visits mid-day for my fur-babies, to walk and feed them lunch. She gave me updates and really put my mind at ease and I knew that my babies were well taken care of. She's the best!!

I’d highly recommend Sarah! I booked her to do drop-in visits for my 8-week old puppy and having a sitter with so much experience has given me such peace of mind. I love the care and attention she gives to my puppy and appreciate her professionalism and detailed updates! Will definitely be booking Sarah again

Taylor is absolutely wonderful. She is very caring and compassionate and comfortable taking care of many different varieties of pets. Taylor watched our fur babies while we were away on an 8 night cruise and made sure everyone was happy and healthy upon our return. I highly recommend Taylor for any of your animal care needs.

Samantha was amazing! We were so fortunate to have Haze in her care. I have a 3 year old German Shepherd with a lot of energy, and she handled him so well. Samantha was attentive, communicative, and took great care of him. I really appreciated the frequent updates and photos too! Would definitely book with her again. Highly recommend! 🐾

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It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.
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How to book dog sitting

1. Search
Browse profiles of sitters near you who offer dog sitting.
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit.
3. Book & Pay
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Popular requests for dog sitting - Windermere
Select a filter and find qualifying sitters offering dog sitting.Sitters in Windermere average 6 repeat dog sitting clients
FAQs for Dog Sitting - Windermere
Frequently asked questions about Rover
The average cost of Dog Sitting in Windermere is $22 per visit as of October 2026. Most bookings cost between $15 and $43 per visit. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of October 2026, there are 5,201 sitters on Rover offering Dog Sitting across Windermere. Enter your ZIP code to see which available sitters are closest to your home.
You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.
Before booking, confirm:
- the timing, length, and frequency of visits;
- the care instructions the sitter should follow;
- which parts of your pet’s usual routine should be prioritized;
- how often you would like to receive messages, photos, or other updates.
Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.
Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Windermere choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!
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 .
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 , which provides up to $25,000 in eligible veterinary care reimbursement.
A Meet & Greet is a casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet or the new environment.
During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first .
While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.
To find sitters in Windermere with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.
Yes, you can find sitters who have experience with handling special pet needs in Windermere. On Rover:
- 89% of sitters can help with special care needs
- 93% can help with giving oral medications or injections
- 96% can help with daily exercise
You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.
Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.
sitters on Rover set their own , which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.
















