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 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: Hi, I'm Ken! With 8 years of pet care experience, I provide top-tier dog walking, pet sitting, and drop-in check-ins tailored to your pet's exact routine. Whether your dog needs an energetic walk to shake off the "ruff" days, or your cat needs some quiet cuddle time during a check-in, I’ve got you covered. Why Choose Me? -8+ Years Experience: Deep understanding of dog and cat behaviors and body language. -Flexible Services: Available for high-energy walks, overnight sitting, or quick potty breaks and feedings. -Safety First: Reliable, fully vetted, and dedicated to keeping your pets secure and happy. I treat every dog and cat like my own family. Book a service today, and let's give your pet the smooth, stress-free day they deserve! I work a steady evening schedule, my routine is perfectly tailored for pets who need dedicated overnight care, morning routines, or daytime attention on my days off. Here is exactly how my availability breaks down: • Mondays & Thursdays (Completely Free): These are my full days off! I am available all day and night for extended playtime, daytime drop-ins, mid-day walks, or a seamless start to an overnight stay. • Wednesday, Friday, Saturday, & Sunday (Evening Workdays With Tuesday as an Occasional Morning): • Mornings & Early Afternoons: Available for morning walks and early drop-in visits before I head out for the evening. • Nights & Overnights: Perfect for overnight House Sitting! I am available to arrive in the late evening to tuck your pets into bed, stay through the night, and provide a full morning routine with breakfast and a walk before leaving. I treat your home with the utmost respect and your pets like members of my own family. Because change can sometimes be 'ruff' for animals, my primary goal is to maintain their familiar habits, scents, and routines as closely as possible while you are away. Here is exactly what you can expect when I care for your pets in your home: • Consistency & Routines: I stick strictly to your established schedule for feeding, medication, crate time, and bathroom breaks. • Active Engagement: I provide active playtime, mental stimulation, and plenty of one-on-one affection. • Thorough Clean-up: I keep all pet areas tidy, including washing food bowls, scooping litter boxes daily, and cleaning up any accidental messes immediately. • Frequent, Detailed Updates: You will receive regular photo and/or video updates through Rover Cards or Messaging along with detailed summaries of how your pet is doing, so you never have to wonder. I also offer meet and greets, so schedule yours today!
“I booked Samanntha to look after my cat Sam for a week while I was on holiday. We emailed back and forth a few times to discuss what I was looking for and when she came to meet Sam he fell in love with her, even offering her his belly for rubs by the end of the meeting. Right then I knew she was the one!! Plus she and I had a wonderful conversation as well! She was great at communicating, cleaned his litter every day, played with him, and sent pics and videos each day, even doing a video chat one day! I would definitely recommend her services, as she is friendly, kind and clearly loves animals!! Thank you, Samanntha!!”

About: I’ve had dogs in my house my whole life! I love all kinds of animals and have even volunteered at an animal shelter in high school. My most recent experience is working at a vet and boarding center. I’ve learned so much more about pet care this past year as my best friend/roommate works at a cat cafe and has a degree in Animal Health. I’ve even started administering medicine! Being with animals is truly the best part of my day! I’m currently working remotely, so I have plenty of free time to take care of your pets throughout the day! I’m available most weekdays and weekends. :) My basic house-sitting service includes staying overnight with your pup so they have company & comfort in their own home, along with daytime care every 3-5 hours for potty breaks, meals, playtime, and cuddles. I currently live with 3 small cats, so I’m very well versed in taking care and providing entertainment for multiple animals throughout the day.
“Nick is the best!! He takes beautiful photos of my Theo at every drop in visit, gives great updates and is so so good with my boy. I’m so grateful for him!”


About: I had a family dog who I love and have been caring for since he was a baby. I recently moved to Orlando and my dog is staying with my family. I love all dogs and have experience with training, desensitizing, and caring for multiple dogs of different breeds. Im so excited to get to know and take care of your dogs soon! I am a full time student in Orlando. So, I will be in class from 8-5 everyday. I am able to take pets on early morning or evening walks. I am also a runner and would love to do short runs with high energy dogs! I am able to do house visits and pet sit at your house through the weekend or weekdays (if your dog is able to be alone from 8am to 5 pm) I understand that each dog will have its own particular needs. Outside of walks, if pet sitting, I think it is important for the dog to have some mental stimulation so I would take time to play mentally stimulating games with your dog!
About: Hi there! I’m Alyssa, a TRUE animal lover. For the past 7 years, I’ve enjoyed caring for pets of all shapes, sizes, and species. Dogs, cats, bunnies, birds…you name it! I open my heart & home to animals in need through volunteer fostering, primarily caring for cats and kittens with medical needs. Full-time pet sitting has allowed me to continue doing what I love most: giving animals the care, attention, and love they deserve. Have a unique pet, or a pet with unique needs? I have extensive experience administering medication, including insulin injections, and I'm happy to meet anxious or nervous pets wherever they're at. I treat every pet as if they were my own, and I'd love nothing more than to become a trusted member of your pet's pack! Pet sitting is my full-time job! I'm flexible, and can typically make a wide variety of days and times work. Just let me know what your animal needs, and I will always do my best to accommodate! I understand some animals may need time to warm up to me! I always follow my client's instructions, and promise to take meticulous care of your fur babies. I am detail-oriented by nature!

“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: I have taken care of dogs since I was a little kid. My godmother used to own five dogs and seven cats back in Brazil. Every time that I would come over to her place I would love to take care of her pets. The best memories I have are from feeding, playing, and having sleepovers with these animals every night. After my godmother passed away, I adopted one of her dogs named Liza. I brought Liza here to the United States with my family and she lived an eighteen year long and happy life! Towards the end of her life, she had vestibular disease. I made sure we were on top of all vet visits, meds and rehab care. She was very important to me so I wanted make sure we gave her the best care. Since then, I have been there for my family and friends to watch their beloved pets. I have experience from cat sitting, dog sitting, and dog walking! I make sure to send my friends and family updates on their fur baby as I know going on vacation can make you miss your pets. So excited for future fur buddies to meet! Hi guys, I am new here!! I work part time and I have full time availability at my day job, but I decided to reserve some time to take care of pets which has always been a dream of mine! I am trying to make this app work and will change my availability on a week to week basis depending on my scheduling at work, but I will be as flexible and as convenient as I can to fit into your schedule! I know how important it is for your pet's happiness to take their daily walks, so during their daily walk I will make sure that they exercise, have enrichment and also have fun with the scenery! If I am doing check ins I will make sure that your pup is happy and also that they have everything that they may need such as food, water and most importantly, are happy!

About: Growing up, we always had a dog or 2 in the house, and I currently have a dog named Meeka. I’ve also dog sat for my friends and family before. I’m currently working part time for the ymca before/after school program a few days a week, so I have a few hours in the middle of the day free to come take care of your fur baby. I have a fenced in yard so my dog can run around. I take her out periodically, give her love and attention and treats. I make sure she has water, and I’ll take her for walks.
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.
“Noelle did a great job of caring for our kitty boys. We really appreciated the daily pictures and coming home to happy cats. Not only were they fed and litter box cleaned, but she spent time with them, giving them some play time and affection. Would definitely book her again.”


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: I’m a caring and dependable pet lover who will treat your dog like family. I’m patient, attentive, and comfortable giving pets plenty of playtime, exercise, cuddles, and attention. I understand that every dog has their own personality and routine, and I’ll make sure they feel safe, comfortable, and loved while you’re away. I have a flexible schedule and can make time throughout the week for walks, drop-ins, playtime, feeding, and giving your pet the attention and care they need. I always put your pet’s safety and comfort first. I follow their normal routine, keep a close eye on them, and make sure they are in a clean, safe, and comfortable environment. I’ll also keep you updated so you know how your pet is doing.

“Katie was a pleasure to meet and attend to my dog's needs. She is extremely reliable and flexible, which I appreciated especially during the holiday season. She sent the cutest pics of my pup and showed her the love she needed while I was away. If I were still living in Orlando, I would book her again and again! Thanks, Katie :)”

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: Hi! I’m Devin, a lifelong animal lover with a soft spot for dogs of every size, shape, and personality. I’ve spent years caring for pets for friends, family, and neighbors — and now I’m opening my doors (and my heart!) to pups on Rover. Whether your dog is a high-energy goofball or a snuggly couch companion, I make sure every dog feels safe, loved, and at home. I've trained my own little pup from 8 weeks old and he's a Shiba (well known for their stubborn personality) I dont work weekends or holidays, plus my lunch breaks are typically on the longer side (1 to 3 hrs). Fitting in check ins, potty breaks and walks are a piece of cake. I believe in positive reinforcement, gentle guidance, and keeping each pet’s individual comfort level in mind. I pay attention to body language and energy, and I always go slow with nervous or shy dogs so they can warm up at their own pace.
The median cost per visit for dog sitting in Windermere is $20
Dog parents share their Rover experiences - Windermere
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! 🐾

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.
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
It's that easy! All payments are processed through Rover's secured platform.
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.



















