Pet Boarding Windermere
Find a loving Windermere pet sitter to watch your cat or dog overnight at your sitter’s home.
Over 2,747 pet parents in Windermere have booked pet boarding
Windermere, Find top rated pet boarding
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Idalis and her family were amazing. We got 2 to 3 updates with photos and videos each day. We immediately noticed how clean their house was when we dropped Bailey off. It was also nice that when we picked Bailey back up that she was pretty much exactly how we dropped her off and was not dirty or stinky. That tells me they took care of her as if she were their own. Will definitely use her again.”
“Jared was really great! I I needed a sitter last minute and luckily he was able to watch my two boys. He was a great communicator and sent me daily pictures of my boys!! I loved that his dogs liked to play with my dogs! I would highly recommend Jared and I will definitely use him again !!”
“Our new puppy found a home away from home staying with Danielle! I can’t recommend her enough. The whole family (including pets!) is so welcoming, we received lots of pictures, videos, and updates while we were gone, and we could easily tell she was in good hands.”
“Jordan was great with Hokie and very responsive both before and during her stay. Hokie has anxiety with thunderstorms which I made Jordan aware of, she was willing to work with her and was observant when a storm was coming to be proactive with ways to calm Hokie. Overall I would definitely board with Jordan again!”
“Execelente, siempre estuvieron en contacto con nosotros para informarnos de Loki, daban paseos y la atención con el el fue muy buena, si volvemos a Orlando repetiremos 100%, muchas gracias!!!”
“Roseli was absolutely AMAZING, this was the first time I was leaving my puppy overnight with someone new and I was a little worried at the beginning but Roseli made this experience so smooth. She sent me constant pictures and videos and you could tell how she loves dogs! Definitely recommend her as your dog will be in the best hands ever!”
“In the hunt for a new person to take care of piper, you have been the standout. After having the same girl for four plus years, there has been some anxiety on my part... We have tried others. The last one Piper had anxiety and came home smelly and in need of a bath. Piper had no hint of stinkyness (is that a word) when she came home after the last nine day stay with you ! Your daily pics were helpful especially for John (hubs). I don't know anything about you.... but I know this. my dog enjoys your home, especially that bed and couch!! Thank you Vanessa.”
About: Hi! I’m Stephanie, a devoted pet sitter and dog mom to Noodles, my long-haired Chihuahua. I provide personalized care tailored to your pet’s needs, whether they’re a playful pup or a senior needing extra TLC. I specialize in small breeds, anxious pets, and medication management. Expect lots of love, attention, and daily photo updates! Your pet’s happiness is my priority! I work from home, which means your pet will get constant attention, love, and care throughout the day. Whether they need regular potty breaks, cuddle sessions, or playtime, I’m here to keep them happy and comfortable. My flexible schedule allows me to cater to your pet’s routine, ensuring they feel safe and stress-free while you’re away! 🐾💛 Your pet’s safety and comfort are my top priorities. In my home, I provide a clean, secure, and pet-friendly space with plenty of supervision, cuddles, and playtime. If caring for pets in your home, I follow your routines closely to ensure a familiar and stress-free experience. I’m experienced with small breeds, anxious pets, and senior care, and I always prioritize safety—whether it’s controlled walks, feeding routines, or medication management. You can trust that your fur baby will be loved and cared for like family! 🐾💛
“This was my first boarding experience for my 1 1/2 year old doggo. I was nervous and she was nervous. I needed more than a boarding option, I needed a family to care for my dog while I had to be out of town. That is what Kallee and Daniel provided, a family that loved her while I was gone. They went beyond what a boarding facility could offer and personally cared for my dog while she went through separation anxiety and missing her family. Sailor became the older sibling she needed and I received not only daily communication but updates and responses as I was going through my own separation issues from her. I couldn't have asked for a better home for my dog to be in while I was away. Their home is a perfect place for an active dog and they are the perfect family to care for an energetic dog especially one who needs support to come out of her shell while her family is away. I couldn't thank them enough for their care for my doggo.”
About: - Certified Dog Trainer | Senior & Puppy Care Specialist | Disney Area Exclusive Thanksgiving & Christmas Boarding – Premium Care for Puppies & Seniors Only 🐾 Traveling for the holidays? Give your most vulnerable furry family members a peaceful, stress-free stay at my private home in Orange County. I do not operate a crowded kennel. I specialize exclusively in the two groups that need the most attentive, gentle oversight: Puppies (under 1 year old) who need strict routine management, and Seniors who require a calm, quiet environment with zero chaos. Why Choose My Holiday Boarding? • Ultra-Limited Spots: I accept a maximum of 3 dogs at any given time to guarantee dedicated, hands-on attention. • Puppy-Safe Environment: Consistent potty routines, crate training maintenance, and zero-compromise supervision for your growing pup. • Senior-Focused Comfort: A quiet, slow-paced home with gentle pacing, easy mobility layout, and meticulous medication schedule management. • Constant Updates: You will receive direct photos and updates throughout Thanksgiving or Christmas so you can enjoy your holiday with peace of mind. Availability: 📅 Now booking for Thanksgiving Week and Christmas/New Year Holiday Weeks. Spots fill up extremely fast due to my strict 3-dog limit. Message me directly today to secure your pet's holiday retreat! #WINDERMERE #WINTERGARDEN #HORIZONWEST #LAKEBUENAVISTA #DISNEYHOTELS #FORTWILDERNESS #DISNEYPETSITTING #RescueDogMom #CertifiedDogTrainerOrlando #PuppyBoardingOrlando #SeniorDogCare As a certified dog trainer and work-from-home business consultant, I structure my entire day around flexibility and care. Because I manage my own schedule, your pet becomes a seamless, prioritized part of my daily routine—never an afterthought. As a certified dog trainer working from home, sharing our lives with animals is an absolute must for my family and me. My entire day is structured to create a safe, trusted environment where your pet is our absolute priority. Because I manage my own business, my early-morning routine is completely flexible. I can easily accommodate early drop-ins right before or after I walk my own dogs, seamlessly weaving positive reinforcement training into our time together to improve behavior. To guarantee total peace of mind, a Meet & Greet is a must for all new clients. This gives us a chance to build real trust, ensures you feel entirely comfortable, and allows me to gather the critical details needed to protect and care for your pet exactly the way you prefer. Think of my service as a Bespoke Concierge for Pets and Pet Parents. I custom-design every walk and drop-in visit around your pet's specific safety and behavioral needs: Tailored Walking Plans: Before we head out, I look closely at your dog's leash habits. Knowing if they are friendly or reactive, hyper-energetic or easily tired, or dealing with specific environmental triggers allows me to manage risks and keep them entirely safe. Secure Drop-In Care: For home visits, I track everything from precise food, water, and medication schedules to their favorite toys. I also proactively verify if your pet is a stealthy escape artist so I can secure the environment.
“Our Murphy was well cared for and most importantly well loved! I am looking forward to having Gloria care for him again. It is a great vacation when your mind is at ease when your fur baby is safe and happy!!”
“Mara and Marco are the best ! Our girl cora had the best time and was so well taken care of . Their home has a spacious backyard for lots of play time and lizard chasing for our girl ! So glad to have found them And will continue to use them any time we need someone to watch Cora”
“Maria took great care of Fluffy, our Cavalier King Charles Spaniel, while we were traveling for a month. She sent regular updates to us and gave fluffy a wash before we picked him up. Thanks, Maria!”
“Dear Carilyn & Jorge thank you so very much for taking care of Chica and Gaia. Thank for constantly communicating with me about their well-being and their day. God Bless your home and family. I could not have been at peace in my vacation if it wasn't for you. Knowing that my pets were being loved and well taken care put at peace.”
“Salomon and family took beautiful care of our Pudd'n girl - they were communicative, professional and what I loved so much: truly organized. If you choose Salomon, know that you're working with someone who's got check-in, care, and check-out down to a science. As someone who has a little bit of social anxiety, I so appreciate this! He took the time ahead of accepting the booking to find out what Pudd'n required for care and then accepted the request. I also appreciated this as it made sure Pud would be well-taken care of and that he wouldn't be overwhelmed. Thank you so much for everything, Salomon!!”
“Linsey agreed to watch my dog Zombie overnight on super short notice. I’m super grateful I found someone so fast, and Linsey is so kind and clearly such a dog person that Zombie loved her instantly. I would definitely book with her again!”
The median cost per night for pet boarding in Windermere is $40
Pet parents share their Rover experiences - Windermere
Julia was fantastic! Caring and kind, my senior cat adjusted well to her and her home after an initial period and he enjoyed the patio especially. Will definitely rebook with Julia for our time away now. It is nice to know raven will be cared for and happy while we are away.
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 :)
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 pets like family
1. Search
Browse profiles of sitters near you who offer pet boarding
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 pet boarding - Windermere
Select a filter and find qualifying sitters offering pet boarding.Sitters in Windermere average 12 repeat pet boarding clients
FAQs for Pet Boarding - Windermere
Frequently asked questions about Rover
The average cost of Pet Boarding in Windermere on Rover is $50 per night as of October 2026. Most bookings cost between $31 and $67 per night. 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.
There are 2,732 sitters on Rover for Pet Boarding in Windermere. About 91% of Windermere sitters can respond to requests in under 60 minutes. Whether you’re planning ahead for holidays, need last-minute care, or need same-day coverage for an urgent trip, you can message multiple sitters at once to find available care.
Once you find the right match, you can arrange a Meet & Greet to ensure they are a perfect fit for your pet’s personality before confirming.
If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.
The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.
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.
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 Meet & Greet .
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. Cats may be required to have Feline Viral Rhinotracheitis and Rabies up to date.
By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.
Emergency support is available by phone or email in English 24/7. When an incident occurs, we recommend that sitters contact our Trust & Safety team immediately so that they can connect your sitter with a board-certified veterinarian or offer other resources to help.
If a sitter needs to cancel at the last minute, Rover’s reservation protection means our team will work with you to find a suitable replacement as quickly as possible.
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