Pet Boarding Windermere
Find a loving Windermere pet sitter to watch your cat or dog overnight at your sitter’s home.
Over 2,699 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.
“Maria was great!! She send pictures and stayed in constant contact! She even let us change our pick up time form noon to 3pm with no issues. We will def be using Maria again!”
“Alberto was absolutely amazing with our dog. He sent videos, pictures and updates every day, and responded immediately each time we reached out. I actually think our dog was sad to leave him! I'd recommend Alberto to anyone looking for a safe, caring place for their pet!”
“You will never find another dog sitter as perfect as Roseli! We were very nervous about leaving our two small dogs with a sitter, figuring no one could love them as much as we do. Roseli happened to be in our search area so I sent her a message and she was great with all of my questions. She invited us to her home so that our dogs could meet her and we could see where they would be staying. Meeting Roseli instantly put our minds at ease. It is evident that she LOVES her pets and the pets that she cares for. Her home is puppy-proofed and we could tell that she was 100% invested in the responsibility we were giving to her. During our time away she sent multiple videos and pictures of our dogs walking, playing, resting and eating. She even cooked special meals for the dogs (with our prior permission)! After all the special treatment they received on their "doggy-vacation", I was surprised they even wanted to come back home! :) Now that we have Roseli, we are looking forward to a few summer getaways without worrying about what we'll do with the dogs. We feel blessed to have found her, thanks to Rover.com! And we highly recommend her to anyone needing a sitter!”
“This was the first time my babies have been with a stranger in their whole lives, and Vanessa kept me updated with photos and was very responsive through texts. I appreciated her last minute availability and will definitely use her again if needing a sitter! My girlies seemed to have really enjoyed themselves!”
“Daijah is very pleasant and accommodating. I booked her very last minute and she was able to accommodate me to the best of her ability. She is clear with communication and keeping me updated on how the day is going with my fur baby! I will definitely be rebooking with her again!”
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! 🐾💛
“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!”
“Carilyn and her family were amazing! Thank you for being flexible with my schedule and for making Bella feel special. I will definitely booking with you again.”
“Sprout was injured when she went to the sitter, so I was a little worried. Clair took care of her and gave her meds when scheduled. When I picked my pup, she looked well and happy.”
“Charity and your family are amazing, they take our little Silver while we took a short vacation, he was always aware of our beloved dog, keeping in touch with us by sending us photos and messages of the care process, they were very affectionate with her and even let her sleep next to them in their bed. I 1000% recommend Charity and her family for the care of your pet. Thank you Charity and family.”
“Julie and her family are wonderful! They are so kind , caring and attentive to my pup’s needs. She is also a great communicator and provides daily updates and photos.”
“Danielle and family were absolutely amazing with our two mini Goldendoodles! From the first meet and greet we knew our girls were going to be in good hands. Danielle texted us everyday during our trip with photos and updates of our girls playing and being loved on!! We have already rebooked with them for our next adventure!”
“Con ella …Como en Casa ???Amor amor amor todo Lo que nuestros Chiquitos necesitan en Nuestra ausencia … Gracias mil Por tus atenciones y por mantenerme al pendiente Siempre Muchas Gracias !!????????✅✅ RECOMENDADA✅✅”
“OMG Leonard is the Best , he is my forever sitter for now on, He was good with my big boy ( cesar) and my little boy ( Taz ) they came home happy and tired from him taking care of them and walking and playing with them for 10 days …. please book him you will not regret it at all❤️❤️❤️❤️❤️”
The median cost per night for pet boarding in Windermere is $40
Pet parents share their Rover experiences - Windermere
Julia's communication is always quick and seamless, and her regular updates and photos give us total peace of mind whenever we're away. She truly understands their personalities, keeping them comfortable, happy, and well-cared for every single visit. It means so much knowing Axel and Raven are in such loving and reliable hands. We will definitely continue booking Julia and can't recommend her enough!
Jonathon & Aimee were awesome sitters for Chip. He spent the weekend with them and as we picked him up, we could tell right away that he had a great time and was really well looked after. They really cared about Chip and we’d happily recommend Jonathon & Aimee to anyone looking for dog sitting.
Every time our dog, Winnie, stays with Sol, we couldn’t be happier with the care she receives! it’s clear that she’s truly loved, and Sol treats Winnie like her own. Throughout the stay, she’s incredibly communicative—sending photos, updates, and little notes that gave us total peace of mind while we were away. Our dog can be a bit shy and standoffish around other dogs at first, but Sol is patient, gentle, and attentive to her and each of her guest's needs. When we came home, Winnie was relaxed, happy, and clearly very well cared for. If you’re looking for someone reliable, kind, and genuinely amazing with pets, look no further. We will definitely be booking with Sol again!
Taryn was absolutely amazing with Kahlua! From the moment we booked, she was attentive, communicative, and so reassuring. She gave the best updates with pictures throughout the day which meant so much to me, especially since Kahlua struggles with anxiety. It was clear that Taryn gave her so much love, patience, and attention. You can truly tell she cares about the dogs she watches. I felt completely at peace knowing Kahlua was in such good hands. I would 1000% book her again!
Dianet was absolutely amazing with our Aiden. She got lots of love, attention and exercise, and even made a new dog friend. Dianet kept us updated throughout Aiden’s stay. We felt very reassured during our trip knowing that she was in good hands with Dianet and her family. Our baby came home a very happy girl! We would 100% recommend :)
This is the second time Rio has stayed with Meredith and her family. We have been looking for a sitter for a while and have finally found an absolute gem! Consistent communication, many pictures, Rio burns so much energy and loves going to their house! We will rebook time and time again, HIGHLY recommend!!!
Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.
Why Choose Rover?
Cashless payments
Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
Meet local sitters who will treat your 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
It's that easy! All payments are processed through Rover's secured platform
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 Boarding - Windermere
Frequently asked questions about Rover
The average cost for Pet Boarding in Windermere on Rover is $49.95 per night (as of September 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Pet Boarding easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Pet Boarding. For more information on service fees, click here .
There are 2,713 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 short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter 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. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.
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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