Dog Boarding Windermere
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 101 pet parents in Windermere have booked dog boarding
Windermere, Find top rated dog boarding
“Jonathon and Aimee were simply amazing! They were so accommodating, kind, and enthusiastic! Our dog was spoiled and treated like royalty. We can't wait to use them again!”
“This is the second time we had Savannah watch Louie and he did amazing. Savannah goes way above making sure that he gets love and attention, medication etc…we will be back again knowing how well he does and how calm he is when we pick him up.”
“We couldn’t be happier with the care Leo received during his 12-day stay. Leaving your dog for that long can be stressful, but we had complete peace of mind knowing he was in such good hands. Leo was well cared for, loved, and treated like part of the family. We received updates, and it was clear that his happiness and well-being were a top priority. Thank you for taking such great care of our boy. We highly recommend you to anyone looking for a trustworthy and caring dog sitter!”
“Chen was wonderful!! So friendly, easy to work with and kept us informed throughout our pup’s stay. He came home relaxed and happy. We already have her booked again! So excited to have found a great new pup sitter!!”
“My rambunctious older corgis are happy and healthy upon returning from Monica’s. She is very thoughtful and gives constant updates. I felt safe leaving them in her hands.”
“Here’s a polished draft of your Rover review: ⸻ Sarah was wonderful with Millie! She watched her for 3 nights and made the whole experience easy and stress-free. Sarah is very friendly and welcoming, and Millie had a great time during her stay. We really appreciated the daily updates and photos—her consistent communication gave us peace of mind while we were away. We’d definitely recommend Sarah and look forward to her caring for Millie again.”
“Idalis was amazing taking care of Rocky for 4 nights while my family went out of town. She sent us updates and pictures every morning and evening. He seemed so happy and had a great time. We will definitely contact Idalis again. ☺️🐶”
“Sol and her family took wonderful care of our dog Penny while we were on a 10-day vacation. We got pictures multiple times a day, and she was always incredibly responsive to messages. Penny had a great time and we’ll definitely be using Sol’s services the next time we need to go out of town.”
“Molly had a good time with Carilyn and Jorge! I received updates throughout the week along with pictures and I felt very comfortable leaving her! She’s going back again in December! Thank you”
“I never used Rover and I was nervous about using this service. Communication with Maria put my mind at ease then after meeting her I was very comfortable lettin her watch my kids. Maria petsit for me for 2 nights while I was in Orlando - not too far from Disney. She is set up for pet care which the area was very clean. I have 3 senior kids (one totally blind, one with issues with black leg movement issues and one with hip issues) and 1 6 yr old that was new to me). She was great with my kids and sent pics and updated me on them. I definitely will use her pet sitting services again when I am back in the area. Highly recommend by me and my 4 kids.”
“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!”
About: I love animals and enjoy spending time with dogs and cats. I am patient, responsible, and caring. I will make sure your pets feel safe, happy, and loved while you are away. 🐶🐱 I love animals and enjoy spending time with dogs and cats. I am patient, responsible, and caring. I will make sure your pets feel safe, happy, and loved while you are away I always make sure pets are safe, comfortable, and happy. I follow the owner’s instructions, provide fresh water and food, keep their space clean, and give them plenty of love and attention.
“Our first time with Linda was a wonderful experience. Our boy Noah loved being with her, and she was excellent to work with. We would highly recommend her to anyone.”
About: I have 2 years of experience caring for pets, and I truly love spending time with them. I enjoy giving them attention, comfort, and lots of love. I care for every pet as if they were part of my own family. I have a flexible schedule and Can care for pets throughout the weekends and weekdays. Feel free to message me to coordínate the Best time for your pet. Your pet’s safety and comfort are my priority. I always make sure they feel secure, supervised, and cared for at all times. I follow your instructions closely, keep routines consistent and Pay attention to any special needs. You Can trust that I will treat your furry family member with respect and love.
“Salomon did an amazing job taking care of our dog, Jaxon 🐾😊 He was kind, attentive, reliable, and truly exceeded our expectations. It gave us so much peace knowing Jaxon was being well cared for and loved while we were away 🌸 We are so grateful and would absolutely recommend him to anyone looking for someone trustworthy and caring with their pets ✨”
“Tetiana took really great care of my Sir. She sent great photos daily and kept assuring me, he was doing great since this was my 1st time being away from him. If i could give her more than 10 stars, I would.”
“Anastasia was amazing with our Puppy. Itwas our 1st time leaving him with an overnight sitter but Anastasia sent pictures daily of their fun walks and snuggles wh I chmade us relax and enjoy our travel!! We will be repeat customers”
“Laura was great with our labradoodle. This was the first time we were needing to leave him outside of family and we were pretty nervous with not knowing how he would be around a new person. She made us feel very comfortable leaving our family dog with her. She has a great backyard for the zoomies! She communicates very well and explains everything you need to know. I will recommend Laura to anyone I know needing pet services and will be using her again! Thanks again for everything, Laura.”
The median cost per night for dog boarding in Windermere is $40
Dog parents share their Rover experiences - Windermere
I am so incredibly impressed with Alberto and with the state of my pup when I picked him up. Normally when we have our dog watched by ANYONE he comes home a bit crazed, stressed, anxious and frankly dirty. When I picked him up after several days with Alberto- our dog was calm and seemed just as he does when he’s home with us. Not only that, but he was clean!!!! Alberto sent us several updates and photos everyday and was incredibly responsive and flexible. He is very polite, professional and friendly. By far- the BEST experience I’ve ever had with someone watching my dog in the entire 8 years we’ve had him and we travel A LOT. Sorry everyone, but we will be booking Alberto all the time from now on- you can’t have him! 😬😂 So grateful!!!
We’ve only had our lab mix for a couple months and were in unfamiliar territory needing to board Luna for a weekend. Salomon was Fabulous. Super responsive and informative. I liked him very much when I dropped Luna off and I received updates and photos a few times over the weekend! Excellent experience !
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!
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 boarding
1. Search
Browse profiles of sitters near you who offer dog 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 dog boarding - Windermere
Select a filter and find qualifying sitters offering dog boarding.Sitters in Windermere average 13 repeat dog boarding clients
FAQs for Dog Boarding - Windermere
Frequently asked questions about Rover
The average cost of Dog Boarding in Windermere is $44 per night as of November 2026. Most bookings cost between $28 and $56 per night. 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 November 2026, there are 2,653 sitters on Rover offering Dog Boarding across Windermere. Enter your ZIP code to see which available sitters are closest to your home.
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.
Every sitter on Rover has their own routine. Depending on the arrangements you agree on before the stay, a sitter can follow your dog’s regular feeding schedule, provide a comfortable place to sleep, offer companionship, and support their usual exercise and play needs.
95% of sitters in Windermere can provide daily exercise during dog boarding stays. Depending on the sitter, their home environment, and your dog’s needs, this may include walks, outdoor play, indoor enrichment activities, or supervised play with compatible dogs. These activities are not automatically included with every booking, so ask the sitter what a typical day looks like.
During the Meet & Greet, discuss your dog’s usual exercise and play routine, whether they can safely interact with other dogs, and any activities or restrictions the sitter should follow. You can also ask the sitter to send photo and message updates during the stay so you can see how your dog is spending their time.
Preparing for drop-off is easy when you have a checklist! To help your dog settle into their Windermere home-away-from-home, we recommend packing:
- Health and safety essentials such as their ID tags, vaccination records, medication, and emergency vet or secondary caregiver contacts.
- Food and gear such as harnesses, collars, food (portioned by day), and an item that smells like you.
- Special instructions such as a list of training cues, medical administration needs, or favorite hang-out spots in your Windermere.
Tip: You can upload your dog’s routine and medical info directly onto their profile so your sitter always has the details at their fingertips.
Yes, you can find sitters who have experience with handling special pet needs in Windermere. On Rover:
- 90% of sitters can help with special care needs
- 94% can help with giving oral medications or injections
- 95% 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.
You and your Windermere sitter can schedule drop-off and pick-up in a way that works best for the both of you—and your dog. Most sitters offer flexible times for drop-off and pick-up but the easiest way to confirm those times will be through in-app messaging. Confirm your arrival time the day of pick-up and drop-off can also help keep the process smooth and organized.
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.
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.
By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.
If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your dog to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your dog is showing signs of possible illness.
For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.
Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.
Adding another pup to the pack? Most sitters and walkers offer a reduced rate for additional dogs. You’ll find these exact rates listed under the "Services" tab on any sitter's profile. Since every dog is unique, final pricing may vary depending on the level of care required.
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