Dog Boarding Windermere
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 2,392 pet parents in Windermere have booked dog boarding
Windermere, Find top rated dog boarding
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“OMG WE LOVE JAMIEEEEEE!!!!! Jamie and her family were amazing in every way!! Jamie is a true dog mom so right from the start you could feel that instant connection!!.. Out little girl Pinky was happy and playing with their dog Evie and fit right in with the rest of the family. She took care of her as it f she was her own,,, It is a beauuutiful atmosphere, a beautiful family and a BEAUTIFUL mom who watched over our little girl with love. We look forward to having Pinky spend more time with Jamie and her family in the near future, Thank you JAMIE you are the BEST!!!!!!!!”
“Chris took great care of our Loki for a few days. Chris has a great set up to meet any dog’s needs and seems very aware of dog behavior. He was great about letting Loki get comfortable and then meeting the dogs for playtime. We got daily pictures and videos, which we appreciate! Loki loved his time at Chris’ house and hopes to come back soon to see Evelyn.”
“We had a great experience with Kymry and look forward to using her again in the future. Olive was well cared for and safe while we were away, and we are so thankful. Excellent communication was so helpful, too.”
“I was very nervous to leave Remy for a week when I went on vacation because he gets very anxious in new places, but Liz made it such a comfortable environment for him. I expected him to not eat and probably have an upset stomach, but he had no issues at all and did great! Liz does a great job caring for the dogs and making them feel at home!”
“Mimi was terrific and Lulu was well taken care of and happy ! She was with 3 other dogs and they all got along ! Thank you Mimi …we will see you again soon xoxo. Lulu & Victoria”
“Savannah was wonderful with our pup, Breezy! This was our first visit to her home, and it was such a positive experience from start to finish. Savannah is kind, positive, and truly listened to all of my instructions and concerns, which gave me great peace of mind. She kept in touch throughout the day and sent pictures, which we really appreciated. Breezy was happy and well cared for, and it was clear she was in great hands. We will definitely use Savannah again and again whenever we’re in the area. Highly recommend!”
“I LOVE HOW I WAS KEPT UPDATED THE ENTIRE STAY ! He took care of my princess like one of his own. I will definitely be re-booking the next time I need a dog sitter ! THANK YOU SO MUCH !!”
“Poliana was really amazing to work with. She took excellent care of my senior dog while we were away. She was very responsive and did not mind me checking in on my sweet girl daily. I received many pictures and even an Easter Greeting on Sunday 😊. My dog also requires medication twice daily and that was not an issue at all. We would not hesitate to book her again in the future. 🐾”
“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.”
“Connor took amazing care of Latte, treating her like his own dog. You can tell he genuinely fell in love with her, which made me feel completely at ease. I received constant updates and photos of Latte looking happy and well cared for, which I truly appreciated. Everything was perfect, and I will definitely continue booking with Connor. Highly recommend!”
“Very happy with the care our dog received with Jerry. He sent us pictures daily of Beckett doing different actives that we looked forward to getting. Jerry is very easy to work with and very accommodating. We will be leaving Beckett with him again if the need arises.”
“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.”
“This is our second time using Jared and what can I say except that he is exceptional. I love all the updates to what my two huskies are up to while under his care. He understands the energy of a husky and my girls love hanging out with his dogs. I would definitely hire again with full confidence that my girls are being well cared for”
“"I recently boarded my dog at Kallee and Daniel twice, and I couldn't be happier with the experience. Kallee was very warm and welcoming at our first Meet & Greet and took the time to get to know my dog. During our two boarding occasions, she provided daily updates and shared photos multiple times a day, which eased my mind while I was away. My dog came home happy with no signs of anxiety. I appreciate Kallee to provide loving environment and accommodate our request to pickup and drop off time change at the last minute. I highly recommend Kallee and Daniel to any pet parent☺️”
“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.”
“We were very happy to have Abby stay with Selenia when we took a week long cruise. We received great reports and pics. Will definitely use Selenia's service again! Thanks Selenia!”
About: I understand that every pet has their own personality, routine, and needs, and I believe they deserve care that’s tailored to them. Whether your pet loves long walks, playtime, quiet companionship, or extra patience, I’ll make sure they feel safe, comfortable, and cared for while you’re away. I’ll follow your pet’s routine closely, respect any special instructions, and keep you updated with regular photos and messages so you always know how they’re doing. I know leaving your pet with someone else is a big decision, and I want you to have complete peace of mind. I treat every pet as if they were my own—with kindness, patience, and lots of affection. My goal is for your pet to feel happy and secure, and for you to return home knowing they received the same love and attention they get from you. Pet care fits naturally into my routine because I have a flexible schedule that allows me to dedicate quality time and attention to each pet I care for. Whether it’s morning walks, midday check-ins, playtime, feeding, or evening cuddles, I’m able to adapt to your pet’s normal routine to help them feel comfortable and at ease. I enjoy spending time with animals, so caring for them is something I genuinely look forward to rather than just fitting into my day. My flexibility also allows me to provide consistent care, regular exercise, and plenty of updates, giving you peace of mind while you’re away. my priority is making sure they feel safe, comfortable, and loved while keeping their routine as consistent as possible. I take the time to learn each pet’s schedule, including feeding times, walks, playtime, medications if needed, and any special instructions you provide. At my home, pets will have a clean, calm environment with plenty of attention and affection. I also have a fully fenced yard where dogs can safely enjoy supervised outdoor time, exercise, and play. They’ll never be left outside unattended, and I’ll always make sure they’re secure and comfortable.
The median cost per night for dog boarding in Windermere is $40
Dog parents share their Rover experiences - Windermere
This was our first time leaving our pup and we couldn’t have picked a better sitter. Monica was phenomenal!! Her communication with us was great, sending videos every day. You could tell she loved on and spoiled our Macie as much as we do. Would highly recommend, we will definitely use her again!!
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!!!
Michael took care of my dogs very well , was super patience and was always sending me pictures and updates of my dogs , he really took time to make them feel like home and my dogs were happy to stay at his place , thank you so much Michael for such a great caregiver for my dogs
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 dogs like family
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
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Popular requests near you
Select a filter and find qualifying Windermere sitters!Sitters in Windermere average 12 repeat dog boarding clients
FAQs for Dog Boarding - Windermere
Frequently asked questions about Rover
The average cost for Dog Boarding in Windermere on Rover is $49.95 per night (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Dog 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 Dog Boarding. For more information on service fees, click here .
As of July 2026, there are 2,656 sitters on Rover offering Dog Boarding across Windermere. Enter your ZIP code to see which available sitters are closest to your home.
Every sitter on Rover has their own rhythm and routine, but most will follow the flow that keeps your dog happiest. Sitters can give meals on your dog's regular schedule, provide a comfortable place for sleep, and plenty of one-on-one attention.
96% of Windermere sitters also include daily walks in the neighborhood during dog boarding stays. You can also request photo and message updates throughout the stay so you can see which Windermere landmarks or neighborhoods your dog is enjoying.
If your dog is a little shy, consider booking a one-night trial stay! This practice run can boost your and your dog’s confidence before your trip.
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.
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.
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