Dog Boarding Windermere
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 2,573 pet parents in Windermere have booked dog boarding
Windermere, Find top rated dog boarding
“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!!”
“Connor was fantastic! He is very communicative and provides lots of photo updates, which is great! My pup, Jake, seemed to have a great time and has made a new best friend!”
“Our little Pug had the best time with Savannah she sent us plenty of pictures and kept us in the loop with how she was doing our whole trip. Her backyard was perfect, fully fenced with turf. Remi came back to us worn out like she went to sleep away camp it was a wonderful experience, when we are back in the area for theme parks we will use Savannah in the future as she is just 2 miles from Universal.”
“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!”
“Great sitter and you get a good family taking care of your dog. I would definitely recommend Poliana and her home for a home boarding. The best thing is she always has someone home, so if you are like me where you work from home and might not have the perfect time to drop off or pick up your dog they are more than happy to work with you. Definitely recommend Poliana for a great sitter to home board your dog with if like me now and then you have to leave town and it gets hard to find a good place to leave your dog. Thank you Poliana and to your family!”
“We left our fur baby with Rennan for 3 days and couldn’t have asked for a better caretaker! He was incredibly attentive and sent us regular updates and pictures, which gave us so much peace of mind. Our pet was clearly happy and well cared for. Highly recommended we’d definitely trust him again!”
“I was so happy to find such a wonderful family to take care of my furbaby. I was able to enjoy myself knowing he was in great hands. They did a great job of sending pics to let me know my baby was happy!”
“Marco and Mara provided wonderful care for Dobby. I received daily updates, and they seemed to care for him like he was their own. Mara asked plenty of good questions when I dropped Dobby off, so it was clear they cared about his wellbeing. Dobby enjoyed their backyard and lots of naps, and he came home safe and happy.”
“Once again Mr. Salomon and his family took very very good care of my Vader! He is always happy when I pick him and that shows me a lot. Thank you again! We will be back.”
“John and his family took such good care of Savannah. I am sure she enjoyed the pool and playing with your children. Thanks again and I will definitely recommend you and use your service again.”
“Mayara has been wonderful from first to last. I had to board my elderly cat, who's never been boarded before, last-minute, and Mayara gracefully handled the late notice, booking hassle and all, and I was so relieved when I saw where Moon Pie would be staying in her home. Clean, comfy, kitty heaven in her own spacious and private office room with extra toys and a sliding glass door looking out at the yard, perfect for soaking up sun- not to mention lots of attention and company from Mayara and her family. The photos, videos and updates were welcome, daily comforts. You can rely on Mayara to take excellent care of your pet, and put your worries to rest. My cat and I were lucky to find her! If I ever need to board Moon Pie again, I'll call on Mayara without hesitation and hope she's got room!”
“Brittany was a lovely sitter! She took care of my pet in every way. I was kept updated over the stay, received pictures, and knew my pet was in a comfortable and safe space.”
“Tia is AMAZING! She made our first time experience with leaving our fur baby easy and stress free. She communicated regularly and took excellent care of our Teddy. A huge thank you for the love and care you showed our sweet Teddy. We would highly recommend and definitely will rebook with Tia. 🐶❤️”
“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.”
“Laura is a GEM! We live in Fort Lauderdale and came to Orlando for universal. I had called our hotel to confirm I could bring my dog zuli but upon arrival they said she couldn’t be in the room without us! I was panicking and tried getting ahold of tons of different sitters with no luck. Then I found Laura. Laura was more than willing to take Zuli last minute (like 30 min notice because of the circumstances). We brought Zuli over and Laura showed us her yard and home so we felt more than comfortable leaving Zuli with her. We got so many pictures and videos of Zuli running in the grass and chilling by the pool and even making a kitty cat friend (which Laura asked permission for ahead of time since not all dogs are good with cats)… she is truly our hero! When we picked up Zuli, she was as happy as can be. I don’t think she wanted to leave… we will need to bring her back to Orlando again just to spend time with Laura. Best dog sitter on rover 100%! Can’t thank her enough! 🩷🐾”
“David is such a kind-hearted person. He communicates often with updates about pictures. I highly recommend David and look forward to booking with him again in the future.”
About: I've grown up with cats and dogs my entire life and have been watching other people's animals for the last 5 years. I've had lots of experience giving dogs medicine as well. I'm available to take your dogs on walks, play extra inside, or just give them some lovies while they're comfy on the couch! I'm new to Rover but excited to get the chance to be a part of your babies day!! I'm a pet owner myself so I understand leaving your baby in the care of another person is scary. If there's anything I can do to make you feel more comfortable please let me know! Thank you for trusting me with their care☺️ I'm off Friday - Sunday so I'll be able to be home all day. Everyone is different but, if your cat/dog likes to play and run around we can go on walks and have some extra playtime, and if they need a little less movement I'll always be there to give them some extra love and let them get comfy! I'm super excited to get to know your baby and help them feel welcomed into my home :) I live in an apartment and have lots of space for them to play inside, but there is also a dog park in the complex that I'd be happy to take them to. There's also lots of walking areas if your pup enjoys going on long walks :) if you prefer, I also have a park not too far that we can drive down to and take walks there as well! I do have a dog and two cats, they're very well behaved and good with other animals, but I also have a separate space for them if your baby prefers to have their own!!
“Iuliia took great care of my Shiba Inu. Emi is a little blind and had to have eye medications administered and Iuliia did a great job at that. We dropped her off at 11AM and picked her up at 11PM since we left late from the amusement park. From the beginning Emi was very happy and we got a lot of pictures and videos while she was in her care. We always knew what was going on with Emi thanks to Iuliia. She is very good with animals i wish i could leave 10 stars”
The median cost per night for dog boarding in Windermere is $40
Dog parents share their Rover experiences - Windermere
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.
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 $50 per night as of October 2026. Most bookings cost between $32 and $67 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 October 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.
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.
96% 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, 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 , 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 .
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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