Dog Boarding Windermere
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 2,516 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.
“Jonathon & Aimee Such a beautiful experience letting our baby on your hands, we are very lucky to find you and be able to be away from him having the peace of mind of knowing he was totally fine. You guys were awesome from the day we contacted you, you were always available for us and keep us updated about Brownie the whole time, we know how comfortable he felt the whole time with you. We loved how attentive, caring, reliable and loving you were throughout this weekend! We really appreciate it. Thank you also for taking the time to send all those cute pics and send brownie home with a goody bag to keep having fun. WHOEVER IS OUT THERE LOOKING FOR A HOME AWAY FROM HOME FOR YOUR BABIES. JONATHON AND AIMEE ARE THE ONES. Thank you guys!🫶🏼🫶🏼🫶🏼”
“100% recommendable. Communication went great. We received pictures and everything to know that our dog was having a good time. Kymry is the kindest person ever”
“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.”
“I highly recommend Poliana. It was my first time using Rover and Poliana made it such a great experience from beginning to end. I was nervous to leave my puppy with someone for the first time, but those nerves were quickly at ease thanks to the great communication and photo/video updates I received each day. Thank you for making it such a great experience. Penny had such a great time and I will definitely book again knowing she will be in such great hands!!”
“Savannah did such a good job watching Doobie! Her space was clean, comfy, and plenty of space to play. She was very communicative and sent plenty of pictures. Doobie had such a great time!”
“Jerry was amazing! This was our first time leaving Ali with a sitter outside our home and we were worried about her. Jerry took great care of her and sent many pictures and videos so we could see that she was happy and having a great time. She loves being outside and with his fenced in yard so she was able to spend lots of time out there playing with his dog. I would highly recommend Jerry and we will definitely be booking again!”
“Idalis and the family were absolutely amazing. Constant communication and beyond accommodating. Captain had so much fun and I think he’s mad I took him from Logan and them!”
“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!”
“Sarah did an amazing job watching Lola. She sent pictures everyday and I know Lola had a good time with Sarah and her family. We will definitely go to Sarah again!!”
“"We could not have asked for a better sitter this past weekend! From the very first update, it was clear that our dog was in incredible hands. We received regular updates and photos, which gave us total peace of mind while we were away. They truly treated our pup like family. We will absolutely be booking again and highly recommend their services to anyone looking for a top-tier, trustworthy sitter!"”
“Connor was a wonderful sitter. My dogs absolutely loved their time with him. He had great communication, took amazing care of them, and sent pictures of the dogs. I highly recommend him and would definitely book him again.”
“Rennan was amazing with Lenny. Who sent me so many pictures that couldn’t be happier. He took Lenny on multiple walks and to the dog park. I am definitely leaving my dog with him 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 !!”
“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!”
“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!”
“Our GSD pup had a sleepover with them and the time of his life with Sailor. We had peace of mind knowing he was being extremely well cared for and looked after!”
The median cost per night for dog boarding in Windermere is $40
Dog parents share their Rover experiences - Windermere
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 dogs like family
1. Search
Browse profiles of sitters near you who offer dog boarding
2. Meet In Person
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3. Book & Pay
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Popular requests for dog boarding - Windermere
Select a filter and find qualifying sitters offering dog boarding.Sitters in Windermere average 12 repeat dog boarding clients
FAQs for Boarding - Windermere
Frequently asked questions about Rover
The average cost for Dog Boarding in Windermere on Rover is $49.95 per night (as of August 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 August 2026, there are 2,620 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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