Dog Boarding Windermere
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 2,680 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.
“Poliana is absolutely amazing. We are repeat customers and she watches our boy regularly! She takes incredible care of him and he always has a great time! I highly recommend her to anyone. No one will take better care of your fur baby!”
“Adreana and her family were awesome. As a first time user of Rover, they helped set me at ease as they took care of Baylor. They didn’t mind the later pickups due to traffic and even understood when I forgot his doggie bag when dropping him off. Words can’t describe how happy I am with Adreana and her family. They have a repeat customer for every time we are on vacation in Orlando.”
“Rennan is awesome! Toby absolutely enjoyed his time with him! Rennan sent in daily updates and was also on top of making sure my puppy was well-fed and stimulated. Highly recommend!”
“First time having someone other than family watch our dog and we would 100% recommend Kymry. She was very nice and we felt completely comfortable leaving our little dog with her! She sent photos every morning, let us come back later than we originally planned on and even washed our dog's blanket before returning it back to us. We would definitely use her services again and can't recommend her enough. Thank you, Kymry!!”
“Savannah is the absolute best! She was able to help me out on very short notice and my dog had the most amazing time staying with her. 10 out of 10 will definitely book again with Savannah.”
“Mimi is so Wonderful, Buttercup made herself at home as if she has know Mini for years. She informed me during buttercups stay and took such wonderful and loving care gif her. Thank you so much !!”
“Monica was absolutely fantastic while caring for our dog, Willa. She was so easy to work with, dependable, and kept us updated every day with messages and photos, which gave us tremendous peace of mind while we were away. It was obvious that Willa was well cared for and receiving lots of attention and love. Monica treated Willa like one of her own, and we could tell how comfortable and happy she was in her care. We are so grateful for everything Monica did and would highly recommend her to anyone looking for a caring, trustworthy pet sitter.”
“Jamie is just wonderful and Buster is like family to her. We are so fortunate to have someone so caring to take care of Buster when we are away. He feels right at home at Jamie’s!”
“Connor was great and also shared pictures. Our dog had unexpected tummy issues when we dropped her off a day before we left and he was amazing taking care of her with a bland diet. We know it might have been tough but Connor was so gracious and understanding with the whole situation.”
“Ariana took wonderful care of my Poppy. She made her feel comfortable and happy. She also sent us pictures of her every day. I am extremely pleased with the care she took of Poppy and will definitely use her again if needed.”
“My dog loves her visits with Sarah and her family and they do an amazing job making her feel welcome and taking care of her. I recommend Sarah to anybody looking to watch their dog while they’re gone.”
“Christopher took good care of Scout for almost 2 weeks while we were out of the country. He made sure she got along with his dogs, went outside in the yard, and had time to play. We really appreciated the photos, videos and updates he provided!”
“Daijah was so great with billy and kept us updated for the whole day. Billy seemed happy to be back with Daijah again, I am confident that your dog is in good hands with her. Highly recommend!”
“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!”
“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.”
“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!”
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 :)
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
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 12 repeat dog boarding clients
FAQs for Dog Boarding - Windermere
Frequently asked questions about Rover
The average cost of Dog Boarding in Windermere on Rover is $50 per night as of October 2026. Most bookings cost between $32 and $67 per night. 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 2,677 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.
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.
<b>Tip:</b> 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.
Connect anywhere with the Rover app
