House Sitting Windemere
Find a loving house sitter to watch over your pets and your home.
Over 7 pet parents in Windemere have booked house sitting
Windemere, Find top rated house sitting
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Kelly was amazing! Right on time to allow me to get to work even with first introductions, very kind, and sends updated pictures throughout the day to keep you as the owner comfortable that your pets are in safe hands! My pets took to her immediately and were very comfortable with her here. Will use again.”
“Karenna did a great job house sitting for our golden retriever and a cat when we were away, she kept us updated with pictures every day and was very communicative. We found the house the way we left and our furry babies well taken care of. I will definitely book with her again!!”
“Jess and Janelle are amazing. My two cats and two dogs LOVE them and are excited when they are cared for by them. I love them as well … they are professional, caring, communicative and thoughtful. Jess and Janelle are my go-tos … always!!!”
“Johnathan was absolutely amazing! My dog Luna is dog reactive and can struggle with meeting new people. Johnathan’s calm demeanor and experience with dogs made all the difference for Luna. What I also really appreciated was the constant updates he would provide through messages AND pictures of Luna through Rover. I was fully able to enjoy my vacation because I knew Luna was in great hands. When I came back home from vacation, Luna was relaxed and calmly chewing on a bone. That was one more confirmation that it was a great experience for Luna!”
About: A friendly, responsible couple who treats every pet like family. We have 6 years of experience with puppies and small dogs. Our family has three dogs and two cats, and we took care of all of them since they were born. We make sure our furry friends have all the care and affection they need. My husband and I have flexible jobs. We can accommodate our time with yours with no issues. We just need a few days in advance for the bookings. We take care of them, and we protect them as if they were our pets. We have a lot of patience and affection for those furry family members of yours.
“Jeff was great. He came by twice before the weekend trip to make sure we were all on the same page and that he was comfortable with our 4 year old Weimaraner. We’ve already rebooked for our next trip and the addition of a puppy!”
“I can’t say enough good things about Serena! She treated my pet like her own—so attentive, patient, and caring. I got regular updates that really put me at ease, and I could tell my dogs and cats were happy and comfortable the whole time. It’s such a relief to have someone so trustworthy. I’ll definitely be booking with her again!”
“Stephanie was so great to work with!! She was super responsive, kept me updated on the pups, and handled my two fur-crazies with ease. Would definitely have her for a doggie sleepover again!”
About: There is nothing I love more than spending time with and taking care of animals. I have owned a plethora of pets in my lifetime. Over the years I have helped take care of 15 rabbits, three dogs, four cats, and a bearded dragon. For nearly all day every day of the past 14 months (and the majority of the past 3 years) I have watched and taken care of an elderly cat and two dogs, one of whom is hyperactive and very anxious. I have lots of experience building relationships of trust with fearful dogs. My childhood dog was deeply traumatized as a pup, but with effort and love she ended up living a full and wonderful life of joy for 15 years! My best friend's dog was aggressive, fearful, and deeply untrusting. It took years of patience and work to get to this point, but we ended up being extremely close and I was dubbed one of his favorite humans! My current dog has a lot of quirks and anxiety, and it has been truly incredible watching her grow and open up to love. I adore everything about caring for pets, even the messy and hard parts. It doesn't matter if they are misbehaving or causing mischief, I always find joy and fulfillment in meeting their needs and working with them. I have experience taking care of a dog with heartworms, keeping her heart rate slow, for 3-4 months. I have experience from when my cat was in recovery from surgery; I administered her medication, fed her by hand, and cleaned her stitches. My dogs love to roughhouse but can sometimes go too far, and I am good at keeping calm and leading the situation if injuries occur. The wellbeing of animals is everything to me, and I will always do my best to make sure pets are getting the love and care they deserve. Animals are just about my favorite part of life! From August 2024 to June 2025, I worked at Best Friends Furever as a dog handler. I spent most of my hours: -Watching, caring for, and playing with the dogs -Practicing their training skills -Handling crisis situations including preventing and breaking up fights -Bonding with fearful high-stress dogs and building trust with them -Assisting customers with pick-up and drop-off -Cleaning/sanitizing play areas and crates -Washing water and food bowls I have completed the PackPro Professional Animal Care Certification Council (PACCC) certified training course for dog daycare, covering topics such as: -Dog body language -Group management -Customer service basics -Fight prevention/protocol I volunteer as a dog walker for the Baltimore County Animal Shelter. I often cat-sit for my friend, and I make sure I am devoting all my time and attention to the cats. I make sure they have enrichment and affection, while also recognizing when they need alone time. Cats are finicky beasts, but every moment they are comfortable and happy is worth it! I have a chronic illness that has caused college to go on the back burner for now, so I have a lot of open time for pet sitting! Despite my health issues, I did well at and really enjoyed my previous job as a dog handler at a daycare for 9 months. Unfortunately, a few months after I left my job in 2025, I had a health incident that set me back a bit; now that I’m on the mend, I am looking for an opportunity to start living a more active and fulfilling life again. I have a lot of free time because of this disability, and now that I have strength back I want to utilize this to do something good. I will work hard and do my best! I will adopt whatever schedule and routine your dog requires; I have experience and training in all kinds of pet care, so there is no such thing as too high maintenance! I am prepared for all aspects of pet sitting.
“Lindsay was absolutely wonderful and took excellent care of our girls! She provided updates and pictures for us daily and appreciate her so much for taking such good care of them! We returned home to happy and relaxed pups and look forward to booking Lindsay again in the future!!”
About: I am currently a school counselor in my 23rd year of service and trying to make some extra income. I love all animals. I have a cat and a border collie and Shih Tzu mix that my family and I recently rescued. I also have a 16 year old daughter who loves animals. I am reliable, flexible, patient, and caring. I have had a dog or cat my entire life. I have cared for many other people’s animals for them over the years. I have given dogs and cats insulin shots and also given medications if needed. I love taking walks and going to the multiple parks in the area. My neighbor is very pet-friendly and walkable. I will treat your pet as my own for the time I am watching them and give it lots of love and affection and care.
“Stokeley did a great job with my dog Rocky. Rocky is older with heath issues and special food requirements, and Stokeley had no issues with the needed care for Rocky. He kept in constant contact with me and gave me regular updates on how Rocky and the day was going. I'd recommend Stokeley for pet sitting and will be using him again for my next trip away.”
“We were so thankful to Jupiter for watching our dog. She was wonderful- communicative, caring, and very respectful of our home! We returned to a happy dog and would definitely use her to sit again.”
“Lara was AMAZING! This was our first time using Rover so we were a little apprehensive but Lara went above and beyond with our pups. She was super communicative and provided daily photos/updates on our dogs throughout the week. Our Golden had a few health issues pop up right before we left for vacay but Lara took great care of her and administered all of the meds every day to ensure she was well on her way back to full health by the time we got home. I have a feeling Lara will be our new go-to pet/house sitter moving forward!”
“Kaitlynn took excellent care of our two cats and was very respectful of our home. It gave me peace of mind to know someone was there the whole time to keep our kitten out of mischief.”
About: I’ve been taking care of animals as long as i can remember. I’ve had lots of animals since i was little that i was responsible for as well as pet sitting for friends,family, neighbors etc. I’m currently unemployed and do college from home, so i have plenty of time to help and take care of your pets when you need I will not be able to have dogs in my home but i can assure you i can be with your fur baby as much as needed as well as taking them on adventures or walks if allowed.
About: I've been a pet parent for 3+ years now. I LOVE my dog Maple and will take care of your dogs like they're my own. I'm open to taking care of all breeds, sizes, and ages - I believe I'm able to adapt to the needs of any dog, from playful discipline for puppies, to gentle care for senior dogs. I also have experience with reactive dogs that I’ve dogsat. Looking forward to meeting you! I have a flexible schedule and am happy to work around your needs whenever possible! This can include early mornings, late nights, and even weekends. I like to have open lines of communication and want to make scheduling as easy as possible for you and your pets! I'm a big believer in bribing dogs with treats and will make sure they feel that they're in good hands. I also love being outdoors and am willing to go on excursions to trails for nice long walks or play time at the park. I’d love to take pictures and give updates on the adventures we go on!
The median cost per night for house sitting in Windemere is $50
Pet parents share their Rover experiences - Windemere
Brooke was amazing! She went above and beyond to make sure my dog was well cared for and she communicated with me everyday. I got lots of pictures and updates on my dogs medication and food and walks. I had never left my dog with someone I didn’t know before, and Brooke made me feel so comfortable. I couldn’t be happier! She also stayed at my home while I was away and left everything super nice and neat, and took great care of everything while I was away. Truly 10/10!!!
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 house sitting
1. Search
Browse profiles of sitters near you who offer house sitting.
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 house sitting - Windemere
Select a filter and find qualifying sitters offering house sitting.Sitters in Windemere average 4 repeat house sitting clients
FAQs for House Sitting - Windemere
Frequently asked questions about Rover
The average cost of House Sitting in Windemere is $67 per night as of November 2026. Most bookings cost between $56 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 November 2026, there are 2,946 sitters on Rover offering House Sitting across Windemere. Enter your ZIP code to see which available sitters are closest to your home.
Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:
- Mail & deliveries: Collecting letters and packages so they don't pile up.
- Plant care: Keeping your indoor or outdoor garden hydrated.
- Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
- Home security: Sitters can stay overnight to keep your home occupied.
The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Windemere walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.
It’s helpful to think of house sitting as a "home base" service. Most sitters in Windemere maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:
- Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
- Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
- Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.
Tip: Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!
Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Windemere choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!
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.
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 pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet 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.
A Meet & Greet is a casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet or the new environment.
During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first Meet & Greet.
sitters on Rover set their own cancellation policy, which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.
Yes, you can find sitters who have experience with handling special pet needs in Windemere. On Rover:
- 89% 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.
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