House Sitting Windemere
Find a loving house sitter to watch over your pets and your home.
Over 190 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.
“Molly was an amazing sitter! She sent me pics of my babies multiple times a day, kept me updated on their feedings and my dogs meds. Enjoyed having her watch over my babies, and def trust her to do it again in the future :3”
“Had a same day request and Kenna was there in a pinch! Total lifesaver... She was excellent with my dog and super super polite. 10 out of 10 will totally book with again!”
“Delaney is amazing! She is so personable and cared for our house and Dog like she was part of our family. She is mature, aware, and I would trust her with our beautiful pup at any time. Cannot wait to book her again and glad to have her part of our circle. Thank you, Delaney.”
“Brittany was able to come last minute to watch my dog while I was out of town for the day. She was very patient and understanding of my old boy and did everything that I asked.”
“Anne went above and beyond our expectations of a house sitter. We received many pictures, videos, and messages while we were away. Our pets were happy and healthy when we arrived home. Can’t wait to book with her again soon!”
“Tori is the absolute best! We have no worries at all when she is taking care of the dogs. She takes them out regularly, plays with them, and treats them like her own. We love her!”
“Samara is an amazing dog whisperer. You can tell she genuinely enjoys what she does and maintains constant communication throughout. I highly recommend anyone looking for a dog sitter, home sitter. Much appreciated Samara!”
“Arturo was fantastic to work with! During our time away he would constantly keep us updated when he would be heading out as well as provide photos of Dottie throughout the day. From our initial meet and greet, we could tell that he and Dottie would get along and from what we heard, she was snuggled up with him all weekend! My partner and I would give him more stars if possible.”
“Sara was an amazing dog sitter to my 2 Labradors. She followed all food and medication instructions, took them on walks when it was cool, and sent me pictures! I loved getting pictures of my girls. She stayed overnight at my house, and she also collected my mail, put the trash containers at the end of the driveway on trash day, and brought any packages into the house. None of these were part of her dog sitting duties. I was very grateful to Sara for all of her help. I will definitely use her again in the future, and I highly recommend her as a responsible dog sitter.”
“Chantell was great with my dogs. She went above and beyond to make sure they were happy, healthy and safe. I would recommend her to anyone who needs a great dog sitter and I will be reaching out to her again. Thank you Chantell”
“Averie REALLY understands dogs and what they need when their owner is gone. She really put her heart into taking care of my dog. I would definitely recommend her for taking good care for your dog. I will be asking for her help again.”
About: I have owned 3 dogs over the past 20 years. I have watched, walked, and cared for the dogs, cats, birds, turtles, and reptiles. I have trained my own pets and I’m very comfortable meeting new animals. I’m a part-time remotely working licensed realtor so I’ve been fingerprinted and FBI background checked for your safety and peace of mind. I’m currently working part-time from home, mostly on my computer so I have plenty of time to play, walk, and care for your pets. I will carefully adhere to your pets’ schedule, routine, and instructions to make sure your pet has a safe and happy experience in my care.
About: I'm a master's degree student and work fulltime but love to help pets on my freetime! While I don't have special skills, i can help with basics and have cared for little to extra large dogs! I've cared for pets my entire life and my family owns a farm so I spend a lot of time caring for animals! I will not be able to provide constant care on weekdays due to my job! I hope to help you and your pets soon! I work full time 8:30-5:00 with children! I'm in school for a master's program but it is virtual so as long as you offer WIFI, it will not be a barrier! My weekends are open but due to my fulltime job, I cannot provide constant care on weekdays! I can help with any pet related needs in home within my experience! This would include cleaning litter boxes, refilling food and water, brushing, letting pets out, and other daily maintenance! I also love to snuggle and play with them!
“Angelica was fantastic! She was very responsive to our short-notice house-sitting request and made us feel completely at ease while we were away. She sent us daily photos and updates of our two dogs, Winston and Coco, which we really appreciated. She took great care of both our pets and our home and promptly let us know of any issues that arose. We came back to happy dogs and a well-cared-for house. We would absolutely recommend Angelica and would be happy to book her again!”
“Alexis was great. Great communication before and during our travels. The dogs were well loved, the house was just as we left it and she kept us in the loop for the whole time we were gone. Will definitely book with her again in the future.”
“Geoff did an amazing job taking care of both of our pit bull mix dogs. He was able to get them to like him and trust in him within minutes and gives multiple updates daily. Our dogs love him! We will definitely choose Geoff again!”
“Ryan was awesome! He was willing to come out same day for me to watch my dog for an unexpected change of plans, on a holiday weekend too! He took care of my doggo and was respectful and responsive to messages the whole time. I will definitely be rebooking Ryan again in the future.”
The median cost per night for house sitting in Windemere is $50
Pet parents share their Rover experiences - Windemere
Delaney is amazing! She is so personable and cared for our house and Dog like she was part of our family. She is mature, aware, and I would trust her with our beautiful pup at any time. Cannot wait to book her again and glad to have her part of our circle. Thank you, Delaney.
Kaitlan was absolutely amazing! She sent us photos and checked in every single day, which gave us so much peace of mind while we were away. We had never used a dog sitter before, and she made it such a wonderful first experience. She also left our house absolutely spotless, which we appreciated so much. We truly couldn’t thank her enough for taking such great care of our home and our pups. Highly recommend!
Chantell was amazing. Our two boys love her. She consistently updated us on how things were at home and with Oak and WInnie, as well as took amazing photos and videos on a multi-times a day basis. We always looked forward to seeing how they were and got lots of pictures of them playing and cuddling and relaxing. Chantell communicated thoroughly about her schedule so we never worried about a thing and our house was left in spotless condition.We know they received the best possible care and I cannot recommend Chantell highly enough.
Ashley was fantastic as a both a home and pet sitter. She takes the cutest little photos, my dogs looked happy and comfortable the entire stay, and she was super response to messages. I have an active dog and a senior dog and she was able to handle all of their needs. I was so relieved when I got home and my dogs seemed to have had a great time and didn't show any signs of anxiety or discomfort. Ashley was such a blessing.
Teresa took wonderful care of our two kitties! They are indoor/outdoor so we needed someone to put in some extra work and she really stepped up! Teresa is super friendly and a great communicator as well. I received daily updates (often more than once a day) that put my mind at ease while we were away. We will definitely use her services again and would highly recommend her to other cat owners.
Elisa did a wonderful job watching our 2 dogs who can take some time to warm up to strangers. She was very kind and patient with them. She kept our house organized and communicated well with us so we felt confident with her care while we were out of town. Will definitely have Elisa again!
Leah & Tyler were awesome with both our puppy and house. When we got home, our Sophie was happier than she has ever been with others staying at house. They truly engaged with our pup and showed her so much love. Our dog has separation anxiety, and I can't think of any better people to stay with her. We are so happy to have found the right folks for our Sophie!
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 pets like family
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 near you
Select a filter and find qualifying Windemere sitters!Sitters in Windemere average 4 repeat house sitting clients
FAQs for House Sitting - Windemere
Frequently asked questions about Rover
The average cost for House Sitting in Windemere on Rover is $44.4 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 House Sitting 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 House Sitting. For more information on service fees, click here .
As of July 2026, there are 4,423 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 short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter 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. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.
Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.
Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.
Yes, you can find sitters who have experience with handling special pet needs in Windemere. On Rover:
- 92% of sitters can help with special care needs
- 96% can help with giving oral medications or injections
- 96% 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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