House Sitting Windemere
Find a loving house sitter to watch over your pets and your home.
Over 170 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.
“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!”
“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!”
“Anne was great with our pup Alex and our 2 cats! Very attentive and considerate. Updated us with photos through out our vacation/honeymoon. Left us a card and thoughtful gift congratulating us on our wedding which was very nice to return to. Would highly recommend her house sitting and watching our pup again!”
“Our dog is fearful of meeting new people and Brandi's calm energy was great for him (and my anxiety about trying a new sitter lol!). She dealt with feeding him turkey through his muzzle and all the other details of a first meeting we wanted to cover. 10 stars on communication and reliability. She did wonderfully with Georgie on our 'trial run' before our longer trip and I'm so happy to have found someone we can trust our anxious fur baby with while we're away.”
“Delanie was absolutely fantastic! She kept us updated throughout our entire trip with frequent messages and lots of photos, which gave us so much peace of mind. She also let us know right away when our senior dog wasn’t feeling like herself and kept us informed on how she was doing. It was clear that she genuinely cared about our dogs and treated them like her own. We came home to happy, well-cared-for pups, and we couldn’t be more grateful. I would absolutely recommend her to anyone looking for a reliable, caring, and communicative dog sitter. Thank you so much for taking such great care of our babies!”
“Arturo was great with our dogs! They both get medicine and one of them had a strict schedule to stick to. Arturo was extremely accommodating and made sure to give them the meds when needed. He’s communicative and this was a great experience!! Would absolutely recommend Arturo!!”
“Annabelle is a perfect find for us! She loved our four-legged babies like her own. We loved that she would send videos and photos each day while we were away! We came home to a clean and picked up home showing she respected our space. She’s also just a sweetheart and she will always be our number one pet sitter!”
“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.”
“Angelica was amazing. She took care of our home and pups as if they were her own. Will for sure book with her again. We got lots of updates and pictures of the fur babies.”
“Geoffrey house-sat for us while we were on a short family trip, and knowing he was home caring for our furbabies really helped put our minds at ease! He was very communicative, and treated our animals like they were his own. We loved receiving pictures and updates on how they were doing, and seeing them enjoying themselves with their new buddy! We appreciated how much he cared for and respected our home, and felt very comfortable with him here. We would DEFINITELY book him again!”
“Heather and her husband were great with our 3 dogs, who are usually a bit nervous around new people. They loved them immediately! Heather was communicative the entire 5 days we were gone which was helpful as we had never left them alone for this long before. Will use again!”
“Averie, did an amazing job watching my two dogs and my home. I came back to happy pups and a perfectly clean house. Highly recommend her services for anyone looking for someone reliable and detail oriented”
“I highly recommend my dog sitter! She did an outstanding job taking care of Triton while I was away. She is always punctual, communicative, and very reliable. Most importantly, she is incredibly sweet, caring, and playful with Triton, which gave me great peace of mind. She followed all of my instructions carefully and kept me updated throughout the entire time. It was clear that she genuinely cared about Triton’s happiness and well-being. I came home to a happy, well-cared-for dog, and I couldn’t have asked for a better experience. Thank you for taking such wonderful care of Triton! I will definitely be using your services again and would highly recommend you to anyone looking for a trustworthy and loving pet sitter. 🐾🐾🐾🐾”
“Robert was amazing!! What a wonderful blessing he was for our Matilda, who is 14 and needs meds and lots of love, as well as taking care of our home while we were gone for over 2 weeks. Such a load off of our shoulders to have him here!! We will definitely be calling him in the future!”
The median cost per night for house sitting in Windemere is $50
Pet parents share their Rover experiences - Windemere
Maggie stayed with my 2 dogs at my house for a week while I traveled to Tokyo for a business trip. I have a hard time leaving them and I honestly didnt worry the entire trip and I was able to focus on work because I had full trust in her! She would send daily recaps at the end of every day with photos and videos, and I can tell my dogs love her. She left the house super clean when I returned and left some homemade treats for the dogs. <3 I could tell they miss her because they were waiting by the door all day! Thank you Maggie for taking amazing care of my children!!
I really enjoyed having Brittany as a house sitter. She had a wonderful rapport with my dog, and did a great job following instructions and providing feedback. We were in regular communication the entire time I was out of town. I would definitely rebook with Brittany the next time I go on vacation!
Annabelle is a perfect find for us! She loved our four-legged babies like her own. We loved that she would send videos and photos each day while we were away! We came home to a clean and picked up home showing she respected our space. She’s also just a sweetheart and she will always be our number one pet sitter!
Delanie was absolutely fantastic! She kept us updated throughout our entire trip with frequent messages and lots of photos, which gave us so much peace of mind. She also let us know right away when our senior dog wasn’t feeling like herself and kept us informed on how she was doing. It was clear that she genuinely cared about our dogs and treated them like her own. We came home to happy, well-cared-for pups, and we couldn’t be more grateful. I would absolutely recommend her to anyone looking for a reliable, caring, and communicative dog sitter. Thank you so much for taking such great care of our babies!
Alexa was absolutely amazing with my dog, Harley! She stepped in to help me at the last minute when I needed a sitter for my vacation, and I couldn’t be more grateful. From the very beginning, Alexa was incredibly communicative and sent me regular updates and lots of pictures of Harley, which gave me so much peace of mind while I was away. It was clear that she genuinely cared about Harley and treated her like one of her own. When I came home, Harley was happy, relaxed, and clearly had been well loved and cared for. Knowing she was in such great hands made it so much easier to enjoy my trip. I would absolutely book with Alexa again and highly recommend her to anyone looking for a trustworthy, dependable, and caring pet sitter. Thank you so much, Alexa, for stepping in on such short notice and taking such wonderful care of Harley!
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!
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 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 for House Sitting in Windemere on Rover is $48.15 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 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 August 2026, there are 4,452 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:
- 91% 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.
Connect anywhere with the Rover app
