House Sitting Windermere
Find a loving house sitter to watch over your pets and your home.
Over 80 pet parents in Windermere have booked house sitting
Windermere, 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.
“Mark has taken care of our dog several times and is always wonderful to work with. He sends lots of pictures and updates, and does a great job of keeping our older dog active and having fun while we're away!”
“Sarah is wonderful! She took excellent care of Ellie and Theo, and excellent care of our home. She lived up to every promise she made. She handled everything that came up competently annd professionally, including a couple of unexpected problems. The dogs were healthy and happy when we got home and our house was very clean and in good order. We will have Sarah come and stay again, without hesitation.”
“We were able to fully enjoy our two-week vacation without a single worry, all thanks to Nick. He took such great care of Winston and gave us the peace of mind we were hoping for. It meant so much to have someone we could completely trust—not just with our dog, but in our home as well. We truly got the best of both worlds with Nick. Thank you for treating Winston like your own and for being so respectful of our home. We’re incredibly grateful!”
“Tiffany was so great! She arrived as promised and even took our dog out one extra time for us since we were returning late. The dog was happy and well- cared for, left the house in great shape. Will definitely use Tiffany again and highly recommend!”
“Alyson stayed at my home x 2 nights with my mischievous Great Dane pup and my 10 year old Doberman. She was prompt with communication and sent updates which allowed me to enjoy my first weekend away in a long time. My dogs were well cared for! I definitely recommend her and will book with her in the future!”
“Nathan was an amazing dog sitter! He took great care of my dog and sent me lots of photo updates throughout my trip. He went above & beyond helping out when I needed an emergency repairman visit to my home while out of town. I will definitely be booking with him again and I highly recommend him to anyone needing a sitter.”
“Brittney was amazing with my fur baby!. She provided tons of updates each day and even a photoshoot! I would definitely recommend Brittney and would book with her again. I came home to a very happy and healthy puppy.”
“Yelena was absolutely wonderful! She responded quickly and was able to accommodate us last minute to watch our fur-babies, which we really appreciated. Throughout the day, she sent us pictures and updates, giving us peace of mind that they were happy and well cared for. She also treated our home with the utmost respect and was such a pleasure to have in our home. We couldn’t have asked for a better pet sitter and would definitely recommend Yelena to anyone looking for someone trustworthy, caring, and dependable. We will absolutely be using her again! 🐾❤️”
“Jonathan did an incredible job again! He has become our “go-to” sitter for our cat and dog. Our animals are so excited to see him and I suspect a little let down when they see us return. Lol. Jonathan provides such wonderful care and attention, sends updates and pics regularly, and it makes taking a family trip so much more relaxing knowing our fur babies are in great care. Can’t recommend him enough!”
“Alexis is amazing. She goes above and beyond. When one of my dogs had an accident she took our carpet to her own place to clean it. We’ve tried several pet sitters but no one leaves our kitties as happy and our place as clean as when Alexis comes to watch them. We will be using Alexis again and again!”
“Liz was wonderful with our doggy! Our senior dog liked her from the moment he met her and was at ease in her presence early on. Liz was especially attentive to taking frequent photos and sending updates daily. When we arrived home, our doggy was comfortable and calm. We are so glad to have found Liz and will be booking with her again very soon!”
About: For over 15 years, I have provided comprehensive, high-quality care for both dogs and cats. My experience ranges from high-energy playtime to specialized senior care and positive reinforcement training. I pride myself on creating a safe, structured, and joyful environment for every pet. What I Offer- Medical & Senior Care: Confident in administering oral medications and skin topicals, as well as managing specialized routines for aging pets. Positive Training: Skilled in teaching basic manners, tricks, and reinforcing good behavior using force-free methods. Play & Enrichment: Expert at reading animal body language to deliver the perfect balance of physical exercise and mental stimulation. Feline Expertise: Experienced in managing cat behavior, specialized diets, and giving space to timid or anxious felines. Whether your pet needs basic puppy training, gentle elder care, or just a fun day of structured play, I adapt my approach to their unique personality. Because my work schedule varies week-to-week, I am highly adaptable and can often accommodate non-traditional times, last-minute requests, and mid-day visits that standard 9-to-5 sitters cannot. I manage my calendar tightly to ensure that when your pet is booked, they get my 100% undivided attention, medical care, and training focus. As a seasoned pet professional specializing in medical administration and behavioral training, I look at safety through a clinical and preventative lens. I do not just watch your pet; I actively monitor their health, behavior, and physical surroundings to prevent accidents before they happen. You can travel with total peace of mind knowing an expert is at the helm.
About: Welcome, Pet Parents! 🐾 Hi everyone! Thank you so much for choosing me as your local pet sitter! ❤️ I’ve been caring for dogs, cats, and other pets for about 10 years, and I’m also a proud Yorkie mom myself. I work from home, which allows me to provide your pets with plenty of attention and a comfortable home environment. I also believe great pet care should be affordable, so I try to keep my rates about $10–$15 below the average local sitter. You’ll receive three updates throughout the day — morning, afternoon, and evening — and I’m always just a text away if you have questions or concerns. **REVIEWS ** Hi pet parents! I love being your go-to pet sitter and always happy to step in when you need last-minute care! Quick favor: Since pet care is my business, 5-star reviews are essential to keep things going. It takes less than 30 seconds to drop a review after our booking, and it helps me out tremendously. Thank you for your continued support! A few friendly house guidelines 🐾 Since I care for multiple pets, I kindly ask for your trust and patience so I can give every pet the attention and care they deserve. All pets in my home are treated with the same love and care. For drop-offs, please follow my instructions and bring your pet to my door unless you have a disability or another circumstance that makes that difficult. When you arrive, please text me rather than knocking or ringing the doorbell. I may be caring for or settling another pet, and unexpected noise can make them anxious. If we've already texted that you're outside, I promise I'll be with you as soon as I safely can!
About: I’ve adored animals my entire life and have taken care of many different types of pets for the last 15 years ranging from my neighbors cats and dogs, to my friends reptiles, and my many pets over the years. Consisting of walking, playing, feeding, bathing, and occasionally overnight stays with their animals. I’ve owned many fish, hamsters, a bunny, duck, and 6 dogs over the course of my life. For the past 8 years I’ve been raising my two beautiful female Rottweilers who are giant teddy bears, full of energy and love. I’m currently working around my full-time job. If you’re looking for care outside of my availability, send me a message and I’ll do my best to accommodate you. Availability: Sunday after 7pm Monday after 5pm Tuesday before noon Wednesday ALL DAY Thursday after 5pm Friday after 3pm Saturday ALL DAY As of now, I offer both dog walking and day visits at your home, and will eventually be offering dog boarding services. I am physically fit to keep up with your dogs no matter their energy level and will give them plenty of exercise during walks throughout your neighborhood or a nearby park. I am well organized and a clean person who will treat your home like my own!
About: I am a vet student in school and I have been caring for my 6 animals for more than 10 years. You can trust me I will be very careful, responsible, and loving towards your animals. I work a part time job as a barista and my mornings and weekends are usually free so I will have a lot of time free to do what I love most and care for your animals! I will care for your animals at your home by feeding/walking them on time and I can put them to bed in their crate if needed or if not then they’ll have a safe space to get their zoomies out and relax!
The median cost per night for house sitting in Windermere is $45
Pet parents share their Rover experiences - Windermere
Elizabeth was amazing!!! She was a great communicator, providing frequent updates and photos of our pets while we were away. She was equally attentive and loving to our dog and our cats. I never worried one bit about their well being because I knew they were in great hands! We will be rebooking!
Michelle was Amazing. So great with our little pup. She was flexible and so accommodating. We were able to do the parks thanks to her accepting a last minute request! She sent us adorable updates. It is clear she loves animals and is so good with both the parents and the furbabies. Thank you, Michelle for helping us have a great vacation!
Thanya went beyond expectations staying at our home and caring for our dog Bogy! She sent many photos, tried many options to get Bogy to take his Meds, my house was well kept! It look just as I left it !!! What a pleasure to come home to ! I highly recommend Thanya and plan on booking with her again!
Yanran cared for my four cats and one dog and we were very pleased with her care. I got photos and updates daily, the pets were all happy when we returned, she let the dog sleep in bed with her as he was obviously missing his family, and the house was clean when we returned. We greatly appreciated her care and will be booking her again soon!
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 - Windermere
Select a filter and find qualifying sitters offering house sitting.Sitters in Windermere average 4 repeat house sitting clients
FAQs for House Sitting - Windermere
Frequently asked questions about Rover
The average cost of House Sitting in Windermere on Rover is $56 per night as of October 2026. Most bookings cost between $30 and $83 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 3,096 sitters on Rover offering House Sitting across Windermere. 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 Windermere 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 Windermere 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.
<b>Tip:</b> 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 Windermere 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 Windermere. 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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