House Sitting Windermere
Find a loving house sitter to watch over your pets and your home.
Over 93 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.
“Karen was fantastic. I think Sophie did not want me to come back from my trip because she got along with Karen so much. Karen was extremely responsible. She walked and played with Sophie all the time. She also took great care of my house!”
“Alyson stayed at our house with our spunky pup for 4 nights. She took good care of both our home and our dog, kept me updated, and we came home to a happy, well-cared-for pup.”
“Shelley was very communicative during her stay. After a rough start for not having the code to our door (completely my fault) things went very smoothly. Daisy and the house were well cared for.”
“Yelena was great, easy to reach and communicate with. Skai loved her and she even left her a new toy to play with! You can tell she is very experienced with dogs especially being that Skai can be very hyper but it did not seem to bother her at all. I would definitely book again, she made things very easy and smooth thank you :)”
“Taylor was amazing! We are new to pet-sitting and have pups that have only ever been watched by friends and family. She was very professional in all interactions from first text to first meeting with us and our dogs, to being able to do a second meet and greet right before our planned vacation to get some alone time with our grumpy older dog. She sent us photos, videos and daily updates. And everything went awesome! House was taken care of, she even watered our plants. I would 100% recommend her and she will be our go-to pet-sitter for future trips.”
About: My first sitting job was at 14 for the neighbors across the street, during a month long trip. I have been sitting for friends on and off for the last 4 years, dogs and cats. I have a lot of experience with senior cats and cats who are on medication. I am currently an independent contractor, working as a performer. When in a show, weekends would be difficult, and at most a show run lasts 5 weeks. I also bartend at a theater, those shifts are only 4 hours, and are also only during the run of a show. My schedule always remains very flexible. Growing up I was the designated dog walker in the family, he was a very excitable and friendly dog so I have a lot of experience with dogs who pull on their leashes. I also was responsible for baths. I also have some experience with multiple dogs at a time, of all sorts of personalities. I have owned at least one cat since I was 6, I'm the girl who seeks out the cat at the party to hang out.
“Elizabeth was great with my three very different personality dogs. They are little with big personalities! She managed them all so well, no accidents in the house, and gave them love as if they were her own. I’m happy to have found someone reliable and patient to be with our pups when we go out of town:)”
“Tiffany was able to help us out last minute when other pet sitting plans fell through and we’re so happy to have found her! She was great with our two pups and sent us pics throughout her stay. She was great at communicating with us before and during and we came home to a clean home and happy pups. We will definitely use her again! Thank you Tiffany for your professionalism and for taking such good care of our pups!”
“Nick was fantastic! I was able to book him day of. He was very nice and flexible. He started getting to know my little Hazelnut right away and she took right to playing with him. He sent several pictures, even one of her asleep which was amazing as she has big puppy energy! Will be very happy to reach out to Nick again!”
“Kaitlyn was amazing with my dogs! She did an outstanding job house sitting and taking care of my two dogs for the weekend. She is a great communicator and sends updates as requested. I will definitely have Kaitlyn back to house sit and take care of my dogs in the future!”
“Nathan is amazing. He took great care of my german shepperd and my 2 cats. He sent me several pictures of them during the day and had great communication. I was able to go on my trip and actually enjoy it, not worrying about them or my house. When I returned everything was cleaned and my pets were happy. My GS loved him. Thank you Nathan! I recommend him without hesitation and I will be contacting him again.”
“Jocelyn made sure our fur babies had all their needs taken care of while we were gone. It helped us enjoy our vacation knowing we could trust they were well cared for. We received lots of picture updates and assuring texts!”
“First time using Rover, super nervous to leave my dog with someone I didn’t know in my hotel but felt it was a better option over doggy daycare! I choose Thanya because of her current work history working with animals as a vet tech! I felt my dog would be safe in her hands with her additional knowledge in her field of work! She made the entire process so easy, she did a meet and greet which she does not have to do which was KEY to meet us, our dog and see the location of where she needs to go vs just showing up the day we needed her. She was very friendly, flexible and on time! She took the trash out which was not asked of her and cleaned up after herself. I know my dog liked her because day 2 he didn’t bark at her when she walked in the door she had gained his trust! She followed eveything asked of her in regards to spuds needs, schedule and my little extra crazy about germs with shoes off in the hotel and washing her hands every time she walked the dog and returned back to the apartment hotel. Highly recommend, we will be using her again the next time we come to Florida and sending her info to friends and family. She is Mahoney & Spud Approved! Worth every penny! Took the best pictures of my dog too one I actually plan to frame when I get home! 🐾”
“I am so glad that I found Diahann to pet/house sit while we were traveling internationally. She was great with our 2 pugs. She was extremely responsible and communicative, sending us daily updates about our girls. Our home was also in perfect condition when we returned. Being a veterinarian myself, I can be picky about who takes care of our dogs, but Diahann definitely passed with flying colors. As long as she is available, she will be my go to pet sitter from now on.”
“Absolutely the best dog, cat and house sitter we've ever had. Wonderful with our sensitive rescue dog. Continued with the training we had started. Took her for long walks. Extra caring for our very old cat and even monitored his weight for us. Found a problem with our jacuzzi that the pool people missed and got them to correct it. Ended up drying all of our bedding and towels at her own home as there was a problem with our dryer on her last day. Left the house spotless and watered the plants. Sent wonderful photos and updates. Excellent communicator and problem solver. Made 9 days of our trip much more enjoyable knowing she was there. Highly recommend.”
“Alexis was amazing! She sent us pictures and kept us updated. The dogs looked so happy!! She stayed at our house, and we came back to a beautiful, clean home. We’d definitely use Alexis again!”
“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!”
“Jonathan was recommended to me by family member and I'm glad they recommended Jonathan. Great communication for planning and during the stay. Will definitely be using Jonathan again.”
About: I’m patient with older dogs and pups just learning, as well as those missing their people and are scared. Grand mom to 4 sweet puppers. Lifetime pet family, we have guinea pigs, hamsters and every kind of dog and cat. I always helped neighbors when the needed pet care as well as years of volunteer work in shelters. Pets are family. I am a retired teacher due to injury and have a home based business so my hours are flexible. With enough notice I will do my best to accommodate care needed. I am unable to care for other pets in my home, we have 7 cats. I will follow all instructions given to lovingly care for your pets at your home
The median cost per night for house sitting in Windermere is $45
Pet parents share their Rover experiences - Windermere
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!
Elizabeth was great with my three very different personality dogs. They are little with big personalities! She managed them all so well, no accidents in the house, and gave them love as if they were her own. I’m happy to have found someone reliable and patient to be with our pups when we go out of town:)
Taylor was amazing! We are new to pet-sitting and have pups that have only ever been watched by friends and family. She was very professional in all interactions from first text to first meeting with us and our dogs, to being able to do a second meet and greet right before our planned vacation to get some alone time with our grumpy older dog. She sent us photos, videos and daily updates. And everything went awesome! House was taken care of, she even watered our plants. I would 100% recommend her and she will be our go-to pet-sitter for future trips.
Lilly is awesome! She took care of Ellie in our home for 5 days and was flexible enough to stretch it a full day when our flights were delayed. She's conscientious, friendly and extremely mature, and she sent us frequent updates and pictures throughout the week. Ellie seemed to love spending time with her, and we felt confident leaving both our pup and our home in her hands. We would not hesitate to use her again!
Maddie was a godsend with all of our pets. We hired her for drop ins to take care of cats while we were on vacation. We emergently needed her to come additional times for dogs as well and she was able to assist while we were out of the country! Pets were well taken care of and I had peace of mind! Would 100% recommend and use her 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 near you
Select a filter and find qualifying Windermere sitters!Sitters in Windermere average 4 repeat house sitting clients
FAQs for House Sitting - Windermere
Frequently asked questions about Rover
The average cost for House Sitting in Windermere on Rover is $51.06 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 3,117 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.
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 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 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 Windermere. On Rover:
- 90% of sitters can help with special care needs
- 95% 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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