House Sitting Windermere
Find a loving house sitter to watch over your pets and your home.
Over 75 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 the perfect dog sitter for Otis! She was so playful and spoiled him with long walks and play time. Her updates made me comfortable on my trip and allowed me to truly enjoy my time knowing Otis was happy and cared for. HIGHLY recommend!”
“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.”
“Alyson was fantastic. Took great care of Bailey and truly cared for her as if she were hers. With a hysterical nickname - you could tell she understood her personality as we do. That level of kindness goes a long way. So greatly appreciated.”
“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!”
“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 :)”
“Sarah was great. We went away for two weeks and had to find a pet sitter last minute. Sarah communicated well, took good care of the pups, and left the house cleaner than when she arrived.”
“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:)”
“Steffanie is a wonderful sitter and I highly recommend her to watch your pets! She is very friendly, professional, self sufficient and a natural with animals. Steffanie stayed in our home for a week and took care of our 2 dogs and 1 cat, she kept us updated with texts and photos to let us know that all was well and gave our dogs extra love during the daily Florida storms. We returned home to a spotless house and happy pets!”
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!
“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! 🐾”
“Nathan took wonderful care of our dog, Koda. He checked in with us regularly and sent lots of pictures. He got Koda out on lots of walks, even in the rain. We came home to a clean house and a happy dog!”
“Jonathan did an incredible job as always! Great communication with pictures each day, and the recaps he sends reassures you that your pets are in great hands. House was in impeccable shape when we returned and we will continue to use his pet services again!”
“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!”
“Ariella was AMAZING. She left the house absolutely spotless and took such great care of our babies. She was great at communicating with us and very responsive. Our cat who doesn’t come out for anyone even loved her! I can’t recommend her enough 11/10!!!”
“Jocelyn did an incredible job with my two pups - both are young with tons of energy. My 3yo border collie was not friendly but Jocelyn easily won her over. I was truly impressed with how she expertly navigated my dog’s behaviors. I received great pictures that highlighted how well cared for they were while I was away. Jocelyn kept them happy, safe and fed. I appreciate Jocelyn”s regular updates and photos. I would 1000% rebook Jocelyn.”
“Taylor took excellent care of our dog and cat! We have quite a few "special" requirements for our senior four-legged family members and Taylor was up for the task. She stayed in our home and fit in like a champ! In fact, we've booked Taylor for another (longer) visit. Thank you, Taylor!”
“Devona was amazing. We needed someone who could stay with our two cone headed dogs after a recent dog attack. She took great care of them and sent many photo updates. Will definitely use her again!”
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.
The median cost per night for house sitting in Windermere is $45
Pet parents share their Rover experiences - Windermere
Hailey is a superb pet and home care pro! Our two dogs just love her! She is kind and playful with them ans obviously loves her work witb them! She stayed at our home foe a week and everything was perfect when we returned. We will continue to use Hailey and you should too!!
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:)
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 for House Sitting in Windermere on Rover is $55.5 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 3,056 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
- 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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