House Sitting Winter Gardens
Find a loving house sitter to watch over your pets and your home.
Over 62 pet parents in Winter Gardens have booked house sitting
Winter Gardens, Find top rated house sitting
Prices are estimates per night for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
About: I genuinely enjoy being around dogs and making them feel comfortable, safe, and loved. I'm active, patient, and love going on walks, playing, or just keeping them company. I'll care for your dog the same way I would my own. Pet care is already part of my everyday life because of my own dog, Taco. He's super active, so walks and park trips are already part of my everyday routine. I genuinely enjoy being around dogs, so dog walking and drop in visits fit naturally into my schedule. I'm available weekday afternoons and anytime on weekends. I always want dogs to feel safe and comfortable around me. On walks, I pay attention to their pace, surroundings, and anything that could stress them out. In a client's home, I follow their routine and make sure their dog feels relaxed and cared for. I treat my dog like they're my own ❤️
About: Hello! I’ve house sat and cared for animals of all ages, including households with multiple cats and dogs, as well as exotic pets. I grew up with a pet husky and miniature poodle, and have experience walking dogs of all sizes and temperaments. I work in the morning/ early afternoon as a Barista ~20 hours a week. I am generally free early morning (before 8am), and afternoon-nighttime. I am off ~3 days a week (usually between Monday-Thursday) during which I can give extra time and attention to pet-care. I have years of experience caring for and walking all kinds of dogs and am very attentive to the emotions and needs of each animal.
“Sarah was very responsive and kind and took great care of our pets and home. I’m very grateful for her communication and reliability, which gave me peace while we were away. Thank you, Sarah!”
“Daisy was a fantastic house and pup sitter. She was super communicative, professional, and was so great with my rambunctious Australian Shepherd. On top all the great care for my pup, she left my house in great shape- clean, tidy. Will definitely hire again.”
About: I've had pets my whole life, and I've always been considered the animal whisperer of my family. I've owned and cared for cats, dogs, birds (parakeets + cockatiels), freshwater fish, toads, ferrets, and event rats! I'm very in tune and informed on common health issues or changes in behavior that may indicate health problems I just recently moved to the El Cajon area and would love to care for your pets :) My availability is currently fully open! Feel free to message me with any concerns or questions! I'm currently job searching since I'm new to California, so my schedule is very open/flexible to any odd times you may need. I'm comfortable with adapting to however you would prefer your pets are looked after and cared for. I'm also happy to help accommodate any current training you may be implementing to help the process. Rest assured your pet will be cared for as if they were my own.
“The communication and updates were exceptional!!! I felt So confident that our pups were being treated well and getting all the love! My rescue pup has never let anyone besides my partner and I touch her, and this weekend tee sent a video of her petting the pup on her bed! Will 100% hire her every time we need pet sitting/drop in needs!”
“100% recommend Alexzandria!! From the time I started messaging her she asked all the right questions about my dogs. She was very flexible and communicated well! I got daily updates without prompt! I was worried about finding someone for 2 dogs, especially one being a puppy but this worked out perfectly!”
About: I’ve been a dog owner for over 15 years. I love the joy they bring to others. I have experience with puppies and senior dogs. I would love to help care for your dog, whether it’s sitting or walking. I am pursuing pet care full time so my schedule is flexible for walks and pet sitting. I will work with you to make sure your dog is taken care of and happy! I am very thorough in making sure every pet has a safe and comfortable space. I have a friendly dog of my own and can bring him along if your pet wants a play buddy!
“Anna was a great help to all of us when she cared for our pups… CC & Gus. She was good with both dogs, kept them happy and safe plus well fed. She seemed to enjoy her time with them and sent pictures. She stayed with them while we were gone a couple of days which made it possible for us to enjoy our time since we knew the dogs were well taken care of. Thanks Anna!”
“Donatella made me feel super comfortable and kept me updated and had open communication throughout her stay with our pup. Will definitely be working with her in the future and would recommend her to anyone.”
“**5 Stars – Excellent Caregiver!** We couldn't be happier with the care our dog received while we were away. Audrey took great care of our dog as if she were her own. She followed all of our instructions, kept us updated with photos, and our dog looked so happy and well-taken care of when we returned. Our home was left spotless, and it was clear that Audrey treated our space with respect. We will definitely be booking with her again for future trips.”
About: Hi! I’m Rhonda, and I understand that pets are family. Whether you’re away for a weekend or an extended trip, I provide dependable pet sitting and house sitting services so you can travel with peace of mind. As a lifelong animal lover and owner, I enjoy caring for pets of all ages and personalities. I am comfortable with both dogs and cats. My goal is to make sure your pets feel safe, comfortable, and loved while you’re away. I am dependable and treat every home and pet with the same care and respect I give my own. I currently have two cats, Gizmo and Truffle, but I have owned many different types of dogs and cats throughout my entire life. I look forward to meeting you and your furry family members! I am currently self-employed part time and primarily work from home, so I am able to be home with your pets the majority of the time. I might be gone for 1-3 hours some days. It varies. I am happy to care for your pets in your home or mine, including staying overnight. Whether your pet loves walks, playtime, cuddles, or simply a familiar routine, I will provide trustworthy care tailored to them. In my home, I currently have two cats, Gizmo and Truffle. I can board your pets in my home as long as they are comfortable with cats. Both my cats tolerate dogs and cats well. I can also stay at your home while you’re away or do drop in visits/walks/feedings, depending on your preference.
“Anna was amazing, not only did she show up on time, but she sent me several check ins throughout the night. She made sure that I knew that my Furkid was happy and safe. She followed the directions I left for her to the T. Anna was extremely punctual and professional. I would highly recommend her to anyone who is in need of pet sitting. She was the epitome of a perfect pet sitter. I will definitely book her again ❤️”
About: I’ve had about 13 dogs of different breeds in my lifetime. Every dog that I’ve had in my life still carry on in my heart. I was responsible for all of my dogs and made sure to attend to their needs in a safe manner. I’m able to work any day of the week as long as it’s 8-3pm. I’m just not available around 4-6, but I am able to care for them in my home if necessary. We have a screen door and our parking lot is gated, so there is no way for them to get through. There is also a park nearby that is great for walking.
“Cristen was excellent with our two Mini Schnauzers! She is very friendly and professional. She went above and beyond our expectations. We have already hired her for our next trip and will continue to request her in the future.”
“Our eperience with Jayna couldn't have been better! Jayna did way more than what was expected. Our baby girl (Lani) was spoiled and well taken care of. Jayna took Lani on her daily walks, snuggled her with blankets at night, sent photo updates of our pup twice a day, and left our home honestly, in better conditions than when we left it! Jayna went above an beyond by bringing in our mail, being on a look out for incoming packages, keeping our backyard grass clean, and leaving my kitchen counters spotless. Couldn't have asked for a better pet sitter. Thanks so much!”
“Bobbie S is an amazing dog sitter. She took such good care of our dogs and followed our instructions to the letter. Our dogs were in such a relaxed and happy mood when we returned just as if we had been there ourselves. 6/5 stars.”
The median cost per night for house sitting in Winter Gardens is $63
Pet parents share their Rover experiences - Winter Gardens
Angela again provided outstanding care to our elderly dog. She left our home in the exact condition she found it, even washed the bathmat. When our return flight was late she even went the extra mile to change her plans and stay later than the original agreement.
The communication and updates were exceptional!!! I felt So confident that our pups were being treated well and getting all the love! My rescue pup has never let anyone besides my partner and I touch her, and this weekend tee sent a video of her petting the pup on her bed! Will 100% hire her every time we need pet sitting/drop in needs!
Angelina was fantastic! We received regular photos showing our dogs happy and being themselves. She stayed in our home for about 10 days and everything was the same as when we left. Hopefully she stays around San Diego and will watch our dogs again in the future. It can be hard to find people to trust to watch your family and stay in your home.
Daisy was great and we would recommend her to anyone. She was our first pet/house sitter ever and she made our experience great. We came home and the house looked just like we left. She was great at sending pictures and video updates while we were away as well. Responsive, friendly, good w/ animals. Would absolutely book again.
We truly trust and appreciate Courtney for taking care of our animals while we were away. We had a last-minute emergency, and thankfully Courtney was able to accommodate us and adjust her schedule to help out. It gave us so much peace of mind knowing our pets were in such caring and capable hands. We are incredibly grateful to have someone we can trust and rely on, and we know our animals will always be well cared for with her. We highly recommend Courtney to anyone looking for a dependable and compassionate pet sitter! 🐾💕
I highly recommend Mandi as a pet and house sitter. Trust me when I say she goes above and beyond on her duties as a pet sitter. Unfortunately, we had a sewer problem at our home during her stay and since we were out of the country, we were able to handle it over the phone and get a plumber in to fix the issue. Mandi was absolutely amazing in communicating and keeping us updated with our pup during our trip. We will definitely have her pet sit again.
Lindsey is our go to sitter and did a great job taking care of our boys as always. She is so sweet with them and sends daily pictures. She is resourceful when challenges come up and you can tell she really loves animals. We always feel at ease when our boys are with Lindsey and highly recommend her :)
Charles took our booking last minute as we had exhausted our options for care for our older reactive pup, he knew what he was doing when it came to the meeting and knew how to handle Avi, Avi loved Charles, and Charles paid close attention to our little needy situation with Avi and executed everything perfectly, will definately book again as im afraid Avi will wonder what happened to his new friend 😁
Cristen again is amazing. We have two Great Danes who demand attention and Cristen steps right up and gives it. We got new place and Cristen did great in it and kept it clean and great. Our kids love having her and are always pooped out when we get back. So glad we found Cristen!!!
I am grateful to Victoria for her care of my dog Ella, a senior girl with multiple health issues requiring careful medication administration. She followed feeding and medication guidelines, got Ella to play, took her for daily walks and responded quickly when asked for updates. This morning, Ella went looking for her in the bedroom, even though I am here! I think that says it all.
Katelin was amazing! She was very communicative throughout the entire stay and kept me updated, which gave me so much peace of mind. It was clear she really cared and was attentive the whole time. I would absolutely book with her again and highly recommend her to anyone looking for a reliable and thoughtful sitter.
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 sitting2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit3. 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 Winter Gardens sitters!Sitters in Winter Gardens average 4 repeat house sitting clients
FAQs for House Sitting - Winter Gardens
Frequently asked questions about Rover
The average cost for House Sitting in Winter Gardens on Rover is $55.5 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 6,351 sitters on Rover offering House Sitting across Winter Gardens. 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 Winter Gardens 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 Winter Gardens 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 Winter Gardens 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 Winter Gardens. On Rover:
- 93% of sitters can help with special care needs
- 95% can help with giving oral medications or injections
- 98% 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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