House Sitting Countryside Woods
Find a loving house sitter to watch over your pets and your home.
Over 109 pet parents in Countryside Woods have booked house sitting
Countryside Woods, 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.
“Alyssa was incredibly communicative and loving to our pup, and when we returned, the house was just as we left it. It’s so special to know your baby is being so well taken care of. Will definitely rebook.”
“Stephanie did an incredible job with our two golden retrievers. She sent me lots of pictures while we were gone and i could tell the dogs were having a great time. She left our house immaculate - it looked better than before we left! She was a pleasure to work with and we will definitely be using her again in the future!”
“Maureen was fantastic! She arrived right on time, kept us updated, and took such great care of our puppies while we were away. It gave us real peace of mind knowing they were in such good hands. We’d absolutely trust her again and highly recommend her to anyone looking for a reliable, caring sitter.”
“Peggy is absolutely amazing. She truly loves animals and treated our pets as if they were her own. She went above and beyond to make sure our pets were happy and comfortable while we were on vacation. She is the perfect sitter and I would give her more than 5 stars if I could. I highly recommend her services.”
“Wow amazing! Amazing communication and even came by for a meet and greet with such short notice. One of our pups had some tummy troubles and she kept us updated the entire time and even made a vet visit on our behalf. The whole process she made a breeze. We will for sure be using again. She loves dogs.. it radiates off her!! Our boys seemed so so happy and we felt comfortable having her stay in our home.”
“Jasmine was just amazing! First time using her to care for our Cavapoo Mavrick and we cold not be more happy. She was very communicative during her entire stay with Mavrick. She sent daily updates and pictures. We will use her again and again.”
“Doug is such a caring person. He took amazing care of our dog and house for more than a week. Our dog absolutely loved him. Moreover he took care of our plants and fish. He also did a very beautiful sketch of our dog. He is so talented! We are highly recommending him!”
About: As a lifelong dog lover and owner for 10 years, I’m now embarking on a new chapter after 24 wonderful years in Chicago. Following a long career in advertising sales, I’m seeking a slower-paced, more fulfilling path — one that lets me combine my reliability with my love for animals. At 49, I bring maturity, responsibility, and genuine care to every pup I watch, ensuring your they are looked after as if they were my own. Also, the doodle you see in some pics is my amazingly chill, gets along with every living thing, sidekick Lambeau. So please note your dog(s) must be okay with other dogs. I'm currently taking some time off and won't be going back to remote work until the fall '26, at the earliest. So I'm very flexible with my time at the moment. I live in an apartment complex (2 bed / 2 bath) with a huge unfenced grassy area off my lanai, that Lambeau and I call our own backyard. I also live across the street from John Chesnut park, in the Tarpon Woods area so Lambeau and I spend lots of time at that huge dog park and/or exploring the various trails. So if you're open to that as well, I'll gladly take your pup(s) over there for some adventures.
“Megan did a fantastic job with our baby. Our baby has a lot of anxiety and we have never left him with a stranger. Clearly he was treated well. Would recommend for sure.”
“Jason was wonderful, patient with our anxious dogs. We lost both our sitters as they moved. So we’re working on finding new sitters. At first our little one was very scared and vicious.. Jason gave him treats and won him over in no time. He just stayed the day, but definitely call him again. He’s definitely a dog whisperer.👍💜🐾”
About: On top of being a vet assistant for almost 10 years now, I have my own 5 pets that I take care of, each with their particular set of needs. I know all about having a specific routine so I’ll make sure things are done exactly as requested! I have two crazy pit mixes at home, but I also had my family Yorkie that I would take care of up until she passed back in 2025. I also have 3 cats, one of them being special needs (CH, IYKYK). I currently work 10 hour shifts, Monday-Thursday as a vet assistant. I normally go home during lunch anyway to let my own dogs out, so I could always try to accommodate extra time to let your dogs out as well if needed. Since I’m very limited on time during those days, I’d have to be relatively close to my job (10-15 min) to be able to provide midday care for everyone. Weekends (including Friday) I have more flexibility though, as my boyfriend would be home to take care of my pets while I take care of yours! I know a pet’s home is the most comfortable environment for them, so I will do my best to keep the comfort level while you are away. I can walk wherever/however long they need, provide adequate play, and just spend as much time as possible so that they never feel alone. I can also do any additional tasks around the home, such as light cleaning and taking care of any plants you may have (watering, etc). I’ll always make sure to tidy up before your arrival, that way you have more time to decompress without worrying about cleaning up after me :)
“You couldn't ask for a better sitter. This was the 1st time we used rover and our dog had never had a sitter. Shawn used his charm and probably patience to win Bernadette over. He also left our house spotless. An all round gentleman. Would hire him again in a nanotechnology second”
“Christine was great with our two pups. She was punctual and treated Gracie and Steve as her own. She always sent us pics and text messages. We would hire Christine again. What a great sitter she was. Hire her you won’t be disappointed”
“Heaven has been truly a blessing for both me and Zeus. Very accommodating to fit my schedule. If you are ever in need of her services, you can not go wrong!”
“It’s hard to put into words how thankful we are for the care our dogs received. Leaving your pets with someone else can always be stressful, but from the very beginning we felt completely comfortable and at ease. Stephanie treated our dogs like family, not just animals she were watching, and that meant everything to us. We got updates, pictures, and could genuinely tell our dogs were happy, relaxed, and loved while we were away. Coming home to pets that were calm, healthy, and clearly well cared for says more than anything else could. It gave us real peace of mind knowing they were in such good hands. You can tell this isn’t just a job for Stephanie — she truly cares about animals and go above and beyond to make sure they feel safe, comfortable, and loved. We wouldn’t hesitate to use her again and highly recommend her to anyone looking for someone trustworthy, dependable, and caring to watch their pets.”
“Melissa is amazing. We have worked with her several times, and this visit was no different. She keeps us well informed and takes wonderful care of our little guy. We appreciate you Melissa!”
The median cost per night for house sitting in Countryside Woods is $50
Pet parents share their Rover experiences - Countryside Woods
Andrea was caring, communicative, professional, dependable, and a pleasure to work with! She responded quickly when I first reached out and generously made time for a meet-and-greet the very next day. This was my first time booking a house sitter and my longest time away from my recently adopted senior kitty, so I was understandably a little nervous. But Daisy immediately greeted Andrea at the door and seemed comfortable with her, which put me at ease. Andrea was attentive to all the little quirks I shared about Daisy, asked thoughtful questions, and was transparent about her daily schedule. She had the flexibility to spend most of the day at my home with Daisy, which was a huge benefit. Throughout my trip, she provided daily photo and video updates and was always quick to respond when we communicated. I also appreciated coming home to a tidy space—Andrea vacuumed, kept the kitchen clean, and took out the trash and recycling. I felt genuinely relieved knowing my cat had loving care and steady companionship while I was away. One of the best signs of how well the stay went was that Daisy was completely herself when I returned, with no apparent signs of stress or separation anxiety after my time away. I would highly recommend Andrea for house sitting and would happily reach out to her again for future stays or drop in visits!
Stephanie was wonderful with all of our babies! This was my first time using someone I didn't know and she exceeded my expectations! She was patient and took great care of them with all of their quirks. She even made friends with our 2 cats who always hide! Will absolutely use her again!
Lydia and Emmitt took amazing care of our puppies while we were on vacation! They sent us updates and photos every day while we were gone. They gave them multiple walks per day and lots of play time. The pups looked like they didn’t even miss us! They stayed in our house for a whole week and left everything exactly as they found it. I don’t think anyone has ever cared for our puppies so well while we were away before!
We were new to Rover and had previously only had family or close friends look after our dogs when traveling. We ran into a last minute bind and needed to find someone to look after our dogs a day before we left. That’s when we were fortunate enough to get paired with Katie. From the first interaction, Katie was responsive, accommodating to our requests, and absolutely wonderful with our very co-dependent dogs. She sent us pictures and check-ins daily which truly exceeded my expectations. She took the best care of our pets while we were away and I’m truly grateful we met Katie. We will absolutely book with her in the future.
Angie was wonderful! She was on-time every time, very polite and always smiling! She house sat for us last minute when another sitter fell through and Dottie too to her right away. Angie was always sending updates and photos from morning to night and we will def. want to work with her again!!
Laryssa was very caring, attentive, and clearly treated our dog like one of her own. Communication was excellent throughout our trip. She kept us updated with messages and photos, which we really appreciated. When we returned home, the house was clean and exactly as we left it. It's such a great feeling to come home to a happy dog. Highly recommend!
Jasmine watched our dog Mickey while we went away for three nights and we were very very happy with the care that she gave him and the updates and photos that she sent to us. She even got him to eat on day one which we did not expect! We’ve been looking for someone for a very long time who we are comfortable with, and we have finally found someone!
Hi Megan!! I had a fantastic experience with you! 😍 This was my first time with a Dogsitter and I could not have found a better one. I went on a trip with my husband and let my two Weimaraners with her for several days and I felt so at ease. She was great with updates and got the best photos we have of the dogs so far!! I will absolutely book her again on next trips as now we have found our Girl! Thank you, Megan and we will see you soon! 💕💕
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