House Sitting Jackson Park
Find a loving house sitter to watch over your pets and your home.

Over 2 pet parents in Jackson Park have booked house sitting
Jackson Park, 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.
“Samantha did a wonderful job during an overnight say with my Sasha. She came to meet Sasha beforehand and get a quick tour of the house and rundown of Sasha's schedule. During her stay, she sent lots of pictures and updates. She also left my home cleaner than when I had left! I am extremely appreciative of Samantha's care that she put towards watching my fur baby.”
“Elizabeth was amazing. We need a last minute dog sitter and she came through and saved vacation! She provided plenty of updates, photos, and videos. Our dog sometimes is a little shy coming out of her crate but she loved Elizabeth. We will definitely use Elizabeth's services again!!”

“Maiah did a terrific job taking care of my dog. She gave us daily updates and photos, left the house clean and even stayed with my dog so she didn’t get lonely! Amazing!”

“Evita was excellent! She is incredibly responsive and communicative. We greatly appreciated regular updates with pictures on how things were going while we were away. Along with our dog being well cared for, our house was also well tended. I will absolutely be reaching back out any time we need a sitter.”

“Wonderful!!! Charlie was so relaxed when I got home which I think speaks volumes to how comfortable he was with Melissa. They played, cuddled and went for a bunch of walks. I loved the photos!!❤️ I will definitely be booking Melissa again for my sweet little peanut!”


About: Animals have always been a huge part of my life! I’ve grown up around dogs of all sizes, especially larger breeds, and have plenty of hands-on experience caring for them. I’ve personally owned two Pit Bulls, one weighing 70 pounds and the other 132 pounds, along with a Pomeranian, so I’m very comfortable handling dogs with different sizes, personalities, and energy levels! My family has always had larger dogs and has trusted me to care for their pets while they’re away. I’ve also helped friends with cat sitting, so my love and experience extend beyond just dogs! For the past year and a half, I’ve been a stay-at-home mom, which has taught me even more about patience, responsibility, and maintaining a loving, attentive environment. I understand that pets are family, and I want every pet in my care to feel safe, comfortable, and loved. Whether your furry friend needs walks, playtime, feeding, companionship, or just some extra love while you’re away, I’ll treat them with the same care and attention I’d give my own pets! As a stay-at-home mom, I have a very flexible schedule that allows me to accommodate a variety of pet care needs throughout the week, including weekdays and could be flexible depending on weekends. I’m happy to provide dog walking, drop-in visits, feeding, playtime, and companionship while you’re away. My 1½-year-old would accompany me during visits, so I ask that pets be comfortable and safe around young children. I understand how important it is to find someone dependable to care for your furry family members, and I’m committed to providing reliable, loving, and attentive care while working around your pet’s individual routine! Your pet’s safety, comfort, and well-being are always my top priorities! While I do not offer pet care in my own home, I’m more than happy to provide care in the comfort of yours, where your pets can remain in their familiar environment and maintain their normal routines. I have experience caring for dogs of all sizes, including large breeds, as well as smaller dogs and cats. I understand that every animal has its own personality, needs, and boundaries, and I always take the time to make sure they feel safe and comfortable. Since my young child accompanies me, I only accept pets that are comfortable around toddlers. I prioritize safe interactions, close supervision, and respecting each animal’s personal space. I’m also happy to follow any specific feeding schedules, walking routines, household rules, or special instructions you provide. My goal is to give you peace of mind knowing your pets are receiving dependable, compassionate care while you’re away!
“Tanya did an absolutely amazing job watching our large household of young and old dogs and cats! She handled medicating the elderly dog, keeping an eye on the still-in-training pup, separating the species as necessary for feeding, even successfully keeping the 13 year old dog from climbing the stairs at night! We felt completely comfortable leaving our menagerie in her care. When COVID necessitated our extending our stay a night, we really appreciated Tanya's flexibility and commitment to care, which she demonstrated by staying an extra day so we could get home safely. She did an excellent job communicating with us daily and left us helpful information about how each pet fared in our absence. We're very grateful to her for giving us peace of mind on our trip!”

“Alissa was great! She really came through for us at the last minute so we were able to enjoy our concert stress free! She kept us updated, and was prompt with her communication! The boys loved her!”

“Adrianne is amazing! She was communicative, asked thoughtful questions during the meet and greet, and ensured meds were delivered to a picky eater. We hope to have her back for future vacations!”

About: I graduated from UW-Milwaukee with a degree in Design and Visual Communications. I am a very outgoing, friendly and loving person. I recently lived with a senior dog, a senior cat, and 3 adult cats! I am very familiar with animal medications including: pill shooters, ear cream, topical skin cream and liquid medicine from the senior animals and my cat Jack who has cardiomyopathy. I understand the importance of animals who have medical needs and schedules. I love providing the care your fur babies need! I work a Mon-Fri work from home job, with flexible hours during the day. During the week days, I availability from 7:00am-8:45am (some earlier mornings can work as well!) 11:00am-2:00pm (for one 30 minute visit during my lunch break) and 6:00pm-9:00pm and weekends are pretty flexible! I am a very active person, and love getting my steps in walking dogs! I currently am not taking any repeating long term bookings. I do not board any animals at my home. I have lived with animals for a little over 7 years. I have house sat for many friends and family, for cats, dogs (corgis, labs, and huskies) and a bearded dragon! I will send lots of pictures for updates during the visits. I understand your pets are your family, and I want to provide the best care possible.

“Rebecca was phenomenal with my little critters! Excellent communication throughout the week and she was able to adjust last minute to needing to give my dog extra TLC and medication. I highly recommend her for your pet-sitting needs!”


“Blythe took such good care of our pets and home. She went out of her way to schedule fun things for our dog, and she clearly loved all the attention, and the cats loved the snuggles. Thank you, Blythe!”

“Tabitha was awesome! One of our dogs is extremely cautious with new people, and Tabitha was so patient and understanding with him. She had the knowledge to work with him communicated with us consistently with any questions. We are very grateful. She was also very respectful of our home and followed any tips/directions we left her with. Would absolutely recommend Tabitha to anyone.”

About: I am a part time college student. I am going to school to get my ECE Degree. I’ve been taking care of dogs since I was 10 by volunteering at humane societies and having my own dogs. I also worked at a doggy daycares throughout Florida and Wisconsin. I love all dogs like they are my children. I would love to own my own rescue center but as of now I want to gain more experience with taking care of different breeds and just express my love of animals to the world. I hope that you choose me to be a temporary parent for your dog and that he or she is in perfect hands and will feel at home. Thank you. Hopefully we speak soon. I work third shift for Target and dog sit during the day. I make sure they are taken out three-four times and feed twice a day. I care for them like they are children. Go on walks, feed, cuddle. Run like crazy and crash from exhaustion. I also love getting to know the dogs personality.

“Maya was so great with our two dogs! She’s incredibly trustworthy, kind, helpful, and communicative. Her dog, Mello, is also such a gem. We really appreciated all her help over the long weekend, and would rebook in a heartbeat!”


About: I have had all sorts of pets since I was a kid - dogs, cats, fish, hamsters - so I understand body language and can know what your animal needs/wants based off that. I also worked at PetSmart, during which I was tasked with taking care of our cats and hamsters; therefore, I have ample experience with a variety of pets needs and personalities. I am currently a student, so my schedule is odd but I have plenty of time to come visit your pets or house sit! I am free everyday mainly midday and in the evening, but I can fit early morning visits as well. I can do any necessary task, be it bathing your pets, walking them, or simply feeding them and letting them out. I will also make sure they feel comfortable and safe with me before moving forward with care.
“Riley is the best - so glad to have her back in Milwaukee. She sends plenty of pictures and can put up with a sassy dog! She is so responsive she even replies while running a half marathon! We love using Riley when we are on vacation.”

The median cost per night for house sitting in Jackson Park is $50
Pet parents share their Rover experiences - Jackson Park
This is the second time Keisha has taken care of our dog Frankie at our house and she will absolutely be our go to if she is available the next time we travel. Our house was also in perfect shape after arriving home Exhausted after our trip. Our dog Frankie was perfectly taken care of! Thanks for everything you do Keisha!!!

Margaret came and stayed 2 nights with our 2 furbabies, ages 8 and nearly 14. I had never needed to find a non-family pet sitter, so I was quit nervous about the whole thing. But Margaret was amazing in so many ways. Our "pups" took to her immediately and so did we. And when we came home we could tell just how well she took care of EVERYTHING for us. I will never hesitate to book her in the future. Now we may even be able to take future short trips, knowing our dear pups are being so well cared for by Margaret.

Stephany did a phenomenal job watching my dogs overnight. I was nervous at first as it was my first time leaving them with someone besides family. However, stephany went above and beyond. Following their usual daily schedules, taking them for walks, and updating me regularly with photos and videos. I could tell that they were comfortable with her and really liked her! I will absolutely re book stephany again in the future, she will take wonderful care of your pets and home while you are away. Thank you Stephany!

Sarah is an absolute star - we’re so lucky to have found her on Rover! Our dogs are so happy and comfortable with her, and we know we can rely on her 100%. Consistent photos and updates, and when we get home, the dogs are so chill that it’s like we never left.

Nicole is absolutely phenomenal! She took such great care of our Siberian kitten. Nicole is very professional, communicative, and you can tell how much she loves what she does! The whole time we were gone she sent us updates and photos. We would 110% recommend Nicole!

Ryan was fantastic! He took great care of our very large dog, who can be reactive at times. I completely trusted him while we were away for a week. We received lots of updates like we asked. He gave our dog medicine without any issues. We came home to a very happy pup and a spotless house. Ryan even got our mail and watered our flowers while we were away, which was super nice. We highly recommend him and already have our next trips booked with him!

Scott was FABULOUS with our dog, Rocket! Rocket is a bit picky, but he wholeheartedly loved Scott, too. Scott had wonderful communication--he gave enough so that I felt reassured that Rocket was doing well, but he also let me just relax while on our trip. He made me feel confident that Rocket was in good hands, and that means the world to me. Scott also took in our mail and watered our garden. Thanks for everything, Scott!

Amanda was wonderful. This was the first time we traveled without our puppy and we were a bit apprehensive. However, Amanda eased our concerns. She arrived a few minutes early which signaled a level of reliability that was very welcome. While we were away, Amanda provided regular updates and pictures. As a result, we were able to enjoy our vacation. And our puppy seemed to genuinely enjoy Amanda. We will definitely use Amanda again. We would feel very comfortable leaving our puppy with her.
Paige is an amazing, young woman and was so loving to my pups. We had a hard journey driving from FL to Milwaukee, and I wanted someone to hang with them while catching up with friends. I could not have picked anyone better. Within minutes, my little Elsa was in love with Paige and King had a new girl friend! I searched the night before and thank God, Paige was the answer :) Obviously, highly recommend Paige.

Sonia and Alex did an absolutely excellent job caring for my dog. He is developmentally delayed, requires daily medication, and is incontinent, so his care takes extra attention and patience. Throughout the 6 days he was with them, they communicated promptly and openly about any challenges that came up, and together we were able to make simple adjustments to ensure his stay was comfortable and successful. They sent pictures frequently, which gave me great peace of mind while I was away. From every photo, it was clear that my dog was happy, well cared for, and comfortable in their care. I am incredibly grateful for the compassion, flexibility, and attentiveness Sonia and Alex showed, and I would wholeheartedly recommend them to anyone—especially those with pets who have special needs.

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