House Sitting Roosevelt Grove

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Roosevelt Grove, 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.

1 / 1
Sitter Profile Image: Emily M.
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Emily M.
Star Sitter
from
$59
per night
5.0 out of 5 stars
38 reviews
9 repeat clients
30 years of experience
Milwaukee, WI, 53213

Emily was exceptional through and through. Great communication and even better care of our home & pups. We will most certainly ask her to care for our boys again!

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Caryn L.
Sitter Profile Image: Ivy G.
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Ivy G.
from
$50
per night
5.0 out of 5 stars
44 reviews
14 repeat clients
20 years of experience
Uptown, Milwaukee, WI, 53210

Ivy was simply the best! Our house was absolutely spotless when we returned and our doggos were absoutely thrilled with their newfound friend. Ivy was really easy to work with, communicative before and during our stay, and sent us photos and updates for the week we were gone. Would absolutely recommend!!!

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Joseph B.
Sitter Profile Image: Alexandra I.
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Alexandra I.
Star Sitter
from
$70
per night
5.0 out of 5 stars
22 reviews
4 repeat clients
11 years of experience
Juneau Town, Milwaukee, WI, 53202

Alex did a great job with Tucker. She bonded with him immediately, he was feed, walked and pampered. Communication was excellent, we got lots of photos and updates. We will definitely use Alex again

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Phil S.
Sitter Profile Image: Keisha P.
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Keisha P.
Star Sitter
from
$45
per night
4.9 out of 5 stars
47 reviews
21 repeat clients
8 years of experience
Clarke Square, Milwaukee, WI, 53204

Keisha was great! She watched our 2 doodles, one with a bit of an attitude! She sent texts when she had questions and sent us pictures. Will definitely book with her again!

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Marie G.
Sitter Profile Image: Charles B.
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Charles B.
Star Sitter
from
$50
per night
5.0 out of 5 stars
111 reviews
20 repeat clients
17 years of experience
Fox Point, WI, 53217

Charley was amazing with our pup Maisy! She was calm and happy when we got home from an 8 day trip. PLUS - our house was spotless! Fantastic job, we will use him again.

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Eliz G.
Sitter Profile Image: Evita E.
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Evita E.
from
$50
per night
5.0 out of 5 stars
12 reviews
1 repeat client
10 years of experience
Sunset Heights, Milwaukee, WI, 53216

Great to communicate with and our pups love her!

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Carley M.
Sitter Profile Image: Stephen & Wipawee D.
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Stephen & Wipawee D.
from
$95
per night
5.0 out of 5 stars
51 reviews
19 repeat clients
5 years of experience
Dineen Park, Milwaukee, WI, 53216

Amelie and Stephen sat for our dog, Dexter, and our cat, Lucy, while we were out of town for a weekend. We felt incredibly assured during our time away that our pets were being well cared for and provided with lots of love. We were given consistent updates on how the stay was going and what our animals were up to. They graciously provided many pictures during the stay that continued to provide us with a sense of calm knowing our fur babies were in very good hands. We have already rebooked with them for a future trip, and will continue to do so! We cannot recommend them enough!

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Kaitlyn F.
Sitter Profile Image: Ashley S.
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Ashley S.
from
$50
per night
5.0 out of 5 stars
17 reviews
8 repeat clients
13 years of experience
Juneau Town, Milwaukee, WI, 53202

Ashley took absolutely excellent care of our cat while we were out of the country for a week! I knew from the moment she met our cat during our meet and greet that our little girl was going to be in great hands. Throughout the trip, Ashley reached out with check-ins and photos reflecting how well she was being taken care of. She also responded quickly to any messages and went above and beyond watching our place. We (and our cat) look forward to seeing her again in the future!

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Jeremiah W.
Sitter Profile Image: Jamila M.
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Jamila M.
from
$65
per night
4.9 out of 5 stars
97 reviews
29 repeat clients
27 years of experience
Washington Heights, milwaukee, WI, 53208

Jeremy was great with our dogs and our home. He encouraged play, comforted them, and ensured they were fed and watered appropriately. His intuition to our dogs behavior was also spot on, it’s obvious he is a great care giver. I would highly recommend him!

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Andrea B.
Sitter Profile Image: Joseph D.
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Joseph D.
from
$28
per night
4.8 out of 5 stars
5 reviews
2 repeat clients
10 years of experience
Wauwatosa, WI, 53213

About: I’ve been looking after fluffy frens of all shapes and sizes from a young age. My time doing a full house/dog sitting gig was for my grandparents and their French bulldog, Sugar (miss you, Sugs!). Since then I have been the go-to for my friends and family for taking care of their for legged family. I make sure your fury family gets the love and care they need, whether you just have one smol dog or a pack of greyhounds. I currently had a stretch of rough health luck, but my ails are your pups gain! I’m currently on the mend, and it’s going well, but between jobs, so my schedule is wide open. I’ll have the time to give your pups the TLC they deserve! Currently unavailable to board pets at my house, but I will make sure to treat all pets in a safe and caring way. I’ll treat them like a newborn baby, because hey, in a way they are!

Sitter Profile Image: Elizabeth J.
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Elizabeth J.
Star Sitter
from
$50
per night
5.0 out of 5 stars
32 reviews
7 repeat clients
17 years of experience
Lower East Side, Milwaukee, WI, 53202

It was our second time hiring Elizabeth, another positive experience. My pooch likes his walks and we are grateful she is ok with taking him. She is great with giving updates and sending photos. Upon return the house was just as we left it.

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Carol M.
Sitter Profile Image: Tishara M.
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Tishara M.
from
$35
per night
5.0 out of 5 stars
4 reviews
1 repeat client
5 years of experience
Midtown, Milwaukee, WI, 53208

Tishara was a wonderful and caring pet sitter. She stayed at our home and ensured our pups were loved on while we were gone. She was quick to communicate with us when needed and shared great photos. One of our dogs requires medicine 2x daily so Tishara made sure she understood how to administer it as well as any emergency contacts she might need while we’re gone. It is so reassuring to know someone is looking after your pets with that much care and concern.

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Megan T.
Sitter Profile Image: Jessica Z.
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Jessica Z.
Star Sitter
from
$64
per night
5.0 out of 5 stars
208 reviews
63 repeat clients
30 years of experience
Lower East Side, Milwaukee, WI, 53202

Jessica was great! Our emotionally needy animals soaked up her attention and loved on her right back. Super great communication throughout the stay, and lots of great photos. Thanks again, Jessica!

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Nicole W.
Sitter Profile Image: Camila S.
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Camila S.
from
$45
per night
5.0 out of 5 stars
9 reviews
2 repeat clients
10 years of experience
Milwaukee, WI, 53209

I couldn’t have picked a better place to leave my dog. I needed a last minute dog sitter and luckily for me Camila was available. When we arrived we were welcomed by Camila and her mom and my dog rushed over happily. Their home is lovely and my dog loved the backyard. Camila makes sure to send updates and pics so I knew my dog was having a great time. I can’t thank Camila and her mom enough for helping us short notice and giving my dog a wonderful stay. I would highly recommend them to anyone!

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Lynne K.
Sitter Profile Image: Jackie C.
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Jackie C.
Star Sitter
from
$90
per night
5.0 out of 5 stars
147 reviews
54 repeat clients
15 years of experience
Brewer's Hill, Milwaukee, WI, 53212

Jackie was amazing with the dogs and you could tell by how calm they were when I got home that they had a great weekend. I would recommend and will have her watch my dogs again.

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Hannah L.
Sitter Profile Image: Catherine R.
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Catherine R.
Star Sitter
from
$70
per night
5.0 out of 5 stars
26 reviews
10 repeat clients
1 year of experience
Murray Hill, Milwaukee, WI, 53211

We could not have asked for a better dog sitter. Catherine stayed at our home with our dog for 12 days and took exceptional care the entire time. She sent daily updates with photos, which gave us peace of mind. Our dog was happy and healthy when we returned. We would absolutely book Catherine again and recommend her to family and friends.

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Meghan M.
Sitter Profile Image: Carrianne L.
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Carrianne L.
Star Sitter
from
$85
per night
5.0 out of 5 stars
189 reviews
47 repeat clients
20 years of experience
Shorewood, WI, 53211

Carrianne did a wonderful job caring for my dog when I went out of town for a weekend. Penny takes some time to warm up to people and Carrianne was very patient and understanding throughout that process. She followed the care instructions I left and sent daily updates with important information (e.g., walks, eating habits, general behavior) with photos. She also stayed overnight in my apartment and left everything really tidy. I couldn't be happier with the care Penny received and will definitely rebook for future travel plans!

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Angela M.
Sitter Profile Image: Rebecca M.
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Rebecca M.
from
$28
per night
5.0 out of 5 stars
6 reviews
2 repeat clients
5 years of experience
Kilbourn Town, Milwaukee, WI, 53203

About: I’ve been caring for dogs for over 5 years, and I truly love getting to know each pet’s personality and routine. Friends, neighbors, and family have trusted me to walk, feed, play with, and stay with their pets while they’re away. I especially enjoy longer stays because it gives dogs time to feel comfortable and settled, and I love being able to build that trust with them. One of my favorite parts is taking dogs on enriching walks, keeping them active, engaged, and happy, and making sure they feel safe, loved, and well cared for while their owners are away. I work remotely, which gives me a flexible schedule and allows me to give pets plenty of attention throughout the day. I’m able to keep up with walks, feeding schedules, playtime, potty breaks, and companionship, especially during longer stays when consistency and routine are important. I always try to make pets feel as comfortable and relaxed as possible by sticking closely to their normal routine and giving them lots of attention and care. I pay close attention to each dog’s personality, energy level, and needs to make sure they feel safe, happy, and comfortable while their owners are away. I’m attentive on walks, respectful of clients’ homes, and committed to providing reliable communication and updates throughout each stay.

Sitter Profile Image: Alhana S.
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Alhana S.
from
$45
per night
4.7 out of 5 stars
7 reviews
4 repeat clients
10 years of experience
Murray Hill, Milwaukee, WI, 53211

Alhana was great with Coco. My little dog was recovering from knee surgery and she followed instructions beautifully for he night I had to be away. Thank you!

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Christine H.
Sitter Profile Image: Emily R.
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Emily R.
Star Sitter
from
$77
per night
5.0 out of 5 stars
101 reviews
28 repeat clients
20 years of experience
Story Hill, Milwaukee, WI, 53213

Emily was prompt, respectful, and communicative. She sent pictures and updates and my dog seemed very comfortable and calm when I returned. I highly recommend Emily and will happily book her again in the future if I need a dog sitter!

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Meredith H.
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The median cost per night for house sitting in Roosevelt Grove is $50

Pet parents share their Rover experiences - Roosevelt Grove

1 / 1
5.0 out of 5 stars

Alena did a great job. Cosmo seemed to be really well taken care of was very calm when we got back. Alena also left the house in great shape.

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Ronald S.
House Sitting
5.0 out of 5 stars

Lily absolutely exceeded my expectations with her attention to detail, genuine care and concern for my pups, and thoroughness! My dogs were well taken care of with feeding, walking (carefully in a heat wave), fireworks, and just general companionship. I also returned to my home probably looking better than how I left it - well cared for, cleaned, and plants alive and well. The daily updates were fantastic and very reassuring. Lily is amazing and I hope we can book again :)

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K D.
House Sitting
5.0 out of 5 stars

Cindy is amazing! She stays in communication your whole trip and provides photo updates. Our fur babies love her so much!

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Jaclyn A.
House Sitting
5.0 out of 5 stars

Nina is kind and caring and communicative. She took great care of my dog and kept me updated while I was gone

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Julia S.
House Sitting
5.0 out of 5 stars

Ivy was the absolute best person to watch our blue heeler, Ringo! We had never left him with anyone other than family before, but Ivy made us feel so calm and confident, sending updates every day and taking Ringo on so many fun adventures. We felt so relieved knowing he was in such good hands and having the time of his life while we were away for 10 days. Words can’t express how grateful we are that our fur baby was so well-loved and taken care of💖

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Maddie M.
House Sitting
5.0 out of 5 stars

Molly is ALWAYS so loving and caring towards Kai and Chloe. I notice the difference. Thank you Molly

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Eric M.
House Sitting
5.0 out of 5 stars

I couldn’t have asked for a better dog sitter! She communicated wonderfully from the start and even met with me ahead of time to get to know my dog’s routine and feel comfortable with the space. While I was away, she sent daily updates with pictures of Stewart completely abandoning dad to cuddle with his new friend! 😂 I wholeheartedly recommend her to anyone looking for a trustworthy and caring sitter.

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Brad B.
House Sitting
5.0 out of 5 stars

Libby house sat and took great care of Jaq over the weekend. She was attentive to his separation anxiety and needs, making sure he felt comfortable while I was away.

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Christina S.
House Sitting
5.0 out of 5 stars

Thomas did a great job taking care of our boys. The dogs got plenty of attention and exercise. He kept the boys on their regular schedule and checked in often with pictures and updates. We hope to book again in the future.

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Alex J.
House Sitting
5.0 out of 5 stars

Davina was truly incredible! I have a dog with many allergies, and is anxious and reactive. She sent me all the updates and he is pooped after her stay. I had such a peace of mind while I was gone, so I cannot recommend Davina enough!! 10/10

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Hailey Q.
House Sitting
5.0 out of 5 stars

Gretchen did a great job watching our anxious dog and two kitties. She kept me updated and always replied promptly when I would reach out. We came home to a well taken care of house. Would recommend her.

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Nikki P.
House Sitting
5.0 out of 5 stars

Esterah was so great with our pets during the house sitting. Our dog is very nervous and she was patient with him when she first arrived. We got lots up updates. She asked questions during the meet and greet and the house sitting which was much appreciated. We came home to a clean house and happy pets!

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Todd S.
House Sitting
5.0 out of 5 stars

Bree did such an amazing job with Lulu while we were in Arizona. I came home to a happy and tired dog. Will definitely be using Bree again for dog sitting and recommend her!!

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Jessica F.
House Sitting
5.0 out of 5 stars

Jamila was amazing with my senior dog Vladimir! She’s helped with feedings and overnights at my house. She is kind, thoughtful, and Vlad loved her! She followed all my instructions and handled my old man with care. We will be asking her to watch Vlad again in the near future! I’m grateful to have found her!

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Marie W.
House Sitting
5.0 out of 5 stars

Nicole was simply fantastic. Walter is a new rescue, and has only been with me for about two weeks before I had to travel for work. Nicole kept all of my anxiety about leaving him at Bay, she was incredibly communicative, very patient with my anxious, crazy boy, and even left me a full page document of notes about her observations on him as I’m continuing to understand who he is. While I was away, I was telling some of the individuals I was with about everything she was doing for Walter and they all begged me to give them her information. Will absolutely be reaching out to Nicole in the future!

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Arianna C.
House Sitting
5.0 out of 5 stars

Jamie was great with our two pups! She kept us updated and sent lots of photos and took good care of our good boy and girl!

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Heather D.
House Sitting
5.0 out of 5 stars

Did a wonderful job taking care of Bernie. Daily updates and pictures. Left the place just how we left it too. Thanks Enrique!!

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Courtney J.
House Sitting
5.0 out of 5 stars

Isabelle and her boyfriend took great care of our puppy. They followed our house rules and went the extra mile to give our high energy puppy plenty of activity while they were house sitting. I would definitely work with them again!

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James P.
House Sitting
5.0 out of 5 stars

Madelyn was a great sitter. She communicated well with me and sent photos of my dachshund so that I could check in with my baby. Very easy to book, does a meet a greet in advance to make things easier!

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Sheri T.
House Sitting
5.0 out of 5 stars

Riley was great with my pets. Very responsive when I asked how they were doing and made sure to communicate with us if she had any questions. Definitely recommend!

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Lexi K.
House Sitting
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Sitters in Roosevelt Grove average 4
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