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.

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Sitter Profile Image: Evita E.
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Evita E.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 18 reviews
3 repeat clients
10 years of experience
Sunset Heights, Milwaukee, WI, 53216

“While Evita watched our pup Molly overnight at our house, she was punctual and communicated well. She also took Molly on a nice long walk each day that pleasantly tuckered her out. Molly seemed calm and happy when we returned home.”

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Alia E.
Sitter Profile Image: Emily M.
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Emily M.
from
$59
per night
5.0 out of 5 stars
• 43 reviews
11 repeat clients
30 years of experience
Milwaukee, WI, 53213

“Emily was great at communicating with us the entire stay, and we could tell from all her updates and pictures that our pups loved having her around. Our flight ended up getting delayed because of the blizzard rolling through Wisconsin this past weekend, and Emily was able to help make sure our pups were let out and fed while we figured out how to get back to Milwaukee. I would absolutely recommend Emily to anyone else looking for expert and friendly care for their pups on Rover. Thank you again!”

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Creighton B.
Sitter Profile Image: Keisha P.
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Keisha P.
Star Sitter
from
$50
per night
4.9 out of 5 stars
• 54 reviews
24 repeat clients
8 years of experience
Clarke Square, Milwaukee, WI, 53204

“Keisha was amazing! She helped us out when another sitter cancelled. She took amazing care of our 2 dogs while we were away! She was very responsive, sent lots of pictures, and kept us posted the whole weekend! She truly understood and embraced my dog’s personalities! I would highly recommend her and will be using her again in the future!”

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Janine P.
Sitter Profile Image: Margaret D.
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Margaret D.
from
$45
per night
5.0 out of 5 stars
• 8 reviews
4 repeat clients
20 years of experience
Cooper Park, Milwaukee, WI, 53222

“She was amazing with Russell and Cora! I felt so comfortable leaving them for so long when she was caring for them!”

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Beth G.
Sitter Profile Image: Joseph D.
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Joseph D.
from
$28
per night
4.9 out of 5 stars
• 8 reviews
2 repeat clients
10 years of experience
Wauwatosa, WI, 53213

“Joe was great with our Fifi, he was really a lifesaver! He stayed at our house as our rescue dog can be a little clingy. I received the cutest pictures and was really able to enjoy myself on vacation knowing she was at home!”

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Candy P.
Sitter Profile Image: Carrianne L.
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Carrianne L.
Star Sitter
from
$85
per night
5.0 out of 5 stars
• 214 reviews
52 repeat clients
20 years of experience
Milwaukee, WI, 53209

“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: Acacia L.
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Acacia L.
Star Sitter
from
$40
per night
5.0 out of 5 stars
• 9 reviews
4 repeat clients
8 years of experience
Milwaukee, WI, 53212

“The best Rover sitter I have had. Communicative, clean, great with Gertie, and an all around kind, responsible, and trustworthy person. Thank you Acacia! It means the world to me 🥰”

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Naomi S.
Sitter Profile Image: Jasmine R.
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Jasmine R.
from
$35
per night
5.0 out of 5 stars
• 85 reviews
8 repeat clients
5 years of experience
Murray Hill, Milwaukee, WI, 53211

“Jasmine is wonderful! She was incredibly responsive, took amazing care of our pup, and left our house in great shape!! We would gladly have her back any time!”

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Kristen A.
Sitter Profile Image: Amanda C.
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Amanda C.
from
$80
per night
5.0 out of 5 stars
• 17 reviews
6 repeat clients
8 years of experience
Milwaukee, WI, 53213

“Amanda was amazing! I was worried our pets wouldn't want us to come home. She was very attentive, timely, did more than asked and was very patient with our crazy bunch. I highly recommend her!”

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

“Jeremy was amazing. He was prompt, insanely responsive, and went above and beyond when we forgot to leave our son’s soccer stuff out for pick up. He even ran to purchase new shin guards when he couldn’t find them for us. This man is truly amazing and we appreciate him watching our three puppies. Our shepherd is usually super depressed when we are away and he looks so happy in all the pictures we received.”

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Amanda B.
Sitter Profile Image: Ashley S.
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Ashley S.
from
$50
per night
5.0 out of 5 stars
• 25 reviews
10 repeat clients
13 years of experience
Juneau Town, Milwaukee, WI, 53202

“Ashley was So responsive and Wonderful with my boys! Thankful she was able to watch them in their house!! Will definitely book again if she is willing to watch them!!”

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Dena K.
Sitter Profile Image: Jessica Z.
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Jessica Z.
Star Sitter
from
$64
per night
5.0 out of 5 stars
• 222 reviews
64 repeat clients
30 years of experience
Lower East Side, Milwaukee, WI, 53202

“Jessica Z stayed in my house with my 14 y/o blind Boston Terrier. She was wonderful. I received daily updates and photos, she clearly took excellent care of my pup. She left my place spotless and I would highly recommend her. She is excellent and I will definitely use her again.”

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Toni P.
Sitter Profile Image: David K.
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David K.
from
$30
per night
45 years of experience
Milwaukee, WI, 53212

About: I don't actually call myself that, that's what my friends say I am. I've literally never met a dog I didn't get on famously with. I respect the fact that they are individuals with their own needs. I don't mean to sound too self assured with the title, but I earned it from friends. Whether it's running on the Lake Michigan shore or just finding a nice sunny spot to sit for a while, your pup is going to have a fulfilling day. I have huge flexibility so no worries! A last minute trip or planned weeks in advance, we can work something out. I'm here for you! Even same day! I strive for communication as much as possible between animal and human. If they're not feeling like socializing, I don't force anything. Everyone has different needs. My experience in a dog daycare really helped me read and understand dog body language to head off any issues that may arise when you're watching 12 dogs.

Sitter Profile Image: Mikalanne T.
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Mikalanne T.
from
$50
per night
5.0 out of 5 stars
• 61 reviews
22 repeat clients
4 years of experience
Riverwest, Milwaukee, WI, 53212

“Mikalanne was great with my senior pups who are definitely creatures of habit. Active communication is so reassuring when I have to be away from my pet family. Highly recommend.”

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

“Elizabeth did the most fantastic job with our dog Annie. She was always fast to respond and sent multiple updates with pictures! Annie can be reactive and has grudges against many of our neighbors dogs so leaving her with someone new for neighborhood walks can be daunting. I felt completely confident in Elizabeth after one walk with her and Annie. We will absolutely be reaching back out to Elizabeth the next time we are looking for a rover! Thank you so much for the best first rover experience.”

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Emma L.
Sitter Profile Image: Celia K.
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Celia K.
from
$40
per night
5.0 out of 5 stars
• 3 reviews
2 repeat clients
3 years of experience
Lower East Side, Milwaukee, WI, 53202

“Celia was great with house sitting and taking care of my elderly dog and two cats!”

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Patti W.
Sitter Profile Image: Abby F.
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Abby F.
from
$20
per night
5.0 out of 5 stars
• 6 reviews
1 repeat client
1 year of experience
Milwaukee, WI, 53222

“Abby did a great job taking care of Levi! She was very kind, communicative, and kept us updated throughout the stay with photos and messages, which we really appreciated. It gave us peace of mind knowing Levi was in good hands.”

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Joseph V.
Sitter Profile Image: Emily R.
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Emily R.
Star Sitter
from
$77
per night
5.0 out of 5 stars
• 104 reviews
29 repeat clients
20 years of experience
Story Hill, Milwaukee, WI, 53213

“We love having Emily stay with our dog and cat when we go out of town! She’s so great with them, we never have to worry about a thing. We always come home to happy animals! She’s also very quick to respond to messages. We love Emily!”

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Kathleen P.
Sitter Profile Image: Murphy N.
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Murphy N.
from
$45
per night
4.9 out of 5 stars
• 15 reviews
4 repeat clients
25 years of experience
Milwaukee, WI, 53208

“Murphy was great with my animals. She was attentive, responsive and I felt comfortable leaving for the weekend knowing my animals were in good hands!”

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Megan G.
Sitter Profile Image: Lily S.
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Lily S.
from
$125
per night
5.0 out of 5 stars
• 68 reviews
18 repeat clients
25 years of experience
Milwaukee, WI, 53212

“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.
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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

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5.0 out of 5 stars

Evita was absolutely amazing with both of our dogs. She took great care of them and even pivoted during unforeseen circumstances to ensure our dogs stayed loved on and safe while we were gone. We will definitely use her again in the future!

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Frances T.
House Sitting
5.0 out of 5 stars

Ivy is amazing with our dogs who are sometimes quite challenging! We trust her to handle any situation that comes up.

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Brent W.
House Sitting
5.0 out of 5 stars

Cindy is amazing. She takes great care of Bear when we are away. Everyday she sends a picture so we know how our baby is doing.

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Craig R.
House Sitting
5.0 out of 5 stars

Marley does such a wonderful job and if she ever decides to change a career, she could make a meant as an animal photographer!

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Eric M.
House Sitting
5.0 out of 5 stars

Nina stayed with our two dogs for a night. We came home to two happy and well cared for pups and a clean house. I would definitely recommend her!

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Sarah M.
House Sitting
5.0 out of 5 stars

Esterah has done house sitting for us multiple times!! She handles our anxious/special dog well, is very attentive to instructions left for the stay, and the house is spotless when we return!!!

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Todd S.
House Sitting
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

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

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
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