House Sitting in Roosevelt Grove, Milwaukee

Find a loving house sitter to watch over your pets and your home.

Search

More resources

A focus on safety

Enjoy photo updates, easy messaging, and the knowledge that every sitter joining Rover needs to pass an enhanced background check.Learn more about RoverProtect

Top rated Roosevelt Grove house sitters

1 / 1
Sitter Profile Image: Emily S.
Verified Enhanced Background Check
Emily S.
Star Sitter
from
$40
per night
5 out of 4.9 stars
23 reviews
17 repeat clients
6 years of experience
West Allis, WI, 53227

Emily did a great job with our older dog. She communicated any concerns she had with him. The house was left in pristine condition. We were thankful to have her staying with Louie.

Profile image
Cheryl D.
Sitter Profile Image: Keisha P.
Verified Enhanced Background Check
Keisha P.
Star Sitter
from
$31
per night
5 out of 5.0 stars
14 reviews
7 repeat clients
8 years of experience
Clarke Square, Milwaukee, WI, 53204

We had Keisha stay for a 7 day sit for our dog and cat. Keisha was incredible and everything we could have ever wanted in a sitter! She sent us updates at least daily, sometimes more with pictures which is what we requested! I made an error and she was flexible with adding another day to her stay! Could not recommend her enough, we will definitely use her again in the future!!

Profile image
Jordyn
Sitter Profile Image: Jasmine T.
Verified Enhanced Background Check
Jasmine T.
Star Sitter
from
$55
per night
5 out of 5.0 stars
9 reviews
4 repeat clients
5 years of experience
Timmerman West, Milwaukee, WI, 53225

Jasmine was amazing! She was extremely communicative and professional. I would absolutely book Jasmine again. She sent tons of photos and updates and my pets loved her!

Profile image
tanya h.
Sitter Profile Image: Melissa H.
Verified Enhanced Background Check
Melissa H.
Star Sitter
from
$60
per night
5 out of 5.0 stars
24 reviews
5 repeat clients
40 years of experience
Milwaukee, WI, 53211

Melissa is genuinely amazing. From the meet and greet to the moment we returned home, I’m so grateful and impressed by her. She kept our boys active and happy (and handled our big puppy so well!) Melissa communicated so well, and we returned to the house just as we left it. Highly recommend Melissa. She really cares about the dogs and making you feel comfortable while you’re away.

Profile image
Claire L.
Sitter Profile Image: Ashley W.
Verified Background Check
Ashley W.
from
$45
per night
5 out of 5.0 stars
14 reviews
5 repeat clients
10 years of experience
Washington Heights, Milwaukee, WI, 53208

As usual, a smooth transaction/stay! We absolutely love Ashley. She is very flexible, punctual and most importantly - clean (we only do home stays). Our pup is always happy to see Ashley and enjoys her company very much.

Profile image
Kristina S.
Sitter Profile Image: Lily S.
Verified Enhanced Background Check
Lily S.
Star Sitter
from
$75
per night
5 out of 5.0 stars
39 reviews
12 repeat clients
25 years of experience
Milwaukee, WI, 53212

As always, Lily goes above and beyond. Helped navigate an u expected, significant GI problem with one of the dogs that required a visit for emergency care and helping mitigate a significant clean-up job. Communicated fantastically throughout the saga

Profile image
Eric M.
Sitter Profile Image: Jessica Z.
Verified Enhanced Background Check
Jessica Z.
Star Sitter
from
$64
per night
5 out of 5.0 stars
152 reviews
46 repeat clients
30 years of experience
Lower East Side, Milwaukee, WI, 53202

Jessica was great! Super communicative and sent lots of pictures! My boys are a handful and don't like strangers, so if she can handle them she can handle any high maintenance pups!

Profile image
Josie H.
Sitter Profile Image: Rachel H.
Verified Background Check
Rachel H.
Star Sitter
from
$30
per night
5 out of 5.0 stars
90 reviews
23 repeat clients
11 years of experience
West Allis, WI, 53214

Rachel was great with our pup and cats, as always! While away we can feel confident the house and pets are being cared for and they all get lots of snuggles!

Profile image
Todd S.
Sitter Profile Image: Joanne & Becky J.
Verified Enhanced Background Check
Joanne & Becky J.
Star Sitter
from
$45
per night
5 out of 5.0 stars
5 reviews
2 repeat clients
20 years of experience
Milwaukee, WI, 53203

Joann and Becky stayed with our dog and cat for almost a week a d they were terrific! They sent lots of updates and pics, and I could see my pets were comfortable, happy and well cared for. I will book with them again in the future. Highly recommend!

Profile image
Sarah O.
Sitter Profile Image: Lenys H.
Verified Enhanced Background Check
Lenys H.
from
$40
per night
5 out of 4.7 stars
9 reviews
3 repeat clients
12 years of experience
Milwaukee, WI, 53211

Lenys did a fantastic job watching my dog Miles. She was very attentive to him, and she provided transparent communication as well as pictures throughout the week. I would highly recommend her.

Profile image
Benjamin J.
Sitter Profile Image: Carrianne L.
Verified Enhanced Background Check
Carrianne L.
Star Sitter
from
$85
per night
5 out of 5.0 stars
32 reviews
8 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!

Profile image
Angela M.
Sitter Profile Image: Addoris D.
Verified Enhanced Background Check
Addoris D.
from
$25
per night
5 out of 5.0 stars
5 reviews
1 repeat client
5 years of experience
Lower East Side, Milwaukee, WI, 53202

About: I’ve taken care of elderly dogs, as well as new puppies, and know how to meet the needs of every unique pet that I work with in my life. I am always conscious about disrupting their routine as little as possible while their humans are gone, and take care to give them as much kindness and love as possible. I work in theatre in the evenings, but have my mornings and afternoons free. I enjoy dog sitting when I don’t have a show, as well as drop in visits and walks to help folks who work a 9-5 job. I always strive to respect and diligently care for the pets in my care. I always write down any instructions I receive, and make sure to cross check that to provide the highest quality care and service for folks. I treat the pets I care for with the kindness, calmness, and love that I would want someone to take care of my own pets.

Sitter Profile Image: Kathryn D.
Verified Enhanced Background Check
Kathryn D.
Star Sitter
from
$65
per night
5 out of 5.0 stars
67 reviews
18 repeat clients
14 years of experience
Milwaukee, WI, 53211

Kathryn has been amazing! She picked up a request super last minute and was so sweet to my pup. She really goes above and beyond what a typical dog watcher would do. Would definitely recommend!!

Profile image
Emily H.
Sitter Profile Image: Emily M.
Verified Enhanced Background Check
Emily M.
from
$38
per night
30 years of experience
Milwaukee, WI, 53213

About: I’ve been pet sitting for over 15 years and have taken care of pets twice that long. I’m a pet owner myself and watch pets for friends and family! I’m self-employed and have a very flexible schedule to meet your pet’s needs! I own a car and am able to make it jobs throughout the week. I’m happy to play with pets, check in on them, let them out for potty breaks or walk them! I love the different personalities of pets and have a passion for animals (I’m a Virgo/earth sign and we love animals!).

Sitter Profile Image: Liz P.
Verified Enhanced Background Check
Liz P.
Star Sitter
from
$60
per night
5 out of 5.0 stars
118 reviews
38 repeat clients
4 years of experience
Riverwest, Milwaukee, WI, 53212

Liz was great at following instructions and was super receptive to any feedback or request. She took care of my boys and the house. She kept me updated and seemed to really care for the boys.

Profile image
Vanessa N.
Sitter Profile Image: Alyssa B.
Verified Enhanced Background Check
Alyssa B.
from
$50
per night
5 out of 5.0 stars
6 reviews
3 repeat clients
10 years of experience
Whitefish Bay, WI, 53217

I loved Alyssa's help taking care of my dog ​​Tango. She did everything I asked her to do. She was very responsible and my dog ​​Tango loved her. During my trip, she sent me photos of Tango's walks with her in the park. 100% recommended.

Profile image
Paulo A.
Sitter Profile Image: Travis H.
Verified Background Check
Travis H.
Star Sitter
from
$62
per night
5 out of 5.0 stars
250 reviews
92 repeat clients
35 years of experience
Riverwest, Milwaukee, WI, 53212

Travis did a great job. He communicated well throughout the entire process and was easy to work with. He provided photos and updates throughout the 3 days he watched our dogs. Will definitely use him again in the future!

Profile image
Robert B.
Sitter Profile Image: Marilia D.
Verified Enhanced Background Check
Marilia D.
Star Sitter
from
$70
per night
5 out of 5.0 stars
60 reviews
15 repeat clients
15 years of experience
Estabrook Park, Milwaukee, WI, 53217

Marilia did a great job staying with our pup and walking , feeding, playing and just being there for him. She spent 3 nights and fleas very responsive and respectful of our home . Was thankful she was available, Will hire again .

Profile image
Jennifer R.
Sitter Profile Image: Jamila M.
Verified Background Check
Jamila M.
Star Sitter
from
$57
per night
5 out of 4.9 stars
80 reviews
24 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!

Profile image
Andrea B.
Sitter Profile Image: Davina A.
Verified Enhanced Background Check
Davina A.
from
$50
per night
5 out of 5.0 stars
4 reviews
18 years of experience
Sherman Park, Milwaukee, WI, 53210

Davina did a great job taking care of our dog while we were gone. She was reliable, flexible, helpful and willing to jump in to problem solve when an unexpected issue came up.

Profile image
Paul S.
1 / 1
View more sitters

Loving house sitters in your neighborhood

Search Results

Sitter Profile Image: Emily S.
Verified Enhanced Background Check
Sitter Profile Image: Emily S.
Verified Enhanced Background Check

1. Emily S.

Star Sitter
Enjoy making pets happy and loved
West Allis, WI, 53227
6.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$40
per night
5 out of 4.9 stars
23 reviews
17 repeat clients
Profile image

Emily did a great job with our older dog. She communicated any concerns she had with him. The house was left in pristine condition. We were thankful to have her staying with Louie.

Availability updated yesterday
Sitter Profile Image: Keisha P.
Verified Enhanced Background Check
Sitter Profile Image: Keisha P.
Verified Enhanced Background Check

2. Keisha P.

Star Sitter
Your Furbabies will Love Me
Clarke Square, Milwaukee, WI, 53204
4.4 mi. away
House Sitting, Drop-In Visits
from
$31
per night
5 out of 5.0 stars
14 reviews
7 repeat clients
Profile image

We had Keisha stay for a 7 day sit for our dog and cat. Keisha was incredible and everything we could have ever wanted in a sitter! She sent us updates at least daily, sometimes more with pictures which is what we requested! I made an error and she was flexible with adding another day to her stay! Could not recommend her enough, we will definitely use her again in the future!!

Availability updated yesterday
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Jasmine T.
Verified Enhanced Background Check
Sitter Profile Image: Jasmine T.
Verified Enhanced Background Check

3. Jasmine T.

Star Sitter
🐈‍⬛Caring for your furry family🐕
Timmerman West, Milwaukee, WI, 53225
4.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$55
per night
5 out of 5.0 stars
9 reviews
4 repeat clients
Profile image

Jasmine was amazing! She was extremely communicative and professional. I would absolutely book Jasmine again. She sent tons of photos and updates and my pets loved her!

Availability updated yesterday
Sitter Profile Image: Melissa H.
Verified Enhanced Background Check
Sitter Profile Image: Melissa H.
Verified Enhanced Background Check

4. Melissa H.

Star Sitter
Their Favorite Pawsome Auntie 🐾
Milwaukee, WI, 53211
4.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
5 out of 5.0 stars
24 reviews
5 repeat clients
Profile image

Melissa is genuinely amazing. From the meet and greet to the moment we returned home, I’m so grateful and impressed by her. She kept our boys active and happy (and handled our big puppy so well!) Melissa communicated so well, and we returned to the house just as we left it. Highly recommend Melissa. She really cares about the dogs and making you feel comfortable while you’re away.

Availability updated yesterday
Sitter Profile Image: Ashley W.
Verified Background Check
Sitter Profile Image: Ashley W.
Verified Background Check

5. Ashley W.

Active person loves active dogs
Washington Heights, Milwaukee, WI, 53208
2.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$45
per night
5 out of 5.0 stars
14 reviews
5 repeat clients
Profile image

As usual, a smooth transaction/stay! We absolutely love Ashley. She is very flexible, punctual and most importantly - clean (we only do home stays). Our pup is always happy to see Ashley and enjoys her company very much.

Availability updated 15 days ago
Sitter Profile Image: Lily S.
Verified Enhanced Background Check
Sitter Profile Image: Lily S.
Verified Enhanced Background Check

6. Lily S.

Star Sitter
Certified Sitter!
Milwaukee, WI, 53212
2.8 mi. away
House Sitting, Drop-In Visits
from
$75
per night
5 out of 5.0 stars
39 reviews
12 repeat clients
Profile image

As always, Lily goes above and beyond. Helped navigate an u expected, significant GI problem with one of the dogs that required a visit for emergency care and helping mitigate a significant clean-up job. Communicated fantastically throughout the saga

Availability updated 7 days ago
Sitter Profile Image: Jessica Z.
Verified Enhanced Background Check
Sitter Profile Image: Jessica Z.
Verified Enhanced Background Check

7. Jessica Z.

Star Sitter
Loving sitter, enthusiastic walker
Lower East Side, Milwaukee, WI, 53202
3.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$64
per night
5 out of 5.0 stars
152 reviews
46 repeat clients
Profile image

Jessica was great! Super communicative and sent lots of pictures! My boys are a handful and don't like strangers, so if she can handle them she can handle any high maintenance pups!

Availability updated today
Sitter Profile Image: Rachel H.
Verified Background Check
Sitter Profile Image: Rachel H.
Verified Background Check

8. Rachel H.

Star Sitter
** Mission: meet ALL the dogs **
West Allis, WI, 53214
5.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$30
per night
5 out of 5.0 stars
90 reviews
23 repeat clients
Profile image

Rachel was great with our pup and cats, as always! While away we can feel confident the house and pets are being cared for and they all get lots of snuggles!

Availability updated 14 days ago
Sitter Profile Image: Joanne & Becky J.
Verified Enhanced Background Check
Sitter Profile Image: Joanne & Becky J.
Verified Enhanced Background Check

9. Joanne & Becky J.

Star Sitter
Wannabe Fur Moms - For Our Fur Fund
Milwaukee, WI, 53203
4.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$45
per night
5 out of 5.0 stars
5 reviews
2 repeat clients
Profile image

Joann and Becky stayed with our dog and cat for almost a week a d they were terrific! They sent lots of updates and pics, and I could see my pets were comfortable, happy and well cared for. I will book with them again in the future. Highly recommend!

Availability updated 19 days ago
Sitter Profile Image: Lenys H.
Verified Enhanced Background Check
Sitter Profile Image: Lenys H.
Verified Enhanced Background Check

10. Lenys H.

Pets don’t need us, we need them!!
Milwaukee, WI, 53211
4.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$40
per night
5 out of 4.7 stars
9 reviews
3 repeat clients
Profile image

Lenys did a fantastic job watching my dog Miles. She was very attentive to him, and she provided transparent communication as well as pictures throughout the week. I would highly recommend her.

Availability updated 3 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Carrianne L.
Verified Enhanced Background Check
Sitter Profile Image: Carrianne L.
Verified Enhanced Background Check

11. Carrianne L.

Star Sitter
Caring for Critters of all Kinds!
Shorewood, WI, 53211
3.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$85
per night
5 out of 5.0 stars
32 reviews
8 repeat clients
Profile image

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!

Availability updated 23 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Addoris D.
Verified Enhanced Background Check
Sitter Profile Image: Addoris D.
Verified Enhanced Background Check

12. Addoris D.

Queer Friendly & Energetic Sitter
Lower East Side, Milwaukee, WI, 53202
4.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$25
per night
5 out of 5.0 stars
5 reviews
1 repeat client

Adi was an absolute gem. My dog Ruby loved her and we were sad when she moved to Chicago. She takes incredible care and was always prompt when messaging me about any issues (Ruby has to take medication every day and she can sometimes be a nightmare about it). Would highly recommend her, especially for your elderly dogs that need a little bit of extra love and attention.

Availability updated today
Sitter Profile Image: Kathryn D.
Verified Enhanced Background Check
Sitter Profile Image: Kathryn D.
Verified Enhanced Background Check

13. Kathryn D.

Star Sitter
Excited to meet your furry friend!
Milwaukee, WI, 53211
3.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$65
per night
5 out of 5.0 stars
67 reviews
18 repeat clients
Profile image

Kathryn has been amazing! She picked up a request super last minute and was so sweet to my pup. She really goes above and beyond what a typical dog watcher would do. Would definitely recommend!!

Availability updated 7 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Emily M.
Verified Enhanced Background Check
Sitter Profile Image: Emily M.
Verified Enhanced Background Check

14. Emily M.

Raised on urban farm, pet sitter
Milwaukee, WI, 53213
3.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$38
per night
2 reviews

From day one, Emily treated Stout like her own. She’s responsible, attentive, and has this magical calming energy that even my high-strung pup couldn't resist. Walks? Always on time. Feedings? Spot on. Belly rubs? Endless. But here's the thing: I think my dog likes her more than he likes me. I once picked him up and he gave me a look like, "Oh... it's you." So yeah. Emily's that good. If you’re looking for someone who’ll love your pet like family and send you the cutest photo updates, Emily is your person.

Availability updated yesterday
Sitter Profile Image: Liz P.
Verified Enhanced Background Check
Sitter Profile Image: Liz P.
Verified Enhanced Background Check

15. Liz P.

Star Sitter
Pet Lover who works from home!
Riverwest, Milwaukee, WI, 53212
3.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$60
per night
5 out of 5.0 stars
118 reviews
38 repeat clients
Profile image

Liz was great at following instructions and was super receptive to any feedback or request. She took care of my boys and the house. She kept me updated and seemed to really care for the boys.

Availability updated 2 days ago
Sitter Profile Image: Alyssa B.
Verified Enhanced Background Check
Sitter Profile Image: Alyssa B.
Verified Enhanced Background Check

16. Alyssa B.

Compassionate Pet Sitter
Whitefish Bay, WI, 53217
3.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5 out of 5.0 stars
6 reviews
3 repeat clients
Profile image

I loved Alyssa's help taking care of my dog ​​Tango. She did everything I asked her to do. She was very responsible and my dog ​​Tango loved her. During my trip, she sent me photos of Tango's walks with her in the park. 100% recommended.

Availability updated 12 days ago
Sitter Profile Image: Travis H.
Verified Background Check
Sitter Profile Image: Travis H.
Verified Background Check

17. Travis H.

Rover 101
Star Sitter
Love & Exercise for your dog or cat
Riverwest, Milwaukee, WI, 53212
3.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$62
per night
5 out of 5.0 stars
250 reviews
92 repeat clients
Profile image

Travis did a great job. He communicated well throughout the entire process and was easy to work with. He provided photos and updates throughout the 3 days he watched our dogs. Will definitely use him again in the future!

Availability updated 7 days ago
Sitter Profile Image: Marilia D.
Verified Enhanced Background Check
Sitter Profile Image: Marilia D.
Verified Enhanced Background Check

18. Marilia D.

Star Sitter
I've had 7 dogs at once. Trust me.
Estabrook Park, Milwaukee, WI, 53217
2.7 mi. away
House Sitting, Drop-In Visits
from
$70
per night
5 out of 5.0 stars
60 reviews
15 repeat clients
Profile image

Marilia did a great job staying with our pup and walking , feeding, playing and just being there for him. She spent 3 nights and fleas very responsive and respectful of our home . Was thankful she was available, Will hire again .

Availability updated 6 days ago
Sitter Profile Image: Jamila M.
Verified Background Check
Sitter Profile Image: Jamila M.
Verified Background Check

19. Jamila M.

Rover 101
Star Sitter
Neighbor providing additional love
Washington Heights, milwaukee, WI, 53208
1.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$57
per night
5 out of 4.9 stars
80 reviews
24 repeat clients
Profile image

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!

Availability updated 24 days ago
Sitter Profile Image: Davina A.
Verified Enhanced Background Check
Sitter Profile Image: Davina A.
Verified Enhanced Background Check

20. Davina A.

Patient, kind, and reliable!
Sherman Park, Milwaukee, WI, 53210
1.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5 out of 5.0 stars
4 reviews
Profile image

Davina did a great job taking care of our dog while we were gone. She was reliable, flexible, helpful and willing to jump in to problem solve when an unexpected issue came up.

Availability updated 6 days ago
Confirmed availability for Memorial Day Weekend

How Rover works

  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

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 house 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.

House Sitting FAQs

Frequently asked questions about Rover

Connect anywhere with the Rover app

Download on the App Store BadgeGet it on Google Play Badge