House Sitting in Jackson Park, Milwaukee

Find a loving dog sitter to watch your dog overnight in your home.

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
Which dates do you need?
What size are your dogs (lbs)?

Search Results

Calendar Recently Updated
Sitter Profile Image: Blythe R.
Verified Background Check
Sitter Profile Image: Blythe R.
Verified Background Check
1.

Blythe R.

Every animal makes me smile!
Bay View, Milwaukee, WI, 53207
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0
133 reviews
60 repeat clients
from
$55
per night

Blythe was great! She took care of our girls while we were away for a quick weekend trip and when we arrived home they were very happy and content and the house was clean and neat. There’s no doubt we’ll be booking with her again!

Calendar Recently Updated
Sitter Profile Image: Jessica Z.
Verified Enhanced Background Check
Sitter Profile Image: Jessica Z.
Verified Enhanced Background Check
2.

Jessica Z.

Loving sitter, enthusiastic walker
Lower East Side, Milwaukee, WI, 53202
House Sitting, Drop-In Visits, Dog Walking
5.0
78 reviews
26 repeat clients
from
$55
per night

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.

Calendar Recently Updated
Sitter Profile Image: Lexi K.
Verified Enhanced Background Check
Sitter Profile Image: Lexi K.
Verified Enhanced Background Check
3.

Lexi K.

Lover of all animals big and small
Cannon Park, Milwaukee, WI, 53214
House Sitting, Drop-In Visits, Dog Walking
5.0
26 reviews
7 repeat clients
from
$35
per night

Lexi is patient and kind! She had to care for my older dog who has heart problems and is needy when I’m gone! She communicated and thankfully helped make me feel comfortable when my dog was less than easy!

Sitter Profile Image: Daniela & Michael P.
Verified Background Check
Sitter Profile Image: Daniela & Michael P.
Verified Background Check
4.

Daniela & Michael P.

Rover 101
Paws Down, the Best in Town!
Milwaukee, WI, 53205
House Sitting, Drop-In Visits, Dog Walking
5.0
275 reviews
158 repeat clients
from
$65
per night

Daniela and Michael are easily the best sitters we have ever had for our dogs. Their care and attention to detail always leave us feeling at ease when we have to leave our pets over a weekend. They will never not be our first choice in house sitting.

Calendar Recently Updated
Sitter Profile Image: Erica L.
Verified Background Check
Sitter Profile Image: Erica L.
Verified Background Check
5.

Erica L.

I'll love them like my own
West Allis, WI, 53227
House Sitting, Drop-In Visits, Dog Walking
5.0
76 reviews
37 repeat clients
from
$37
per night

Erica was great! She kept me updated and sent pictures and videos and my dog looked happy and well cared for. Would not hesitate to book her again!

Calendar Recently Updated
Sitter Profile Image: Stephen & Wipawee D.
Verified Enhanced Background Check
Sitter Profile Image: Stephen & Wipawee D.
Verified Enhanced Background Check
6.

Stephen & Wipawee D.

Pawfessional w/ Love & Care <3
West Allis, WI, 53227
House Sitting, Drop-In Visits, Dog Walking
5.0
41 reviews
17 repeat clients
from
$65
per night

Stephen and Wipawee watched my dog and my sister’s dog at my house while we went away on a family vacation. The dogs were well cared for, had plenty of attention and were taken great care of! Couldn’t have asked for better sitters.

Sitter Profile Image: Rachel H.
Verified Background Check
Sitter Profile Image: Rachel H.
Verified Background Check
7.

Rachel H.

** Mission: meet ALL the dogs **
West Allis, WI, 53214
House Sitting, Drop-In Visits, Dog Walking
5.0
73 reviews
22 repeat clients
from
$27
per night

I can't say enough about how great Rachel is! Bunnies are very hard to care for, and she does it at an all-star level. We came home to clean, happy bunnies and a beautifully cared for home. She sent great updates every day that made us smile! We will have her back every time we need a sitter.

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Jenn S.
Verified Enhanced Background Check
Sitter Profile Image: Jenn S.
Verified Enhanced Background Check
8.

Jenn S.

Dog lover and cat mom of 3❤️
West Allis, WI, 53227
House Sitting, Drop-In Visits, Dog Walking
5.0
29 reviews
9 repeat clients
from
$60
per night

Jenn is amazing!! I have 2 cats and an anxious dog. She treated them all with so much love and cared for them while I was out of town.Updates and pictures every day!!

Calendar Recently Updated
Sitter Profile Image: Felicity W.
Verified Enhanced Background Check
Sitter Profile Image: Felicity W.
Verified Enhanced Background Check
9.

Felicity W.

Animals are my full time passion 🤍
St Francis, WI, 53235
House Sitting, Drop-In Visits, Dog Walking
5.0
21 reviews
10 repeat clients
from
$50
per night

Felicity was great! My pup loved her and was well taken care of while we were away. She has watched her twice now and we would definitely book again! She stayed at our home and the house was in great shape when we got home.

Sitter Profile Image: Cindy H.
Verified Enhanced Background Check
Sitter Profile Image: Cindy H.
Verified Enhanced Background Check
10.

Cindy H.

Reincarnated Dog Here!
wauwatosa, WI, 53213
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
18 reviews
3 repeat clients
from
$55
per night

Cindy was great with our two dogs. They haven’t ever been watched by anyone other than family, so we were nervous having someone else watch them. Cindy was very communicative and made us feel at ease while being away from them. From the pictures sent, it seems as though they had a great time!

Calendar Recently Updated
Sitter Profile Image: Leandrea R.
Verified Enhanced Background Check
Sitter Profile Image: Leandrea R.
Verified Enhanced Background Check
11.

Leandrea R.

Rover 101
your pets are my priority.
Muskego Way, Milwaukee, WI, 53204
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
85 reviews
32 repeat clients
from
$60
per night

Leandrea has watched our dog twice now and has done a wonderful job helping him be comfortable and happy when we're away. She communicates regularly and provides updates. We'll definitely be booking with her again!

Calendar Recently Updated
Sitter Profile Image: Kira W.
Verified Enhanced Background Check
Sitter Profile Image: Kira W.
Verified Enhanced Background Check
12.

Kira W.

Flexible Scheduling, Cats and Dogs
Lenox Heights, Milwaukee, WI, 53210
House Sitting
5.0
3 reviews
1 repeat client
from
$40
per night

Kira was amazing with our quirky doggo. We couldn't have asked for a better experience. She provided daily updates and loved on our pup while we were away for a long weekend. Upon returning home, we could tell puppers was anxiety free and our home was in excellent order. 1000% would use Kira again.

Calendar Recently Updated
Sitter Profile Image: Bret H.
Verified Enhanced Background Check
Sitter Profile Image: Bret H.
Verified Enhanced Background Check
13.

Bret H.

Work from home and reliable
Bay View, Milwaukee, WI, 53207
House Sitting, Drop-In Visits, Dog Walking
5.0
3 reviews
2 repeat clients
from
$50
per night

Thank you for the great support for Schooner. He appeared happy and rested when I returned.

Sitter Profile Image: Molly O.
Verified Background Check
Sitter Profile Image: Molly O.
Verified Background Check
14.

Molly O.

All the walks and all the cuddles
Wick Field, Milwaukee, WI, 53208
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
22 reviews
10 repeat clients
from
$55
per night

Molly did a great job watching our three bulldogs for a long weekend. She sent lots of pics and responded quickly any time I sent a question or note. Two of our girls have had some weird behaviors around meal time right before we left and she rolled with it with ease (and everyone ate all meals under her care). Definitely would hire her again!

Calendar Recently Updated
Sitter Profile Image: Jess W.
Verified Enhanced Background Check
Sitter Profile Image: Jess W.
Verified Enhanced Background Check
15.

Jess W.

Human Available for All Pet Needs
West Allis, WI, 53214
House Sitting, Drop-In Visits, Dog Walking
5.0
5 reviews
from
$50
per night

Jess was a life saver! We had a last minute cancellation from our other sitter and Jess was up for it without even meeting us in person. She has a natural gift to bond and earn trust with fur babies. We are so glad we found each other. Our cat was stuck to her the entire time and she spent almost everyday and night with our baby. Couldn’t have asked for anything more. She engaged in play whenever he asked for it and followed through with our cat diet religiously. She sent us pics everyday to reassure us. We would definitely have her again and recommend her to anyone looking for an experienced animal lover to take care of their fur baby

Calendar Recently Updated
Sitter Profile Image: Sarah J.
Verified Enhanced Background Check
Sitter Profile Image: Sarah J.
Verified Enhanced Background Check
16.

Sarah J.

I’m awkward with humans.
West allis, WI, 53219
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
60 reviews
25 repeat clients
from
$25
per night

Sarah was awesome with my puppies and they both seems to love her. She gave them medications and hugged then as they need too. Thank u for your attention and for being patient with their needs, Sarah! I recommend Sarah for every pets and pet parents.

Sitter Profile Image: Amanda B.
Verified Enhanced Background Check
Sitter Profile Image: Amanda B.
Verified Enhanced Background Check
17.

Amanda B.

Have loved animals since birth.
Greenfield, WI, 53220
House Sitting, Drop-In Visits, Dog Walking
5.0
85 reviews
29 repeat clients
from
$28
per night

Amanda was awesome - she came to the house to meet us and Hutch about a month ahead of our trip; was very communicative- sent daily notes and photos and spoiled him rotten. We were thrilled and look forward to using her again.

Calendar Recently Updated
Sitter Profile Image: Miranda O.
Verified Background Check
Sitter Profile Image: Miranda O.
Verified Background Check
18.

Miranda O.

All Dogs go to heaven
Bay View, Milwaukee, WI, 53207
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
150 reviews
78 repeat clients
from
$70
per night

Miranda house sat my dog and cat over the weekend. I come home to happy, relaxed pets which I appreciate. She also is quick to respond to messages. I highly recommend reaching out if you're looking for somebody to trust your pets with.

Calendar Recently Updated
Sitter Profile Image: Allie C.
Verified Enhanced Background Check
Sitter Profile Image: Allie C.
Verified Enhanced Background Check
19.

Allie C.

I love all animals ❤️
Jackson Park, Milwaukee, WI, 53215
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
2 reviews
from
$40
per night

Allie was just great with our 3 labs. They have a lot of energy and the youngest dog 2.5 can be a handful. But she listens to Allie. Allie did a whole week for us, plus weekends here and there. She also filled in for us when we needed someone to stop by at lunch time when our work schedules got crazy. She followed our instruction sheet and we just loved having her care for our furbabies. She sent pics for us too. 5 Stars!! Or is that 5 paws? 😁

Sitter Profile Image: Samantha B.
Verified Background Check
Sitter Profile Image: Samantha B.
Verified Background Check
20.

Samantha B.

Animal lover for both dogs or cats
White Manor, Milwaukee, WI, 53219
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0
12 reviews
3 repeat clients
from
$45
per night

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.

Search Map

When it comes to house sitting, dog owners in Jackson Park, Milwaukee, WI love Rover.com. Over 1,089 owners have reviewed sitters in Milwaukee, giving them an average rating of 5.0/5. The cost of house sitting in Jackson Park may surprise you - in a good way. That's because there's a house sitter on Rover for nearly every price range and lifestyle. Curious about how much it you can expect to pay for house sitting on Rover? Check out our average house sitting rates to get an idea before you start a conversation with a sitter.

Rover.com is the simple, savvy way to find and book Jackson Park house sitting. It's easy to find the perfect house sitter: many sitters on Rover have a long history of dog sitting, and 95% of reviewed stays have received a perfect five-star rating. When you book house sitting in Jackson Park, Milwaukee, WI on Rover, your dog will enjoy a loving staycation, right in your home. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Every dog sitter on Rover has the option to complete a free background check. Stays are booked on Rover every minute of every day, and more than 92% of the population lives within a short drive of one of the more than 65,000 sitters who've listed their services on Rover. 95% of reviewed stays have received a perfect five-star rating. When you book with one of our trusted Jackson Park house sitters on Rover, your dog gets the loving care they deserve, and you get peace of mind.

A Daily Treat: A Blog by Rover

Rover's got you covered, even when you don't need a pet sitter or dog walker. Check out our blog for pictures of adorable dogs, help on your biggest dog-related questions, and more:

Book a Stay, Donate to a Cause

Sit a Dog, Save a Life lets you raise money for local dogs-in-need by doing something you do already: asking your neighbors to watch your dog instead of leaving them in a kennel. Many Rover sitters in Jackson Park, Milwaukee donate a percentage of their earnings to nonprofits through Sit a Dog, Save a Life. When you book with a sitter who has the Rover Donation Badge on their profile, you're helping dogs in need, right here in Milwaukee.

We're proud to support over 200 organizations across the nation, including:

House Sitting