Pet Sitting & Drop Ins in Washington Heights, Milwaukee

Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
One Time
Repeat Weekly
Which dates do you need?
What size are your dogs (lbs)?
To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

Search Results

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

1. Karsyn R.

Rover 101
Star Sitter
Dog Buddy & Reliable Care
Milwaukee, WI, 53207
5.0 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
156 reviews
51 repeat clients
from
$18
per visit

Karsyn was a great friend to Simba while we were away for a few hours! She was super responsive when we reached out for the initial visit and was very kind. Simba warmed up to her friendly personality right away, so we felt relieved when leaving him. Will definitely be using Karsyn 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.

Star Sitter
Loving sitter, enthusiastic walker
Lower East Side, Milwaukee, WI, 53202
4.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
98 reviews
33 repeat clients
from
$20
per visit

She was great and got along, so well, with Blue. Sent all the pictures and all the updates. And gave awesome feed back. Will be using Jessica again

Calendar Recently Updated
Sitter Profile Image: Kathy S.
Verified Enhanced Background Check
Sitter Profile Image: Kathy S.
Verified Enhanced Background Check

3. Kathy S.

Rover 101
Star Sitter
Patient walker and caregiver.
Wauwatosa, WI, 53213
1.2 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
50 reviews
17 repeat clients
from
$16
per visit

I am so grateful I found Kathy when looking for a sitter to check in on my cat! My cat was recently prescribed meds that need to be administered every 12 hours. Kathy didn't bat an eye at helping with meds and was punctual for each check-in. She went above and beyond in every way while I was out of town, and her communication was excellent. I won't hesitate to have her check-in on my cat again in the future, and would I recommend her to others in a heartbeat!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Leandrea R.
Verified Enhanced Background Check
Sitter Profile Image: Leandrea R.
Verified Enhanced Background Check

4. Leandrea R.

Rover 101
Star Sitter
your pets are my priority.
Muskego Way, Milwaukee, WI, 53204
3.7 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
106 reviews
37 repeat clients
from
$15
per visit

Great communication always on time if there were any questions she asked. Very friendly and very good with the dog. Would highly recommend her for taking care of your dogs. Always sent pictures and an update on what was going on.

Sitter Profile Image: Lexi K.
Verified Enhanced Background Check
Sitter Profile Image: Lexi K.
Verified Enhanced Background Check

5. Lexi K.

Star Sitter
Lover of all animals big and small
Cannon Park, Milwaukee, WI, 53214
2.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
42 reviews
12 repeat clients
from
$16
per visit

She did so good with my evil cat and even brought in a package and put my robot camera back on the charger. We met up before my vacation and did a quick review of what was needed. I felt comfortable knowing she was there for my cat :)

Calendar Recently Updated
Sitter Profile Image: Emily V.
Verified Enhanced Background Check
Sitter Profile Image: Emily V.
Verified Enhanced Background Check

6. Emily V.

Star Sitter
Caring, active, & attentive sitter
Brewer's Hill, Milwaukee, WI, 53212
3.4 mi. away
Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
18 reviews
3 repeat clients
from
$14
per visit

Emily was wonderful during our drop in visit! She took Pickles for a walk and played with Brownie! We look forward to her next drop in visit and appreciate her help taking care of our little ones!

Calendar Recently Updated
Sitter Profile Image: Lindsey F.
Verified Enhanced Background Check
Sitter Profile Image: Lindsey F.
Verified Enhanced Background Check

7. Lindsey F.

Star Sitter
Your best friends new best friend!
Wauwatosa, WI, 53213
1.9 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
26 reviews
3 repeat clients
from
$15
per visit

I would recommend Lindsey to anyone. We hired her for three drop-in’s over the weekend and she was timely, respectful, had great communication throughout the process. It felt as though a family member was taking care of our dogs.

Sitter Profile Image: Lillith L.
Verified Background Check
Sitter Profile Image: Lillith L.
Verified Background Check

8. Lillith L.

Star Sitter
ABC VA Certified and ❤️ all animals
Milwaukee, WI, 53208
0.3 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
12 reviews
7 repeat clients
from
$19
per visit

I recently adopted my dog so I was nervous to introduce more humans so soon. But I didn’t have to worry with Lillith. She’s knowledgable and you can tell how much she loves dogs. Maverick can’t wait to see you again!

Calendar Recently Updated
Sitter Profile Image: Natalie F.
Verified Enhanced Background Check
Sitter Profile Image: Natalie F.
Verified Enhanced Background Check

9. Natalie F.

Star Sitter
Lover of all animals big or small!
Wauwatosa, WI, 53226
2.7 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
20 reviews
2 repeat clients
from
$18
per visit

Thank you! I will definitely keep you in mind for future visits. ?

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

10. Kristine K.

Star Sitter
Experienced dog & cat mom
Merrill Park, Milwaukee, WI, 53208
1.8 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
18 reviews
13 repeat clients
from
$16
per visit

We are so glad Kristine was available on Christmas Day to check on our cat. She came a few days prior on late notice for a meet and greet and provided a nice update!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Maggie S.
Verified Enhanced Background Check
Sitter Profile Image: Maggie S.
Verified Enhanced Background Check

11. Maggie S.

I'll Treat Your Dog Like My Own
Milwaukee, WI, 53213
1.2 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
6 reviews
1 repeat client
from
$15
per visit

Maggie is the best! She is a true dog lover and she is our automatic go-to whenever we need a dog sitter. She has always given our pup the best care from the puppy days into his senior years. We trust her to stay at our house, and he has also done extended stays at her place. Can’t say enough great things about her!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Kaitlin G.
Verified Enhanced Background Check
Sitter Profile Image: Kaitlin G.
Verified Enhanced Background Check

12. Kaitlin G.

Mom to animals, teacher to humans
Wauwatosa, WI, 53213
1.1 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
21 reviews
2 repeat clients
from
$18
per visit

I’ve worked with Kaitlin multiple times now - she’s awesome! She’s reliable and communicative, she’ll hang out with your pets and make sure to send photos :) 10/10 person

Calendar Recently Updated
Sitter Profile Image: Heidi N.
Verified Enhanced Background Check
Sitter Profile Image: Heidi N.
Verified Enhanced Background Check

13. Heidi N.

Pet loving medical student
Washington Heights, Milwaukee, WI, 53208
0.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
14 reviews
3 repeat clients
from
$20
per visit

Heidi was really great with our dog, Hazel! Excellent communication and so nice to deal with. She took good care of Hazel during our day away. Will definitely book again!

Calendar Recently Updated
Sitter Profile Image: Danica V.
Verified Enhanced Background Check
Sitter Profile Image: Danica V.
Verified Enhanced Background Check

14. Danica V.

Star Sitter
PAWsitively reliable med student!
Wauwatosa, WI, 53226
2.0 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
20 reviews
7 repeat clients
from
$25
per visit

Danica stopped in to feed my kitties and did an incredible job. She took lots of photos and was very communicative. I felt very happy to see my boys getting lots of love and pets. I will definitely be booking with her again!

Sitter Profile Image: Aly L.
Verified Enhanced Background Check
Sitter Profile Image: Aly L.
Verified Enhanced Background Check

15. Aly L.

Star Sitter
Warning! Pets are spoiled here!
Washington Heights, Milwaukee, WI, 53208
0.4 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
27 reviews
11 repeat clients
from
$20
per visit

Ally was super friendly & easy to work with, very thorough communication and made us feel at ease. We will use her for ALL of our needs. Highly recommend.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Lance C.
Verified Enhanced Background Check
Sitter Profile Image: Lance C.
Verified Enhanced Background Check

16. Lance C.

Coffee loving dog walker!
Enderis Park, Milwaukee, WI, 53210
1.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
3 reviews
from
$14
per visit

I had an amazing experience with Lance as my dog sitter! He was incredibly attentive to my furry friend's needs and went above and beyond to ensure their comfort and happiness while I was away. Lance provided regular updates and even sent adorable photos of my pup enjoying their time together. I felt completely at ease knowing that my dog was in such capable and caring hands. I highly recommend Lance to anyone in need of a reliable and compassionate dog sitter.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jeremy M.
Verified Background Check
Sitter Profile Image: Jeremy M.
Verified Background Check

17. Jeremy M.

Rover 101
Neighbor providing additional love
Washington Heights, milwaukee, WI, 53208
0.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
51 reviews
21 repeat clients
from
$20
per visit

Jeremy was an amazing cat sitter! Both my cats were immediately comfortable and really grew to like Jeremy’s daily visits and play time. Super responsive and always sending lots of pics for me to check in on- it’s was such a relief to have them in Jeremy’s care. Highly recommend!!!

Sitter Profile Image: Sylvia G.
Verified Background Check
Sitter Profile Image: Sylvia G.
Verified Background Check

18. Sylvia G.

Here to help with your pet needs!
Washington Heights, Milwaukee, WI, 53208
0.5 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
1 repeat client
from
$11
per visit

About: Animals are my passion while my full time position is in healthcare. I’ve been around animals my entire life and truly try to create a deep bond with every animal I work with. I’m here to give your animal all the scratches and cuddles they want! I have two dogs of my own, 5 and 6 years old. They both are very friendly with other animals and love to play. I have a fenced in yard for your dog to run freely and get all the sniffing they want in! I work 12 hour shifts Friday through Sunday. I am completely available Monday through Thursday at any time of the day. I am here to love your animal! I have a fenced in yard and two friendly pups to keep them entertained. I keep my dogs on a schedule with food, potty breaks, and walks; I can do the same for your dogs given the information!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Alex S.
Verified Enhanced Background Check
Sitter Profile Image: Alex S.
Verified Enhanced Background Check

19. Alex S.

New Walker on the scene!
Uptown, Milwaukee, WI, 53210
0.5 mi. away
Drop-In Visits, Dog Walking
10 years of experience
from
$20
per visit

About: Hello! My name is Alex! I have two older chihuahua mixes who are rescues. I also have experience dropping in to friends’ houses to feed and walk their animals when they are out of town. I thought I’d parlay my love of animals and experience with helping friends out into a fun side gig! I work from home Mondays-Wednesdays and Fridays 7am-4pm and have availability for walks early morning, mid day, and after work. I love pets and am very calm and collected. I am very open to following any and all desired steps you want in order to care for your furry children. I respect and love animals and and very calm and respectful of animals’ cues.

Sitter Profile Image: Lou H.
Verified Enhanced Background Check
Sitter Profile Image: Lou H.
Verified Enhanced Background Check

20. Lou H.

I’m a long time dog lover!
Wauwatosa, WI, 53213
0.7 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
31 reviews
3 repeat clients
from
$14
per visit

Lou was prompt and great to work with! She stopped by before the day she was needed and got to know the dogs and was reliable! Will book again!

Search Map

Rover also offers Pet Sitting & Drop Ins in these neighborhoods:

Rover also offers other services in Washington Heights:

Dog owners in Washington Heights, Milwaukee, WI love booking pet sitting with sitters on Rover.com. Over 1089 pet owners have reviewed pet sitters in Milwaukee, giving them an average rating of 5.0/5 stars. Booking pet sitting can be super affordable, no matter where you live. Trust us, we think you'll be pleasantly surprised. Curious what it might cost to book pet sitting with Rover? Check out our average pet sitting rates to get an idea before reaching out and starting a conversation with a pet sitter near you in Washington Heights.

Never beg a friend to drop in on your pets while you're on vacation again. With Rover, you can find the perfect Washington Heights, Milwaukee pet sitter in seconds. Sitters on Rover are pet lovers, who will be happy to sit dogs, cats, caged pets, and even horses while they take care of your home. By removing common pet care obstacles, Rover ensures pets nationwide are happy and well-cared for even when their human is away, and empowers pet lovers to live happy and fulfilling lives. Founded on the belief that everyone should have the opportunity to experience the unconditional love of a pet, Rover makes it easy for you to reach trusted pet sitters in Washington Heights, Milwaukee who can provide the care your pet needs, when they need it.

Drop-In Visits