Pet Sitting & Drop Ins in Maitland Park, 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)?

Search Results

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Sitter Profile Image: Karsyn R.
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Sitter Profile Image: Karsyn R.
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1. Karsyn R.

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

Karsyn is great! She put up with our mischievous cats, sent lots of pictures and was super responsive! Definitely have her watch your fur babies :)

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Sitter Profile Image: Kailey S.
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Sitter Profile Image: Kailey S.
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2. Kailey S.

Committed to making your pet happy
Oak creek, WI, 53154
5.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
69 reviews
14 repeat clients
from
$17
per visit

Kailey was awesome! She came by for a meet and greet and took great care of our pup when we had to go away at the last minute. Very informative and sent lots of pics, we felt really comfortable knowing he was being taken care of. Thanks Kailey!!

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Sitter Profile Image: Devon W.
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Sitter Profile Image: Devon W.
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3. Devon W.

Rover 101
Lover of all creatures!
Milwaukee, WI, 53207
4.1 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
47 reviews
21 repeat clients
from
$15
per visit

Devon did a great job dropping in on our dogs while we were on vacation. They had very good communication, promptness, and even though our pups can be a handful Devon had no problem taking care of them.

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Sitter Profile Image: Leandrea R.
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Sitter Profile Image: Leandrea R.
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4. Leandrea R.

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

Leandrea did a superb job with my kitty Sunny! I was anxious about leaving him due to him just having surgery a couple of days prior, but I was immediately put at ease with her quality of care! I would recommend her to anyone looking for care for their pet! I will definitely be booking for all my pet needs in the future! Thank you for being so wonderful!

Sitter Profile Image: Michele M.
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Sitter Profile Image: Michele M.
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5. Michele M.

15+ yr pet owner & dog foster
Milwaukee, WI, 53221
1.8 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
22 reviews
10 repeat clients
from
$20
per visit

Michele did an AMAZING JOB, she took care of my dogs at the last minute while I underwent a minor emergency procedure at the hospital. She fed them, played with them and took them out 3 times a day. I am so appreciative of her help and look forward to rebooking her, I definitely recommend her!

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Sitter Profile Image: Elba M.
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Sitter Profile Image: Elba M.
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6. Elba M.

Rover 101
Wiggle waggle and roll!
Cudahy, WI, 53110
2.9 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
129 reviews
50 repeat clients
from
$20
per visit

Bella has stayed with Elba several times, she always comes home happy and well taken care of. She also comes home very tired as she goes on many walks and hangs out at the dog park! Elba is very flexible with her schedule and always sends updates to let me know how Bella is doing. I would highly recommend Elba!

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Sitter Profile Image: Deanna S.
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Sitter Profile Image: Deanna S.
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7. Deanna S.

I will provide unconditional love.
Greendale, WI, 53130
5.0 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
7 repeat clients
from
$18
per visit

Deanna did a great job taking care of our dog and cat while we were away for a weekend. She always provided updates and photos and my dog and cat absolutely adore her! Will hire her again when we are in need of her services.

Sitter Profile Image: Julia R.
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Sitter Profile Image: Julia R.
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8. Julia R.

I have experience for dogs
Cudahy, WI, 53110
2.9 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
10 reviews
3 repeat clients
from
$20
per visit

Julia has been SUCH a huge help to me with my dog Payton. She’s very responsive, reliable, kind, sends the cutest pics while I’m away at work and takes amazing care of P. I would recommend her for any service you may need :)

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Katie N.
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Sitter Profile Image: Katie N.
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9. Katie N.

Here kitty kitty (and doggies too!)
Greendale, WI, 53129
3.6 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
39 reviews
10 repeat clients
from
$20
per visit

Katie took great care of my cat! She did everything I asked for and also made sure everything was in order throughout the house for her! Sophie loves when she visits!

Sitter Profile Image: Alexy & Dylan G.
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Sitter Profile Image: Alexy & Dylan G.
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10. Alexy & Dylan G.

Animals are my passion and joy!
Milwaukee, WI, 53207
3.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
12 reviews
5 repeat clients
from
$11
per visit

Alexy & Dylan are sweet! they took great care of my girl’s needs while I was away & sent plenty of pictures. I will contact them for future needs. 💜

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Sitter Profile Image: Elaine P.
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Sitter Profile Image: Elaine P.
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11. Elaine P.

Experienced & loving pet owner!
Milwaukee, WI, 53207
2.4 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
15 reviews
6 repeat clients
from
$17
per visit

As always, very dependable and my girls love her! Kaia and Pepper were well taken care of and I looked forward to reading the check in notes and seeing their pictures. I can appreciate the thoughtfulness and care Elaine provides. I will continue to use Elaine whenever she is available. 😊

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Hannah K.
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Sitter Profile Image: Hannah K.
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12. Hannah K.

Rover 101
I will treat your dogs like my own!
Cudahy, WI, 53110
3.2 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
386 reviews
184 repeat clients
from
$25
per visit

We can’t thank Hannah enough! Our older pup can be quite the handful for most people, but Hannah made her so at ease. Thank you Hannah for taking such wonderful care of our 2 pups and keeping their humans at ease while they were away!!!

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Sitter Profile Image: Amanda D.
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Sitter Profile Image: Amanda D.
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13. Amanda D.

Experienced pet owner
South Milwaukee, WI, 53172
3.8 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
7 reviews
2 repeat clients
from
$13
per visit

Amanda was an excellent sitter! She sent a lot of updates and had great communication!

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Sitter Profile Image: Christine H.
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Sitter Profile Image: Christine H.
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14. Christine H.

Experienced Dog Foster
Greenfield, WI, 53221
1.9 mi. away
Boarding, Drop-In Visits
5.0 out of 5 stars
28 reviews
9 repeat clients
from
$20
per visit

Came on short notice and did a great job!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Markita H.
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Sitter Profile Image: Markita H.
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15. Markita H.

Friendly/Compassionate/Responsible
Saint Francis, WI, 53235
3.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
70 reviews
6 repeat clients
from
$17
per visit

Markita was excellent-gave lots of great care and attention to my cats and great communication. I appreciate that she makes sure to know your exact communication and update preferences since many owners may differ on the level of detail and specificity of updates on the visits. I definitely will be a repeat customer!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Rebecca S.
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Sitter Profile Image: Rebecca S.
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16. Rebecca S.

PAWSitively the Best!
Town Of Lake, Milwaukee, WI, 53207
2.6 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$15
per visit

Rebeccca is excellent with dogs! She is a loving dog owner of two who takes her dogs on ample walks and excursions. Rebecca makes sure to fill their days with love and fun. She has experience house training dogs, providing boarding for other dogs, and walking multiple dogs at a time. I highly suggest going with her!

Sitter Profile Image: Nicole D.
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Sitter Profile Image: Nicole D.
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17. Nicole D.

Your dog will be loved!
Greenfield, WI, 53221
1.3 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
9 reviews
2 repeat clients
from
$20
per visit

Without a doubt, the best pet sitter in the area. I was very happy to find Nicole, she is a true dog lover and takes amazing care of my dog, Kona. Kona wags her tail and is excited to stay with Nicole. Nicole will text over a picture and send me information on how Kona is doing. Nicole cares for Kona, the way I would. I never worry about Kona when Nicole is around. Thank you so much for giving me "Peace of Mind" while I'm out of town.

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Sitter Profile Image: Felicity W.
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Sitter Profile Image: Felicity W.
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18. Felicity W.

Animals are my full time passion 🤍
St Francis, WI, 53235
2.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
24 reviews
11 repeat clients
from
$20
per visit

Felicity is always so professional and quick to respond! I made an appointment 20 min before the requested time and she made her self available immediately. Lexi always looks forward to her visits!!

Sitter Profile Image: Kirstie K.
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Sitter Profile Image: Kirstie K.
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19. Kirstie K.

Rover 101
Let’s get off on the right paw 🐾
Clayton Crest, Milwaukee, WI, 53221
1.0 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
109 reviews
64 repeat clients
from
$20
per visit

Kirstie was a great Rover. She really pampered my pup. She brought her own dogs with her for Mia to play with. My dog looks like she had a blast! I would definitely recommend Kirstie!

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Sitter Profile Image: Marissa N.
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Sitter Profile Image: Marissa N.
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20. Marissa N.

Compassionate & Caring Animal Lover
Goldman Park, Milwaukee, WI, 53221
0.7 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
2 reviews
from
$20
per visit

Marissa is one of the most caring people I know, she will shower your pet with love. You will not have to worry while you are away, Marissa will take great care of your fur baby.

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

Rover also offers other services in Maitland Park:

Pet parents turn to sitters on Rover.com when they're looking for pet-sitting. 1089 owners have reviewed sitters in Maitland Park, Milwaukee, WI, giving them an average rating of 5.0/5. Since 92% of pet owners live within a short drive of a sitter on Rover, it's easy to find the perfect pet sitter near you. 95% of reviewed stays have received a perfect 5-star rating. Wondering how much you can expect to pay on Rover.com? Check out our average pet sitting rates to get an idea before you start a conversation with a pet sitter. Exchange messages from your sitter's profile, ask to schedule a free in-person Meet & Greet, and book and pay on Rover. You'll receive adorable photo updates, premium insurance, and world-class support.

The next time you head out of town and need someone to take care of your pets and check in on you home, turn to Rover. It's easy to find a loving Maitland Park pet sitter on Rover who'll give your pet one-on-one attention while you're away, and take care of your home. Search from hundreds of trusted pet sitters in Maitland Park, Milwaukee, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet(s). We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your house and pet sitter all through Rover: it's easy, safe, and cashless. You'll have the peace of mind knowing that your sitter has free premium insurance, a team of safety experts available 24/7, and will send you cute photo updates throughout the stay. Rover is the easiest way to find trustworthy Maitland Park pet sitters and avoid the kennel.

Drop-In Visits