Pet Sitting & Drop Ins in Fairfield, Milwaukee

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

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

Search Results

Confirmed availability: Memorial Day
Kadijah L.
I’m a dog lover! ?Lincoln Creek, Milwaukee, WI, 53216
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Kadijah was great! Would definitely feel comfortable having her board my dog again and would recommend her to any friends or family that needed a dog boarded. … (more)

from
$60
per night
Confirmed availability: Memorial Day
Cindy T.
2.
TOTAL DOG LOVER :)Wauwatosa, WI, 53222
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Our one year old German Shepherd had a wonderful weekend with Cindy and her family. We loved getting pics and updates about his stay. I would recommend Cindy … (more)

from
$35
per night
Rhonda G.
3.
Love to walk and cuddle.Whitefish Bay, WI, 53217
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Rhonda took very good care of Pickles. She sent lots of pictures. Took her on lots walks, and gave her a lot of attention. Very satisfied with the care Pickles … (more)

from
$30
per night
Kim M.
4.
Kim 
Verified Enhanced Background Check
Fenced yard and lots of love!Timmerman West, MILWAUKEE, WI, 53225
Dog Boarding

Kim and Joe watched our pups at the last minute and were so wonderful! Our dogs have quite a bit of specific instructions and needs and they were so accommodati… (more)

from
$27
per night
Confirmed availability: Memorial Day
Michelle B.
For the Love of the Dog-WI™Pheasant Run, Milwaukee, WI, 53224
Dog Boarding

We loved the fenced in yard and pool for the dog to play in! Our pup seemed like he had a great time with Michelle! We will be boarding with Michelle again. (more)

from
$38
per night
Calendar Recently Updated
6.
We’ll Keep Their Tail WagginMenomonee Falls, WI, 53051
Dog Boarding, Drop-In Visits, Doggy Day Care

My first time using Rover and it was a great experience with Angela! After my picky/ missy pup got settled in she did great and nice and tired coming home too. … (more)

from
$35
per night
Calendar Recently Updated
7.
Jan 
Verified Background Check
I am a pet lover; home full timeWhitefish Bay, WI, 53217
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Jan is the best dog sitter. Our dog adores her. She sent great photos throughout and took fantastic care of our 3 year old, high energy dog. We highly, highly r… (more)

from
$45
per night
8.
I Absolutely Love Fur Babies ❤️❤️Hampton Heights, Mikeaukee, WI, 53218
Dog Boarding
14 years of experience

About: I’ve known how to care and create bonds with animals at a very young age. I’m 34 and we’ll seasoned with pets of all ages. I really enjoy the persona… (more)

from
$60
per night
Calendar Recently Updated
9.
Multiple walks and cuddles!Washington Heights, Milwaukee, WI, 53208
Dog Boarding, Doggy Day Care

Deann was great! She sent us updates and pictures of walks and playing. I know that Waski had a great time with the other dogs too. Thanks a bunch! (more)

from
$35
per night
Calendar Recently Updated
Two for one love!Brookfield, WI, 53005
Dog Boarding

Rebecca and Bobby were amazing! They treated our dog like their own, sent us updates and pictures throughout! We couldn’t of asked for better care for our dog. … (more)

from
$50
per night
Calendar Recently Updated
11.
Work from home dog lover!Glendale, WI, 53217
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Kelsey was wonderful - she responded to all of my messages in record time. She was able to take in our dog on the short notice and was very accommodating. ( we … (more)

from
$30
per night
We’ll meet your dog's needs!Grasslyn Manor, Milwaukee, WI, 53216
Dog Boarding, Drop-In Visits, Dog Walking

Elizabeth and her family are awesome. She took excellent care of Lovey and kept me updated with daily pictures and messages. I would rebook without hesistatio… (more)

from
$32
per night
Calendar Recently Updated
Open and flexible dog attendeeKilbourn Town, 53233, WI, 53233
Dog Boarding, Doggy Day Care, Dog Walking

Isabella was amazing! She help us out with taking care of our little pup Bigos on last minute request. She was very flexible and easy to communicate and Bigos w… (more)

from
$35
per night
Calendar Recently Updated
14.
Kathy's Home Away From HomeBrown Deer, WI, 53223
Dog Boarding, Doggy Day Care

We had a great experience with Kathy. I felt that Molly was in good hands the entire time we were gone. Molly doesn't like to be left alone so it was comforting… (more)

from
$25
per night
Confirmed availability: Memorial Day
15.
Wee looove the fur babies ♥️Kops Park, Milwaukee, WI, 53222
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Yisel took amazing care of my dog! She provided many updates and was super detailed! Would highly recommend! (more)

from
$40
per night
Calendar Recently Updated
16.
Place your trust in me...Mequon, WI, 53092
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Cindy is fantastic! Best dog sitting experience ever. This was the first time we used Rover and we couldn't have asked for a better sitter for our dog. Cindy… (more)

from
$50
per night
Calendar Recently Updated
17.
Home full time, LOVE dogs!!!Glendale, WI, 53209
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Auria was excellent. Her communication skills were great (very important). She easily accommodated special requests - such as taking a birthday photo of my dog… (more)

from
$45
per night
Calendar Recently Updated
18.
I love pets! Pets are family :)Avenues West, Milwaukee, WI, 53233
Dog Boarding, Drop-In Visits, Dog Walking

Megan has been a dog lover since she was a toddler. She grew up with a dog from birth and later helped raise a puppy starting at 10 years old. Over the years … (more)

from
$35
per night
Calendar Recently Updated
19.
Dog lover work from homeWest Allis, WI, 53214
Dog Boarding, Doggy Day Care

Jill took wonderful care of our pup in the week that he stayed with her. I was nervous about being separated from Macchi for the first time since we adopted him… (more)

from
$45
per night
Calendar Recently Updated
20.
Accommodating, responsible, lovingKops Park, MILWAUKEE, WI, 53222
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Sara was such a great choice for my dog. It was very late notice but she really came through and took great care of Bubba. She updated me multiple times during … (more)

from
$34
per night

In Fairfield, Milwaukee, WI, dog lovers trust Rover.com for their pet sitting needs. Over 1,089 pet owners have reviewed pet sitters in Milwaukee, giving them an average rating of 5.0/5 stars. Booking pet sitting in Fairfield can be incredibly affordable, no matter what price range you're looking for. Curious about what it might cost to book pet sitting in Milwaukee on Rover? Check out our average pet sitting rates to get an idea before reaching out and beginning a conversation with a sitter.

Rover.com is the simple, savvy way to find and book Fairfield, Milwaukee drop in pet sitting. It's easy to find the perfect pet sitter. Many sitters have offered pet sitting on Rover for years, and 95% of reviewed stays have received a perfect five-star rating. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Pet sitters on Rover have the option to complete a free background check, which you can see from their background check badge. Pet sitters are booked on Rover every minute of every day, and 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, so you're sure to find the perfect pet sitter in Fairfield, Milwaukee . When you book with one of our trusted pet sitters on Rover you get peace of mind that your home and pets are in loving hands.

A Daily Treat: A Blog by Rover

Rover's got you covered, even when you don't need a dog sitter. 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 Fairfield, 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.

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