House Sitting in Freedom Village, 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)?
To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

Search Results

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

1. Lily S.

All-Day in Home Care For Critters
Milwaukee, WI, 53212
8.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
12 reviews
8 repeat clients
from
$60
per night
Profile image

Lily was a blessing for our family!! This was the very 1st time we have used rover. We ended up adopting a dog 2 weeks before a preplanned vacation. Lily was so patient and understanding with us as we had very little information about our new family member when we booked with her. We were able to leave her with notes on training our new dog had and we gave her the ability to address and immediate concerns with positive training as she saw fit to help her week go smoothly. Lily was able to help bridge the gap with consistent training while we were gone to ensure we didn’t lose precious training time. She was also able to pivot and help address any behavioral issues or quirks that arose that we were unaware of. She even sent us videos and a great description of how she addressed them. She sent updates everyday and didn’t hesitate to reach out with questions. She put away our grocery order before we arrived and made sure to have the house cleaned up and even washed the towels I left out for her. We definitely will be booking with her again.

Confirmed availability: Juneteenth
Sitter Profile Image: Jeanee S.
Verified Enhanced Background Check
Sitter Profile Image: Jeanee S.
Verified Enhanced Background Check

2. Jeanee S.

Star Sitter
Pets just get me!
Menomonee Falls, WI, 53051
6.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
12 reviews
6 repeat clients
from
$50
per night
Profile image

Jeanee is amazing! She took the best care of our pets, provided frequent updates, and was honestly a joy to communicate with! She will most definitely be my first choice for future pet sitting needs.

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

3. Jessica Z.

Star Sitter
Loving sitter, enthusiastic walker
Lower East Side, Milwaukee, WI, 53202
9.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
105 reviews
35 repeat clients
from
$59
per night
Profile image

Jessica has taken care of our cats, pup, and home while we’re traveling multiple times. She is such a wonderful sitter, and we’re really grateful to have found her. We highly recommend her to anyone looking for someone reliable, communicative, and wonderful to work with!

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

4. Jackie C.

Looking forward to meet your pet!
Brewer's Hill, Milwaukee, WI, 53212
9.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
74 reviews
22 repeat clients
from
$65
per night
Profile image

Jackie is incredible! Great communication, she is punctual, sent so many pictures, and best part was my pup was so happy. I definitely recommend! Thanks again Jackie!!

Calendar Recently Updated
Sitter Profile Image: Ali M.
Verified Background Check
Sitter Profile Image: Ali M.
Verified Background Check

5. Ali M.

I love dogs, cats, and herptiles !
Milwaukee, WI, 53211
8.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
37 reviews
19 repeat clients
from
$65
per night
Profile image

I would absolutely book with Ali again! We did a meet and greet before and my dog absolutely loved Ali. I got text updates and photos while I was away too which was awesome. Ali is great - highly recommend!

Confirmed availability: Juneteenth
Sitter Profile Image: Cody C.
Verified Enhanced Background Check
Sitter Profile Image: Cody C.
Verified Enhanced Background Check

6. Cody C.

Great Pyrenees lover
Cedarburg, WI, 53012
8.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
10 reviews
3 repeat clients
from
$47
per night
Profile image

Cody is a great caregiver. This was the second time we'd utilized their services. Our dogs were well cared for and communication was excellent. We will definitely be booking again soon.

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

7. Abby S.

Owner away? I walk, sit and stay.
Cedarburg, WI, 53012
9.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
2 repeat clients
from
$55
per night
Profile image

Abby stayed at our house and watched a new dog (1 month with us) while we took our second dog with us. We didn't want to leave both dogs together for the first time as we are still learning how they interact. Everything went great, plenty of updates and pics. No issues despite us not quite knowing how the new dog would behave with us gone. He's a big Bullmastiff and loves attention. Abby wasn't intimidated by a big dog. House and dog were just as we left it. Definitely will use her again for house/dog sitting.

Calendar Recently Updated
Sitter Profile Image: Beth P.
Verified Enhanced Background Check
Sitter Profile Image: Beth P.
Verified Enhanced Background Check

8. Beth P.

Summer/weekend house sitting
Milwaukee, WI, 53210
7.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
2 repeat clients
from
$60
per night
Profile image

Beth is a Godsend! She stayed at our home for five days and took exceptional care of our many animals: our dog, cats, rabbits, Guinea pig and fish. We came back to a tidy house and relaxed animals. She took our dog on two mile walks and sent photos and updates regularly. We couldn’t have asked for a better sitter. She is kind and considerate. We highly recommend Beth!

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

9. Amber S.

Experienced Sitter & Animal Lover
Mequon, WI, 53092
5.8 mi. away
House Sitting, Dog Walking
5.0 out of 5 stars
12 reviews
1 repeat client
from
$50
per night
Profile image

Everything went great and Amber was very great with communicating with us. Arrived home to all 4 pets happy and healthy and our house in the same condition we left it:)

Calendar Recently Updated
Sitter Profile Image: Debbi O.
Verified Enhanced Background Check
Sitter Profile Image: Debbi O.
Verified Enhanced Background Check

10. Debbi O.

Rover 101
Star Sitter
Care for Your Furry Family Member!
THIENSVILLE, WI, 53092
4.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
120 reviews
43 repeat clients
from
$68
per night
Profile image

Debbi was great and very attentive with my dogs while I was away for the weekend! Even though she did not stay over, my dogs were walked and given many exercises to work out any wiggles. She provided many updates and even suggested tips and tricks for my pup with separation anxiety. I would 1000% book dog-sitting with her again in the future.

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

11. Nicole K.

Dog loving teacher off for summer!
Germantown, WI, 53022
7.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
10 reviews
2 repeat clients
from
$30
per night

Nicole is excellent with dogs. She is caring and compassionate with dogs and is very reliable.. I know my dog is always in good hands with Nicole!

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

12. Tegra R.

Star Sitter
The right Mama to care 4 your baby
Milwaukee, WI, 53223
2.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
22 reviews
10 repeat clients
from
$28
per night
Profile image

Tegra made me feel comfortable with leaving my senior pup. She provided photos and communicated with me when the many times I reached out to check in on Tedi. I came home to a happy pup!

Sitter Profile Image: Katelyn A.
Verified Enhanced Background Check
Sitter Profile Image: Katelyn A.
Verified Enhanced Background Check

13. Katelyn A.

Eat. Play. Love.
Bayside, WI, 53217
4.0 mi. away
House Sitting, Dog Walking
5.0 out of 5 stars
11 reviews
9 repeat clients
from
$65
per night
Profile image

Katelyn was friendly and easy to communicate with. She sent us updates and pics of our pups every other day while we were on vacation (she also seemed respectful of wanting to let us truly enjoy our time away). The house was left very clean when we returned and our boys were happy and loved!

Calendar Recently Updated
Sitter Profile Image: Jeff G.
Verified Enhanced Background Check
Sitter Profile Image: Jeff G.
Verified Enhanced Background Check

14. Jeff G.

Care for dogs like they're children
Glendale, WI, 53209
3.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
38 reviews
10 repeat clients
from
$68
per night
Profile image

Jeff was amazing! We were very nervous about a dog sitter having never used one before. Jeff was great at making us feel comfortable and at ease during our week long trip overseas. The daily updates were greatly appreciated. Our dog can take time to warm up but seemed to like Jeff right away. At a certain point we thought our dog was having a better time than us on our trip. He also made our cats very comfortable. When we got home the place was spotless, going above and beyond to give us a nice home to return to. We will definitely use Jeff in the future for any of our pet sitting needs.

Confirmed availability: Juneteenth
Sitter Profile Image: Dawn U.
Verified Enhanced Background Check
Sitter Profile Image: Dawn U.
Verified Enhanced Background Check

15. Dawn U.

Laid back furbaby care.
Menomonee Falls, WI, 53051
4.9 mi. away
House Sitting, Drop-In Visits
5.0 out of 5 stars
1 review
from
$50
per night

About: I am currently accepting clients who want in-home or drop-in care. No cats please. I have been a dog owner for over 25 years, as well as growing up with dogs in my home. I love to follow their lead with their activity needs - whether it be a rowdy romp in the back yard, a energetic walk (weather permitting) or a relaxing day of being a couch potato. We currently have 2 rescue furbabies who gets along with other dogs and like to interact with our fur guests. Will only be caring for one furbaby family at a timne. No other pets in the home, no children and no smoking. We have a fenced in back yard and are not far from several dog parks, if that is an approved activity by the dog owner. I have a very flexible part-time schedule, so I can usually work around your schedule and care needs. For in home care I will come and go throughout the day with frequent check ins per your preference, as well as meals and overnight care. I am currently offering drop-in care for potty breaks and/or meals plus play time, and in your home days and overnight pet care. No cats in the home please.

Confirmed availability: Juneteenth
Sitter Profile Image: Odessa B.
Verified Enhanced Background Check
Sitter Profile Image: Odessa B.
Verified Enhanced Background Check

16. Odessa B.

Can't wait to meet your furbaby!
Brown Deer, WI, 53223
0.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
4 reviews
from
$63
per night

Odessa has pet sit for me multiple times, and has done a wonderful job in doing so. At the time I had a Great Dane/English Mastiff mix (Koba), 2 chihuahuas (Bella and Beast), and a boxer (Sparky). Koba had chronic ear infections and a fungal skin infection, that would flare up. Odessa would keep up with cleaning his ears, giving the proper dosage of medicine, and bathing for his skin. She also maintained a proper feeding schedule for all of my dogs. I’ve known Odessa, for a long time and know she cares very deeply about pets, even those that aren’t hers. She is an incredibly hard worker, and anybody would be lucky to have her take after their pets.

Confirmed availability: Juneteenth
Sitter Profile Image: Jenn L.
Verified Enhanced Background Check
Sitter Profile Image: Jenn L.
Verified Enhanced Background Check

17. Jenn L.

I like big mutts, and I cannot lie.
Mill Valley, Milwaukee, WI, 53224
4.2 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
6 reviews
2 repeat clients
from
$63
per night
Profile image

Jenn was so great with my very spoiled Great Pyrenees at her home Christmas weekend. She was so good at communicating and sending pictures the weekend she was with him. I felt she genuinely cared so much about Koda and us too. I will definitely be contacting her again on our next travels. Thanks again Jenn!

Confirmed availability: Juneteenth
Sitter Profile Image: Clare K.
Verified Enhanced Background Check
Sitter Profile Image: Clare K.
Verified Enhanced Background Check

18. Clare K.

No animal is too big or small!
Mequon, WI, 53097
4.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
1 repeat client
from
$50
per night

About: I have worked with all animals, from dogs and cats, to rats, turtles, hamsters, rabbits and fish! I have worked at a Humane Society, and love volunteering my time to work with animals. I have experience administering medication, as well as working with animals that have a bit of an attitude. I enjoy training dogs, and sitting on the coach and watching a movie together! While I have a full time job, I am able to commit all of my other time to petsitting! I do not board in my home, but I have a reliable car that allows me to travel and spend the night in your home. That means less stress on your furry companions! While I do not provide care in my home, I prefer to meet families and their animals in advance so that we are able to discuss the little things about your animals. I love getting to know their quirks, and the best way to do that is talking to owners. I enjoy long walks with the dogs, and snuggling with cats and other animals!

Sitter Profile Image: Olivia W.
Verified Enhanced Background Check
Sitter Profile Image: Olivia W.
Verified Enhanced Background Check

19. Olivia W.

Passionate Pet Enthusiast
Heritage Heights, Milwaukee, WI, 53224
3.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
2 reviews
from
$29
per night

We cannot give enough praise to Olivia for watching our three dogs over winter break in 2023. We have one rescue, Rex, who was abused before he became part of our family and he is very protective of us and aggressive towards strangers. With her experience and interest in dogs, Olivia knew exactly how to interact with Rex and it only took an hour or so before they were good buddies! I'm sure our mouths dropped in amazement, because that really had never happened before. Throughout or trip, Olivia kept us well informed and sent us pictures of the pups happily hanging out with her. Olivia is always welcome back at our home and I thinks the dogs already adopted her anyway! Olivia is a lovely person who is great with dogs. She is easily 11 out of 10 stars!

Confirmed availability: Juneteenth
Sitter Profile Image: Jessica s.
Verified Enhanced Background Check
Sitter Profile Image: Jessica s.
Verified Enhanced Background Check

20. Jessica s.

Provide care and comfort!
Whispering Hills, Milwaukee, WI, 53223
0.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
7 reviews
from
$32
per night

Jessica is someone you can trust with your pup. She took care of my Chihuahua for 3 days, received good communication, and everything went smooth. Will be contacting her again in the near future!

Search Map

Rover also offers House Sitting in these neighborhoods:

Rover also offers other services in Freedom Village:

Pet parents in Freedom Village, Milwaukee, WI love dog sitters on Rover.com. 1089 owners have reviewed sitters in Milwaukee, giving them an average rating of 5.0/5. 95% of reviewed stays have received a perfect 5-star rating, and 92% of pet parents live within a short drive of a dog sitter on Rover. That means Rover is the perfect place to go when you're search for loving, safe care for your best friend. Wondering how much you can expect to pay for a day on Rover? Check out our average house sitting rates to get an idea before you start a conversation with a sitter.

Never beg a friend to watch your dog again. With Rover, you can find your the perfect Freedom Village house sitter in seconds. When you book house sitting on Rover, your dog will enjoy a loving, relaxing stay in their own home. If you're looking for care for pets other than dogs, you can find a pet sitter who offers care for cats, caged pets, and even horses. No matter what, you'll know that your pet is getting loving care. By removing common pet care obstacles, Rover ensures dogs nationwide are happy and well-cared for even when their human is away, and empowers dog lovers to live happy and fulfilling lives. Founded on the belief that everyone should have the opportunity to experience the unconditional love of a dog, Rover makes it easy for you to reach trusted house sitters in Freedom Village, Milwaukee who can provide the care your dog needs, when they need it.

House Sitting