House Sitting in Havenwoods, 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
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Sitter Profile Image: Lily S.
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Sitter Profile Image: Lily S.
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1. Lily S.

Compassion, Experience, Flexibility
Milwaukee, WI, 53212
5.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
4 repeat clients
from
$50
per night

This was Lily’s first time house sitting Kai and she exceeded my expectations. She clearly developed a great connection with Kai, did a really nice job keeping me connected/informed, and overall left the house looking like it did when I left. I so much enjoyed her texts, pictures and video clips. Thank you Lily!

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Sitter Profile Image: Jessica Z.
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Sitter Profile Image: Jessica Z.
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2. Jessica Z.

Loving sitter, enthusiastic walker
Lower East Side, Milwaukee, WI, 53202
6.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
93 reviews
31 repeat clients
from
$59
per night

Our family had recently experienced a loss of our other pet. It was a tough time for travel but Jessica supported our other pet while we were away. She kept us informed and made the world of difference being away during such a difficult time.

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Sitter Profile Image: Jeanee S.
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Sitter Profile Image: Jeanee S.
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3. Jeanee S.

Pets just get me!
Menomonee Falls, WI, 53051
8.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
10 reviews
5 repeat clients
from
$40
per night

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.

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Sitter Profile Image: Rachel H.
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Sitter Profile Image: Rachel H.
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4. Rachel H.

** Mission: meet ALL the dogs **
West Allis, WI, 53214
7.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
77 reviews
22 repeat clients
from
$30
per night

Rachel was absolutely amazing! She was really great at communicating and sending lots of pictures throughout the stay. Most notably, she went above and beyond to care for my dog when she was dealing with anxiety while I was gone by going for more walks and time at the dog park. All in all, she will be my sitter of choice whenever I go out of town.

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Sitter Profile Image: Jackie C.
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Sitter Profile Image: Jackie C.
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5. Jackie C.

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

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!!

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Sitter Profile Image: Ali M.
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Sitter Profile Image: Ali M.
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6. Ali M.

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

Ali was so great with both our house and our dog while we were away from home for 6 days! It was obvious from the Meet & Greet that Ali is very comfortable around dogs and a great presence for them - ours is a bit anxious around strangers but immediately warmed up to Ali and seemed very comfortable with her! She was very responsive/communicative (and sent us plenty of pics :)) and did all our house tasks as expected. Will absolutely book Ali again, thanks for taking such good care of our Tito!

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Sitter Profile Image: Katie K.
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Sitter Profile Image: Katie K.
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7. Katie K.

Friend to felines & all animals
Menomonee Falls, WI, 53051
5.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
2 repeat clients
from
$50
per night

Katie was amazing! She played fetch with our dogs, snuggled with our new kitten, and took very good care of our home while we were gone. I would highly recommend Katie for your pet care!

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Sitter Profile Image: Allison S.
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Sitter Profile Image: Allison S.
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8. Allison S.

Guaranteed tail wags!
Avenues West, Milwaukee, WI, 53233
6.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
21 reviews
7 repeat clients
from
$30
per night

Allison did a great job taking care of our 2 fur kids while we were on a weekend getaway. And she kept our house in great condition. Thank you!

Sitter Profile Image: Katelyn A.
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Sitter Profile Image: Katelyn A.
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9. Katelyn A.

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

Katelyn is fantastic! She's incredibly responsive and caring. She came to meet the dogs beforehand, so we could chat which was awesome. One of our dogs in incredibly anxious and wary of strangers, and Katelyn's calm demeanor won her over! We already booked Katelyn for the near future.

Sitter Profile Image: Daniela & Michael P.
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Sitter Profile Image: Daniela & Michael P.
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10. Daniela & Michael P.

Rover 101
Paws Down, the Best in Town!
Milwaukee, WI, 53205
5.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
282 reviews
160 repeat clients
from
$65
per night

Daniela was great with our two little fur babies! We have never left them at home before, and Dani was a godsend, giving us the ability to finally take a vacation! She stayed in our home to make the dogs more comfortable, which was awesome! Dani gave them all the cuddles and attention that my spoiled little dogs needed! Thank you! I hope she is available next time we go on vacay, (now that I feel like we CAN!) Thank you, thank you!!

Sitter Profile Image: Marie H.
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Sitter Profile Image: Marie H.
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11. Marie H.

Your Pets New Favorite Sitter :)
Martin Drive, Milwaukee, WI, 53208
5.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
3 repeat clients
from
$45
per night

Marie is a great sitter and I plan to use her for any future dog sitting needs. I have an elderly dog and it always makes me nervous to leave her, so it’s great to find someone I feel comfortable leaving her with. She gives many updates and pictures too which I love! I highly recommend her.

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Sitter Profile Image: Casandra E.
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Sitter Profile Image: Casandra E.
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12. Casandra E.

Dog mom dog lover
Milwaukee, WI, 53208
5.3 mi. away
House Sitting
5.0 out of 5 stars
5 reviews
from
$33
per night

Cassandra was great! She spent a lot of time with our animals and sent me updates frequently. She went above and beyond to make sure the dogs got a walk in everyday. She left the house exceptionally clean. I felt very at ease knowing she was caring for our pets. I would definitely reach out to her and hire her again. Thanks Cassandra!

Sitter Profile Image: Beth P.
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Sitter Profile Image: Beth P.
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13. Beth P.

Summer/weekend house sitting
Milwaukee, WI, 53212
5.3 mi. away
House Sitting
5.0 out of 5 stars
7 reviews
2 repeat clients
from
$60
per night

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!

Sitter Profile Image: Cindy H.
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Sitter Profile Image: Cindy H.
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14. Cindy H.

Reincarnated Dog Here!
wauwatosa, WI, 53213
4.7 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
30 reviews
8 repeat clients
from
$70
per night

We had a great experience with Cindy. She took care of our furbabies like they were her own. Excellent communication, got daily pictures and updates. I did not have to worry at all will 100% rebook with Cindy.

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Sitter Profile Image: Lance C.
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Sitter Profile Image: Lance C.
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15. Lance C.

Coffee loving dog walker!
Enderis Park, Milwaukee, WI, 53210
3.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$28
per night

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.

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Sitter Profile Image: Ariela M.
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Sitter Profile Image: Ariela M.
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16. Ariela M.

Experienced Veterinary Technician
Grantosa, Milwaukee, WI, 53222
4.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
8 reviews
4 repeat clients
from
$55
per night

Ariela is great! She is super kind and knowledgeable about animals! I felt extremely safe and good about leaving my puppy in her care! I highly recommended her!

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Sitter Profile Image: Hanna B.
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Sitter Profile Image: Hanna B.
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17. Hanna B.

Lover of all furry friends
Whitefish Bay, WI, 53211
4.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
9 reviews
6 repeat clients
from
$50
per night

Hannah did a great job with an overnight stay carrying for our elderly dog and our puppy. The dogs were happy when we got home and the house was well cared for. Thank you, Hannah!

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Sitter Profile Image: Marilia D.
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Sitter Profile Image: Marilia D.
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18. Marilia D.

I've had 7 dogs at once. Trust me.
Estabrook Park, Milwaukee, WI, 53217
3.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
29 reviews
7 repeat clients
from
$65
per night

My kitties had a great time with their new friend Marilia. When Marilia came back to the house, even my shy Chico cat came to see her. So I guess the cats say it all. When they come to the door to greet the pet sitter, that is all I need to say. They love her.

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Sitter Profile Image: Jeff G.
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Sitter Profile Image: Jeff G.
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19. Jeff G.

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

Jeff was a wonderful sitter!! We will absolutely be asking him to dogsit again soon! He came to meet us a week ahead of time to learn about Winnie’s routine, confirmed the sitting the day before, and maintained great communication throughout her care. She has separation anxiety but she calmed down very quickly with Jeff and snuggled him all night. He ensured that timing was flexible and we felt so confident leaving our disabled pup with Jeff! Definitely recommend!

Sitter Profile Image: Jill B.
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Sitter Profile Image: Jill B.
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20. Jill B.

Fun Loving, Honest, and Reliable
Glendale, WI, 53217
2.6 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$65
per night

Hello Pet Owners, Jill is an amazing Dog Walker :) She understands the individual needs of each dogs capabilities to make sure she walks them in a safe and healthy environment. She is patient & a great trainer to make sure they respond to her commands during their exercise routine. Jill will make sure to clean up after the pets and be courteous to other pedestrians walking past the dogs during the walks. Your Pets are in good hands with Jill. Cheers, Dave

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Rover also offers House Sitting in these neighborhoods:

Rover also offers other services in Havenwoods:

Pet parents turn to sitters on Rover.com when they're looking for house-sitting. 1089 owners have reviewed sitters in Havenwoods, 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 house 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 house sitting rates to get an idea before you start a conversation with a house 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.

Rover offers the perfect alternative to dog kennels. The next time you head out of town and need someone to take care of your dog and your home, turn to Rover for your Havenwoods, Milwaukee house sitting needs. On Rover, it's easy to find a loving dog sitter in Havenwoods, Milwaukee, WI who'll give your dog one-on-one attention while you're away, and your dog can enjoy a sweet staycation, right at home. Search from hundreds of trusted Havenwoods house sitters near you, read sitter profiles, and reach out to sitters who seem like a good fit for you and your dog. 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 dog's stay all through Rover: it's easy, safe, and cashless. You get free premium insurance, a team of safety experts available 24/7, and cute photo updates throughout the stay. It's the easiest way to find trustworthy house sitters in Havenwoods, Milwaukee, WI for your dog: people who'll treat him like family.

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