House Sitting in Havenwoods, Milwaukee

Find a loving dog sitter to watch your dog overnight in your home.

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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
7 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.

Star Sitter
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
97 reviews
33 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.

Star Sitter
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
12 reviews
5 repeat clients
from
$40
per night

Jeanee was the most incredible dog sitter we have ever had. Lilly got to go on many adventures and walks. Once Lilly got to know Jeanne, she asked if Lilly could with on errands, Lilly loves car rides. I suggested if she wanted to take her home to introduce Lilly to her furbaby - she could give it a shot. Keeping in mind that Lilly is food & person possessive and can be aggressive with older dogs, but Jeanee knew exactly how to handle her. It worked out so well that Lilly stayed at her home the remaining 6 days! Her dog really enjoyed having another dog around. She took Lilly's bed, food, treats and favorite stuffie to her house, so Lilly felt right at home. It really helped Lilly, she wasn't constantly watching for us, missing us and she ate so well. We had constant communication and updates. Anytime I sent a message she responded very quickly. This was the most confident and secure we have ever felt on our vacation. It made for a very relaxing and fun vacation. Knowing we now have an incredible sitter for Lilly, we are looking to book future vacations. 100% recommend!! Your furbaby will be in incredible hands!!

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Sitter Profile Image: Katie K.
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Sitter Profile Image: Katie K.
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4. 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
6 reviews
3 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!

Sitter Profile Image: Rachel H.
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Sitter Profile Image: Rachel H.
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5. Rachel H.

Star Sitter
** 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 goes above and beyond every time she house sits for us. I hate leaving my pets, but I feel so much better knowing she’s there. She keeps us updated every day, and we always come home to a very happy dog and cat!

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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 is amazing! Very nice, punctual and great communicator! She sent lots of pictures. When I got home my house waa as clean as I left it, waa like no-one had been there. My puppy was super happy too. Definitely recommend and I will use Ali again

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jackie C.
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Sitter Profile Image: Jackie C.
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7. 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
69 reviews
22 repeat clients
from
$65
per night

I am a first time user of Rover.com and was nervous about leaving my dogs with someone the dogs and I didn't know. The meet and greet with Jackie helped put my mind at ease. Jackie did an amazing job taking care of my 2 dogs at my house for a little over 2 weeks. One the dogs does not trust people. It did not take him long to warm up to her, which says that she has good, calm energy. It was great that the dogs could be at home and she would come to them. I think this made the dogs less anxious. She sent us great pictures and promptly responded to texts. I would highly recommend Jackie and I would definitely use her again.

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Sitter Profile Image: Daniela & Michael P.
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Sitter Profile Image: Daniela & Michael P.
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8. 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 so great with my dog Joanie. She came over for a meet and greet beforehand, which I really appreciated. She took her for a walk and was great with her. She took lots of photos, sent notes and was really responsive. I will absolutely have her watch Joanie again!

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Sitter Profile Image: Riley N.
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Sitter Profile Image: Riley N.
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9. Riley N.

Star Sitter
Animal lover since birth! PETS=FAM
Milwaukee, WI, 53212
5.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
10 reviews
4 repeat clients
from
$60
per night

Our boys are crabby old men and pretty high maintenance. Riley won them over though! She was so patient and they eventually started warming up to her. Will definitely rebook!

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Sitter Profile Image: Danica V.
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Sitter Profile Image: Danica V.
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10. Danica V.

Star Sitter
PAWsitively reliable med student!
Wauwatosa, WI, 53226
5.9 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
20 reviews
7 repeat clients
from
$46
per night

Danica is consistent and professional throught the Rover experience. I've been burned before with previous dog sitters that have been inconsistent and unresponsive, but Danica is always punctual and quick to respond to any concerns/needs. I trust her to be with my pups when they are most stressed and take care of them when I'm away. That peace of mind is priceless and I love having Danica over to watch my pups.

Sitter Profile Image: Beth P.
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Sitter Profile Image: Beth P.
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11. 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!

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Sitter Profile Image: Erica L.
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Sitter Profile Image: Erica L.
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12. Erica L.

Rover 101
Pro. Dog Handler with WFH job!
Park West, Milwaukee, WI, 53206
4.0 mi. away
House Sitting, Drop-In Visits
5.0 out of 5 stars
84 reviews
29 repeat clients
from
$75
per night

Erica was so great with our pups! Even taking care of a new puppy, dealing with all that chaos, potty training etc. We got lots of pictures, updates and communication, and look forward to having her stay with our pups again.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Sam P.
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Sitter Profile Image: Sam P.
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13. Sam P.

Rover 101
Loving, Responsive, Knowledgeable.
Hawthorne Glen, Milwaukee, WI, 53208
5.4 mi. away
Boarding, House Sitting, Drop-In Visits
5.0 out of 5 stars
120 reviews
58 repeat clients
from
$80
per night

Sam far surpassed our expectations! Noodles is a “handful” to say the least! He’s not quite a year and a half and still acts like a puppy in all ways. He’s also very hesitant around other dogs, which comes off as aggressive. Her first of many pictures sent to us was Noodles “calmly” sitting right in the middle of three others dogs during a pack walk! He came out of this weekend with new friends, human and four-leggers! We’ve already booked Sam for another weekend of “Noodle sitting” as well as dog walking and training! Couldn’t be happier for us and Noodles~ The McBride’s

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
31 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.

Confirmed availability: Memorial Day Weekend
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
3 reviews
from
$38
per night

Lance has watched my dog Lupe a number of times. My dog loves him! He gets a lot of love, walks, and hang out time. He's very responsible, asks all the right questions and provides updates to make sure my wife and I are never concerned. I highly recommend Lance if you want peace of mind while you're away.

Sitter Profile Image: Katelyn A.
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Sitter Profile Image: Katelyn A.
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16. 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.

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Sitter Profile Image: Ariela M.
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Sitter Profile Image: Ariela M.
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17. 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!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Marilia D.
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Sitter Profile Image: Marilia D.
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18. Marilia D.

Star Sitter
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

Marilia did a great job staying with our pup and walking , feeding, playing and just being there for him. She spent 3 nights and fleas very responsive and respectful of our home . Was thankful she was available, Will hire again .

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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

So happy we found Jeff. He not only took care of our little fur angels, but he took packages for us. The girls loved him, he stayed the whole weekend. When we returned the girls were calm and content, and Jeff even left a detailed log of their weekend activities. Happy to say we will book again!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Lillian R.
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Sitter Profile Image: Lillian R.
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20. Lillian R.

Owner away? I walk, sit and stay!
Lincoln Park, Milwaukee, WI, 53209
2.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
15 years of experience
from
$40
per night

About: Growing up with animals has given me a lifetimes worth of pet care experience! Determined to care for your furry family as if they are my own. I currently have an open schedule to assist with whatever your pet family may need. Walks, check ins, overnights, I can accommodate them all for you! I have experience taking care of my own dog and cats, all rescues from different backgrounds. I am able to adapt my care style to fit the needs of your pets.

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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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