House Sitting in Freedom Village, Milwaukee

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Top rated Freedom Village house sitters

1 / 1
Sitter Profile Image: Addoris D.
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Addoris D.
from
$50
per night
5 out of 5.0 stars
10 reviews
1 repeat client
5 years of experience
Lower East Side, Milwaukee, WI, 53202

Did a great job managing our house full of animals while we were away for two weeks. We came home to happy healthy animals, and I could tell they'd been well-cared for!

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Nikki C.
Sitter Profile Image: Ashley W.
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Ashley W.
from
$45
per night
5 out of 5.0 stars
15 reviews
5 repeat clients
10 years of experience
Washington Heights, Milwaukee, WI, 53208

As usual, a smooth transaction/stay! We absolutely love Ashley. She is very flexible, punctual and most importantly - clean (we only do home stays). Our pup is always happy to see Ashley and enjoys her company very much.

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Kristina S.
Sitter Profile Image: Paul S.
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Paul S.
Star Sitter
from
$50
per night
5 out of 5.0 stars
47 reviews
23 repeat clients
20 years of experience
Germantown, WI, 53022

Paul took great care of our two puppies while we were on vacation! He sent multiple updates daily with pictures, and they were extremely well cared for. We never had to worry about them, and we were able to enjoy our vacation! I would leave my pets with Paul anytime!!

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Brian or Sarah L.
Sitter Profile Image: Cody C.
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Cody C.
Star Sitter
from
$55
per night
5 out of 5.0 stars
88 reviews
23 repeat clients
5 years of experience
Cedarburg, WI, 53012

Cody was great with our dogs. She communicated and updated me on them regularly. She took care of the house as well. I would use her again and recommend her!

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Kayla C.
Sitter Profile Image: Tegra R.
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Tegra R.
Star Sitter
from
$40
per night
5 out of 5.0 stars
43 reviews
14 repeat clients
30 years of experience
Milwaukee, WI, 53223

Tegra was amazing with our quirky doggo. We couldn't have asked for a better experience. Tegra provided updates and loved on our pup while we were away for almost two weeks. Upon returning home, we could tell puppers was anxiety free and our home was in excellent order. 1000% would use Tegra again.

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Bret K.
Sitter Profile Image: Jamila M.
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Jamila M.
Star Sitter
from
$57
per night
5 out of 4.9 stars
83 reviews
24 repeat clients
27 years of experience
Washington Heights, milwaukee, WI, 53208

Jamila was responsible, respectful and communicative. She was on time and sent plenty of updates. Our dogs seemed to be very comfortable with her.

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Claire M.
Sitter Profile Image: Jeanee S.
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Jeanee S.
from
$65
per night
5 out of 5.0 stars
18 reviews
8 repeat clients
25 years of experience
Menomonee Falls, WI, 53051

Jeanne is AMAZING. We got home to happy dog, clean house, an awesome day by day journal, and near daily check ins (that we kept requesting and appreciating). Jeanne is an awesome communicator, kept our house in immaculate condition, and all was well during our vacation. We will 100% use her again and knowing we have a great sitter for Winnie makes me even more inclined to book a future vacation. 100% recommend.

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Lizzy K.
Sitter Profile Image: Charles B.
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Charles B.
Star Sitter
from
$28
per night
5 out of 5.0 stars
57 reviews
9 repeat clients
17 years of experience
Fox Point, WI, 53217

Could not recommend more! Was amazing with my dog and when I got stuck and had to stay an extra day got me out of a tight spot by continuing to look after my dog! I would recommend to anyone and will be using again!

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Vicki W.
Sitter Profile Image: Amanda C.
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Amanda C.
from
$65
per night
5 out of 5.0 stars
13 reviews
2 repeat clients
8 years of experience
Milwaukee, WI, 53213

Amanda was an amazing in-house sitter for our dog. This was our first time booking on Rover, and our little guy can be a handful sometimes, but Amanda immediately put our worries at ease. Our meet & greet helped acclimate everyone and once we were on our trip, I appreciated the daily updates with photos. When our flight was delayed, she was extremely flexible about staying another night in case we couldn't make it back. The communication was fantastic and she went above and beyond with our dog's care. She is also a very polite house guest. I couldn't recommend Amanda enough and I would 100% book with her in the future.

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Delaney B.
Sitter Profile Image: Jaclyn O.
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Jaclyn O.
from
$50
per night
5 out of 4.9 stars
82 reviews
36 repeat clients
25 years of experience
Park Knoll, Milwaukee, WI, 53225

Jaclyn was awesome! She took tons of pictures for me, and gave tons of love to to my two pups. I couldn’t ask for anything better than that! Thank you

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Carolyn B.
Sitter Profile Image: Katelyn A.
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Katelyn A.
Star Sitter
from
$85
per night
5 out of 4.9 stars
21 reviews
14 repeat clients
8 years of experience
Bayside, WI, 53217

Katelyn is great! We’ve had her to our house twice now to stay overnight with our girls. She sends updates throughout the stay and our girls always seem to be very happy after a weekend with her.

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Michaela M.
Sitter Profile Image: Joan P.
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Joan P.
from
$35
per night
5 out of 5.0 stars
9 reviews
1 repeat client
20 years of experience
Grantosa, Milwaukee, WI, 53222

Joan stayed for 3 days with my dog Charlie at my house. She was timely, responsive and took excellent care of both my home and my dog. I would absolutely ask Joan to pet/house sit for me again. Charlie is an old guy who can have separation anxiety causing him to pee in the house. Joan did such a great job making him feel safe and happy.

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Jessica R.
Sitter Profile Image: Jasmine T.
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Jasmine T.
Star Sitter
from
$55
per night
5 out of 5.0 stars
15 reviews
6 repeat clients
5 years of experience
Timmerman West, Milwaukee, WI, 53225

Jasmine communicated with us frequently about the things that concerned us most. Our girls enjoyed their time with her and behaved well. She made sure medication was administered as requested and kept our little one in her cone. We would recommend Jasmine.

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Michele M.
Sitter Profile Image: Stephen & Wipawee D.
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Stephen & Wipawee D.
from
$95
per night
5 out of 5.0 stars
49 reviews
19 repeat clients
5 years of experience
Dineen Park, Milwaukee, WI, 53216

Amelie and Stephen sat for our dog, Dexter, and our cat, Lucy, while we were out of town for a weekend. We felt incredibly assured during our time away that our pets were being well cared for and provided with lots of love. We were given consistent updates on how the stay was going and what our animals were up to. They graciously provided many pictures during the stay that continued to provide us with a sense of calm knowing our fur babies were in very good hands. We have already rebooked with them for a future trip, and will continue to do so! We cannot recommend them enough!

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Kaitlyn F.
Sitter Profile Image: Jeff G.
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Jeff G.
from
$70
per night
5 out of 4.9 stars
53 reviews
13 repeat clients
15 years of experience
Glendale, WI, 53209

Jeff stayed at our house to take care of our dog Frankie while we were on vacation. After a day of traveling, it was so nice to come home to a happy, healthy Frankie and a house that looked the same, or maybe even better than when we left!! Jeff sent updates on Frankie to us often with videos and pictures! It is obvious that he really cares for and loves animals!! I am always a little nervous leaving my house and loved dog to someone else for an entire week, but I won't feel that way next time we ask Jeff!! He was absolutely great with Frankie!

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Mark M.
Sitter Profile Image: Yolanda W.
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Yolanda W.
Star Sitter
from
$90
per night
5 out of 5.0 stars
144 reviews
57 repeat clients
35 years of experience
Brown Deer, WI, 53223

About: Animals have always been a part of my life. They show us so much love. Who are we not to give it back in return. Since the passing of our long time dog (Roc,15) we’ve been watching our friends and family dogs while they’re out of town. In each case the owners return with their dogs a little hesitant about wanting to return home. LOL. I work from home and I have no plans of switching to another job that would require me to go into the office. Therefore, I have plenty of time to play with your big and little babies. I also like to take walks at minimum twice a day. This is a perfect time for your fur babies to stretch their legs. After a nice long walk I clean their paws to make sure they leave the yucky stuff outside. I have a designated area where they can sleep. However, I like to keep them close to me during the day while I’m working. I think it sets them up for a positive visit. They immediately become part of the family. I also have the flexibility to take them out throughout the day. There is a highly recommended veterinarian within a two minute driving distance and maybe a ten minute walk in the event of an emergency.

Sitter Profile Image: Selena M.
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Selena M.
from
$28
per night
1 repeat client
8 years of experience
Calumet Farms, Milwaukee, WI, 53224

About: I often take care of my mom’s senior dog. He requires a lot of attention due to his health and getting around. I love to be an assistant to him. I work from home on Mondays and Fridays and I am often free during the weekends. I can make sure I have enough time available for any of your needs. I live in a pet friendly apartment. I don’t live near any busy streets and can take a dog on a nice stroll around my neighborhood. I can keep animals in crates, if requested.

Sitter Profile Image: Cynthia E.
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Cynthia E.
from
$28
per night
40 years of experience
Mequon, WI, 53092

About: I have many years of pet care experience, I grew up on a farm,I have a calm caring approach I'm dependable and full of heart! I'm currently in between jobs so I have plenty of time for your fur baby for walks , belly rubs, treats & tail wags everything we're together! Safety is always a priority!! Love and affection & pets happiness is very important to me - treat them like family - because they are!

Sitter Profile Image: Perseus M.
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Perseus M.
Star Sitter
from
$85
per night
5 out of 5.0 stars
34 reviews
7 repeat clients
15 years of experience
Milwaukee, WI, 53223

About: 🐾 Buddy’s Boarding — Where Pets Feel at Home Hi! We're Percy and Darik — two experienced pet lovers offering premium dog boarding from our home in Brown Deer. One of us is home full-time, giving us the flexibility to provide reliable, personalized care for every pup we host. 🐶 Why pet parents love Buddy’s Boarding: • Spacious yard with a partially fenced area for play and potty breaks • Flexible pick-up/drop-off times with clear communication • Convenient location — just 10 minutes from I-43 and Hwy 41 • Quiet, dog-friendly neighborhood with sidewalks and green space • Two attentive, dog-experienced sitters under one roof • Access to a dog-friendly pool (summer months only, supervised, optional) ✨ Our Story Buddy’s Boarding is named after the dog that started it all. At 10 years old, I found Buddy as a stray near my dad’s business and begged my mom to let us keep him. She said yes — and from that moment on, my bond with animals was sealed. That connection still fuels the love and care we give every dog who stays with us. Whether your pup is active and playful or chill and cuddly, we tailor each stay to their needs. Let us know your dog’s routine and preferences — we’re happy to accommodate. We can’t wait to welcome your dog into our home. 🐾 👉 Send us a request to get started — we’d love to meet your pup! Pet care fits seamlessly into our daily routine. My partner Darik works from home as a graphic designer, so there’s always someone present to supervise and care for the dogs. I work part-time as a dog handler in the mornings, which means I bring both experience and structure to our day. Between the two of us, we’re able to give pets plenty of attention, play, and potty breaks throughout the day — with flexibility for early drop-offs, midday walks, and evening wind-downs. It’s a rhythm that’s built around making dogs feel safe, happy, and at home. Safety We prioritize safety by pet-proofing our home, keeping hazardous items out of reach, and supervising pets at all times. Whether it’s backyard play or a leashed walk, we ensure dogs are always in secure, pet-friendly environments. We also tailor safety measures to each dog’s personality, energy level, and needs. Trust Building trust with both pets and their people is at the heart of what we do. We take time to understand each dog’s routine and preferences, and we maintain regular communication with pet parents — sharing updates and photos so they always feel connected and confident in our care. Environment Our home is clean, cozy, and designed with dogs in mind — with plenty of space to move, comfy spots to rest, and loving attention throughout the day. We create a calm, positive environment and adjust our approach to meet each dog where they’re at. If we’re caring for pets in their home, we follow their routine closely to ensure they feel safe, secure, and comfortable in their own space.

Sitter Profile Image: Jessica s.
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Jessica s.
from
$36
per night
5 out of 5.0 stars
33 reviews
5 repeat clients
10 years of experience
Whispering Hills, Milwaukee, WI, 53223

About: Have owned all types of animals all my life and grown up with them. Always ready to meet a new friend and establish new animal relationships I work an 8-5 job with an hour lunch break. I can follow strict schedules and maintain flexibility. I can accommodate special needs. I am home most nights and weekends. I can provide love and care to your pet and a comforting environment. Playing with them and marking sure they are happy and healthy in different settings

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Sitter Profile Image: Addoris D.
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Sitter Profile Image: Addoris D.
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Addoris D.

Queer Friendly & Energetic Sitter
Lower East Side, Milwaukee, WI, 53202
10.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5 out of 5.0 stars
10 reviews
1 repeat client
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Did a great job managing our house full of animals while we were away for two weeks. We came home to happy healthy animals, and I could tell they'd been well-cared for!

Availability updated yesterday
Sitter Profile Image: Ashley W.
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Sitter Profile Image: Ashley W.
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Ashley W.

Active person loves active dogs
Washington Heights, Milwaukee, WI, 53208
8.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$45
per night
5 out of 5.0 stars
15 reviews
5 repeat clients
Profile image

As usual, a smooth transaction/stay! We absolutely love Ashley. She is very flexible, punctual and most importantly - clean (we only do home stays). Our pup is always happy to see Ashley and enjoys her company very much.

Availability updated 42 days ago
Sitter Profile Image: Paul S.
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Sitter Profile Image: Paul S.
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Paul S.
Star Sitter

Home full time, flexible schedule
Germantown, WI, 53022
6.9 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5 out of 5.0 stars
47 reviews
23 repeat clients
Profile image

Paul took great care of our two puppies while we were on vacation! He sent multiple updates daily with pictures, and they were extremely well cared for. We never had to worry about them, and we were able to enjoy our vacation! I would leave my pets with Paul anytime!!

Availability updated today
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Cody C.
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Sitter Profile Image: Cody C.
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Cody C.
Star Sitter

Great Pyrenees lover
Cedarburg, WI, 53012
8.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$55
per night
5 out of 5.0 stars
88 reviews
23 repeat clients
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Cody was great with our dogs. She communicated and updated me on them regularly. She took care of the house as well. I would use her again and recommend her!

Availability updated 9 days ago
Sitter Profile Image: Tegra R.
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Sitter Profile Image: Tegra R.
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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
from
$40
per night
5 out of 5.0 stars
43 reviews
14 repeat clients
Profile image

Tegra was amazing with our quirky doggo. We couldn't have asked for a better experience. Tegra provided updates and loved on our pup while we were away for almost two weeks. Upon returning home, we could tell puppers was anxiety free and our home was in excellent order. 1000% would use Tegra again.

Availability updated 4 months ago
Sitter Profile Image: Jamila M.
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Sitter Profile Image: Jamila M.
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Jamila M.
Rover 101
Star Sitter

Neighbor providing additional love
Washington Heights, milwaukee, WI, 53208
8.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$57
per night
5 out of 4.9 stars
83 reviews
24 repeat clients
Profile image

Jamila was responsible, respectful and communicative. She was on time and sent plenty of updates. Our dogs seemed to be very comfortable with her.

Availability updated 11 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Jeanee S.
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Sitter Profile Image: Jeanee S.
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Jeanee S.

Pets just get me!
Menomonee Falls, WI, 53051
6.0 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$65
per night
5 out of 5.0 stars
18 reviews
8 repeat clients
Profile image

Jeanne is AMAZING. We got home to happy dog, clean house, an awesome day by day journal, and near daily check ins (that we kept requesting and appreciating). Jeanne is an awesome communicator, kept our house in immaculate condition, and all was well during our vacation. We will 100% use her again and knowing we have a great sitter for Winnie makes me even more inclined to book a future vacation. 100% recommend.

Availability updated today
Sitter Profile Image: Charles B.
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Sitter Profile Image: Charles B.
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Charles B.
Star Sitter

Pet lover ready 2 watch your bestie
Fox Point, WI, 53217
5.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$28
per night
5 out of 5.0 stars
57 reviews
9 repeat clients
Profile image

Could not recommend more! Was amazing with my dog and when I got stuck and had to stay an extra day got me out of a tight spot by continuing to look after my dog! I would recommend to anyone and will be using again!

Availability updated 13 days ago
Sitter Profile Image: Amanda C.
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Sitter Profile Image: Amanda C.
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Amanda C.
Rover 101

Trusted, Loving Care for Your Pets!
Milwaukee, WI, 53213
7.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$65
per night
5 out of 5.0 stars
13 reviews
2 repeat clients
Profile image

Amanda was an amazing in-house sitter for our dog. This was our first time booking on Rover, and our little guy can be a handful sometimes, but Amanda immediately put our worries at ease. Our meet & greet helped acclimate everyone and once we were on our trip, I appreciated the daily updates with photos. When our flight was delayed, she was extremely flexible about staying another night in case we couldn't make it back. The communication was fantastic and she went above and beyond with our dog's care. She is also a very polite house guest. I couldn't recommend Amanda enough and I would 100% book with her in the future.

Availability updated 6 days ago
Sitter Profile Image: Jaclyn O.
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Sitter Profile Image: Jaclyn O.
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Jaclyn O.

The Friendly, Neighborhood Pet Lady
Park Knoll, Milwaukee, WI, 53225
4.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$50
per night
5 out of 4.9 stars
82 reviews
36 repeat clients
Profile image

Jaclyn was awesome! She took tons of pictures for me, and gave tons of love to to my two pups. I couldn’t ask for anything better than that! Thank you

Availability updated 7 days ago
Sitter Profile Image: Katelyn A.
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Sitter Profile Image: Katelyn A.
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Katelyn A.
Star Sitter

Eat. Play. Love.
Bayside, WI, 53217
4.0 mi. away
House Sitting, Dog Walking
from
$85
per night
5 out of 4.9 stars
21 reviews
14 repeat clients
Profile image

Katelyn is great! We’ve had her to our house twice now to stay overnight with our girls. She sends updates throughout the stay and our girls always seem to be very happy after a weekend with her.

Availability updated 2 days ago
Sitter Profile Image: Joan P.
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Sitter Profile Image: Joan P.
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Joan P.

Dogs are my BFF!
Grantosa, Milwaukee, WI, 53222
6.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$35
per night
5 out of 5.0 stars
9 reviews
1 repeat client
Profile image

Joan stayed for 3 days with my dog Charlie at my house. She was timely, responsive and took excellent care of both my home and my dog. I would absolutely ask Joan to pet/house sit for me again. Charlie is an old guy who can have separation anxiety causing him to pee in the house. Joan did such a great job making him feel safe and happy.

Availability updated 3 days ago
Sitter Profile Image: Jasmine T.
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Sitter Profile Image: Jasmine T.
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Jasmine T.
Star Sitter

🐈‍⬛Caring for your furry family🐕
Timmerman West, Milwaukee, WI, 53225
5.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$55
per night
5 out of 5.0 stars
15 reviews
6 repeat clients
Profile image

Jasmine communicated with us frequently about the things that concerned us most. Our girls enjoyed their time with her and behaved well. She made sure medication was administered as requested and kept our little one in her cone. We would recommend Jasmine.

Availability updated 34 days ago
Sitter Profile Image: Stephen & Wipawee D.
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Sitter Profile Image: Stephen & Wipawee D.
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Stephen & Wipawee D.

Pawfessional w/ Love & Care <3
Dineen Park, Milwaukee, WI, 53216
6.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$95
per night
5 out of 5.0 stars
49 reviews
19 repeat clients
Profile image

Amelie and Stephen sat for our dog, Dexter, and our cat, Lucy, while we were out of town for a weekend. We felt incredibly assured during our time away that our pets were being well cared for and provided with lots of love. We were given consistent updates on how the stay was going and what our animals were up to. They graciously provided many pictures during the stay that continued to provide us with a sense of calm knowing our fur babies were in very good hands. We have already rebooked with them for a future trip, and will continue to do so! We cannot recommend them enough!

Availability updated 8 days ago
Sitter Profile Image: Jeff G.
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Sitter Profile Image: Jeff G.
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Jeff G.

Care for dogs like they're children
Glendale, WI, 53209
3.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$70
per night
5 out of 4.9 stars
53 reviews
13 repeat clients
Profile image

Jeff stayed at our house to take care of our dog Frankie while we were on vacation. After a day of traveling, it was so nice to come home to a happy, healthy Frankie and a house that looked the same, or maybe even better than when we left!! Jeff sent updates on Frankie to us often with videos and pictures! It is obvious that he really cares for and loves animals!! I am always a little nervous leaving my house and loved dog to someone else for an entire week, but I won't feel that way next time we ask Jeff!! He was absolutely great with Frankie!

Availability updated today
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Yolanda W.
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Sitter Profile Image: Yolanda W.
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Yolanda W.
Star Sitter

I miss our pup & hope 2 spoil yours
Brown Deer, WI, 53223
1.4 mi. away
Boarding, House Sitting, Doggy Day Care
from
$90
per night
5 out of 5.0 stars
144 reviews
57 repeat clients

I can’t say enough about Yolanda and her wonderful services Often having big dogs like Rottweilers its extremely hard to find care for them while attempting to vacation but thanks to Yolanda , I was able To be at peace while away. She took care of my babies(dogs) as if they were hers, even going as far as sending me pictures and videos of my pets during the duration of my vacation. I highly recommend her services. Especially for larger breeds of dogs. Thanks Again.

Availability updated today
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Selena M.
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Sitter Profile Image: Selena M.
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Selena M.

I can help with your fur babies.
Calumet Farms, Milwaukee, WI, 53224
2.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$28
per night
4 reviews
1 repeat client

Selena and Maui has a truly special bond. The excitement that he shows towards her is a clear sign of affection and a happy anticipation. Patience is key when working with such enthusiastic energy and she has that. It's wonderful that they have such a positive connection.

Availability updated 12 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Cynthia E.
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Sitter Profile Image: Cynthia E.
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Cynthia E.
Rover 101

Loving Care when you're not there!
Mequon, WI, 53092
2.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$28
per night
2 reviews

Cynthia is a wonderful human being who loves all animals, specially dogs. I've known her for almost 30 years and have seen her with her dogs and other people's dogs. You wouldn't know which one was hers because she spoiled them all. Cynthias energy is calm and patient, which is great energy around dogs, but she is also goofy and fun in a way that every dog would love. I've trusted her with every dog I've had.

Availability updated 5 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Perseus M.
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Sitter Profile Image: Perseus M.
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Perseus M.
Rover 101
Star Sitter

Caring & Respectful Animal Lover
Milwaukee, WI, 53223
0.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$85
per night
5 out of 5.0 stars
34 reviews
7 repeat clients

As someone very nervous about leaving my cats while on vacation, I knew I needed to find someone I could trust. Perseus watched my three cats on short notice and took the time to understand their individual needs and very specific feeding schedules. One of my cats only eats one type of food and changes her mind every other day, another needs to eat behind a closed door so the others won't eat their food, and one of them is very shy around strangers and I was worried he wouldn't eat while I was gone, but Perseus was patient and made my scaredy-cat feel right at home. Upon my request, he agreed to send daily updates on the cats so I could be assured they were being well-cared for, and he was happy to confirm all the tedious things I asked for to make my cats as comfortable as possible in someone else's home. He was personable, kind, and patient with both me and my cats, and made me feel more comfortable with leaving my babies with a stranger! At the end of the week, he didn't feel like a stranger anymore but someone I could genuinely trust.

Availability updated today
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Jessica s.
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Sitter Profile Image: Jessica s.
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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
from
$36
per night
5 out of 5.0 stars
33 reviews
5 repeat clients

Jessica is an outstanding dog sitter! She has been gracious enough to watch my dog Cowboy several times. :) She is very professional and courteous. Would highly recommend Jessica for any petsitting needs!

Availability updated 9 days ago
Confirmed availability for Labor Day Weekend

How Rover works

  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

Why Choose Rover?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • Reservation protection

    It doesn’t happen often, but if your house sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

House Sitting FAQs

Frequently asked questions about Rover