Pet Sitting & Drop Ins In Havenwoods

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

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Top rated Havenwoods pet sitters

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Sitter Profile Image: Aidan H.
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Aidan H.
Star Sitter
from
$22
per visit
4.9 out of 5 stars
35 reviews
12 repeat clients
12 years of experience
Menomonee River Hills, Milwaukee, WI, 53224

Aidan always takes the best care of our pups while we are away!! Very attentive, excellent communication, so helpful. Would absolutely recommend and plan to use again when needed.

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Sarah M.
Sitter Profile Image: Genesis A.
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Genesis A.
from
$25
per visit
5.0 out of 5 stars
10 reviews
5 repeat clients
10 years of experience
Thurston Woods, Milwaukee, WI, 53209

Great communication, very easy to work with!

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Andrea L.
Sitter Profile Image: Paul Y.
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Paul Y.
from
$25
per visit
3 years of experience
Town And Country Manor, Milwaukee, WI, 53223

About: I provide friendly, professional, and truly attentive care, noticing your dog’s needs and moods. My approach is calm, balanced, and consistent, following your routines closely so pets feel safe, comfortable, and relaxed. I treat every dog with respect, giving them confidence and happiness while you’re away. I currently offer part-time dog sitting and walking, with availability continuing to expand as my Rover schedule grows. My mornings and weekends vary week to week, but I may be able to accommodate requests on a case-by-case basis. Feel free to reach out to check availability. As a dog owner myself, I understand the importance of reliable, attentive care and aim to provide flexible, high quality support tailored to your dog’s needs. I provide calm, attentive care in your dog’s own home, respecting boundaries and following your instructions closely. Every dog receives consistent, thoughtful handling to feel secure and comfortable while in my care. Even dogs with minor behavioral quirks are managed safely, so owners can feel confident that their pets are well cared for, calm, and respected.

Sitter Profile Image: Yolanda W.
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Yolanda W.
Star Sitter
from
$30
per visit
5.0 out of 5 stars
197 reviews
83 repeat clients
35 years of experience
Brown Deer, WI, 53223

Sooo grateful we found this sitter. She is caring, reliable and does an amazing job with our senior dog. Highly recommend.

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Melissa E.
Sitter Profile Image: Charles B.
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Charles B.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
110 reviews
20 repeat clients
17 years of experience
Fox Point, WI, 53217

Did a wonderful job! Thorough and flexible! Was there to let our dogs out but was friendly with our cats too! All our dogs loved having him over!

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Teanna F.
Sitter Profile Image: Alyssa B.
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Alyssa B.
from
$20
per visit
5.0 out of 5 stars
9 reviews
3 repeat clients
10 years of experience
Glendale, WI, 53209

About: I have been passionate about animals, big and small, my entire life! I have volunteered at humane societies, fostered animals in need, cared for the pets of family members and friends, interned at AZA-accredited zoos, and worked at wildlife sanctuaries. Currently I am a full-time licensed wildlife rehabilitator caring for injured and orphaned Wisconsin wildlife with the goal of releasing them back into the wild, but I have previously worked with a variety of domestic animals both in my personal and in my professional life. I am well versed in animal behavior, body language, and positive reinforcement. I promise to treat (and spoil) your pets like they are my own! At the moment I have 3 sweet cats, a high-energy dog, a mischievous chinchilla, and a gentleman of a ball python! Please do not hesitate to reach out and get to know me more! I currently work 4 days of the week at my full time job so I am only available select days. I am eager to spend time with your pets, however, so if my schedule shows I am unavailable, please reach out anyway as I try to be as flexible as possible! It is extremely important to me to use Fear Free tactics when interacting with any animal. Gaining the trust of you and your pet are my top priority!

Sitter Profile Image: Anya P.
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Anya P.
Star Sitter
from
$24
per visit
5.0 out of 5 stars
55 reviews
15 repeat clients
12 years of experience
Brown Deer, WI, 53209

Once again Anya saved me with a couple last minute drop ins. She was also super helpful with some unexpected errands and tasks around the house.

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Chris C.
Sitter Profile Image: Monae H.
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Monae H.
from
$15
per visit
6 years of experience
Thurston Woods, Milwaukee, WI, 53209

About: I stand out as a dog sitter through a lifelong connection with dogs, developed since a young age, combined with six years of hands-on experience training dogs of all breeds and temperaments. I’ve also taken the initiative to study dog nutrition in depth, allowing me to confidently understand what dogs should and should not eat. Additionally, I have experience safely administering medications, ensuring every dog in my care stays healthy, comfortable, and well-supported. I have an open schedule as far as now, so i am available to fit into what schedule is needed from me. Pet care fits into my daily schedule!! I provide attentive, personalized care tailored to each dog’s needs, including easy crating when required. I’m happy to stay full-time if needed. Whether your dog loves playtime, outdoor adventures, learning new skills, or simply relaxing and cuddling while watching shows, I adapt to their mood to ensure they feel safe, happy, and comfortable.

Sitter Profile Image: Stephen & Wipawee D.
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Stephen & Wipawee D.
from
$25
per visit
5.0 out of 5 stars
51 reviews
19 repeat clients
5 years of experience
Dineen Park, Milwaukee, WI, 53216

Stephen and Amelie are the best! They take excellent care of our babies and our home when we’re away and make us feel completely comfortable when we need to travel without the pups. Our dogs love them too!

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Laura B.
Sitter Profile Image: Elijah X.
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Elijah X.
from
$15
per visit
3 years of experience
Menomonee River Hills, Milwaukee, WI, 53223

About: I have had multiple dogs through out my life. During high school my family had 4 dogs in the house which were 3 Labs and 1 Bully mix. Since my wife and I moved out we currently live with our doghter, Nala. We also recently adopted our cat, Neo who is sweet and loving towards other dogs. I usually take my dog out during the morning around 7am to 8 am, during the afternoon after the dogs have breakfast, once again during 4 or 5pm, and then one final time before we head to bed around 8pm or 9pm. This is a daily routine for Nala and I that we have stuck to since she was a puppy and works great for us over all. We usually walk around the block or play in the background as sometimes she doesn't need to potty and just needs that outside enrichment. I currently have a fenced yard for the back yard if the dogs do plan to play. The only part that is not fenced up is the driveway, but for the most part Nala and I do walk so that she can get some steps in and also so she won't poop too much in the backyard. If I am visiting your home I will come respectfully and walk your dog with Nala or without what ever your preference is and also give a detailed check-in of your dog to put your mind at ease.

Sitter Profile Image: Fonshe B.
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Fonshe B.
from
$25
per visit
5.0 out of 5 stars
2 reviews
12 years of experience
Silver Spring, Milwaukee, WI, 53218

About: I’ve taken care of dogs, since I was 13yrs old. We always kept a dog growing up which made me fall in love with them. I’m currently open and available anytime between 9:30am-4:00pm and 5:30p-9:00p. Monday-Friday and I’m available from 9am-9pm Saturday and Sunday. I can also be on a need be schedule as well. I have a small friendly Yorke that will keep your dog company while being cared for. I have have nice size bag yard but it is not fully fenced in. I also have a park about a minute away from home walking distance.

Sitter Profile Image: Angela M.
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Angela M.
from
$18
per visit
5.0 out of 5 stars
3 reviews
2 repeat clients
15 years of experience
Whitefish Bay, WI, 53217

Angela was great. The animals loved her and she left good descriptions and pictures with every visit.

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Aidan F.
Sitter Profile Image: Montserrat R.
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Montserrat R.
from
$16
per visit
5.0 out of 5 stars
3 reviews
1 repeat client
10 years of experience
Golden Valley, Wauwatosa, WI, 53222

About: I’m the designated dog walker for family and friends because I love going on walks, and dogs love coming with me! I grew up with a dog but only have two cats of my own— so I miss having that four-legged friend to go with me! I’d love to take your dog out for a walk/run, or just let them stretch their legs. Cat owners, I’m happy to give your kitties as much or as little space as they need while making sure they feel the love :) I don’t work Fridays or Saturdays, so I am free to help anytime then! Definitely looking to fill my Fridays up with some time outside, and I’d love to take your dog with me - or check in on your cat! I usually walk my parent’s and brother’s dogs (about 80 lbs each) so I know how to handle bigger dogs on leashes who tend to stray from the sidewalk. I can clean up after them, feed them, and give them all the pets! For my cats at home, I love to play with strings or catnip - and can cater to their personality as need be.

Sitter Profile Image: Alyssa S.
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Alyssa S.
from
$15
per visit
5.0 out of 5 stars
7 reviews
3 repeat clients
4 years of experience
Glendale, WI, 53217

Alyssa was great! Did exactly what I asked her to do during her drop-in visits with my cat. I definitely recommend her!

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Mary S.
Sitter Profile Image: Ruby M.
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Ruby M.
from
$28
per visit
5.0 out of 5 stars
19 reviews
6 repeat clients
13 years of experience
Milwaukee, WI, 53209

Ruby was great taking care of our dog Georgia!

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Marissa W.
Sitter Profile Image: Camila S.
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Camila S.
from
$25
per visit
5.0 out of 5 stars
9 reviews
2 repeat clients
10 years of experience
Milwaukee, WI, 53209

Camila was terrific with our puppy! Gave detailed notes and great communication.

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James P.
Sitter Profile Image: Nariya W.
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Nariya W.
from
$25
per visit
5 years of experience
Garden Homes, Milwaukee, WI, 53209

About: I am a former dog handler that worked at a doggy day care where I cared for multiple dogs daily, managing different temperaments and energy levels. I’m experienced in supervising play, maintaining safety, and keeping dogs calm, comfortable, and well cared for. I’ve also owned dogs and cats in my lifetime as well! Genuinely an animal lover. I’m available for morning and evening visits on weekdays, and I have open availability on weekends. I offer flexible scheduling for walks, drop ins, and pet sitting, and I do my best to accommodate each pet’s routine. I prioritize a safe, calm, and clean environment. I’m attentive to each pet’s behavior and needs, follow routines closely, and make sure every pet feels comfortable, secure, and well cared for.

Sitter Profile Image: Rachelle P.
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Rachelle P.
from
$14
per visit
5.0 out of 5 stars
2 reviews
10 years of experience
Brown Deer, WI, 53223

About: I've grown up with pets ever since I was little. I've been trusted even from young ages to walk, feed, and clean up after dogs. I've never had a bad experience and I'm always willing to encounter any and every kind of dog out there with lots of love and care! I have my own pet at home, had him for 10 years. Even after so long, it's so easy and even fun sometimes to do the little things for your pets like feeding them, walking them, and just making sure you spend some quality time with them! There's never a moment I don't want to be around my pet, or any pet for that matter! I always think the key to good pet care is real love and attention. Watching for what your pets want and giving them it will make them happy. If it's attention, bring on the cuddles! If it's a walk, let's do it! And that goes for pets that aren't mine as well. I always care for them like they're mine, and will pay attention to what they want as well as what their owners know is best too!

Sitter Profile Image: Charlotte M.
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Charlotte M.
from
$17
per visit
5.0 out of 5 stars
107 reviews
9 repeat clients
12 years of experience
Milwaukee, WI, 53210

Charlotte came to do a meet and greet, and then was very quickly available for a drop in visit! She has great communication and Lenny loves her!

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Danielle P.
Sitter Profile Image: Cynthia E.
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Cynthia E.
from
$20
per visit
5.0 out of 5 stars
14 reviews
6 repeat clients
40 years of experience
Fox Point, WI, 53217

Cynthia is doing great with my reactive dog!! Thank you.

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Peggy K.
1 / 1
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Havenwoods pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

As always, we had a wonderful experience leaving our fur babies with Aidan! Very communicative, attentive to our pets needs, and goes above and beyond to make us feel comfortable while we are away.

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Sarah M.
Drop-In Visits
5.0 out of 5 stars

Yolanda was amazing with our three high energy dogs! When we first met her and her husband, we could tell right away they were great people and our dogs took right to them. Even our dog that is sometimes shy around new people seemed completely at ease with them. She was available on short notice and took lots of great photos of the first visit. Our dogs looked very happy and relaxed. We would definitely recommend Yolanda!

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Michelle C.
Drop-In Visits
5.0 out of 5 stars

As always Katie is amazing. Our girls love spending time with Katie. She sends us plenty of updates pictures and videos. They love their play time with Katie as well.

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Alberto F.
Drop-In Visits
5.0 out of 5 stars

Angela is our go-to sitter for our greyhounds. She loves dogs and does such a phenomenal job. We never worry when they are in her care.

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Rebecca A.
Drop-In Visits
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How Rover works

  1. 1. Search

    Read verified reviews by pet parents like you and choose a 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 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!

The median cost per night for pet sitting in Havenwoods is $20

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 pet 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.

Sitters in Havenwoods average 6
repeat pet sitting clients

Pet Sitting FAQs

Frequently asked questions about Rover

Pet sitters on Rover are free to set their rates. The median cost to hire a pet sitter in Havenwoods on Rover as of Jun 2026 was about $20 per night, after factoring in Rover’s service fees. A pet sitter’s rate may also change as you customize your booking to fit your and your pet’s needs.

If you’re searching for a Havenwoods pet sitter for the first time, visit the pet sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a pet sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 2,205 pet sitters in Havenwoods. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass a background check for you and your pet’s safety.

Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, 86% of Havenwoods pet sitters respond in under an hour.

Pet sitters in Havenwoods have an average of 16 years of experience. Pet sitters with repeat customers have an average of 6 repeat clients. Experience can vary from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when you compare pet sitters in Havenwoods.

Rover makes it easy to find Havenwoods pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:

  • Pets of all ages and abilities, including puppies
  • Pet parents looking for a safe, loving alternative to a kennel
  • Pets who’d love to socialize with their pet sitter’s pets

There are 2,205 pet sitters in Havenwoods on Rover, so you’re sure to find the perfect match for your pet! In Havenwoods, 95% of pet sitters offer daily exercise, 97% offer medication administration, and 92% have experience with senior pets and pets with special needs. We know each pet is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass background checks for you and your pet’s safety.

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your pet sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.