Dog Sitting Bayside

Book a Bayside dog sitter to watch your dog in your sitter’s home or yours.

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Over 23
pet parents in Bayside have booked dog sitting

Bayside, Find top rated dog sitting

Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Angela M.
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Angela M.
from
$18
per visit
5.0 out of 5 stars
5 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: Elaina H.
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Elaina H.
from
$15
per visit
10 years of experience
Glendale, WI, 53217

About: I’ve dog sit for families since I was a teenager, and I’ve always been very reliable. I’ve had all different types of breeds of dogs growing up as well. I currently work as a teacher; so I’m off for the summer. I can help any time! I can be there as early as needed. I love walking dogs and am always very interactive with all animals. I’ll never left them get bored and think stimulation for them is very important.

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 responsive and took excellent care of my cat with attention to detail and his unique needs.

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Jenelle D.
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: 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: Aidan H.
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Aidan H.
Star Sitter
from
$20
per visit
4.9 out of 5 stars
43 reviews
12 repeat clients
12 years of experience
Menomonee River Hills, Milwaukee, WI, 53224

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.
Sitter Profile Image: Sydney H.
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Sydney H.
from
$15
per visit
4.0 out of 5 stars
3 reviews
1 year of experience
Mequon, WI, 53092

Sydney was very responsive and reliable. She sent great pictures and timely updates!!

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Samantha K.
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

An excellent sitter!

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Andrea L.
Sitter Profile Image: Auria R.
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Auria R.
from
$45
per visit
5.0 out of 5 stars
162 reviews
70 repeat clients
40 years of experience
Glendale, WI, 53209

Auria was a competent, caring, and thoughtful dog sitter. She sent us numerous pictures and detailed updates as to how Lily was doing. I would highly recommend her and have already booked another stay! We truly felt as though Lily was in excellent hands.

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Maryanne M.
Sitter Profile Image: Makayla W.
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Makayla W.
from
$15
per visit
10 years of experience
Mequon, WI, 53092

About: I have had many dogs in my lifetime from childhood and as an adult and love to give dogs the love and compassion they deserve I am a new physician assistant graduate and do not start my new job for quite a few months so I have quite the down time to take care of pets! I have a dog myself and ensure I will care for your dogs with the same amount of love, compassion and care! I also have a background in healthcare

Sitter Profile Image: Ana B.
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Ana B.
from
$19
per visit
5.0 out of 5 stars
220 reviews
38 repeat clients
11 years of experience
Shorewood, WI, 53211

Ana was a great friend to our dog when we were gone. She provided thorough updates and cute photos each time she visited and was a reliable, sweet sitter!

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Stephanie B.
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: Nicole & Scott G.
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Nicole & Scott G.
Star Sitter
from
$40
per visit
5.0 out of 5 stars
14 reviews
5 repeat clients
30 years of experience
Glendale, WI, 53209

About: My husband and I have grown up with dogs. Although we don't currently have a dog, our family loves to fill the need for a dog by dog sitting and dog walking for friends and family. Our children adore dogs and love to treat visiting dogs as if they were our own. We are both home based and available during the day. I'm a stay at home mom that is able to let your pet out regularly. We have a large family (4 kids) and my husband works remotely, so although we are busy, someone is often home. We have a large, unfenced yard for your pup to play in. Walks, play and running outside are a standard part of our outdoor environment.

Sitter Profile Image: Melissa H.
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Melissa H.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
57 reviews
22 repeat clients
40 years of experience
Murray Hill, Shorewood, WI, 53211

Melissa was very attentive to my cats while I was away for a week! She administered their medication, played with them, and made sure they were happy as can be :) Highly recommend!

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Grace F.
Sitter Profile Image: Jessica s.
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Jessica s.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
56 reviews
18 repeat clients
10 years of experience
Whispering Hills, Milwaukee, WI, 53223

She was very helpful! It didn't work out with my dogs being at her house so we worked it out to her dropping in on them at my house to take care of them. She's one of the best!

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Anna B.
Sitter Profile Image: Whitney H.
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Whitney H.
from
$25
per visit
5.0 out of 5 stars
6 reviews
30 years of experience
Mequon, WI, 53092

About: I provide attentive, compassionate, and reliable care for dogs of all breeds and sizes. I specialize in creating a safe, comfortable environment—whether in your home or mine—ensuring pets receive plenty of exercise, affection, and individualized attention. With strong communication skills and a genuine love for animals, I keep pet parents updated and at ease throughout every stay. Whether it’s daily walks, overnight stays, or special care routines, I’m committed to treating every dog like family. I have a flexible work schedule so I’m able to provide breaks and attention as needed throughout the day. I am able to attend to your pet as needed. I have a large back yard that the dogs can play in. I also have the Oak Leaf trail next to my house we can go on frequent walks!

Sitter Profile Image: Rachel S.
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Rachel S.
from
$14
per visit
8 years of experience
Shorewood, WI, 53211

About: From family pets, growing up on a farm, pet sitting in college, to multiple years taking care of animal ambassadors as a naturalist, I've been working with and caring for critters of all sorts for nearly as long as I can remember! For critters in the pet category, I have been caring for indoor cats since 2018, from kittens to seniors and every stage in between, including administering medications. My family has had medium/large dogs (rottweilers, labs, and border collie and boxer mixes) my whole life but I have also pet sat for smaller breeds like Boston terriers and cavalier king Charles spaniels. My time as a naturalist gave me experience working with not only varied species, but varied personalities. From grumpy skunks to mischievous snakes and dramatic birds, I have extensive experience across the gambit. It also provided experience with very specific care instructions and detailed documentation. I like to provide pet parents with a thorough summary of my time with their pet so they don't have to worry while they're away. My schedule varies week to week from periods of no availability to periods of open availability, I will make sure to keep things updated so you know what to expect! In fall of 2025, I finished my 2,200+ mile thru hike of the Appalachian Trail. What does that mean for pet care? I LOVE to walk and do so whenever I get the chance! I would love to have your pet join me! I am very detail oriented and will follow your care instructions to a T! I also provide my pet parents a detailed summary of my visit for peace of mind, every time!

Sitter Profile Image: Perseus M.
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Perseus M.
Star Sitter
from
$65
per visit
5.0 out of 5 stars
78 reviews
23 repeat clients
10 years of experience
Milwaukee, WI, 53223

Percy and Darik were great with Baron while I was out of town! They were quick to respond and made sure I knew how Baron was doing and when they would be dropping in to take care of him. I appreciate all the love they gave him - he was in good hands!

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Haley K.
Sitter Profile Image: Travis H.
Verified Background Check
Travis H.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
355 reviews
111 repeat clients
35 years of experience
Riverwest, Milwaukee, WI, 53212

Travis helped us with hour-long drop in visits during the work day. We contacted him with short notice and he was quick to reply and help! Very friendly and professional, and he sent us great pictures of our pup.

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Kirstyn W.
Sitter Profile Image: Emily R.
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Emily R.
from
$14
per visit
1 repeat client
10 years of experience
Williamsburg, Milwaukee, WI, 53212

About: I’ve grown up with pets my whole life, dogs all through my childhood and cats all through my adult life. I have experience with caring for multiple animals and training as well. I have an open schedule at the moment, working on school online so I have a lot of free time. I love to walk dogs and sit at your home, as I have a shy kitten at home who doesn’t mix well with other animals. I love to make your animal comfortable, and I understand not everybody’s will warm up to you right away. I make effort to keep in contact with you to make sure your pet’s needs are all met.

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The median cost per visit for dog sitting in Bayside is $20

Dog parents share their Rover experiences - Bayside

1 / 1
5.0 out of 5 stars

Suzi was extremely accommodating and took great care of our dogs. We will be happy to book her again.

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Will N.
Drop-In Visits
5.0 out of 5 stars

The best pup sitter we could ask for. So reliable, compassionate, plays with them, updates us & takes the cutest photos.

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

Lenys was great! She spent the extra time with our pups and took such good care of them. We highly recommend her!

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Jon I.
Drop-In Visits
5.0 out of 5 stars

We love Mia! I’m the kind of dog mom who can’t leave her baby easily. From our first meeting we knew Mia was the girl for us. She is caring, attentive & most important, Roxy approved. We will be hiring her many more times. I can’t recommend her enough!

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Angela K.
Drop-In Visits
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Book with peace of mind

  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

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 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.

Meet local sitters who will treat your dogs like family

  1. 1. Search

    Browse profiles of sitters near you who offer dog sitting
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform

Sitters in Bayside average 6
repeat dog sitting clients

FAQs for Drop-In Visits - Bayside

Frequently asked questions about Rover

The average cost for Dog Sitting in Bayside on Rover is $19.98 per visit (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Dog Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Sitting. For more information on service fees, click here .

As of July 2026, there are 2,149 sitters on Rover offering Dog Sitting across Bayside. Enter your ZIP code to see which available sitters are closest to your home.

A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.

Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Bayside stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.

Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.

Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Bayside choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!

Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.

A Meet & Greet is a short introductory meeting between you, your dog, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.

To find sitters in Bayside with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.

Yes, you can find sitters who have experience with handling special pet needs in Bayside. On Rover:

  • 92% of sitters can help with special care needs
  • 96% can help with giving oral medications or injections
  • 95% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.

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