Dog Sitting Whitefish Bay

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

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Over 102
pet parents in Whitefish Bay have booked dog sitting

Whitefish Bay, 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.

1 / 1
Sitter Profile Image: Emily B.
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Emily B.
from
$12
per visit
6 years of experience
Riverwest, Milwaukee, WI, 53212

About: ** Discounted rates as I built up reviews on this app!** I’m a true animal lover ready to give your pets the next best thing to your own love! My experience spans singlehandedly training a puppy during my teen years, caring for a 3 legged rescue, and my recent every day and extended dog sitting for my roommate’s 80 lb reactive Pitbull, I’m ready and happy to handle just about anything with compassion, care, and dedication! As a retail worker, my schedule stays flexible, so I’m a perfect candidate for both midday visits or long term stays. Whether your dog needs a multi mile walk or a quick potty break, I’m ready to make it work! As someone who also has childcare experience, I know how to be an unobtrusive, responsible, and respectful guest in your home. I value strong communication and can easily adjust my typical care style to your preferences and boundaries. I’ll be sure to always wipe those paws before letting your pup loose :)

Sitter Profile Image: Jessica K.
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Jessica K.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
44 reviews
12 repeat clients
15 years of experience
Northpoint, Milwaukee, WI, 53211

Jessica took great care of my cat! It was clear from the daily cards that my cat warmed up to her quickly, and they spent good quality time snuggling and playing together.

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Justin C.
Sitter Profile Image: Lisa R.
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Lisa R.
Star Sitter
from
$13
per visit
5.0 out of 5 stars
51 reviews
19 repeat clients
45 years of experience
Fox Point, WI, 53217

Lisa was outstanding with our doggies! Great communication with us and paid close attention to the little details that made them feel comfortable. Would highly recommend her!

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Mary F.
Sitter Profile Image: Travis H.
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Travis H.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
363 reviews
112 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: Evelyn E.
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Evelyn E.
from
$20
per visit
5.0 out of 5 stars
4 reviews
2 repeat clients
5 years of experience
Milwaukee, WI, 53211

About: I grew up with two cats and two dogs, so I’ve been around pets for most of my life! I got my own dog five years ago, and I have been taking care of her ever since. I love any and all types of pets, and I have am flexible with times and can accommodate mamy different schedules. Along with taking care of my own dog, I am available throughout the day to stop in and check on/walk dogs. I am also available any day to stay over as a sitter. My one and only priority would be taking care of your pet. I would never be intrusive or inappropriate in your home. I would treat it with the respect I would want from a sitter.

Sitter Profile Image: Jessica Z.
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Jessica Z.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
211 reviews
63 repeat clients
30 years of experience
Lower East Side, Milwaukee, WI, 53202

Jessica is reliable and responsive, and takes great care of my kitty. I will continue to ask her to take care of Rocco every time I go out of town. Thank you Jessica!

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Michelle L.
Sitter Profile Image: Hope S.
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Hope S.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
56 reviews
27 repeat clients
15 years of experience
Riverwest, Milwaukee, WI, 53212

Hope is so great with our dogs! Both of our dogs have different medical needs, so finding the right sitters can be difficult. She has great communication and has very quickly figured out how to balance the time and attention each of our dogs need. So easy to work with! We love having her stay with them for longer days and quickly breaks!

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Sarah R.
Sitter Profile Image: Kalina M.
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Kalina M.
from
$17
per visit
8 years of experience
Upper East Side, milwaukee, WI, 53211

About: Hi! I'm Kalina. I've been around animals my whole life, and they've always been a huge part of it. I've worked with rescue dogs and have experience with pets of all different personalities, so I know that every animal deserves patience, understanding, and care that's tailored to them. I have two cats and a deaf dog of my own, so I understand how much trust it takes to leave your pets with someone else. My deaf pup has taught me a lot about paying attention to body language, being patient, and finding what works best for each individual pet. Whether your pet is full of energy and loves to play or would rather curl up on the couch, I'm happy to follow their routine and make sure they feel comfortable while you're away. I'll treat them like they're my own and keep you updated with plenty of photos and messages so you never have to wonder how they're doing. I know our pets are family, and my goal is to make sure they feel safe, loved, and well cared for until you're back home. Care for your pet fits naturally into my daily routine because I have a very open and flexible schedule. That allows me to be available for morning, afternoon, evening, and weekend visits, and I can easily adjust my day to meet your pet's needs. Whether it's a walk, a drop-in visit, or spending extra time keeping your fur baby company, I'm happy to work around their routine to help them feel comfortable, happy and cared for. When I'm caring for pets in your home, my goal is to keep their routine as normal as possible so they feel safe and comfortable while you're away. I'll carefully follow any instructions you leave regarding feeding, walks, medications, potty breaks, playtime, and any other special needs or preferences. I've been around animals my whole life and have experience working with rescue dogs. My mom also fosters dogs, and I've cared for many of her foster dogs while she's away. That experience has taught me to be patient with dogs who may be shy, anxious, or still adjusting to new people and environments. I treat every home with respect and every pet like they're my own. I'll make sure they get plenty of attention, exercise, and affection, and I'll keep you updated with photos and messages so you can feel confident they're happy and well cared for while you're away.

Sitter Profile Image: Jodi C.
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Jodi C.
from
$18
per visit
5.0 out of 5 stars
36 reviews
11 repeat clients
40 years of experience
Harambee, Milwaukee, WI, 53212

Reliable and easy to communicate with! Would book her again!

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Jackie M.
Sitter Profile Image: Nevaeh T.
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Nevaeh T.
from
$17
per visit
5.0 out of 5 stars
26 reviews
6 repeat clients
6 years of experience
Milwaukee, WI, 53211

Nevaeh was awesome! She sent us text updates including pictures/videos the whole time giving us peace of mind. Our dog Mallie loved her! Would definitely recommend!

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Cheyenne D.
Sitter Profile Image: Rachel S.
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Rachel S.
from
$15
per visit
5.0 out of 5 stars
4 reviews
8 years of experience
Shorewood, WI, 53211

Rachel did an excellent job watching my cats. She showed up on schedule and provided thorough daily updates and pics. I would strongly recommend her.

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Nick D.
Sitter Profile Image: Carole C.
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Carole C.
Star Sitter
from
$30
per visit
5.0 out of 5 stars
189 reviews
41 repeat clients
23 years of experience
Murray Hill, Milwaukee, WI, 53211

Very responsive and attentive. I booked them last minute for an evening visit and they responded right away! They gave lots of picture/text updates and I felt like my pup was in great hands.

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Lauren C.
Sitter Profile Image: Heidi H.
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Heidi H.
from
$25
per visit
20 years of experience
Shorewood, WI, 53211

About: I’m a very active Shorewood nurse who is absolutely crazy about dogs!!! I look forward to giving your pet the same TLC our 2 rescue mutts enjoy with our family. I love being out and about in our local neighborhoods in any weather (I am a heart MN gal) and am happy to provide a walk, jog, or drop by for some laid-back company. I’m happy and comfortable working with dogs large and small, as we have a Setter-mix and Chihuahua at home. My variable nursing schedule allows me lots of flexibility to help your fury family member almost any time of day. Let’s connect so I can make sure your lovely pets get the attention they deserve while you go about your busy day. I’m a nurse and work night shift. I have lots of daytime and varying flexibility and also a daughter who loves helping and learning about pets just like her mom. I would love and care for your pet as if they were my own, with attention to detail and routine that’s needed to make them feel at home.

Sitter Profile Image: Aj S.
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Aj S.
from
$16
per visit
2 years of experience
Shorewood, WI, 53211

About: I have a dog of my own named Charlie! He is a 3 year old tripod pitbull mix that is the love of my life. I am able to lift him up (52lbs) when he needs the extra help, so I am able to lift dogs if needed. I just graduated with my BFA in Musical Theatre and minor in Dance Performance. I am available Monday-Friday as early as 6:30am-1pm. My schedule will shift from time to time as I am an actor and will be in shows. I care a lot about pet safety and wellbeing. When an animal is in my care, they are my number 1 priority. Any little change in demeanor that seems off or anything that seems off with the pet, their parent will be notified and updated right away. This is because this is what I would want for my dog. I know that my dog means the whole world to me and that when he is not with me, I want the best for him and for him to be comfortable and cared for.

Sitter Profile Image: Laura R.
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Laura R.
from
$26
per visit
5.0 out of 5 stars
7 reviews
20 years of experience
Shorewood, WI, 53211

About: 20+ years experience caring for dogs and cats of all sizes, ages, and breeds! Professional, punctual, caring, and fun! My services are especially catered to meet your pets needs. Experienced with administering medications and older aged animals as well. Daily pics and report will be provided to owners each day you are away! Enrichment, toys, and treats are supplied. I look forward to working with your furbabies! I'm currently doing this full-time time so I will have plenty of time to play with your pups! I'm also available weekends and holidays. 🐶❤️ I have no kids or pets. Your pet will be pampered and treated as one of my very own! As well as receiving 1:1 attention and lots of TLC. Dogs are allowed on the furniture and bed. Snuggles are welcome.

Sitter Profile Image: Hanna C.
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Hanna C.
from
$15
per visit
4.9 out of 5 stars
45 reviews
5 repeat clients
10 years of experience
Riverwest, Milwaukee, WI, 53212

Hanna did a wonderful job taking care of my two cats while I was away on vacation! She was prompt, communicated very well, and sent lots of photos. I would highly recommend her to anyone looking for a pet sitter!

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Aisling N.
Sitter Profile Image: Mikalanne T.
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Mikalanne T.
from
$18
per visit
5.0 out of 5 stars
55 reviews
19 repeat clients
4 years of experience
Riverwest, Milwaukee, WI, 53212

About: I have grown up with dogs all my life. Every time I get the opportunity to watch a fur baby, I treat them like they are my own. I have done some dog/puppy training as well, and I've always gotten great reviews on what one's pet can do by the time they go home (If interested) My schedlue is fairly flexible. I am able to move clients around depending on your availability. This is my full-time gig as of now, so I take lots of pride in the care I provide to your pet(s). I have currently moved to Riverwest, this came with a fenced in backyard (yayyyy)! I live close to lots of parks, dog park (Rover west), and trails.

Sitter Profile Image: Miranda E.
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Miranda E.
from
$20
per visit
5.0 out of 5 stars
10 reviews
17 years of experience
Riverwest, Milwaukee, WI, 53212

Miranda was prompt, communicative, and reliable! She clearly loves dogs! We will definitely request her services again.

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Rebecca S.
Sitter Profile Image: Laci P.
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Laci P.
from
$20
per visit
5.0 out of 5 stars
2 reviews
10 years of experience
Shorewood, WI, 53211

Laci was so sweet to work with and our dogs were in great hands! High recommend!

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Kelley M.
Sitter Profile Image: Auria R.
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Auria R.
from
$45
per visit
5.0 out of 5 stars
165 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.
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The median cost per visit for dog sitting in Whitefish Bay is $20

Dog parents share their Rover experiences - Whitefish Bay

1 / 1
5.0 out of 5 stars

We had a great experience with Travis, and will absolutely book with him again. He was responsive, easy to communicate with, and kept us updated while we were away. Our dogs were happy, healthy, and well cared for when we returned, which gave us a lot of peace of mind. We highly recommend him to anyone looking for a reliable and caring dog sitter.

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Jennica W.
Drop-In Visits
5.0 out of 5 stars

Carrianne is truly the cat whisperer! She sends me several pictures of my cats playing and interacting with her. They always hide when anyone else comes over. They adore her!

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Cheryl A.
Drop-In Visits
5.0 out of 5 stars

Angela was wonderful! She treated our puppies with so much love and care during her drop-in visit. She spent quality time playing with them, giving them lots of hugs and attention, and it was clear she genuinely enjoys being around dogs. She was also very accommodating, responsive, and easy to communicate with throughout the entire process. We felt completely at ease knowing our puppies were in such caring hands. We would absolutely book Angela again and highly recommend her to anyone looking for a reliable and compassionate pet sitter!

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Ai B.
Drop-In Visits
5.0 out of 5 stars

Jessica was great with my German shepherd, my dog has been going through some health issues and when I went out of town for 4 days I needed someone to come take care of her 3 times a day and mix up her special food, take her for walks and monitor her potty breaks. Jessica was also super flexible with the timing of her visits and made this potentially stressful time super easy for me and my dog. 5 stars. Would reccomend her to anyone.

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

Ana is a great sitter, she watched Nico while I was away for work and is very communicative and sweet! She is amazing with dogs! I would definitely recommend her.

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

Bria was great with our dog Mallie! We really appreciated her picking up a last minute request from us & taking the time to meet Mallie beforehand. She communicated quickly and left detailed feedback on her visit while we were out, which gave us peace of mind that our baby was in good hands. Will definitely be working with Bria again!!

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Cheyenne D.
Drop-In Visits
5.0 out of 5 stars

Katie provided peace of mind and lots of great love and attention to my two dogs. I can’t wait to have her help again in the future!!

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

Christie did a phenomenal job taking care of our pup! She is great with him and very communicative throughout each drop in.

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Samantha L.
Drop-In Visits
5.0 out of 5 stars

Maggie was easy to work with, very responsive, and had an amazing time with my pup. Would love to have her watch my dog anytime!

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Bo B.
Drop-In Visits
5.0 out of 5 stars

Lisa was outstanding with our doggies! Great communication with us and paid close attention to the little details that made them feel comfortable. Would highly recommend her!

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

We loved having Elizabeth as a rover for the past year and half. Posie was always excited to see Elizabeth and she always communicated quickly with me for any bookings and details. I would highly recommend!!

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Cassie D.
Drop-In Visits
5.0 out of 5 stars

Megan was fantastic! Buddy was so happy hanging out with her. She sent lots of photos and videos and took great care of him!

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Susannah K.
Drop-In Visits
5.0 out of 5 stars

Jan always takes great care of our 3 dogs. She keeps them on their schedule and gives them lots of love. When we get home the dogs are always relaxed and happy.

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Diane H.
Drop-In Visits
5.0 out of 5 stars

Melissa is a wonderful dog sitter and I can’t recommend her enough. She treated our pup as if he was her own and was very communicative with me throughout her visits. Looking forward to working with her again ☺️

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Samantha L.
Drop-In Visits
5.0 out of 5 stars

Vicki is amazing! My little Roxy warmed up to her quickly. It’s obvious she has much love in her heart for animals. Vicki is calm and nurturing. Vicki is also very responsive and on time. I felt comfortable leaving my Roxy with her right away.

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Angela K.
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
5.0 out of 5 stars

Casey is always caring, trustworthy and respectful of our home and our dogs needs. I know our dog is well taken care of with Casey

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Jill H.
Drop-In Visits
5.0 out of 5 stars

Kim was attentive to my dog’s needs and gave her the attention and snuggles she needed when I was out of town.

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Jennifer R.
Drop-In Visits
5.0 out of 5 stars

Really appreciate the extra flexibility coming a little later than we originally discussed to give the babies dinner!

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Josie H.
Drop-In Visits
5.0 out of 5 stars

Madison was incredibly helpful when we needed a couple last minute drop ins for our dog. She sent photos with the report card and you can tell our pup is happy. I would recommend her to anyone!

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Lindsey A.
Drop-In Visits
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  • 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?

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    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

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Popular requests for dog sitting - Whitefish Bay

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Sitters in Whitefish Bay average 6
repeat dog sitting clients

FAQs for Drop-In Visits - Whitefish Bay

Frequently asked questions about Rover

The average cost for Dog Sitting in Whitefish Bay on Rover is $21.4 per visit (as of August 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 August 2026, there are 2,165 sitters on Rover offering Dog Sitting across Whitefish Bay. 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 Whitefish Bay 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 Whitefish Bay 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 Whitefish Bay 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 Whitefish Bay. 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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