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
5.0 out of 5 stars
1 review
1 repeat client
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: Dani P.
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Dani P.
from
$20
per visit
5.0 out of 5 stars
10 reviews
2 repeat clients
9 years of experience
Glendale, WI, 53209

About: Hello! I come from a family of dog lovers currently with 20 doggies in just my imitated family plus close aunts/uncles and cousins. We have quite the hectic family holidays. I've had lots of dog sitting experience between all those pups as well as being on Rover for 9 years now. My favorite pup is my border collie/aussie mix, Piper. She’s a rescue, almost 8 years old and all energy all the time. She’s keeps me active and taught me how to keep dogs physically and mentally exercised. I’m super easy going, just let me know how I can help you and your furry friends! I am fully self employed, pet sitting and dog walking is my main gig! I am able to do walks and drop in visits 7 days a week and I am open for doggie day care on weekdays. Dogs will always be kept on leash unless in a secure, fenced in area with me. Every animals needs are different, I am happy to hear every details about your pet to know how to best care for them. Happy to feed and care for any additional pets (fish, birds, etc.) during my visits as well!

Sitter Profile Image: Linda V.
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Linda V.
from
$15
per visit
5.0 out of 5 stars
3 reviews
6 years of experience
Riverwest, Milwaukee, WI, 53212

Linda was able to come visit my puppy very last minute and I appreciate her availability. She answered promptly to my questions and kept me updated during the visit. I was nervous as this was my first time using Rover, but she was very kind and understanding.

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Silvia C.
Sitter Profile Image: Jessica Z.
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Jessica Z.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
217 reviews
64 repeat clients
30 years of experience
Lower East Side, Milwaukee, WI, 53202

Jessica was a great find for our drop in visit needs for our two cats. She was punctual, caring, and provided great care as well as updates and tons of pictures. We recommend her to other families in need of drop-in care.

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Mary Lou K.
Sitter Profile Image: Jodi C.
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Jodi C.
from
$18
per visit
5.0 out of 5 stars
37 reviews
13 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: Carole C.
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Carole C.
Star Sitter
from
$30
per visit
5.0 out of 5 stars
190 reviews
41 repeat clients
23 years of experience
Murray Hill, Milwaukee, WI, 53211

Carole is a fantastic pet sitter. Timely, efficient, very communicative and a great companion for our dogs. Would recommend without hesitation. Thank you!

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Randy P.
Sitter Profile Image: Keira S.
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Keira S.
from
$22
per visit
5.0 out of 5 stars
2 reviews
10 years of experience
Shorewood, WI, 53211

About: I have extensive experience in pet sitting, having raised my own dogs from puppies to adulthood. I have a 10 year old small Cockapoo and an 8 year old big Golden Doodle, both of whom I've cared for since they were born. Additionally, I have a highly energetic Blue Heeler, so I'm well knowledged in managing dogs with high energy levels. My skills include basic training for puppies, ensuring they learn good behaviors early on, and providing gentle, attentive care for senior dogs. I absolutely love dogs and will make sure they revive the love and attention that they very much deserve. Pet care is a big part of my daily life. I make sure to spend quality time with my dogs every day, whether it's walking, feeding, or playing with them. I ensure pets are comfortable by maintaining a clean, safe environment, providing regular meals, exercise, and playtime, and giving them lots of love and attention.

Sitter Profile Image: Hanna C.
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Hanna C.
from
$16
per visit
4.9 out of 5 stars
46 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: 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: Anna S.
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Anna S.
from
$25
per visit
5.0 out of 5 stars
31 reviews
9 repeat clients
12 years of experience
Fenway-Kenmore, Fox Point, WI, 53217

Anna was responsible and great with my dog! She consistently provided updates and photos, which were reassuring. I would highly recommend Anna, and I will definitely use her in the future!

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Ashtyn G.
Sitter Profile Image: Devashi G.
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Devashi G.
from
$30
per visit
5.0 out of 5 stars
2 reviews
2 years of experience
Glendale, WI, 53217

About: I helped raise my own two family dogs and ensured that they were always walked, bathed, fed, and happy. It's also a habit of mine to go take the extra step like wiping my dogs and make sure they are clean after they've been outside. I've also taken care of my neighbor's dogs alongside our own family dogs, so I have experience handling multiple pets at once. I work full-time, Monday through Friday, while working from home 2-3 days a week. I also go to workout classes in the evening. Normally, if working from home, I take the dogs out for a walk in the morning. On other days, I take them for a walk in the evening. I normally take pets out 3 times a day, once in the morning, afternoon, and night. I make sure the dogs have a dedicated spot for food and bed. I have both a park and a dog park, 5-10 minutes away from my apartment, which I can take the pets to for a walk or some dog play time. There are also multiple yard-like grass areas where the dogs are meant to do their business. If pets stay with me for longer than two weeks, I bathe them every other week.

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

Ana is the best! She helped me out multiple times this week with little notice. I love how I can rely on her to take the best care of my bulldog! Thanks Ana!

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Chelsea M.
Sitter Profile Image: Mikalanne T.
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Mikalanne T.
from
$18
per visit
5.0 out of 5 stars
57 reviews
20 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: Christie O.
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Christie O.
from
$19
per visit
5.0 out of 5 stars
18 reviews
3 repeat clients
20 years of experience
Milwaukee, WI, 53211

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.
Sitter Profile Image: Allison Z.
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Allison Z.
from
$14
per visit
1 repeat client
25 years of experience
Glendale, WI, 53217

About: I have watched friends and neighbor's pets for years and decided to sign up with Rover. I love all animals. I have 1 dog and 1 cat, and they are family. I will walk, love and play with all pets staying with me and follow instructions given by their owners. I can watch puppies that are really like toddlers or older wiser members of your families. I am comfortable giving medications if needed. Most will sleep on my bed and yes, they are allowed on my furniture, but they are welcome to sleep or nap wherever they would like. I want you to go on vacation knowing they are happy and having a vacation of their own. I have a morning routine which includes a long walk, depending on temperature, playing in the yard with my dog and another walk usually late afternoon. Walks include walks around my neighborhood and also at parks. While your dog is in my care, I will not be going to any dog parks with them. I will have our dogs meet prior to accepting a job. They can play in my yard and once we are both comfortable with their meeting, we can schedule a time for drop off or pick up. While in my home they will be treated with love and respect. Walks and playtime throughout the day. They are allowed to sleep or hang out wherever they would like.

Sitter Profile Image: Adrianna H.
Verified Background Check
Adrianna H.
from
$15
per visit
4.9 out of 5 stars
9 reviews
1 repeat client
15 years of experience
Milwaukee, WI, 53209

So caring... Thanks Adri!

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Luana S.
Sitter Profile Image: Patrick B.
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Patrick B.
from
$15
per visit
5.0 out of 5 stars
2 reviews
5 years of experience
Whitefish Bay, WI, 53217

About: I've taken care of dogs for around 5 years now and I enjoy taking them out on walks. I find dog walks calming and can take several hour long walks if needed. What I love to do best on my breaks is spend time with my dog, giving him walks. So I always have plenty of time to take care of pets. I can easily cater to your dog's needs when it comes to walks and house sitting. Just tell me how to typically take care of your dog and I'll do exactly that.

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: Auria R.
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Auria R.
from
$45
per visit
5.0 out of 5 stars
166 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

Linda was able to come visit my puppy very last minute and I appreciate her availability. She answered promptly to my questions and kept me updated during the visit. I was nervous as this was my first time using Rover, but she was very kind and understanding.

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

Jan was a perfect Dogsitter for my 3 year old St. Bernard who doesn’t always like everyone. She instantly got along with him & knew just what to do regarding care. Sent me photos of sessions. Definitely would recommend!

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

Angela took wonderful care of Elliott during her twice-daily visits. She showed tremendous patience with him and let him warm up to her at his own pace. By her final visit, he allowed her to pet him and take him into the yard—a big accomplishment! She also thoughtfully handled a few extra details around the house. I truly appreciated her reliable and compassionate care. I highly recommend.

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Kim S.
Drop-In Visits
5.0 out of 5 stars

Carrianne was the best! She was very flexible and our girl really loved her visits! Carrianne’s communication is top notch too. Felt very informed and assured that Frannie was being well taken care of. Highly recommend and will absolutely hire her again.

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Terese P.
Drop-In Visits
5.0 out of 5 stars

Lisa is the best, my dog is a little quirky and does not warm up to new people easily and he let her clean and wrap a wound he got on his leg and let her hand feed him! She went above and beyond in every possible way and I could not have asked for a kinder and more competent sitter for Arrow! Highly recommend!! ❤️

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

Emily was great with Teddy! She kept us updated, followed his routine, and took great care of him. Teddy seemed really comfortable with her. We’d definitely book with her again! 🐾

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

Mika agreed to a last minute drop-in and I’m incredibly grateful! They were attentive at the meet and greet, and took great care of our many critters!

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Hope S.
Drop-In Visits
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

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

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

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
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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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