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 121
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: Dani P.
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Dani P.
from
$20
per visit
5.0 out of 5 stars
11 reviews
3 repeat clients
9 years of experience
Glendale, WI, 53209

Excellent communication and very happy with how well Dani helped us out!

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Chris R.
Sitter Profile Image: Travis H.
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Travis H.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
371 reviews
115 repeat clients
35 years of experience
Riverwest, Milwaukee, WI, 53212

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.
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: Jodi C.
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Jodi C.
Star Sitter
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: Anna S.
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Anna S.
from
$25
per visit
5.0 out of 5 stars
31 reviews
10 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: Jessica Z.
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Jessica Z.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
221 reviews
64 repeat clients
30 years of experience
Lower East Side, Milwaukee, WI, 53202

Jessica is terrific! She is so good with my senior cat and takes great care of her when I’m out. Her communication is very timely and you can count on her to be there. I have booked her several times and will continue to do so.

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Debra L.
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: Joseph Q.
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Joseph Q.
from
$16
per visit
14 years of experience
Downer Woods, Milwaukee, WI, 53211

About: I’ve got a lot of experience with cats—I have two of my own (6 years old and 1 year old), and they’re basically family to me. I’m used to all kinds of personalities, from super playful to more shy or independent. I also grew up with Maltese dogs, so I have experience walking and caring for dogs too. I’ll make sure your pet is fed, comfortable, and cared for, whether that means playtime, attention, or just giving them space. I’ll treat your home with respect and care for your pets like they’re my own. I work full time currently but i am off on the weekends to care for your pets while your away on a weekend getaway. I am available the whole day unless i have something scheduled but ill work with you if thats the case. ill care for your pets as if they were my own and care for your place, ill keep it clean and maintain the litter and cats happy during my time with them.

Sitter Profile Image: Olivia K.
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Olivia K.
from
$25
per visit
5.0 out of 5 stars
5 reviews
1 repeat client
5 years of experience
Shorewood, WI, 53211

About: I’ve been caring for pets for the past 13 years, starting with walking my neighbors’ dogs multiple times a week and stopping by to let them out when their owners were away overnight. Since then, animal care has been a constant part of my life. I’ve helped care for my own dogs in every way—from off-leash walks and swimming to bathing and attending vet appointments. My family and I have also fostered dogs ranging from 8-week-old puppies to senior pups, giving me experience with dogs of all ages and needs. In addition to dogs and cats, I have extensive experience working with horses. I also have a laid-back tabby cat of my own who’s more like a dog than a cat. I’m a huge animal lover and always care for pets as if they were my own—providing the same attention, patience, and love I’d want someone to give my animals. I’m currently a full-time student at UWM, but I have a very flexible schedule. I attend classes three days a week, and most of my coursework can be done on my laptop. This allows me to spend plenty of quality time with your pet throughout the day and easily accommodate feedings, walks, playtime, and check-ins. I care for every pet as if they were my own. I understand that for most people, pets are family, and I treat them with the same love, respect, and attention I give my own animals. When I’m caring for pets , I prioritize their safety, comfort, and routines so they feel secure and well cared for at all times.

Sitter Profile Image: Jasmine R.
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Jasmine R.
from
$16
per visit
5.0 out of 5 stars
85 reviews
8 repeat clients
5 years of experience
Murray Hill, Milwaukee, WI, 53211

jasmine was INCREDIBLE! she was super accommodating to my last minute booking and responded very quick to all of my messages! my cats are super shy, so i wasn’t expecting them to come out for her, but she managed to get a few pictures of them which made my day! she went above and beyond and i’d 10000% recommend booking her.

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Addy P.
Sitter Profile Image: Annika H.
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Annika H.
from
$14
per visit
8 years of experience
Shorewood, WI, 53211

About: I’ve had dogs ever since I was born: a black lab and then two beagles! It was often my responsibility to care for them until my parents got home and we’ve pet sit ourselves before too. I love dogs, so I’d love to help anyone out who has one! I reserve my bookings just for weekends, as I’m busy pretty much all day and night throughout the week! I keep myself very busy! I would love to check in on your pet during the weekends though! It would be my pleasure! I always make sure that the pets are well attended to and that they are my priority. They will always have the appropriate food and attention necessary for them.

Sitter Profile Image: Lenys H.
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Lenys H.
from
$30
per visit
4.9 out of 5 stars
31 reviews
11 repeat clients
12 years of experience
Shorewood, WI, 53211

We were visiting from out of town and needed a dog sitter while we were gone for many hours at a wedding. Lenys was so nice. She came by in the morning to meet us and our dog. Then, she came over in the evening to walk him, play with him, and give him food. We especially loved the photos. Thank you, Lenys! We will definitely hire you again when we are back in town.

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Amy C.
Sitter Profile Image: Chanell W.
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Chanell W.
from
$13
per visit
2 years of experience
Milwaukee, WI, 53209

About: My Name is Chanell I graduated from Whitefish Bah High School and also volunteered at the Racine Humane Society and the Spay and Neuter Clinic in West Allis. i worked at the VCA Milwaukee Emergency Center for Animals as a vertical assistant however I used to work at the WVRC as a vet assistant also. I love all pets short, tall and all breeds and I am eager to make your pet my friend and gain your trust as a worker. I have a very flexible schedule since I started school full time and am dedicated most of my days to that. I am available during the morning and evenings. I always watch after pets like they are my own, with the right amount of food, exercise and love I know I can be your pets best-friend and a trustworthy worker.

Sitter Profile Image: Gabriel T.
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Gabriel T.
from
$25
per visit
4.9 out of 5 stars
17 reviews
4 repeat clients
7 years of experience
Upper East Side, Milwaukee, WI, 53211

Gabriel is awesome! Took great care of my cat on super short notice, was communicative, and sent great photos!

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Shelby L.
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: Mikalanne T.
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Mikalanne T.
from
$18
per visit
5.0 out of 5 stars
61 reviews
22 repeat clients
4 years of experience
Riverwest, Milwaukee, WI, 53212

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.
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: 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: Alhana S.
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Alhana S.
from
$25
per visit
4.8 out of 5 stars
8 reviews
5 repeat clients
10 years of experience
Murray Hill, Milwaukee, WI, 53211

Alhana was awesome! I would certainly boon with her again ☺️

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Karlee S.
Sitter Profile Image: Auria R.
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Auria R.
from
$45
per visit
5.0 out of 5 stars
167 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

Ana gave excellent care to our dog while we were away! She was timely and sent detailed reports and pictures each time she dropped in to take care of our dog. She also gave our dog lots of attention and snuggles! I would highly recommend her for any of her services!

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

Bria B was exceptional, flexible and amazingly attentive to our dog, Lenny Bruce, and senior cat, Sam. She stayed extra and checked in multiple times when Lenny Bruce was struggling with a thunderstorm. We are so appreciative for her visits and would definitely rebook her for future visits.

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Morgan K.
Drop-In Visits
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

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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  • 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

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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 September 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 September 2026, there are 2,111 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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