Dog Walking Sugar Island

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Sugar Island, Find top rated dog walking

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

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Sitter Profile Image: Amanda C.
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Amanda C.
from
$20
per walk
30 years of experience
Neosho, WI, 53059

About: I have had pets all my life. I have 5 of my own dogs of various shape and size and foster for a couple different rescues! I am very flexible, I'm available most of the time and love to meet new pets. I try to fit the needs of pet owners where I can. I don’t plan on doing any home care. I have 5 dogs of my own and also foster. This just isn’t possible at this time.

Sitter Profile Image: Natalie K.
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Natalie K.
from
$14
per walk
5.0 out of 5 stars
7 reviews
2 repeat clients
12 years of experience
Oconomowoc, WI, 53066

Was great!l and fast response!!

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Natalie H.
Sitter Profile Image: Sadie S.
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Sadie S.
from
$20
per walk
5.0 out of 5 stars
13 reviews
4 repeat clients
16 years of experience
Watertown, WI, 53094

Sadie is so sweet and kind! She's great with my highly energetic dog, Scout. She walks him all around my neighborhood and is kind to all of our neighbors she meets on our walk. She's very dependable and has great communication skills. I am so glad I found her to help me with Scout!

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Sandy G.
Sitter Profile Image: Cooper B.
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Cooper B.
from
$18
per walk
5.0 out of 5 stars
7 reviews
1 repeat client
10 years of experience
Hartland, WI, 53029

About: I've been taking care of all types of animals for several years. Including snakes, lizards, cats dogs, and even a tarantula. I've provided exercise, care and the same love I have for my animals at home. I care daily for my own two cats, and work part time as a pet/ house sitter. Please check with me for my upcoming availability. I can rearrange my schedule to suit your needs. I will take care of your animal's needs with attention and care. Whether that means following a special meal plan, going on ten walks a day, or anything else they require. I’m happy to provide references from past clients. If you ever have any questions or concerns, feel free to call or text me anytime. My phone is always open to you.

Sitter Profile Image: Brendan B.
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Brendan B.
from
$10
per walk
2 repeat clients
1 year of experience
Hartland, WI, 53029

About: I'm comfortable with feeding, administering medications, and walks for dogs and cats. I understand how important it is to follow each pet's routine and making them feel safe and comfortable while your away. I'm flexible and available for any time of the week, including weekends. I'm happy to work with your schedule for drop-ins, walks, and extended care. When caring for pets in homes, I treat your space with respect and follow your instructions carefully. I stick to your pet's regular routine for feeding, walking, potty breaks, and playtime to keep things consistent and stress free.

Sitter Profile Image: Brandi K.
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Brandi K.
from
$12
per walk
5.0 out of 5 stars
2 reviews
1 repeat client
4 years of experience
Iron Ridge, WI, 53035

Brandi was great with my 3 dogs. She was on time. Was able to meet the dogs and I before the first day. There was an issue with the neighbors dog jumping my fence when she was out with my 3 dogs. She handled the situation very well! She sent me a lot of pictures also! I would have Brandi come back and take care of my dogs again!.

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Teresa S.
Sitter Profile Image: Bayli M.
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Bayli M.
from
$16
per walk
5.0 out of 5 stars
1 review
1 year of experience
Oconomowoc, WI, 53066

About: Hi! 🐾 I’m a teacher with summers off and a lifelong animal lover. As a dog mom myself, I know how important it is to have someone you trust caring for your pets. Whether your pet needs walks, playtime, cuddles, or dropin visits, I’ll make sure they feel safe, loved, and well cared for while you’re away. I can’t wait to meet your furry family members! 🐶🐱💕 During July, I teach summer school, so I’m available anytime after 12 PM for walks, drop-ins, and pet care. In August, my schedule becomes much more flexible, allowing for additional daytime availability. Once the school year begins, I’ll primarily be available on weekends and for evening/late-night care. As a teacher and animal lover, I enjoy spending my free time caring for pets and making sure they get plenty of attention, exercise, and love. I treat every pet like my own! I maintain routines, provide loving care, and create a safe, comfortable environment where pets feel happy and cared for while their families are away.

Sitter Profile Image: Ella W.
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Ella W.
from
$14
per walk
5.0 out of 5 stars
3 reviews
10 years of experience
Oconomowoc, WI, 53066

My pup absolutely adored Ella! She was so excited to see her and just wanted to play and play. Ella gave me lots of picture and video updates and I could tell she treated my pup just like she would her own. Super easy to get along with a took great care of my baby!

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Julia M.
Sitter Profile Image: Ramsey S.
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Ramsey S.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
53 reviews
12 repeat clients
40 years of experience
Oconomowoc, WI, 53066

Ramsey is fantastic! She was able to watch our 2 month old puppy on short notice and gave us updates every day. Will definitely be booking with her again!

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Lyndsay L.
Sitter Profile Image: Katelyn W.
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Katelyn W.
from
$15
per walk
5.0 out of 5 stars
29 reviews
13 repeat clients
8 years of experience
Oconomowoc, WI, 53066

Katelyn is great with our dog. I appreciate her fitting us into her schedule and coming to walk him while we’re away at work.

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Marissa P.
Sitter Profile Image: Yasmin U.
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Yasmin U.
from
$45
per walk
5.0 out of 5 stars
2 reviews
4 years of experience
Watertown, WI, 53094

About: With years of hands-on experience caring for both dogs and cats, I bring a well-rounded and deeply committed approach to pet care. I am the owner of Oh My Paws, a pet-sitting business I started during college, and have worked as a kennel technician, dog handler for Can Do Canines, and am currently completing an apprenticeship at a Humane Society. These roles have given me experience with a variety of temperaments, medical needs, and behavioral challenges. What truly sets me apart is my background in dog behavior and training. I am currently studying to earn my CPDT-KA (Certified Professional Dog Trainer – Knowledge Assessed) certification and have experience training service dogs through the Falcon Fetch program. This gives me a unique ability to understand body language, reduce stress in pets, and ensure a safe, enriching environment during their care. Pet care is a central part of my life and something I prioritize in my weekly routine. I have very open availability on weekends (Saturday–Sunday), and I’m also available on Mondays if needed. This flexibility allows me to provide consistent and dependable care, whether it’s for daily visits, overnights, or last-minute bookings. Because I run my own pet-sitting business and am actively involved in training and animal welfare work, I structure my schedule around the pets I care for. I take the time to provide each animal with individualized attention, exercise, enrichment, and a calm, safe environment. Whether caring for pets in my home or in a client’s home, safety and trust are always my top priorities. I begin with a detailed intake to learn about each pet’s routine, medical needs, triggers, and preferences, and I tailor my care accordingly. I use positive reinforcement and clear communication to build trust with animals, helping them feel safe and comfortable. In a client’s home, I maintain their pet’s usual routines as closely as possible to reduce stress. I’m respectful of the home environment, leave things exactly as I found them, and provide regular updates with photos and notes for peace of mind.

Sitter Profile Image: Raegan S.
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Raegan S.
from
$25
per walk
5.0 out of 5 stars
2 reviews
9 years of experience
Oconomowoc, WI, 53066

About: I’ve take care of dogs my whole life. I’ve taken care of puppy’s to senior dogs. I groom, clean up, and shower them in love I work part time but have a bunch of free time to take care of dogs. I am commuting to college so when school starts but I still have plenty of time to take care of dogs I always show dogs love and give them space when needed. I have two dogs and many more before that, so I have experience with dog behavior

Sitter Profile Image: Malarie B.
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Malarie B.
from
$25
per walk
10 years of experience
Oconomowoc, WI, 53066

About: I am outgoing, energetic, and a happy over achieving girl! You can always trust me. I’ve had dogs between golden retrievers, beagles , labs, blue healers, German Shepard’s I’ve dog sat and have been around them all! And let’s just say they love me :) So I do have a crazy job, so if you’re looking for someone to be there all day I won’t be your girl, I usually work 6-10 hours every day tue-Friday my hours vary depending on the day of the week my thursday hours (12-8)(fri8-3)(every other Saturday 8-2) (Sunday off) Mondays I work one Monday a month (4 hours) (tue 9-5 sometimes vary)(wed 8-8) I do massage therapy full time. But when I dog sit I only go to work and tend to your dogs! I make no plans and hangout with my furry friends all my free time I walk my dogs every day! I keep the homes clean just like you left them! And I’ll give the dogs all the love and snuggles in the world

Sitter Profile Image: Charles W.
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Charles W.
from
$20
per walk
5.0 out of 5 stars
8 reviews
1 repeat client
18 years of experience
Watertown, WI, 53098

About: I have always had dogs in the household ever since I was born. More specifically my family had my sister and I grow up around Black Labs the entirety of my life. Neighbors as well as my immediate family have relied on me to take care of their animals. Whether it be a short walk or staying with them for an extended period of time, I was their guy! I have an extremely open/flexible schedule. I am self employed so I pretty much choose when I want to work my other job. Taking care of animals via Rover will take top priority unless my job situation changes. If that occurs I will make sure to update my profile accordingly! I have no other animals/roommates in my apartment. So your dog/cat will get all the undivided love and attention they deserve while you're away. Same rules apply if I am asked to dog/cat sit at a clients home!

Sitter Profile Image: Cindy S.
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Cindy S.
from
$28
per walk
5.0 out of 5 stars
51 reviews
14 repeat clients
45 years of experience
Oconomowoc, WI, 53066

Cindy is reliable and great with our dogs!

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Gina R.
Sitter Profile Image: Katy Z.
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Katy Z.
from
$25
per walk
1 repeat client
20 years of experience
Neosho, WI, 53059

About: I have one or two dogs since I was a little girl. I currently have 2 rescues who I love very much! I have helped watch neighbors dog a few times, and now Would like to make some money doing what I love. Dogs are absolutely man’s best friend. I could never live without a dog in my life. I currently work full time, I work until 4 M-F. I am available on the weekends to do drop in care, dog walking or overnights I would care for dogs in your home, and make sure their every need is taken care. I will treat them like my own. I am willing to walk, bath, snuggle ,and give them my full attention

Sitter Profile Image: Anna H.
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Anna H.
from
$25
per walk
5.0 out of 5 stars
6 reviews
3 repeat clients
12 years of experience
Oconomowoc, WI, 53066

Anna took the best care of Winston! Our puppy can be shy and nervous, but she treats him like one of her own regardless and we are so thankful to have her spend time with him while we are at work. Thank you again Anna!

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Kristen M.
Sitter Profile Image: Malia K.
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Malia K.
from
$20
per walk
10 years of experience
Oconomowoc, WI, 53066

About: Hi there! My name is Malia, and I’m a dedicated dog lover ready to care for your furry friends as if they were my own. With a reliable, caring, and energetic approach, I ensure your pup gets the attention, exercise, and love they deserve while you’re away. Whether it’s long walks, playtime, or cozy companionship, I customize my care to match your dog’s unique needs and personality. I’m experienced with dogs of all sizes and energy levels, from playful puppies to senior companions. Why choose me? • Flexible availability to fit your schedule • Passionate about creating a safe and happy environment for pets • Plenty of outdoor activity and cuddles guaranteed Let’s chat to discuss how I can help you and your pup! I am a stay at home mom who is raising a beautiful baby boy ! Easy to make my own schedule! Always can be home! I am always watching the dogs, when outside must be on a leash and being watched as well! When inside always entertained and monitored throughout the day

Sitter Profile Image: Deann S.
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Deann S.
from
$25
per walk
5.0 out of 5 stars
3 reviews
2 repeat clients
27 years of experience
Watertown, WI, 53094

About: I've had dogs my whole life! Most have been middle size dogs - lab mixes, etc. I have experience with taking care of all size of pets though.I also walked dogs at a local humane society until I adopted my own bundle of joy! I have dog sat for all different sizes and types of dogs and genuinely enjoy being around them. Like I said above - I sometimes prefer dogs over people haha! I would love to get back into walking and socializing dogs looking for good homes! I love being able to help them find new homes! I just have a connection with dogs and love being around them! I currently work during the day but am free nights and weekends and would love to meet your member(s) of the family! :)

Sitter Profile Image: Amber P.
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Amber P.
from
$40
per walk
5.0 out of 5 stars
6 reviews
2 repeat clients
28 years of experience
Oconomowoc, WI, 53066

About: I have grown up with all kinds of animals, dogs being the main one. Love carin for dogs and always making them feel loved, even when owners may have to be away. What better way to spoil your pet then to make sure they have a great day too! I am the kind of person that would go to a party and hang out with the dog. I have excoerience in caring for both people and animals and hope that I may be able to help care for more. I will always be focused on what you are looking for for your dog and making sure that they get the time and love they deserve each day. Hope to talk to you soon. ? ❤️ We are a working household but have staggered start and end times so very little time is left alone. During that time dogs can remain out if possible or can be crated. Our dogs are crate trained for this time as well, though not always done. We have two friendly, though large dogs to keep yours company. We also have 2 cats, but can be placed in a different area of the house as needed. Have 2 meal times per day and can adjust to fit needs. Always have water available and frequent outside time.

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The median cost per walk for dog walking in Sugar Island is $20

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Popular requests for dog walking - Sugar Island

Select a filter and find qualifying sitters offering dog walking.

Sitters in Sugar Island average 3
repeat dog walking clients

FAQs for Dog Walking - Sugar Island

Frequently asked questions about Rover

As of August 2026, there are 1,293 sitters on Rover offering Dog Walking across Sugar Island. Enter your ZIP code to see which available sitters are closest to your home.

Whether you want a solo or group walk depends on your dog's personality. Solo walks can be beneficial for dog parents with reactive dogs, puppies, or dogs who are anxious around unfamiliar animals. Many dog walkers on Rover offer private, one-on-one walking services.

Group walks are a good fit for social dogs who enjoy structured walks. If your dog prefers the energy of a group stroll, ask your dog walker about group walks in your Sugar Island. Since all dog walkers are local, they may have a neighborhood dog who is a good walking companion to yours.

For dog walking services, you can request a report card update with specifics about your dog’s walk. Report cards require photos and can include a map of the walking route , total walk time, poop and pee breaks, and distance traveled, so you know exactly where your dog has been walking in Sugar Island.

Got specific details you'd like the dog walker to include? Message them in the app before your dog’s walk begins.

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.

Every walker 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 .

Yes, you can find walkers who have experience with handling special pet needs in Sugar Island. On Rover:

  • 95% of walkers can help with special care needs
  • 98% can help with giving oral medications or injections
  • 99% 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.

A Meet & Greet is a short introductory meeting between you, your dog, and a walker. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your walker 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 walker questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and walkers 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.

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 walker.

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