House Sitting in Havenwoods, Milwaukee

Find a loving dog sitter to watch your dog overnight in your home.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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Available this weekend
1. Miranda

All dogs welcome & Lots of play

Whitefish Bay, WI, 53217

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

About: Hi i'm Miranda, I love all dogs, (small, large, active, lazy). I'm a current dog owner myself of a Labrador retriever. I love going to all dog p... (more)

2. Morgan

Fun spirited and energetic! ??‍♀️

Wauwatosa , WI, 53213

House Sitting, Drop-In Visits, Dog Walking

"Morgan has dog sat for us multiple times. She has done everything from stopping by to let the dogs out and check their water and give a quick belly rub and t... (more)"

3. Sarah

Give your dog a great stay-cation!

Menomonee River Hills, Milwaukee, WI, 53225

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

5 repeat clients

"Sarah was great with our pup, Ruby! She stayed with her while we were away on vacation and it's obvious Ruby had a good time while we were away! We received ... (more)"

4. Isaiah

A Good Time Training and Playing

Riverwest, Milwaukee, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"My two dogs loved Isaiah right away. He's very caring, laidback, and easy to work with! He followed our instructions, sent updates, and kept the house neat &... (more)"

5. Madeline

Madeline's Dog Care

Lower East Side, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

About: I am a student at the Milwaukee School of Engineering in downtown Milwaukee. I lead a very active lifestyle so getting your pet the proper amount o... (more)

6. Kelsey

Dog lover in need of a dog friend!

Wauwatosa, WI, 53213

House Sitting, Drop-In Visits, Dog Walking

"Kelsey was great! My cavapoo, who sometimes can be anxious, warmed right up to her! Kelsey was responsive with communication before and during the stay. I wo... (more)"

7. Kelsey

PreVet Student, Dedicated Caregiver

Riverwest, Milwaukee, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Kelsey was fantastic. When she came for our meet and greet she took notes and got to know my dogs and I well. She read through their profiles before coming... (more)"

8. Jenny

Has loved dogs since childhood!

Riverwest, Milwaukee, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

"Jenny took care of my dog Sonny. He's a larger dog. A boxer mix. She did a great job house sitting and watching our dog. I would hire her again. (more)"

9. Sonja

Passionate about life with animals!

Riverwest, Milwaukee, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

"Loved the photo updates and my pups were well taken care of! Highly recommend- very flexible. (more)"

10. Steven

Top notch, experienced dog care

Lower East Side, Milwaukee , WI, 53202

House Sitting, Drop-In Visits, Dog Walking

9 repeat clients

"Steven did an excellent job caring for our little girl. She was a happy girl while we were gone-which was 10 days, that turned into 11, due to our cancelled ... (more)"

11. Brenna

Dog Walker / Babysitter

Saint Joseph, Milwaukee, WI, 53210

House Sitting, Drop-In Visits

4 repeat clients

"Brenna took great care of my pup (and my apartment) while I was out of town for three nights. She was nice enough to send daily photo updates, and was a grea... (more)"

12. Lauren

Experienced Dog Sitter and Lover

Wauwatosa, WI, 53213

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Lauren loves all animals, but she especially loves dogs. Her dog, Alfie, is the most pampered pooch ever! Lauren has provided care for numerous dogs, and s... (more)"

13. Meagan

Will love your furbabies as my own.

Saint Amelian's, Milwaukee , WI, 53222

Dog Boarding, House Sitting, Drop-In Visits

"Meagan has proved love and care for my dog for 10 years since he was born. She has a dog of her own that is 1 year old that she trained by herself. She has g... (more)"

14. Nicole

Will work for snuggles & long walks

Uptown, Milwaukee, WI, 53210

House Sitting, Drop-In Visits

1 repeat client

"We have an initially apprehensive pup, who can be quite vocal and intimidating (even though he's actually a big softy), and Nicole handled the situation so w... (more)"

15. Melissa

Registered Nurse who loves dogs

Mequon, WI, 53092

Dog Boarding, House Sitting, Dog Walking

2 repeat clients

"I cannot recommend Melissa enough. She is responsible, organized, deeply caring, and loves to take care of dogs (and cats)! I would absolutely trust any of... (more)"

16. Erica

Energetic & Compassionate Dog Lover

Riverwest, Milwaukee, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

"I have known Erica for years and she is without a doubt my go to dog lady!! My husband and I go out of town a lot for his job, so our two dogs, Dozer and Die... (more)"

Available this weekend
17. Kalee

Passionate dog lover

Grantosa, Milwaukee, WI, 53222

House Sitting, Drop-In Visits, Dog Walking

"Thanks for watching my husky while I was away kalee! Knowing how much my dog sheds, I didn't expect to come back to a groomed and washed dog. If you are look... (more)"

18. Shane

Experienced dog handler/pre vet

Hampton Heights, Milwaukee, WI, 53218

House Sitting, Drop-In Visits, Dog Walking

"Shane watched my two dogs, dachshund and mini pincher, while I went on a three day trip to Chicago. Shane checked in regularly with me, kept to the schedule ... (more)"

19. Andrea

My dogs are my world.

Melody View, Milwaukee, WI, 53224

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

About: My name is Andrea and I have two dogs of my own and I love them more than anything in the world. Your dogs will be safe with me because I would tak... (more)

20. Wanda

I love taking care of pets.

Whitefish Bay, WI, 53217

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"I first met Wanda Foy twenty years ago. We both were teaching in a parochial school working with young children. Wanda was easy going, kind and gentle towa... (more)"

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Learn About Premier

Pet parents turn to sitters on Rover.com when they're looking for house-sitting. 1,089 owners have reviewed sitters in Havenwoods, Milwaukee, WI, giving them an average rating of 5.0/5. Since 92% of pet owners live within a short drive of a sitter on Rover, it's easy to find the perfect house sitter near you. 95% of reviewed stays have received a perfect 5-star rating. Wondering how much you can expect to pay on Rover.com? Check out our average house sitting rates to get an idea before you start a conversation with a house sitter. Exchange messages from your sitter's profile, ask to schedule a free in-person Meet & Greet, and book and pay on Rover. You'll receive adorable photo updates, premium insurance, and world-class support.

Rover offers the perfect alternative to dog kennels. The next time you head out of town and need someone to take care of your dog and your home, turn to Rover for your Havenwoods, Milwaukee house sitting needs. On Rover, it's easy to find a loving dog sitter in Havenwoods, Milwaukee, WI who'll give your dog one-on-one attention while you're away, and your dog can enjoy a sweet staycation, right at home. Search from hundreds of trusted Havenwoods house sitters near you, read sitter profiles, and reach out to sitters who seem like a good fit for you and your dog. We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your dog's stay all through Rover: it's easy, safe, and cashless. You get free premium insurance, a team of safety experts available 24/7, and cute photo updates throughout the stay. It's the easiest way to find trustworthy house sitters in Havenwoods, Milwaukee, WI for your dog: people who'll treat him like family.

A Daily Treat: A Blog by Rover

Rover's got you covered, even when you don't need a pet sitter or dog walker. Check out our blog for pictures of adorable dogs, help on your biggest dog-related questions, and more:

Book a Stay, Donate to a Cause

Sit a Dog, Save a Life lets you raise money for local dogs-in-need by doing something you do already: asking your neighbors to watch your dog instead of leaving them in a kennel. Many Rover sitters in Havenwoods, Milwaukee donate a percentage of their earnings to nonprofits through Sit a Dog, Save a Life. When you book with a sitter who has the Rover Donation Badge on their profile, you're helping dogs in need, right here in Milwaukee.

We're proud to support over 200 organizations across the nation, including: