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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1. Sandy

Mature & Special Needs Dogs Welcome

Story Hill, Milwaukee, WI, 53208

Dog Boarding, House Sitting

18 repeat clients

"Sandy was terrific with my dog who suffers from separation anxiety. Buff typically stops eating for 2 - 3 days when I am away and then it takes her several d... (more)"

2. Melissa

Dog loving nurse, large fenced yard

Mequon, WI, 53092

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

27 repeat clients

"I highly recommend Melissa. I sincerely appreciated the communication leading up to and during her time sitting our puggle Cody. I look forward to working ... (more)"

3. Emily

Caring, Committed & Active

Avenues West, Milwaukee, WI, 53233

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"My now husband and I were getting married and we really wanted pictures with our dog, Willow, and someone had suggested we look into using Rover. We found E... (more)"

4. Maureen Casey

Love to get outside with your pup!

Wauwatosa, WI, 53213

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

2 repeat clients

"Maureen was the best! She took such great care of our Schatzi!! She updated us with pictures as well which was really nice to see. We would highly recommend ... (more)"

Confirmed Thanksgiving Availability
5. Heather

Dog handler -vet tech-dog lvr4lyfe!

Brewer's Hill, Milwaukee, WI, 53212

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

2 repeat clients

"Heather sends great updates and lots of photos and it’s clear my pup loved her instantly. It’s hard to tell there’s even been anyone in my house as she lives... (more)"

6. Hannah

Working part time, love walks

Murray Hill, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Hannah did a wonderful job housesitting for our home and our dog, Sterling, for two and a half weeks! She is very friendly and kind and responds to messages ... (more)"

7. Yessenia

Home full-time- Years of experience

Riverwest, Milwaukee, WI, 53212

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

1 repeat client

"Yessenia has been watching my babies for a long time, she's like family. I have been comfortable leaving them with her since day one. They always seem so com... (more)"

8. Wanda

I love taking care of pets.

Whitefish Bay, WI, 53217

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

4 repeat clients

"Very flexible and accommodating. Made our dog feel comfortable, and made us feel assured he was being well-cared for. (more)"

Confirmed Thanksgiving Availability
9. Sara

Lifetime dog lover

Wauwatosa, WI, 53222

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

11 repeat clients

"Sara took great care of my pets while I was away at work. She sent me pictures and updates throughout the day so I knew they were being loved on. :-) (more)"

Confirmed Holiday Availability
10. Jazmine

I have a passion for animals!

Bradley Estates, Milwaukee, WI, 53223

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

2 repeat clients

"Jazmine is a very knowledgeable and friendly sitter. It made me feel so much better knowing my munchkin could be in his own environment while I was gone. (more)"

11. Rachel

Experienced dog handler-dog lover

Golden Valley, Milwaukee, WI, 53222

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"She was amazing! I was so worried about my pups but she calmed my nerves. She sent me messages daily with updates. She was professional with everything. Appo... (more)"

Confirmed Thanksgiving Availability
12. Lisa

What beats the love of a dog?

Kops Park, Milwaukee, WI, 53222

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: My name is Lisa, and I love dogs! Pretty sure everyone here says that. I would like to watch your dog in your home because the less their world i... (more)

13. Kevin

Your Dog Loves Me!!!

Shorewood , WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"I got my Border Collie Jessie as a one year old rescue. Due to mistreatment or misunderstanding of the breed, she is very sensitive to the people around her.... (more)"

14. Joshua

Outdoorsy dog lover

Thurston Woods, Milwaukee, WI, 53209

House Sitting, Drop-In Visits, Dog Walking

"Josh was an absolute joy to work with. He took GREAT care of my 2 English Mastiffs (which is not a small job to take-on). I was very nervous leaving town f... (more)"

15. Cynthia

Willow's Way Dog Haven!

Wauwatosa, WI, 53213

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

"Highly recommended. They came for a meet and greet prior (more)"

16. Amari

Love & Care for your fur babies!

Vogel Park, Milwaukee, WI, 53225

House Sitting, Drop-In Visits, Dog Walking

"I’ve known Amari for a few years now and I just want to say what an amazing girl. She’s very hardworking, caring,respectful, and responsible especially when ... (more)"

Confirmed Thanksgiving Availability
17. Darby

A Dog's Best friend

Milwaukee, WI, 53217

House Sitting, Drop-In Visits, Dog Walking

About: I have been watching dogs for about three years now, and every owner has asked me to watch their dogs again! I love playing with dogs, and being ac... (more)

18. Meagan

Will love your furbabies as my own.

Arlington Gardens, Milwaukee, WI, 53222

Dog Boarding, House Sitting, Drop-In Visits

"She was more than happy to watch my Hugo while I was out of town for just over a week. She took excellent care of him and was able to manage his severe alle... (more)"

19. Stephanie

Dogs all breeds and sizes welcome!

Menomonee River Hills, Milwaukee, WI, 53224

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

"Stephanie is really great with my dog and cats. She has always been really caring and compassionate towards my pets. She really goes off her way to make sure... (more)"

20. Sandy

I'll love your dog like you do.

Silver Spring, Milwaukee, WI, 53218

House Sitting, Drop-In Visits, Dog Walking

"I have known Sandy for a long period of my life. She is one of the most courageous and caring people I know. Sandy's very determined and will always complete... (more)"

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: