House Sitting In Highwood Estates

Find a loving house sitter to watch over your pets and your home.

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Top rated Highwood Estates house sitters

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

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Sitter Profile Image: Mallory S.
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Mallory S.
Star Sitter
from
$47
per night
5.0 out of 5 stars
43 reviews
14 repeat clients
30 years of experience
West Allis, WI, 53719

Mallory is so nice! She ensured that Kermit was comfortable despite fireworks and a thunderstorm in the same weekend. She sent us updates twice a day to reassure us that he was doing okay.

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Miranda D.
Sitter Profile Image: Emily M.
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Emily M.
Star Sitter
from
$59
per night
5.0 out of 5 stars
33 reviews
8 repeat clients
30 years of experience
Milwaukee, WI, 53213

Emily did a great job watching my pups, and chickens. Easy and quick communication, she took the pups on some adventures as well. Highly recommend her and would use her again.

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Lauren S.
Sitter Profile Image: Justine R.
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Justine R.
from
$60
per night
20 years of experience
Euclid Park, Milwaukee, WI, 53227

About: I’ve been a devoted animal lover and pet owner for as long as I can remember. From dogs and cats to caring for pets with unique personalities and needs, animals have always been a huge part of my life. Currently, I share my home with a lovable, mischievous hound mix who keeps me on my toes and a cat who completely stole my heart. A few years ago, I lost my soul dog, Jersey, and that experience deepened my understanding of the special bond we share with our pets. I know firsthand how difficult it can be to leave them behind and trust someone else with their care. That’s why I treat every pet as if they were my own—with patience, affection, attention, and plenty of love. Whether your pet needs a quick drop-in visit, playtime, cuddles, a walk, or simply a friendly face while you’re away, my goal is to make them feel safe, happy, and cared for. I also know how important peace of mind is for pet parents, so you can expect regular updates, photos, and communication throughout my visits. Because I work from home, I have a flexible schedule that often allows me to accommodate drop-in visits and pet care needs throughout the day. I’m committed to providing dependable, compassionate care and building a trusting relationship with both you and your pets. I look forward to meeting your furry family members and becoming someone you can count on whenever you need a helping hand! 🐾❤️ I work from home and have a decently flexible schedule. I have a young son and pets of my own but thankfully I share these responsibilities with my rockstar husband so I will be able to care for your fur babies. I understand that having a stranger in your home can be a little uncomfortable. I will 💯 respect your space and keep things clean in order for your while you are gone. Please let me know your preferences for my stay.

Sitter Profile Image: Jenn S.
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Jenn S.
Star Sitter
from
$70
per night
5.0 out of 5 stars
117 reviews
34 repeat clients
40 years of experience
West Allis, WI, 53227

Jenn was wonderful! She was dependable and super responsive. She sent us frequent photo updates as well which made us feel comfortable knowing our dog was in great hands while we were away

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Kristen A.
Sitter Profile Image: Keisha P.
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Keisha P.
from
$45
per night
4.9 out of 5 stars
45 reviews
19 repeat clients
8 years of experience
Clarke Square, Milwaukee, WI, 53204

We were very happy with the communication and attention to detail while watching bella. Not only did she take great care of our dog but also our house 🧡 we would definitely recommend her and use her in the future

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Amy G.
Sitter Profile Image: Melissa F.
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Melissa F.
from
$68
per night
5.0 out of 5 stars
4 reviews
3 repeat clients
25 years of experience
WEST ALLIS, WI, 53227

Melissa was amazing with our two labs. She took impeccable care of them and our home. She is conscientious, organized and soooo kind! Our girls loved her. Lots of pictures and updates. Our minds were at ease during our last minute getaway! Would absolutely recommend!

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Wendy P.
Sitter Profile Image: Maya M.
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Maya M.
Star Sitter
from
$55
per night
5.0 out of 5 stars
12 reviews
2 repeat clients
10 years of experience
Greenfield, WI, 53228

Maya was so great with our two dogs! She’s incredibly trustworthy, kind, helpful, and communicative. Her dog, Mello, is also such a gem. We really appreciated all her help over the long weekend, and would rebook in a heartbeat!

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Audrey J.
Sitter Profile Image: Adrianne R.
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Adrianne R.
from
$50
per night
5.0 out of 5 stars
19 reviews
1 repeat client
20 years of experience
Franklin, WI, 53132

Andrianne was wonderful! She was communicative throughout her time with Tex. Pictures often! She Not only took good care of our precious dog, but Our Home as well! I would highly recommend Adrianne for your pet sitting needs! We will definitely be using her again! Words I would use to describe her: kind, trustworthy,friendly!

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Pamela W.
Sitter Profile Image: Lexi K.
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Lexi K.
Star Sitter
from
$75
per night
5.0 out of 5 stars
137 reviews
46 repeat clients
10 years of experience
Cannon Park, Milwaukee, WI, 53214

Lexi was great with my particular and somewhat shy senior dog. We planned drop-ins prior to the full weekend, which worked great for Lexi and my Coco to get to know each other a little. Lexi is very responsive and gave updates. I will feel more comfortable taking trips and time away with Lexi caring for my girl!

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Mary M.
Sitter Profile Image: Joseph D.
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Joseph D.
from
$28
per night
4.8 out of 5 stars
5 reviews
2 repeat clients
10 years of experience
Wauwatosa, WI, 53213

About: I’ve been looking after fluffy frens of all shapes and sizes from a young age. My time doing a full house/dog sitting gig was for my grandparents and their French bulldog, Sugar (miss you, Sugs!). Since then I have been the go-to for my friends and family for taking care of their for legged family. I make sure your fury family gets the love and care they need, whether you just have one smol dog or a pack of greyhounds. I currently had a stretch of rough health luck, but my ails are your pups gain! I’m currently on the mend, and it’s going well, but between jobs, so my schedule is wide open. I’ll have the time to give your pups the TLC they deserve! Currently unavailable to board pets at my house, but I will make sure to treat all pets in a safe and caring way. I’ll treat them like a newborn baby, because hey, in a way they are!

Sitter Profile Image: Sarah J.
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Sarah J.
from
$50
per night
5.0 out of 5 stars
508 reviews
89 repeat clients
5 years of experience
West allis, WI, 53219

Sarah is the best! This was the longest we’ve been away from our dog, and we came home to a happy, comfortable dog and a clean house to boot! Our vacations are always so much more enjoyable because we know Sarah is doing a killer job taking care of our pup :) thank you Sarah!

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Hannah T.
Sitter Profile Image: Amanda S.
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Amanda S.
from
$55
per night
5.0 out of 5 stars
40 reviews
9 repeat clients
10 years of experience
West Allis, WI, 53219

Amanda is wonderful! Great communicator and is so thoughtful with each of our individual pups. We have a senior dog and Amanda is very patient and caring with her. We would absolutely hire again.

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Katie W.
Sitter Profile Image: Scott S.
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Scott S.
from
$40
per night
5.0 out of 5 stars
17 reviews
4 repeat clients
15 years of experience
Honey Creek Parkway, Milwaukee, WI, 53214

Scott was our first introduction to Rover. We really appreciated that he could come on short notice to sit with our 22-week old puppy. We loved Scott's relaxed and gentle way with our dog who is so excited to meet someone new, but is still in manners training in how to greet people. Scott quickly picked up on what we were trying to teach and went along with that routine. Scott arrived on the dot of our agreed time and we plan to ask him to come again!

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Maree E.
Sitter Profile Image: Audrey N.
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Audrey N.
from
$28
per night
1 year of experience
Greenfield, WI, 53228

About: I’ve been the go-to pet sitter for my family and friends for years because I actually enjoy the 'tricky' stuff. From helping my own senior dog with bladder issues to winning over an abused, reactive Rottweiler, I have a lot of heart for pets that need a little extra patience. I’m also totally comfortable with bearded dragons and cats! I’m used to walking dogs in areas without fences, so I’m very careful on the leash and always keep safety first. I’ve had to clean up after bad sitters so I'll make sure your house stays spotless and your pets stay happy while you’re gone! Animals are a huge part of my daily life, so I build my schedule around making sure they feel safe and cared for. I’m currently available Monday-Sunday with Flexible Hours and am always happy to help with last-minute requests or holiday bookings when you're in a pinch. Which is perfect for seniors needing extra potty breaks or reactive pups who need a calm, un-rushed walks. I make your pet's routine my top priority every single day! Safety is Always my top priority, but keeping your pets happy is a close second! Whether I’m hanging out with your cat, dog, or bearded dragon (exc. I stick strictly to the routine you’ve set so they feel totally secure while you're gone. Since I’m used to walking pups in areas without fences, I’m always extra careful to double-check leashes and harnesses before we head out the door. I’m also a bit of a neat freak so I’ll make sure your home is pet-proofed and leave it even cleaner than I found it. I’m a big believer in open communication, so expect plenty of photo updates of your best friends (scales or fur!) so you can relax knowing they’re in great hands!

Sitter Profile Image: Patricia N.
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Patricia N.
Star Sitter
from
$40
per night
5.0 out of 5 stars
102 reviews
30 repeat clients
30 years of experience
Franklin, WI, 53132

Patricia was very attentive and detail oriented, and she made sure to cover all of her bases when preparing to care for our pup. She is experienced and professional. I would absolutely hire her again and recommend her to others!

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Lauren P.
Sitter Profile Image: LilyAnn R.
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LilyAnn R.
from
$32
per night
5.0 out of 5 stars
4 reviews
5 years of experience
West Allis, WI, 53219

Lily was great! Our dogs were well cared for, and it was clear that Lily took great care of them. We will absolutely be using her again. She is so nice, communicative, professional, and accommodating.

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Kaye R.
Sitter Profile Image: Jordan D.
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Jordan D.
from
$50
per night
5.0 out of 5 stars
7 reviews
1 repeat client
7 years of experience
Avenues West, New Berlin, WI, 53151

Jordan was fantastic! She did a great job housesitting and taking care of our dog and other animals while we were away. Our dog is very anxious when separated from us, and hasn't done well boarding in the past. This was our first experience with a sitter in home, and Jordan made the process super easy! Winston loved her, Jordan kept us up to date with regular communication...I can't say enough good things! We'll definitely re-book with her in the future! Thanks Jordan!

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Jennifer M.
Sitter Profile Image: Marilia D.
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Marilia D.
from
$75
per night
5.0 out of 5 stars
81 reviews
25 repeat clients
15 years of experience
Wilson Park, Milwaukee, WI, 53221

Marilia communicated often sending updates and pictures, and was very open to our instructions and the pets’ daily routines. We felt good that Marilia would care for them well while we were able to focus on our flight process without having to worry if the pets were eating and going potty when they needed to. Thank you so much for looking after them!

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Stefanie V.
Sitter Profile Image: Elizabeth J.
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Elizabeth J.
Star Sitter
from
$50
per night
5.0 out of 5 stars
32 reviews
6 repeat clients
17 years of experience
Lower East Side, Milwaukee, WI, 53202

It was our second time hiring Elizabeth, another positive experience. My pooch likes his walks and we are grateful she is ok with taking him. She is great with giving updates and sending photos. Upon return the house was just as we left it.

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Carol M.
Sitter Profile Image: Krystle S.
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Krystle S.
from
$50
per night
4.3 out of 5 stars
11 reviews
4 repeat clients
10 years of experience
Honey Creek Manor, Milwaukee, WI, 53220

About: I love any type of dog, any type of dog is welcome in my home for caring, people I know describe me as a nice loving person . I work from home on my own time, I am self employed, dog sitting will fit in my schedule routine just perfectly right to welcome any dog. Anything the owner does for the care of there dog fits right in with me, communication on how you would like for me to take care of your dog is the key, I would love for your dog to feel right at home .

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Highwood Estates pet parents share their Rover experiences

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5.0 out of 5 stars

As with last time, everything was perfect! Amazing communication throughout the stay. Sharing everything from updates on our moody dog’s tummy issues to funny anecdotes! Even our most shy cat deems Emily a quality caretaker! So much so that he makes his presence known and allow for pets!

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Jensen M.
House Sitting
5.0 out of 5 stars

Amazing sitter for Bear and Oakley she gave lots of updates and cleaned up after Bear when he had an accident! Loads of pictures both dogs were happy to see her as always! I definitely recommend

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Megan G.
House Sitting
5.0 out of 5 stars

Maya was AWESOME! We needed a last minute Rover to stay at our house and watch our 2 pups for a night and she was such a good fit for the job. Super communicative & sweet — we always received the cutest pupdates. Our dogs were 100% in great hands & we’ll definitely be booking with Maya in the future! 😊

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Jenna H.
House Sitting
5.0 out of 5 stars

Second time Melissa has cared for our pups Oakley and Nala (2 labs)! This time with one recovering from ACL surgery. She followed the plan perfectly and the girls absoutley LOVE HER, Daily detailed updates , photos and walk maps were sent. We came home to perfect pups and a spotless home. Thank you Melissa for loving our girls when we were away 💗💗 She is amazing,

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Wendy P.
House Sitting
5.0 out of 5 stars

Rachel has house sat for us a number of times and our pets love her. We feel comfortable knowing Sully the dog and the cats are well taken care of. We arrive home to a clean house! Thank you, Rachel!

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Todd S.
House Sitting
5.0 out of 5 stars

Amanda was wonderful. This was the first time we traveled without our puppy and we were a bit apprehensive. However, Amanda eased our concerns. She arrived a few minutes early which signaled a level of reliability that was very welcome. While we were away, Amanda provided regular updates and pictures. As a result, we were able to enjoy our vacation. And our puppy seemed to genuinely enjoy Amanda. We will definitely use Amanda again. We would feel very comfortable leaving our puppy with her.

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Kerry H.
House Sitting
5.0 out of 5 stars

Nicole is awesome ! I felt more than comfortable leaving my baby in her care ! She sent me lots of pics a videos and kept me in the loop ! She was super nice and very professional !! You can tell she really cares about furrbabies !

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Emily Z.
House Sitting
5.0 out of 5 stars

Kim did a great job boarding my two frenchies! She sent updates/photos, asked questions if she had any and really learned my pups through and through! Would definitely book again and recommend 💗🐶

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Liz F.
House Sitting
5.0 out of 5 stars

Hannah always goes above and beyond, and knowing that she is taking care of Kai gives me such peace of mind! She is truly great with animals, and treats them like one of her own. I cannot recommend her enough!

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abigail b.
House Sitting
5.0 out of 5 stars

Went on vacation from April 8 - 16 and hired Jenn as a pet sitter at my house. I cannot say enough how nice, thoughtful and caring she was. She took great care of my elderly dog and 2 cats. Jenn got my very shy cat to come out in 1 day. Amazing! She sent pics and notified everyday on how they were doing. I felt as ease being gone. I would definitely hire Jenn again and recommend her to anyone. She left my house just the way it was when I left. I would give her 6 stars if I could Thank you Jenn for taking such good care of my babies ❤️

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Jane H.
House Sitting
5.0 out of 5 stars

Cary was an excellent dog sitter! She cared for my dog for 7 days while I was out of the country, and this was my first time being away from my dog. She was very thoughtful about sending regular updates throughout the day, which gave me so much peace of mind. Cary stayed at my home and took great care of both my dog and my space. She kept everything clean and even washed my sheets before I returned, which I truly appreciated after a long day of traveling. It’s clear she genuinely cares and treats your pet like her own. I highly recommend her to anyone looking for a reliable and caring dog sitter!

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Seryna G.
House Sitting
5.0 out of 5 stars

She did an amazing job with our boy, Koda! We were nervous being away from him for a whole week, but she did such a good job of being with him, communicating with us of updates as well! We will definitely be using her again in the future!

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Brittney R.
House Sitting
5.0 out of 5 stars

We use Amanda multiple times a year and she is great! I love the daily photos of our pup, and I know she with take great care of our big guy. Thanks, Amanda!

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Erin F.
House Sitting
5.0 out of 5 stars

Caitlyn was once again outstanding. She provided excellent care for our five dogs and accommodated our newest addition on short notice. She handled Mayhem’s medications perfectly (which is an absolute necessity as she has Addison’s Disease) and shared lots of regular photo updates, which we greatly appreciated during our 10-day absence. Our dogs clearly adore her and are always excited to see her. This is our fourth time using Caitlyn, and we hope she’ll continue to sit for us! I really can’t say enough good things!

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Cam H.
House Sitting
5.0 out of 5 stars

Stephanie was amazing with our dogs! She was on time, communicative, helpful, and easy to get along/work with. We would absolutely have her over to hang with the dogs again. Thank you Stephanie!

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Kaye R.
House Sitting
5.0 out of 5 stars

Alexis saved the day when we had a last-minute cancellation for a long trip. She was wonderful and spent lots of time with our pets, sending updates and giving them lots of love!

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Cassandra D.
House Sitting
5.0 out of 5 stars

Caitlyn checks in once a day with pictures, which I really appreciate, and is super communicative. She’s catsit for me twice now and does a great job - I will absolutely continue to schedule with her!

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Tressa S.
House Sitting
5.0 out of 5 stars

Ashley took absolutely excellent care of our cat while we were out of the country for a week! I knew from the moment she met our cat during our meet and greet that our little girl was going to be in great hands. Throughout the trip, Ashley reached out with check-ins and photos reflecting how well she was being taken care of. She also responded quickly to any messages and went above and beyond watching our place. We (and our cat) look forward to seeing her again in the future!

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Jeremiah W.
House Sitting
5.0 out of 5 stars

Samantha was great. The dogs loved her from the meet and greet and she was in constant communication sending lots of pictures. Had complete piece of mind with her watching them.

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Scott B.
House Sitting
5.0 out of 5 stars

I always feel so comfortable leaving my dog and my home in Holly's care. Communication is excellent, as is reliability and a willingness to go the extra mile.

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Anne T.
House Sitting
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  1. 1. Search

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  2. 2. Meet & Greet

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House Sitting FAQs

Frequently asked questions about Rover

If you’re searching for a Highwood Estates house sitter for the first time, visit the house sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a house sitter before, learn more about how to do this in the Rover app or on your computer.

Rover makes it easy to reach out to multiple house sitters about your booking. Typically, house sitters on Rover respond in under an hour.

Experience can vary widely from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when comparing house sitters available in Highwood Estates.

Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Highwood Estates house sitters are great for:

  • Dogs who’d prefer to stay on their home turf
  • Cats and caged pets
  • Pet parents on a tight schedule
  • Keeping an eye on your home and plants while you’re away

Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.