House Sitting Greendale

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

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Over 72
pet parents in Greendale have booked house sitting

Greendale, Find top rated house sitting

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

1 / 1
Sitter Profile Image: Elizabeth H.
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Elizabeth H.
Star Sitter
from
$75
per night
5.0 out of 5 stars
228 reviews
44 repeat clients
9 years of experience
Muskego, WI, 53150

Elizabeth watched our puppy overnight for NYE. She kept us updated and sent pictures. We appreciated the last minute help especially for the holiday!

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Hockey 2.
Sitter Profile Image: Jenn S.
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Jenn S.
Star Sitter
from
$70
per night
5.0 out of 5 stars
129 reviews
35 repeat clients
40 years of experience
West Allis, WI, 53227

Jenn is a amazing! She is the most kind and compassionate woman. This is the very first time we have ever left our two rescue dogs, so I wasn’t sure what to expect with our two pups and how they would react to anyone other than family watching them. she watched them for two stretches of time periods, one stretch of time was for a few hours while we were at a rehearsal dinner and with a second stretch of time it was for over 12 hours at our daughters wedding. The first stretch of time they barked continuously, and poor Jenn soldiered through like a champ, unscathed. I was afraid she wouldn’t show up the next day, but there she was bright and early the next day, ready to meet the challenge! Within 10 minutes, she texted me with a photo that our two beautiful pups were fast asleep and quiet. She had a wonderful day. It just took a while for them to get used to being with someone other than their owners. She was wonderful, kept us up-to-date throughout our time away. With photos and brief updates. Highly recommend, if I could leave more than five stars, I would!⭐️

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Sherrie A.
Sitter Profile Image: Alissa A.
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Alissa A.
Star Sitter
from
$70
per night
5.0 out of 5 stars
13 reviews
3 repeat clients
20 years of experience
Greenfield, WI, 53221

Alissa was great! She really came through for us at the last minute so we were able to enjoy our concert stress free! She kept us updated, and was prompt with her communication! The boys loved her!

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Cue T.
Sitter Profile Image: Keisha P.
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Keisha P.
Star Sitter
from
$50
per night
4.9 out of 5 stars
50 reviews
22 repeat clients
8 years of experience
Clarke Square, Milwaukee, WI, 53204

Keisha is wonderful! Our pups are very shy but Keisha did a great job helping them warm up. She is sweet, communicative and flexible, and even sent us pics of the girls while she was watching them!

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

Sarah took good care of my precious Joey and my home while I was on a vacation. She sent updates and gave him lots of love. I appreciate her professionalism .

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

We came home to 4 happy healthy fur babies from our week long vacation. Lots of photos and check ins were sent to ease our mind. Our bed sheets were washed and bed re-made, house stayed clean. There is no doubt I will use Pat again. AMAZING!!

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Jen M.
Sitter Profile Image: Audrey N.
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Audrey N.
from
$28
per night
5.0 out of 5 stars
6 reviews
2 repeat clients
1 year of experience
Greenfield, WI, 53228

Audrey took excellent care of my babies so I could have a mini getaway, she made my boys happy and feel loved.

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Kelly S.
Sitter Profile Image: Samantha S.
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Samantha S.
from
$33
per night
5.0 out of 5 stars
6 reviews
2 repeat clients
10 years of experience
Bay View, Milwaukee, WI, 53207

Sam was great with our rambunctious pup! She was so attentive to Walter, sent daily updates and photos, and left our home in stellar shape. Thank you!

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Livia A.
Sitter Profile Image: Emily M.
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Emily M.
from
$59
per night
5.0 out of 5 stars
41 reviews
10 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: Blythe R.
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Blythe R.
Star Sitter
from
$75
per night
5.0 out of 5 stars
209 reviews
72 repeat clients
7 years of experience
South Milwaukee, WI, 53172

We can’t say enough good things here. We had a really bad boarding experience and needed to do something different. We were a little hesitant with having someone in our home but Blythe was awesome. We have a large dog who is pretty needy and a little old man. She took pics, gave us updates and did everything we asked and our home looked the exact way we left it. Would highly recommend!

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Kasie S.
Sitter Profile Image: Anna S.
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Anna S.
Star Sitter
from
$45
per night
5.0 out of 5 stars
15 reviews
4 repeat clients
5 years of experience
Oak creek, WI, 53154

Anna was wonderful. She was a great communicator and sent me a daily picture and update of how my dog was doing or what they did that day. I felt very comfortable with Anna watching my dog and would definitely use her again.

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Ashley P.
Sitter Profile Image: Melissa F.
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Melissa F.
from
$68
per night
5.0 out of 5 stars
6 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: Makayla D.
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Makayla D.
from
$75
per night
5.0 out of 5 stars
30 reviews
13 repeat clients
20 years of experience
Muskego, WI, 53150

Makayla is great. She’s the best we’ve found on Rover yet.

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Amanda B.
Sitter Profile Image: Abigail B.
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Abigail B.
Star Sitter
from
$70
per night
5.0 out of 5 stars
71 reviews
16 repeat clients
18 years of experience
Muskego, WI, 53150

Abigail did a fantastic job with our pups! She was kind, trustworthy, and clearly cared about providing the best care possible. I really appreciated her communication throughout — she even let us know that our fridge was acting up and helped us find a solution while we were away. We felt completely at ease knowing our dogs were in great hands!

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Gretchen Z.
Sitter Profile Image: Heidi B.
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Heidi B.
from
$50
per night
5.0 out of 5 stars
45 reviews
15 repeat clients
32 years of experience
Caledonia, WI, 53402

Heidi was truly amazing… She really took great care of my little guy while he was in recovery after an unexpected surgery. She kept me in the loop on everything that was happening and really helped keep my mind at ease when I was unable to be there. Very grateful to have found her, and will definitely use again in the future.

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Jennifer G.
Sitter Profile Image: Rebecca M.
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Rebecca M.
Star Sitter
from
$38
per night
5.0 out of 5 stars
12 reviews
4 repeat clients
5 years of experience
Kilbourn Town, Milwaukee, WI, 53203

Rebecca was phenomenal with my little critters! Excellent communication throughout the week and she was able to adjust last minute to needing to give my dog extra TLC and medication. I highly recommend her for your pet-sitting needs!

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Kristina P.
Sitter Profile Image: Alexandra I.
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Alexandra I.
Star Sitter
from
$80
per night
5.0 out of 5 stars
31 reviews
6 repeat clients
11 years of experience
Juneau Town, Milwaukee, WI, 53202

Alex did a great job with Tucker. She bonded with him immediately, he was feed, walked and pampered. Communication was excellent, we got lots of photos and updates. We will definitely use Alex again

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Phil S.
Sitter Profile Image: Laurie P.
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Laurie P.
Star Sitter
from
$75
per night
5.0 out of 5 stars
119 reviews
49 repeat clients
36 years of experience
Historic Third Ward, Milwaukee, WI, 53202

Laurie was amazing with our senior citizen dog Jada. She is timid and doesn’t bond easily, but Laurie became a member of the family. Our Great Dane normally only talks to a very few people that she knows well. Jada really like Laurie because she spoke to her with a “woo-woo”. Laurie was also the perfect house guest, leaving a clean and tidy house when she left. We are definitely planning to re-book.

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Kathy P.
Sitter Profile Image: Ashley S.
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Ashley S.
from
$50
per night
5.0 out of 5 stars
21 reviews
9 repeat clients
13 years of experience
Juneau Town, Milwaukee, WI, 53202

Ashley was So responsive and Wonderful with my boys! Thankful she was able to watch them in their house!! Will definitely book again if she is willing to watch them!!

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Dena K.
Sitter Profile Image: Emily R.
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Emily R.
Star Sitter
from
$77
per night
5.0 out of 5 stars
103 reviews
28 repeat clients
20 years of experience
Story Hill, Milwaukee, WI, 53213

Emily is incredible with my senior dog, Bernie. She's gentle and patient and is understanding of the unfortunate accident or 2 requiring clean up on some visits. I have peace of mind knowing she will be there for Bernie!

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Kim A.
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The median cost per night for house sitting in Greendale is $50

Pet parents share their Rover experiences - Greendale

1 / 1
5.0 out of 5 stars

Alyssa was absolutely amazing. When we had the meet and greet, I loved her from the very start. We have two Maltese, which are tightly bonded to my husband and I, not wanting anyone in our space. But with her great communication skills, loving and kind personality, she had them cuddling up on the sofa soon into the day. We enjoyed messaging her and receiving pictures from her. she is a wonderful person and would love becoming a friend of hers! I highly recommend her, she would be my first choice having her as a caregiver for my dogs.

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Audrey H.
House Sitting
5.0 out of 5 stars

Kailynn was so kind and understanding about us leaving our Maggie for the first time and rearranged her schedule to accommodate us since we needed someone here the entire time. I couldn’t be happier with her services and will definitely be seeking her out for the next time. Also felt very confident in getting ahold of her for check ins. 10 STARS if they went that high ❤️

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Mary P.
House Sitting
5.0 out of 5 stars

Alexandra was a pleasure to work with and took excellent care of our dog Rocky. We received great updates while she house sat for us, and we came back to a spotless home and happy pup. Would absolutely have her house sit for us again, and recommend her to others!

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David B.
House Sitting
5.0 out of 5 stars

Stephanie was a great sitter. She helped me out when I was in a pinch due to last minute cancellation. She was able to get a meet and greet in timely and sit for me that weekend. She was prompt, professional, all around great! Will forsure use her services again!

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Jenna Z.
House Sitting
5.0 out of 5 stars

Aubrey was amazing. My doggies were comfortable with her right away. She treated my home with respect and it was even cleaner when I got back. Will be hiring her again!

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Antonia R.
House Sitting
5.0 out of 5 stars

We feel so incredibly lucky to have found Justine! She watched our 10 month old puppy, Rumi, for the weekend and truly went above and beyond. Leaving your pup and your home in someone else's hands can be stressful, but Justine gave us total peace of mind - we knew right away he was in the best hands! She kept us connected the entire time with constant updates and photos. Rumi even got to meet her family briefly, and I can tell he absolutely loved it, especially hanging out with her son! To top it off, when Rumi had a minor issue with an itchy ear, Justine stepped right in with excellent preventative care, keeping him comfortable until we could get him to the vet on Monday. Rumi clearly had a fantastic weekend. We couldn't ask for a more trustworthy, communicative, and caring sitter - highly recommended!

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Sofia K.
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

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

Sonia and Alex did an absolutely excellent job caring for my dog. He is developmentally delayed, requires daily medication, and is incontinent, so his care takes extra attention and patience. Throughout the 6 days he was with them, they communicated promptly and openly about any challenges that came up, and together we were able to make simple adjustments to ensure his stay was comfortable and successful. They sent pictures frequently, which gave me great peace of mind while I was away. From every photo, it was clear that my dog was happy, well cared for, and comfortable in their care. I am incredibly grateful for the compassion, flexibility, and attentiveness Sonia and Alex showed, and I would wholeheartedly recommend them to anyone—especially those with pets who have special needs.

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Gwen P.
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

Adrianne is amazing! She was communicative, asked thoughtful questions during the meet and greet, and ensured meds were delivered to a picky eater. We hope to have her back for future vacations!

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Beth K.
House Sitting
5.0 out of 5 stars

Anya did a great job with our dog! Even when the power went out due to a wind storm she helped make sure the house was good/safe while taking care of the dog. 10 out of 10, would recommend.

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Kyle S.
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

Emma did an amazing job watching my animals and housesitting!! I think my dog and cats probably love her more than me🤣

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Donna L.
House Sitting
5.0 out of 5 stars

Alex did an awesome job caring for our cats and our home while we were away for almost 2 weeks. Sometimes our cats get anxiety when we go out of town but I could tell our cats were comfortable with her when she came for the initial visit before we left and all 3 cats seemed to be happy and content when we arrived back home which was pleasant to come home to. We highly recommend Alex for overnight visits!

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Chelsea H.
House Sitting
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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 pets like family

  1. 1. Search

    Browse profiles of sitters near you who offer house sitting
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit
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Popular requests for house sitting - Greendale

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Sitters in Greendale average 4
repeat house sitting clients

FAQs for House Sitting - Greendale

Frequently asked questions about Rover

The average cost for House Sitting in Greendale on Rover is $44.4 per night (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of House 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 House Sitting. For more information on service fees, click here .

As of August 2026, there are 1,370 sitters on Rover offering House Sitting across Greendale. Enter your ZIP code to see which available sitters are closest to your home.

Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:

  • Mail & deliveries: Collecting letters and packages so they don't pile up.
  • Plant care: Keeping your indoor or outdoor garden hydrated.
  • Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
  • Home security: Sitters can stay overnight to keep your home occupied.

The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Greendale walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.

It’s helpful to think of house sitting as a "home base" service. Most sitters in Greendale maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:

  • Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
  • Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
  • Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.

Tip: Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!

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 Greendale 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!

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 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 .

If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.

For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.

Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.

A Meet & Greet is a short introductory meeting between you, your pet, 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.

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.

Yes, you can find sitters who have experience with handling special pet needs in Greendale. On Rover:

  • 90% of sitters can help with special care needs
  • 96% can help with giving oral medications or injections
  • 96% 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.

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