House Sitting Five Points

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

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Over 408
pet parents in Five Points have booked house sitting

Five Points, 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: Ann A.
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Ann A.
Star Sitter
from
$82
per night
5.0 out of 5 stars
121 reviews
45 repeat clients
10 years of experience
Madison, WI, 53719

Ann did a fantastic job dog sitting our very high energy and dog-reactive pup in our home for five days! She sent so many pictures and we could tell our pup was content/happy and so well taken care of. Ann also reached out to ask clarifying questions when needed and was very responsive. I highly recommend Ann!

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Claire G.
Sitter Profile Image: Jacki J.
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Jacki J.
from
$40
per night
5.0 out of 5 stars
6 reviews
25 years of experience
Maple-Prairie, Madison, WI, 53719

Jacki is amazing!!!! I cannot say enough good words about her! She provides constant updates with great information about the my pets and lots of very cute photos! She made me feel super confident that my pets are well taken care of so I don’t have to worry about them. There’s always an update coming my way right when I wanted to check. She also has great attention to details and noticed that I had a perishable package delivered. She checked in with me to get my permission for next steps and I really appreciate how she approached that situation. It is an amazing experience having Jacki as a sitter. I would highly recommend her to anyone considering.

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Maggie L.
Sitter Profile Image: Anna H.
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Anna H.
from
$38
per night
5.0 out of 5 stars
16 reviews
3 repeat clients
2 years of experience
Verona, WI, 53593

Anna did an outstanding job of caring for and entertaining our energetic 5 month old yellow lab puppy. She even took time to work on commands with our girl! Our pup is always excited and happy to see Anna. Thanks!

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Ben D.
Sitter Profile Image: Sidney M.
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Sidney M.
Star Sitter
from
$50
per night
5.0 out of 5 stars
6 reviews
4 repeat clients
6 years of experience
Madison, WI, 53711

Sidney was amazing! She sent me pics and updates of my pup and took great care of him while I was away, I would 100% recommend her!!

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Hannah M.
Sitter Profile Image: Jess B.
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Jess B.
Star Sitter
from
$74
per night
5.0 out of 5 stars
56 reviews
17 repeat clients
10 years of experience
Madison, WI, 53719

Jess is the absolute BEST! She’s so good with my two doggos and so responsive when she takes care of them both on short walks and overnight 10/10 would recommend!

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Alana M.
Sitter Profile Image: Lauren R.
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Lauren R.
from
$40
per night
5.0 out of 5 stars
9 reviews
4 repeat clients
16 years of experience
Verona, WI, 53593

Lauren was fantastic with our pup! He loved spending time with her and can’t wait to see her again :)

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Nikki S.
Sitter Profile Image: Tucker S.
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Tucker S.
from
$42
per night
5.0 out of 5 stars
6 reviews
10 years of experience
Orchard Ridge Community, Madison, WI, 53711

Tucker was amazing — he took great care of my fur baby and provided pics regularly AND he was gracious and unflappable in the face of some unforeseen challenges. Flexible, great communicator, and left the house cleaner than he found it. Great with following directions and proactively taking care of all the things — he even noticed the light on the automatic feeder and refilled it before I even messaged him about the notification I’d received. Perhaps best of all, he saw AJ for the loving, playful kitty that he is—so I knew AJ was feeling comfortable and that he was in good, kind hands. Would definitely recommend to others and would be glad to have his help again!

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Sarah G.
Sitter Profile Image: kylie l.
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kylie l.
from
$58
per night
5.0 out of 5 stars
87 reviews
26 repeat clients
1 year of experience
Madison, WI, 53719

Kylie was very communicative and really helped us out with a last minute booking on a holiday. She was punctual, sent great updates, and instantly put our senior dog at ease. We were nervous using Rover for the 1st time, but we would highly recommend her services and will absolutely call her again the next time we need someone.

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Sean P.
Sitter Profile Image: Allegra R.
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Allegra R.
Star Sitter
from
$65
per night
5.0 out of 5 stars
131 reviews
53 repeat clients
29 years of experience
Faircrest, Madison, WI, 53705

I interact with you very well, and vice versa. You are our go-to sitter of all time, now with Teddy as with Cindy. You are so tender and wise with our dogs.

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Dietrich G.
Sitter Profile Image: Megan B.
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Megan B.
from
$65
per night
5.0 out of 5 stars
10 reviews
8 years of experience
Madison, WI, 53719

Megan took excellent care of my pups while I was away. One of my dogs became ill right before I left. She kept me updated on his condition and her concerns, as well as handling my sassy girl! I will definitely use her services again! My pups loved her.

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Leah H.
Sitter Profile Image: Louisa M.
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Louisa M.
Star Sitter
from
$60
per night
5.0 out of 5 stars
89 reviews
24 repeat clients
3 years of experience
Midvale Heights Community, Madison, WI, 53711

Our pups had a great experience with Louisa over the two days we were out of town. We came back to two happy and well cared for little guys. I loved the daily pictures, nice personal touch. Louisa checked in with us making sure we’re made it back. Very grateful!

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Tara
Sitter Profile Image: Evelin C.
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Evelin C.
from
$42
per night
5.0 out of 5 stars
14 reviews
4 repeat clients
3 years of experience
Verona, WI, 53593

Great experience! Our sitter took wonderful care of our two Labrador puppies—playing with them in the yard, giving them a special treat, and keeping them happy and content. We loved receiving photos of them playing and resting peacefully. Highly recommend!

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Ben D.
Sitter Profile Image: Poorna D.
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Poorna D.
from
$55
per night
5.0 out of 5 stars
5 reviews
3 repeat clients
12 years of experience
Verona, WI, 53593

Poorna was so kind and accommodating! She was super patient with my anxious pups, and made sure to send daily pictures and updates. Will definitely rebook in the future!

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Rachel V.
Sitter Profile Image: Ann M.
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Ann M.
Star Sitter
from
$28
per night
5.0 out of 5 stars
5 reviews
3 repeat clients
30 years of experience
Fitchburg, WI, 53593

Ann did an excellent job in taking care of Indy!! She frequently kept us updated with pictures. Indy was very comfortable and safe with Ann.

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Vinoth G.
Sitter Profile Image: Annalesse B.
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Annalesse B.
from
$35
per night
5.0 out of 5 stars
3 reviews
5 years of experience
Madison, WI, 53719

Annalesse did a great job with our two dogs! She had good communication and she stayed to our dog’s schedule with their medicine they have to take twice daily. We got a picture everyday and an update with how they were doing.

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Claire B.
Sitter Profile Image: Amy F.
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Amy F.
from
$40
per night
5.0 out of 5 stars
11 reviews
1 repeat client
30 years of experience
Meadowood, Madison, WI, 53711

We couldn't have asked for a better experience with our recent Rover sitter! She was absolutely fantastic while watching our dog, Scooby, for the week. From the start, she excelled at being adaptable, seamlessly adjusting to Scooby’s routine and needs without any issues. We also truly appreciated the frequent, reassuring text messages and photos she sent throughout the week, which gave us total peace of mind while we were away. Most importantly, she provided Scooby with an incredible amount of love, affection, and exercise—he was a very happy pup when we returned. We highly recommend her services to anyone looking for a caring and reliable sitter!

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Zachary M.
Sitter Profile Image: Stephany D.
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Stephany D.
from
$45
per night
4.9 out of 5 stars
60 reviews
14 repeat clients
13 years of experience
madison, WI, 53719

Stephany watched our dog over the weekend and was great! She always communicated in a timely manner and even sent us some photos of our pup while we were gone. It was clear our dog and our house were well taken care of. Highly recommended!

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Jacob F.
Sitter Profile Image: Michelle S.
Verified Background Check
Michelle S.
Star Sitter
from
$60
per night
5.0 out of 5 stars
136 reviews
55 repeat clients
4 years of experience
Madison, WI, 53719

Michelle stayed at our home for 7 days and was really fabulous! We met ahead of time and she reviewed all of our dogs needs, medical conditions, and routines. She is exceptionally professional and has attention to detail. Was very comfortable administrating medications and taking care of any special needs We will most definitely use her for future dog sitting! Our dogs missed her when we returned!

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Dawn C.
Sitter Profile Image: James W.
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James W.
from
$30
per night
5.0 out of 5 stars
10 reviews
2 repeat clients
50 years of experience
Verona, WI, 53593

James was great! He came over to meet our 3 cats before his overnight stay which helped us feel more comfortable. He swept and cleaned, everything is just as we left it! He was great at communicating check in and questions , provided photos which was so cute and much appreciated! 10/10 would recommend and book again

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Grace R.
Sitter Profile Image: Maya F.
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Maya F.
from
$148
per night
5.0 out of 5 stars
157 reviews
53 repeat clients
26 years of experience
Westhaven Trails, Madison, WI, 53719

I think my cats might like Maya more than me 🤣 She's always so good at following up after each visit with details and pictures, which puts us at ease. Even when I change the instructions in their plan, Maya is sure to review those changes and carry them out flawlessly. She communicates any time she has questions. She even informs us of any unusual litter box activity, which is so helpful with kitties that have health issues! Thanks Maya!

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Heather S.
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The median cost per night for house sitting in Five Points is $50

Pet parents share their Rover experiences - Five Points

1 / 1
5.0 out of 5 stars

Jolie goes above and beyond to make sure my pups are doing well while I'm away. Especially appreciate her navigating July 4 with them!

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Erick S.
House Sitting
5.0 out of 5 stars

Jacki provided great care to our English bulldog. Provided regular updates and pictures and was proactive in her communication. We’d love to have her again!

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Allison B.
House Sitting
5.0 out of 5 stars

Burgail is reliable, communicative, thoughtful, and clearly cared about making our dog feel comfortable. We truly appreciate the excellent care and would gladly recommend Burgail to anyone looking for a trustworthy pet/house sitter. Thank you so much!

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Bingjie Z.
House Sitting
5.0 out of 5 stars

Anna was just what we were looking for. Good Communication, good pre-visit and left the house clean and fresh (washed sheets and remade the bed!). The dog seemed very happy and got lots of exercise😜. Also we were a little late looking for help and worried that we may not find anyone…. Rover worked out so well. Thankyou to you all. We had a relaxing fun time knowing our dog and house were well taken care of❤️

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Laura R.
House Sitting
5.0 out of 5 stars

Annalesse did a great job with our two dogs! She had good communication and she stayed to our dog’s schedule with their medicine they have to take twice daily. We got a picture everyday and an update with how they were doing.

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Claire B.
House Sitting
5.0 out of 5 stars

Kira took great care of our dogs while we were out of town for a family event. Workers in the area were distressing to the dogs but she was able to distract them and keep them happy. She rolled with the changes we recently made to the feeding routine and everything was great!

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Mary A.
House Sitting
5.0 out of 5 stars

Ann did an excellent job in taking care of Indy!! She frequently kept us updated with pictures. Indy was very comfortable and safe with Ann.

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Vinoth G.
House Sitting
5.0 out of 5 stars

Tucker was amazing — he took great care of my fur baby and provided pics regularly AND he was gracious and unflappable in the face of some unforeseen challenges. Flexible, great communicator, and left the house cleaner than he found it. Great with following directions and proactively taking care of all the things — he even noticed the light on the automatic feeder and refilled it before I even messaged him about the notification I’d received. Perhaps best of all, he saw AJ for the loving, playful kitty that he is—so I knew AJ was feeling comfortable and that he was in good, kind hands. Would definitely recommend to others and would be glad to have his help again!

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Sarah G.
House Sitting
5.0 out of 5 stars

Azaria agreed to take over care of our pets very last minute, when our booked sitter was delinquent and couldn’t be reached for more than 12 hours. She was very communicative and took good care of our pets from there on. Kept our house in good condition as well for the stay! Would definitely recommend.

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James W.
House Sitting
5.0 out of 5 stars

We have booked Steph many times to sit for our dog and she takes excellent care of both our pup and house. She is reliable, attentive, and prompt to reply to messages. She is our go to Rover and the first person we reach out to when we need a dog sitter.

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Lexi D.
House Sitting
5.0 out of 5 stars

Emma was a great sitter! We will definitely use her again! She sent lots of updates and our guy was very happy the whole time. She also kept our house very clean.

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Laurel S.
House Sitting
5.0 out of 5 stars

Super communication and easy to work with. Kept us updated through text messages and pictures. Would love to work with her again and highly recommend!

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Ben B.
House Sitting
5.0 out of 5 stars

Ann took great care of our dogs over a long weekend, including our elderly dog. Would definitely hire again!

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Stacey B.
House Sitting
5.0 out of 5 stars

Great job with our two dogs. Spent lots of time at our house over a long weekend. Sidney was flexible with our schedule (even when I scheduled for the wrong weekend). 10/10 would book again.

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Duncan P.
House Sitting
5.0 out of 5 stars

Lauren was fantastic with our pup! He loved spending time with her and can’t wait to see her again :)

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Nikki S.
House Sitting
5.0 out of 5 stars

Maria did a great job. We needed a last minute house sitter for our 2 German Shepherds, who are sweet but not low maintenance :). We came home to happy non-anxious doggos, and the house seemed in better shape than we left it. Thanks Maria!

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Alison B.
House Sitting
5.0 out of 5 stars

Lisa did a terrific job with our fur babies! She was very careful and caring with them, kept us posted with the right amount of details, and kept the home really clean. Would definitely have her sit for us again!

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James W.
House Sitting
5.0 out of 5 stars

James was great! He came over to meet our 3 cats before his overnight stay which helped us feel more comfortable. He swept and cleaned, everything is just as we left it! He was great at communicating check in and questions , provided photos which was so cute and much appreciated! 10/10 would recommend and book again

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Grace R.
House Sitting
5.0 out of 5 stars

This was my second time booking with Monica and she delivered wonderful care to my large pack once again! Highly recommend!

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Elizabeth K.
House Sitting
5.0 out of 5 stars

Mandi was excellent! Her communication was impeccable something that we have struggled with past sitters. She was a natural with our two small dogs and gave us the peace of mind we have been looking for. We will definitely use her again!!

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Tracy Y.
House Sitting
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Book with peace of mind

  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • 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?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • 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.

How Rover works

  1. 1. Search

    Browse profiles of sitters near you who offer house sitting
  2. 2. Meet & Greet

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform

Sitters in Five Points average 4
repeat house sitting clients

FAQs for House Sitting - Five Points

Frequently asked questions about Rover

The average cost for House Sitting in Five Points on Rover is $49.66 per night (as of July 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 July 2026, there are 849 sitters on Rover offering House Sitting across Five Points. 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 Five Points 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 Five Points 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 Five Points 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 Five Points. On Rover:

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