House Sitting Five Points

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

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Over 420
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
$85
per night
5.0 out of 5 stars
129 reviews
49 repeat clients
10 years of experience
Madison, WI, 53719

Ann did a great job caring for our dog and even made friends with our very shy cat. She was very responsive and sent lots of updates, which were very reassuring since this was the first time we’ve left our dog at home overnight. Our dog was happy and calm when we returned. We will definitely rebook with her if she is available!

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Carol H.
Sitter Profile Image: Louisa M.
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Louisa M.
Star Sitter
from
$60
per night
5.0 out of 5 stars
92 reviews
25 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: Poorna D.
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Poorna D.
from
$55
per night
5.0 out of 5 stars
6 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
8 reviews
4 repeat clients
30 years of experience
Fitchburg, WI, 53593

Ann was wonderful with our puppy. She was very responsive to our messages and flexible when we needed to change things. We felt our puppy was in great hands when we were away and she even taught her a few commands. Will definitely recommend her to others.

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Kyle T.
Sitter Profile Image: Hanna P.
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Hanna P.
from
$40
per night
5.0 out of 5 stars
5 reviews
2 repeat clients
6 years of experience
Madison, WI, 53719

Hanna was awesome with all the doggies while we were away, she kept us updated every day with photos and comments. Thank you for taking care of them!

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Mik R.
Sitter Profile Image: Jacki J.
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Jacki J.
from
$40
per night
5.0 out of 5 stars
9 reviews
2 repeat clients
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: 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 quick to respond to our texts and sent us the most adorable pics of our pup so we could see how happy he was. We will definitely be hiring her again.

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Todd B.
Sitter Profile Image: Amy F.
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Amy F.
from
$40
per night
5.0 out of 5 stars
17 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: Annalesse B.
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Annalesse B.
from
$35
per night
5.0 out of 5 stars
9 reviews
1 repeat client
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: Brienna T.
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Brienna T.
from
$50
per night
10 years of experience
Madison, WI, 53719

About: Hi! I’m a reliable, caring dog lover who treats every pup like my own. Whether it’s walks, playtime, or cuddle time, I’ll make sure your dog feels safe, happy, and loved while you’re away. I’ll follow your pet’s routine and keep you updated so you can have peace of mind! I'm a part-time student who takes morning classes Monday-Thursday. I am typically at home the majority of the day, but if I am ever away I will return home for about an hour to take any guests out during lunch (12-1PM). Weekends, I am mostly free. Drop-off/pick-up can be anytime! My schedule is pretty flexible during weekends so if you need a specific time, I can make it work. I'm very accommodating. Just let me know in advance when you are thinking about booking and I can check my schedule for that day. If you have a busy schedule, I can also pick-up and drop-off for free! Let me know what your fur-baby's routine is like (sleep, eat, play schedule). I hope to make your fur-baby comfortable while you are away. For DROP-INS: I have experience with drop-ins for dogs, cats, and fish! If you would like me to do a short walk during the 30 minute drop-in for your pup, let me know! I typically like to refresh their water, give a treat (if you allow it), and make sure they go potty! For cats, I will make sure their water & food is replenished and will clear out litter boxes! I will also water your plants, bring in your mail/newspapers (if requested). Thanks for considering me! Let’s set up a Meet & Greet! **Holiday Rates will also be applied for Easter, Mother’s Day, and Father’s Day weeks/weekends** I’m currently working part time with plenty of time for fuzzy friends! I haven’t found my perfect pet just yet, so I have lots of love to give! I have loads of experience training young and old pups, no matter the service your looking for I would love to incorporate good habits for your pet!

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

Great sitter - of house and dog. Friendly and kind; Chico was happy and healthy when we returned and my house was exactly as I left it. I would recommend Megan to anyone and hope to reunite Megan and Chico again!

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Alex D.
Sitter Profile Image: Emma W.
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Emma W.
from
$85
per night
5.0 out of 5 stars
17 reviews
5 repeat clients
12 years of experience
Madison, WI, 53719

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.
Sitter Profile Image: Sidney R.
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Sidney R.
from
$50
per night
5.0 out of 5 stars
84 reviews
33 repeat clients
20 years of experience
Middleton, WI, 53562

Sidney took great care of my house and dogs while I was away for a few days. I will definitely work with Sidney again if I get the opportunity to!

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Cale H.
Sitter Profile Image: Sidney M.
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Sidney M.
Star Sitter
from
$50
per night
5.0 out of 5 stars
7 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: Quinn M.
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Quinn M.
from
$20
per night
8 years of experience
Madison, WI, 53719

About: I have been surrounded by and have taken care of dogs since getting my family’s two dogs when I was around 11 or 12 years old. Even since moving out, my family has relied on me to take care of them on vacations, extended work trips, etc. I now have two cats of my own, and love any opportunity to meet new animals. I am currently traveling the country, and looking to explore new places! I’ve found that pet-sitting is an excellent way to do so, with the side bonus of getting to meet new furry friends along the way! I am very intentional about adapting to each pet’s individual needs - whether they’re a fast friend or needs some space to figure me out first, my top priority is establishing trust with your fur baby. From there, I can ensure that I give them the proper love and care they deserve.

Sitter Profile Image: Christian O.
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Christian O.
from
$28
per night
5.0 out of 5 stars
2 reviews
1 repeat client
15 years of experience
Summit Woods, Madison, WI, 53711

About: Currently in medical school so looking to make some extra money. I’m always the first one asked to watch pets for friends, family, and classmates. I’ve got my own fur babies but I can never get enough and love to help ensure other peoples pets are well taken care of when they are away. I love to send photos to update owners. I’m currently in school with a reduced schedule for the summer so I’m able to have a flexible schedule right now. Come fall things will be different I’m used to working with pets who have all manner of needs and personalities. I’ve always been good about making a good bond with new pets and respecting their personal space while also keeping them entertained and safe.

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

Evelin is so sweet with my dogs! They love hanging out with her! She is super communicative and sends frequent updates. I’d recommend her to anyone!

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Mary Kate 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: Michelle S.
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Michelle S.
Star Sitter
from
$75
per night
5.0 out of 5 stars
138 reviews
56 repeat clients
4 years of experience
Madison, WI, 53719

Michelle was fantastic. Kept us up to date with what was happening and sent lots of pics. We felt very comfortable with her in our home and with our pup. Would definitely use her again.

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Katrina K.
Sitter Profile Image: Tucker S.
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Tucker S.
from
$48
per night
5.0 out of 5 stars
9 reviews
2 repeat clients
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.
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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

Ann was so communicative, patient, and respectful of our home and pets. I am so grateful to have found her!

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Vidya G.
House Sitting
5.0 out of 5 stars

Melvin stepped in on very short notice and took great care of my two big dogs. He stayed at the house and left it in great shape when he left. The dogs liked him and were in great shape when I got home. Thanks to Mel for saving the weekend for us.

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ann s.
House Sitting
5.0 out of 5 stars

Lisa did a great job with our 8 month old Golden Retriever while we were gone for a week, providing daily updates. She took care of our home as well and it looked the same as it did the day we left! We recommend Lisa and would hire her again.

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Lynn B.
House Sitting
5.0 out of 5 stars

Azaria did a great job house sitting with Ollie. This was my first experience with Rover, and it was nice to meet Azaria before we left on our trip. She sent daily pictures and updates. The house was very tidy when we returned. Will definitely choose her again.

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Maureen L.
House Sitting
5.0 out of 5 stars

Anna took great care of our pup and our home! She applied eye medication and was great about communication. We would love to have her back again sometime.

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Allison B.
House Sitting
5.0 out of 5 stars

Annalesse is an amazing sitter! She has become my regular sitter and she connects so well with my dog and I am able to travel with confidence!

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Jett M.
House Sitting
5.0 out of 5 stars

I'd give Emma 10 stars if that was an option. Emma stayed at my home for 6 nights, to care for my 6.5 year Frenchie who required special attention and Tess, the newest member of my pack weighing in at 11lbs at only 3 months. Emma clearly understood my concerns with leaving a new pup and resident pooch who were still getting acquainted, and gave both pups the love they were accustomed to, collectively and on a solo basis. Emma vacuumed and made sure my home was clean and in the same condition I left it for her, my plants were watered and the garbage was taken out. Yay! Both pups seem very happy and stress free when I got home, for which I couldn't be more happy. Side note: I'm sure there's a bit of sticker shock with Emma's fee, but her premium is well deserved and earned and I have no hesitation to contact Emma for future house and puppy/dog sitting needs.

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Susan D.
House Sitting
5.0 out of 5 stars

Hanna was awesome with all the doggies while we were away, she kept us updated every day with photos and comments. Thank you for taking care of them!

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Mik R.
House Sitting
5.0 out of 5 stars

Camille did a great job taking care of Sandy and my home! She kept in touch as requested and helped me feel confident that Sandy was in good hands while we were out of the country(and out of touch at times). I was comfortable trusting Camille with Sandy's daily care for several weeks and also medical care if needed. Camille is welcome back in my home and I will invite her to take care of Sandy the next time we need a sitter. Thank you!

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Rita W.
House Sitting
5.0 out of 5 stars

Anne continues to be an amazing pet sitter. We had a very last minute need and she was willing to work with us. Keira loves when she comes over and has gotten very comfortable with her.

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Kyle T.
House Sitting
5.0 out of 5 stars

Our pup was in great hands with Lauren when we were out of town for a few nights. We came home to a happy and healthy girl! Thanks again!

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Nicole K.
House Sitting
5.0 out of 5 stars

As always, Jolie did an excellent job taking care of my dogs while I was away. Appreciate her thoughtful care!

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Erick S.
House Sitting
5.0 out of 5 stars

Ava was wonderful. She was able to pick up our request right away with very short notice. She requested a meet and greet beforehand (which I greatly appreciated). She asked great questions and quickly bonded with our puppy. She sent texts and picks over the course of the weekend. I would highly recommend!

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Pam M.
House Sitting
5.0 out of 5 stars

Evelin was an absolute rockstar. She sat for our two older dogs and a rambunctious young one. We joked that the dogs are going to have unrealistic expectations of us now because Evelin was SO attentive with them. She sent constant pictures, and they were clearly loving the attention and love. She clarified any questions she had, and we felt totally confident that the dogs were in great hands—she followed up that she was following our instructions for feeding and meds. We would hire Evelin again immediately, and I’d recommend her to any pet parents, even if your dogs have some extra needs. If we go on a trip again, she’s our first call!

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Lauren G.
House Sitting
5.0 out of 5 stars

Maya did a wonderful job with our very senior dog. She took care of all his needs while we’re gone and even did a nail trim. Communication was great. Looking forward to having her help us out again.

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Karen R.
House Sitting
5.0 out of 5 stars

Anna is the best! She’s a great communicator and our cats love her. That’s why she’s been our go-to sitter for several years now!

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Claire W.
House Sitting
5.0 out of 5 stars

My dogs both were very happy in Jesse's care. She communicates frequently with pictures. Would use again.

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Brenda W.
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

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
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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

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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

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Popular requests for house sitting - Five Points

Select a filter and find qualifying sitters offering house sitting.

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 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 827 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:

  • 96% 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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