House Sitting Five Points

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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
$95
per night
5.0 out of 5 stars
139 reviews
53 repeat clients
10 years of experience
Madison, WI, 53719

Great experience with Ann watching our dogs and house for two nights. Very responsible, shared updates with photos, would hire again without hesitation.

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Benjamin L.
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: Louisa M.
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Louisa M.
Star Sitter
from
$60
per night
5.0 out of 5 stars
94 reviews
26 repeat clients
3 years of experience
Midvale Heights Community, Madison, WI, 53711

Louisa was kind, responsive and took extra care to come to our hotel to watch our dog on our wedding day. We could not recommend her more highly 💜

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Angie A.
Sitter Profile Image: Evelin C.
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Evelin C.
from
$42
per night
5.0 out of 5 stars
17 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: Tucker S.
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Tucker S.
Star Sitter
from
$48
per night
5.0 out of 5 stars
12 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.
Sitter Profile Image: Lauren R.
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Lauren R.
Star Sitter
from
$50
per night
5.0 out of 5 stars
14 reviews
5 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: kylie l.
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kylie l.
from
$58
per night
5.0 out of 5 stars
88 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: Poorna D.
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Poorna D.
from
$55
per night
5.0 out of 5 stars
8 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: Amy F.
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Amy F.
from
$40
per night
5.0 out of 5 stars
18 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: 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: Stephany D.
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Stephany D.
from
$45
per night
4.9 out of 5 stars
61 reviews
14 repeat clients
13 years of experience
madison, WI, 53719

Stephany is fantastic! She did amazing staying with our senior kitty and sent plenty of pics. It didn’t even look like he missed us! She also took great care of our home. Highly recommend!

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Paula G.
Sitter Profile Image: Austin M.
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Austin M.
Star Sitter
from
$65
per night
5.0 out of 5 stars
9 reviews
2 repeat clients
29 years of experience
Park Ridge, Madison, WI, 53719

About: Caring for dogs isn't just something I do. It's something I'm genuinely passionate about. I have experience caring for dogs of all ages, personalities, and energy levels, from young puppies learning routines to senior dogs who need a little extra patience and attention. I understand that every dog is different, and I take the time to get to know each pet's unique needs. I'm comfortable with feeding schedules, administering oral medications, crate training, basic puppy training, leash walking, playtime, and providing plenty of love and attention. I'm also attentive to changes in behavior or health and believe it's important to catch anything unusual early and communicate it with owners right away. I know how stressful it can be to leave your pet with someone else, so I make it my priority to provide a safe, clean, and calm environment where they feel comfortable. Whether your dog loves long walks, playing fetch, or simply relaxing with company, I'll make sure they receive the care and attention they deserve. Communication is very important to me. I'll provide regular updates, photos, and messages so you can enjoy your time away knowing your pet is in good hands. My goal is to care for every pet as if they were my own and give owners complete peace of mind. Pet care is already a major part of my daily routine. My day is structured around caring for dogs, so adding walks, drop-in visits, daycare, or boarding fits naturally into my schedule. Because I'm already following consistent routines for feeding, exercise, potty breaks, playtime, and cleaning, I'm able to provide dependable, attentive care throughout the day. I have a flexible schedule that allows me to give pets the time and attention they deserve rather than leaving them alone for long periods. Whether your pet needs a consistent routine, extra exercise, medication, or simply companionship, I'm committed to making sure they feel safe, comfortable, and well cared for while you're away. Safety and comfort are my top priorities when caring for pets, whether in my home or a client’s home. I make sure every pet is in a clean, secure, and calm environment where they can feel relaxed and stress-free. I follow each pet’s routine closely, including feeding schedules, potty breaks, exercise, and any special instructions provided by the owner. I pay close attention to behavior and overall well-being so I can quickly notice if something seems off and communicate right away. In my care, pets are never left unattended for long periods. I supervise interactions, provide structured playtime, and ensure a safe environment at all times—especially when introducing pets to new surroundings or other animals. I also respect the client’s home fully when providing in-home care, keeping everything clean, secure, and exactly as I found it. I understand how important trust is when someone allows you to care for their pet or enter their home, and I take that responsibility seriously. My goal is to make sure pets feel safe, loved, and comfortable, while giving owners complete peace of mind through clear communication and reliable care.

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

Maya did a fantastic job taking care of my kitty Princess, who has some special needs and requires daily medications. She was super responsive and sent me daily updates and pictures so I did not worry. Thanks again for taking such good care of my sweet girl!

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Meagan K.
Sitter Profile Image: Elizabeth M.
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Elizabeth M.
from
$50
per night
5.0 out of 5 stars
10 reviews
2 repeat clients
10 years of experience
Madison, WI, 53711

Lizzy was great with our elderly dog. She has multiple daily meds and a special diet, and actually got a little bit sick while we were gone. Lizzy was kind and patient with her. We got daily updates and pictures and felt totally comfortable while we were away. Zeba was happy and relaxed when we got back and had obviously been well cared for. We'll definitely use Lizzy again!

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Christy S.
Sitter Profile Image: Tatyana K.
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Tatyana K.
Star Sitter
from
$55
per night
4.9 out of 5 stars
78 reviews
24 repeat clients
4 years of experience
Fitchburg, WI, 53713

Tatyana was great with my pups! She provided the perfect amount of updates and even left me flowers and a note congratulating me on my first home purchase ☺️

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Samantha K.
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: James W.
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James W.
Star Sitter
from
$30
per night
5.0 out of 5 stars
12 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: 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: May N.
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May N.
from
$30
per night
5.0 out of 5 stars
2 reviews
1 repeat client
2 years of experience
Middleton, WI, 53562

About: My pet-sitting experiences include looking after both cats and dogs day to day and for extended periods of time. When taking care of cats, I make sure they have clean water and food at all times; keep their environment clean; watch over them and see if they are healthy; and interact with them by playing with them on a daily basis. I also have experience caring for dogs of various sizes and energy levels. Making sure their fed, walked, groomed, and cleaning up any messes/ their environment. In addition always making sure they have access to clean drinking water and providing plenty of playtime and attention. I occasionally take care of a family friend’s dog who has arthritis. I help keep her comfortable through gentle massages, giving her medication as directed, and hand-feeding her when necessary. In doing so, I learned to be patient and attentive in caring for an animal's individual needs. What sets me apart is my genuine love for animals. I always go the extra mile into taking good care of animals, ensuring their safety, and comfort in the absence of their owners. I treat every pet as if they were my own and doing everything I can to ensure their happiness. I am extremely flexible with regards to my schedule, and can be available for the most part of the day. I wake up early, so feeding and taking the animals for walk won't be a problem at all. When caring for pets in a client’s home, I value their safety, trust, and maintaining a calm and familiar environment for their pet. It is important for me to carefully follow all the instructions concerning their feeding schedule, treatment, taking medication, and other specific care. It goes without saying that I make sure that the pets receive proper meals and have clean water to drink. I also try to keep the house as clean as possible, including litter boxes for cats and any messes that may occur. I also observe the pets to ensure everything seems normal and they’re healthy. I believe that building trust with both pets and owners is essential, I’ll always provide them with updates and photographs about the current condition of the pets. My goal is to make sure their pet is cared for and mostly importantly happy.

Sitter Profile Image: Christine H.
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Christine H.
from
$60
per night
5.0 out of 5 stars
2 reviews
10 years of experience
Fitchburg, WI, 53719

About: I'm an animal lover who has years of experience with dogs, cats, and rabbits! I educate myself on animal behavior and find that it really helps me be able to meet their needs. Not afraid to administer medication or go the extra mile for whatever a loved pet needs. I'm available every single day of the week - morning, midday, and evenings. I sometimes take an hour or so of classes in the evening which are extremely easy to work around, I'm very flexible and typically don't travel for holidays. I'm completely ready to adhere to any standards that clients have in their home. I am very communicative and will reach out if instructions need clarification.

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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

My cat, Sunny, seemed very happy and comfortable with Ann! She sent me pictures regularly, was very responsible, and was always easy to communicate with. I felt completely at ease knowing Sunny was in good hands. I’ll definitely reach out to Ann again the next time I need a cat sitter!

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Jin
House Sitting
5.0 out of 5 stars

Jesse was absolutely amazing with Snowy! Her communication was great, and I loved getting all the frequent picture updates while I was away. She was super punctual, paid really close attention to Snowy's routine, and showered her with love. I couldn't have asked for a better sitter and will 100% be booking with her again!

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Elaine P.
House Sitting
5.0 out of 5 stars

Austin took great care of our bulldog, Uecker and provided us updates throughout about how he was doing!

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Allison B.
House Sitting
5.0 out of 5 stars

Annalesse was so sweet and attentive while caring for our 15yr old beagle. We received plenty of updates and pictures and our mind was at total ease knowing she was there! She asked good questions and left the house nice and clean for us! We will most definitely be rebooking, thanks annalesse!!!!

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Kelly R.
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

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

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
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  • 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

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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 $48.5 per night (as of September 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 September 2026, there are 811 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:

  • 94% of sitters can help with special care needs
  • 98% 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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