House Sitting in Five Points

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

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Top rated Five Points house sitters

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

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Sitter Profile Image: Ann A.
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Ann A.
Star Sitter
from
$82
per night
5.0 out of 5 stars
120 reviews
42 repeat clients
10 years of experience
Madison, WI, 53719

Ann was so great! Haze LOVES her. She accommodated to Hazel’s separation anxiety and other quirks so well and sent plenty of updates and pictures. My flight was delayed and Ann was able to stay an extra night, we really appreciate her flexibility!

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Paige H.
Sitter Profile Image: Sidney M.
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Sidney M.
from
$45
per night
5.0 out of 5 stars
4 reviews
1 repeat client
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: Louisa M.
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Louisa M.
Star Sitter
from
$60
per night
5.0 out of 5 stars
88 reviews
24 repeat clients
3 years of experience
Midvale Heights Community, Madison, WI, 53711

Louisa and her daughter did a great job of communicating with me, though their stay was short. My cat loved the attention they gave her. Her coat was beautifully soft and clean from all the brushing. I would definitely schedule them again when I am out of town.

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Judy B.
Sitter Profile Image: Allegra R.
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Allegra R.
Star Sitter
from
$65
per night
5.0 out of 5 stars
125 reviews
50 repeat clients
29 years of experience
Faircrest, Madison, WI, 53705

Allegra is a blessing to all dogs everywhere. If you and your dog have the opportunity to meet Allegra...do it. We left Arya overnight for the first time ever and couldn't have had a more pleasant experience. I hope that next time we go out of town Allegra is available.

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Jordan W.
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

This was our first experience with Rover with our labrador girls, including a 3 month old puppy and a 10 1/2 year-old, and Anna did a great job! Thank you for starting us off with Rover on such a positive note!

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Ben D.
Sitter Profile Image: Tucker S.
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Tucker S.
from
$38
per night
10 years of experience
Verona, WI, 53593

About: I have had dogs since my childhood and have worked with breeds of different sizes and backgrounds, including some with special needs. In my home life, I have two cats that I adore and spend much of my free time with. I’m available all day on weekends, as well as from 5:30pm onward on weekdays (typically). If you have specific requirements for your animal let me know and we can create a schedule that works best for you! I can perform any specific needs that your pet may need. One of my own pets has special medical requirements, so I am familiar with taking care of animals that need extra care.

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

Michelle did a great job watching my golden doodle! She made sure to ask lots of questions about his feeding and walking schedule and sent me daily pictures and updates during her stay. I would absolutely ask her to watch Vash again!

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Kastyn M.
Sitter Profile Image: ariel s.
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ariel s.
from
$47
per night
5.0 out of 5 stars
9 reviews
2 repeat clients
20 years of experience
Madison, WI, 53711

Ariel was great watching my dog. She's blind and sometimes needs a little extra love.

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Martha T.
Sitter Profile Image: Jacki J.
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Jacki J.
from
$40
per night
5.0 out of 5 stars
4 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: Kaitlyn J.
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Kaitlyn J.
Star Sitter
from
$50
per night
5.0 out of 5 stars
25 reviews
6 repeat clients
15 years of experience
Madison, WI, 53705

Kaitlyn was great with the dogs right from the meet and greet. She handled their different personalities and medical needs perfectly. She did all that was asked and more. Thank you for allowing me the peace of mind to enjoy this week with friends!!

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Sharon S.
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: 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: Kyra H.
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Kyra H.
from
$50
per night
4.9 out of 5 stars
18 reviews
2 repeat clients
9 years of experience
Verona, WI, 53593

We are so extremely pleased with the petsitting services Kyra provided while staying overnight to care for our 11 year old 60 lb lab mix Macy who had surgery three weeks prior. Kyra is so very kind and wonderful with our dog and she administered Macy’s daily arthritis meds. I know Macy misses Kyra already and so do I. Do not hesitate to have Kyra assist with your house and petsitting needs. She’s wonderful and we highly recommend her!

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Tammy & Mike S.
Sitter Profile Image: Natasha H.
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Natasha H.
from
$60
per night
4 years of experience
Verona, WI, 53593

About: Your pets health and wellbeing is my top priority. I take the time to connect with them and be there for them while you are away. It can be an anxious time for pets, but I am calm, patient, and compassionate towards them. I have experience caring for family pets big and small, working dogs, and horses/goats while owners are away for extended periods of time. My first dog was a loving, energetic German Shorthaired Pointer who taught me self awareness as a pet owner. I currently work a seasonal position 7am to 3:30pm during Monday-Friday and I am available to house/pet sit while you’re away. Just send me a message and we can talk about how I might best help your family’s most important member :) Caring for your pet is a very important job that I take seriously. When I am with them I take the time to play/interact with them and make sure they are getting enough physical and mental exercise.

Sitter Profile Image: Ann M.
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Ann M.
from
$28
per night
5.0 out of 5 stars
3 reviews
1 repeat client
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: 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
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.
Sitter Profile Image: Katie T.
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Katie T.
from
$60
per night
5.0 out of 5 stars
42 reviews
9 repeat clients
5 years of experience
Westmorland, Madison, WI, 53711

Katie took excellent care of our dogs and our home. We felt very comfortable with her and the dogs took to her right away. She took them for walks and sent pictures too! Thank you Katie!

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Dawn S.
Sitter Profile Image: Nicole W.
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Nicole W.
from
$35
per night
5.0 out of 5 stars
10 reviews
4 repeat clients
5 years of experience
Madison, WI, 53705

We (and our dogs) loved having Nicole sit for us. She is an excellent communicator and took care of our pups like they were her own. I’d absolutely have her stay with our dogs again—and based on their lukewarm reaction to us coming home, I think they’d like to see her again too. 🤣

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Kim B.
Sitter Profile Image: Julia M.
Verified Background Check
Julia M.
from
$50
per night
5.0 out of 5 stars
3 reviews
1 repeat client
8 years of experience
University Apartments, Madison, WI, 53705

Julia was so pleasant and professional! She asked great questions to prepare for her time with Princeton, and you could tell she really cared - Princeton warmed up to her immediately :) I highly recommend Julia and would definitely hire her again!

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Aisha B.
Sitter Profile Image: Jess B.
Verified Enhanced Background Check
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.
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Five Points pet parents share their Rover experiences

1 / 1
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

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.
House Sitting
5.0 out of 5 stars

Annalesse did so great with our 2 cats and 2 dogs. She is reliable and came on time. An expert at following instructions; everyone got their supplements with meals and treats daily. She sent us picture updates every day & was able to medicate and take time to let our shy/finicky cat eat as well which meant a lot. 10/10 would book with her again!

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Jasmyne S.
House Sitting
5.0 out of 5 stars

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.
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

Kira is awesome! She took great care of my pets and sent lots of updates with pictures. The pets were happy and the house was clean when we got back. Highly recommend Kira if you’re looking for a reliable sitter!

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Laura D.
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
5.0 out of 5 stars

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.
House Sitting
5.0 out of 5 stars

Jesse was great while she stayed overnight with my cat while I was on vacation. She sent pictures and videos, kept my place clean, and washed the sheets when she left. Thanks, Jesse!

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Chelsea B.
House Sitting
5.0 out of 5 stars

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.
House Sitting
5.0 out of 5 stars

McKayla was awesome! She gave our 6 month old border terrier rescue the exercise she needed while we were out of town on a weekend trip. 2-3 mile walks and many trips to the dog park. She also looked after our two older cats who are still getting used to the puppy. I was surprised to find that there was a lack of cat distress remnants (iykyk) when we returned. Everyone was fed, watered and happy! She was even able to be flexible with our late departure and later than expected return time. Definitely recommend!

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Chris T.
House Sitting
5.0 out of 5 stars

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.
House Sitting
5.0 out of 5 stars

Michelle took great care of our dog. She is clearly experienced with animals and knows what questions to ask to be sure she is providing the best care. She was very communicative and we felt our dog was in good hands throughout her stay.

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Gary B.
House Sitting
5.0 out of 5 stars

Azaria was great again. She sent cute photos, was very communicative, and my house was the same as I left it. I'll definitely invite her to house/dog sit again! Thank you Azaria!

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Marit S.
House Sitting
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Find pet care near you

How Rover works

  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

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

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 house 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.

Sitters in Five Points average 4
repeat house sitting clients

House Sitting FAQs

Frequently asked questions about Rover

House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Five Points on Rover as of Jun 2026 was about $50 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.

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

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

As of Jun 2026, there are 767 house sitters in Five Points. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.

Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 89% of Five Points house sitters respond in under an hour.

House sitters in Five Points have an average of 15 years of experience. House sitters with repeat customers have an average of 4 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Five Points.

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

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

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

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

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