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
$95
per night
5.0 out of 5 stars
• 146 reviews
54 repeat clients
10 years of experience
Madison, WI, 53719

“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
Sitter Profile Image: Tucker S.
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Tucker S.
Star Sitter
from
$48
per night
5.0 out of 5 stars
• 13 reviews
2 repeat clients
10 years of experience
Orchard Ridge Community, Madison, WI, 53711

“Tucker did a great job watching Zoe & Mocha - regularly sent photos, provided updates from each visit, and was very communicative in providing care.”

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

“Louisa and her daughter Samantha are wonderful. I had to book them last minute, they were flexible, on time, and respectfully did what I asked them to do! They are very patient with my 7 yr old lab and my 9 week old lab puppy (we all know how naughty and energetic they can be). I received several updates during their overnight stay, and both of my girls were very content when I got home from work. Definitely would recommend them!”

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Jennifer V.
Sitter Profile Image: Amy F.
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Amy F.
from
$40
per night
4.9 out of 5 stars
• 19 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: Hanna P.
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Hanna P.
from
$40
per night
5.0 out of 5 stars
• 7 reviews
3 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: Stephany D.
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Stephany D.
from
$50
per night
4.9 out of 5 stars
• 62 reviews
15 repeat clients
13 years of experience
madison, WI, 53719

“Stefany took great care of our dogs and house while we were away. The pups were happy and healthy when we got back and it was great not having to wash sheets or dishes after a long trip. We will definitely use her again!”

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Meg G.
Sitter Profile Image: Lauren R.
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Lauren R.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 17 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: 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: Emma E.
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Emma E.
from
$28
per night
9 years of experience
Madison, WI, 53719

About: I’ve taken care of dogs and cats ever since I was 12! I help my neighbors, family, and friends whenever I can. I love all animals :) I have 4 cats of my own! I’m currently working full time Monday-Friday 10:30am to 7pm! I have plenty of time in the morning before work for pet care and after work. I'm not able to host pets at my home, but I bring the same level of care and attention directly to yours. I'm happy to follow your routine exactly — feeding, walks, playtime, medication, and all the snuggles your pet needs to feel safe and loved while you're away. I'll keep you updated with photos and check-ins so you always know how your fur baby is doing! :)

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: Lynne O.
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Lynne O.
from
$60
per night
5.0 out of 5 stars
• 8 reviews
1 repeat client
30 years of experience
Fitchburg, WI, 53711

“Asked question about the girls to get to know them. Provided a lot of pictures while we were gone.”

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Barb R.
Sitter Profile Image: Brienna T.
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Brienna T.
from
$50
per night
5.0 out of 5 stars
• 4 reviews
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: Lisa T.
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Lisa T.
Star Sitter
from
$90
per night
5.0 out of 5 stars
• 7 reviews
3 repeat clients
2 years of experience
Madison, WI, 53719

“Lisa was great! Our two dogs were very happy, and we would be glad to have Lisa help out again. She left our place better than it was before!”

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Stacy B.
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: Annalesse B.
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Annalesse B.
from
$35
per night
5.0 out of 5 stars
• 12 reviews
2 repeat clients
5 years of experience
Madison, WI, 53719

“Annalesse was amazing watching my kitties and dog. My places was in great shape and everyone seemed very happy :) I was able to relax while away and will rebook!!”

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Cailin C.
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 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.
Sitter Profile Image: Katie T.
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Katie T.
from
$30
per night
5.0 out of 5 stars
• 3 reviews
1 repeat client
4 years of experience
Madison, WI, 53713

“Katie was wonderful and took excellent care of my cat, dog, and house during a weekend away. She was very communicative and sent lots of photos, which I really appreciated.”

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Cydney N.
Sitter Profile Image: Ann M.
Verified Enhanced Background Check
Ann M.
Star Sitter
from
$28
per night
4.9 out of 5 stars
• 14 reviews
6 repeat clients
30 years of experience
Verona, 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: Oliver A.
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Oliver A.
from
$50
per night
5.0 out of 5 stars
• 11 reviews
2 repeat clients
10 years of experience
Bram's Addition, Madison, WI, 53713

“Oliver did an excellent job taking care of our dog! Great communication while we were away and sent lots of cute pictures.”

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Keelin M.
Sitter Profile Image: Briana L.
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Briana L.
Star Sitter
from
$40
per night
4.9 out of 5 stars
• 28 reviews
8 repeat clients
10 years of experience
Madison, WI, 53711

“Briana took great care of our cats and our house! When we arrived back from our trip, things were clean and our boys were in good spirits. We know they were comfortable with Briana.”

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William M.
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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

Hanna did a great job staying at our house and caring for our dogs, we’d happily book with her again! She sent regular updates and communication was timely and professional.

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Julie W.
House Sitting
5.0 out of 5 stars

Jesse sat for our 2 kitties for 3 weeks! She was absolutely fabulous! Regular check-ins, going the extra mile in every way to make the cats happy and making us feel comforted that she was taking tender loving care of them. She sent pics frequently and was conscientious about their meds and habits. Don’t hesitate to Grab Jesse she is a gem!!!

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Terri & Jeffrey H.
House Sitting
5.0 out of 5 stars

Quinn is amazing. Our girl Freddie had the best time and was so happy she had someone visit and watch her while we were away on a trip. Quinn took great care of her and left our home clean and well cared for. Great communication and extremely accommodating to whatever Freddie needed as well!

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Sydney L.
House Sitting
5.0 out of 5 stars

Stephany communicated well, showed up on time, and took good care of my pets during my trip. Aa an example, she noticed the cat fountain had stopped, and set out an extra bowl of water for them so they'd be ok until I got home.

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David B.
House Sitting
5.0 out of 5 stars

Poorna did an incredible job overnight sitting for our two dogs, Chopper and Ophelia, while we were away on vacation. She provided lots of updates and many great pics of them while we were away unprompted, and was an amazing guest in our house as well. We would recommend her to anyone and will be booking with her in the future.

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Jace M.
House Sitting
5.0 out of 5 stars

We felt very comfortable leaving our 2 puppies in the care of Mara and Dirk. They communicated with us daily and handled them like pros. Would highly recommend - they quickly created a bond with our pups and were very caring and responsible.

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Broni W.
House Sitting
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

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

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
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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.

Meet local sitters who will treat your pets like family

  1. 1. Search

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

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

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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 $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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