House Sitting Five Points

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

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Over 408
pet parents in Five Points have booked house sitting

Five Points, Find top rated house sitting

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

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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
125 reviews
47 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
7 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: Anna H.
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Anna H.
from
$38
per night
5.0 out of 5 stars
18 reviews
3 repeat clients
2 years of experience
Verona, WI, 53593

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

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Ben D.
Sitter Profile Image: Annalesse B.
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Annalesse B.
from
$35
per night
5.0 out of 5 stars
5 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: Louisa M.
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Louisa M.
Star Sitter
from
$60
per night
5.0 out of 5 stars
91 reviews
25 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: Hanna P.
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Hanna P.
from
$40
per night
5.0 out of 5 stars
2 reviews
1 repeat client
6 years of experience
Madison, WI, 53719

Hanna communicated regularly and left the space as she found it.

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Wade U.
Sitter Profile Image: Amy F.
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Amy F.
from
$40
per night
5.0 out of 5 stars
14 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: 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: 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: Allegra R.
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Allegra R.
Star Sitter
from
$65
per night
5.0 out of 5 stars
136 reviews
53 repeat clients
29 years of experience
Faircrest, Madison, WI, 53705

Allegra was absolutely wonderful when house sitting our dog franklin over a long weekend. She took on the additional challenge of caring for him when he was on heartworm treatment and did a great job attending to his special medication and low exercise needs. We came back to a happy dog and we know he was well cared for. She sent multiple picture updates each day. We will definitely contact her again in the future to watch franklin!

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Kelsey K.
Sitter Profile Image: Evelin C.
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Evelin C.
from
$42
per night
5.0 out of 5 stars
15 reviews
4 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.
from
$42
per night
5.0 out of 5 stars
8 reviews
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: kylie l.
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kylie l.
from
$58
per night
5.0 out of 5 stars
87 reviews
26 repeat clients
1 year of experience
Madison, WI, 53719

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

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Sean P.
Sitter Profile Image: Maddi S.
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Maddi S.
from
$50
per night
5.0 out of 5 stars
7 reviews
2 repeat clients
10 years of experience
Fitchburg, WI, 53575

Maddi was excellent! She sent us regular updates and was very professional. Maddi made sure our dogs and house were well cared for while we were away.

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Travis T.
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 was wonderful with my dog and a great communicator. She sent lots of updates and I could tell she was taking great care of him. She went above and beyond! I would definitely utilize her again.

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Susana S.
Sitter Profile Image: Mara S.
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Mara S.
from
$50
per night
5.0 out of 5 stars
21 reviews
8 repeat clients
7 years of experience
Verona, WI, 53593

Mara took care of our dog and 3 cats at our house for a week while we were on vacation. She communicated with us throughout the week and we came home to happy pets and the house as we had left it. Would definitely book again.

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Lindsay W.
Sitter Profile Image: Michelle S.
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Michelle S.
Star Sitter
from
$75
per night
5.0 out of 5 stars
137 reviews
56 repeat clients
4 years of experience
Madison, WI, 53719

I’m so glad Michelle was able to help us when we were in a pinch to find care for our 4 month old puppy! She communicates very well and I really enjoyed all of the picture updates she sent throughout the day! She’s very courteous as well and asked for permission before using our appliances, etc. We will definitely request Michelle to come back in the future!! :)

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Isabella W.
Sitter Profile Image: Kyra H.
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Kyra H.
from
$50
per night
4.9 out of 5 stars
20 reviews
3 repeat clients
9 years of experience
Verona, WI, 53593

Kyra did such a wonderful job house sitting with our dog Sadie! She was well cared for and we got updates every day— she seemed very happy and calm the entire visit. We will definitely be booking with Kyra again for our next trip!

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Megan H.
Sitter Profile Image: Abby L.
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Abby L.
from
$40
per night
5.0 out of 5 stars
6 reviews
3 repeat clients
16 years of experience
Junction Ridge, Madison, WI, 53717

We were lucky enough to get Abby at the last minute to dog sit (and house sit) for us, and we couldn't be happier. Our golden took a liking to her right away and it was obvious how good she is with animals. Moby can have a bit of separation anxiety, and yet, with Abby, he was in the best of hands. She cared for him as if he were her own, sent adorable pictures, and was easy to reach the entire time of our trip. The house was spotless when we returned. I highly recommend Abby and plan to call her again when I plan our next get-a-way.

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

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

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

Pet parents share their Rover experiences - Five Points

1 / 1
5.0 out of 5 stars

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

Anna was flexible with our meet and greet time and great at communicating throughout the entire process! Our dogs and cat were in fantastic hands. She was great at making sure we knew things were going well, and handled the care of our senior dog (who needs medications)! We are so thankful for her help and will be booking again!

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Katherine L.
House Sitting
5.0 out of 5 stars

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.
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

Pets always have a great time with Ann! She’s super communicative and send lots of photos! Never have to worry when she watches out pets!

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Brianne M.
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

Annalesse did a great job taking care of my dog while I was out of town at a wedding. It was my first time leaving my dog with stranger and I was nervous but annalesse did a great job of ensuring Bandit was well cared for! I received plenty of pictures and my girl had a great time!

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Jett M.
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
5.0 out of 5 stars

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

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Sarah G.
House Sitting
5.0 out of 5 stars

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

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James W.
House Sitting
5.0 out of 5 stars

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

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Lexi D.
House Sitting
5.0 out of 5 stars

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

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Laurel S.
House Sitting
5.0 out of 5 stars

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

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Ben B.
House Sitting
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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 $49.66 per night (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of House Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for House Sitting. For more information on service fees, click here .

As of July 2026, there are 849 sitters on Rover offering House Sitting across Five Points. Enter your ZIP code to see which available sitters are closest to your home.

Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:

  • Mail & deliveries: Collecting letters and packages so they don't pile up.
  • Plant care: Keeping your indoor or outdoor garden hydrated.
  • Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
  • Home security: Sitters can stay overnight to keep your home occupied.

The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Five Points walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.

It’s helpful to think of house sitting as a "home base" service. Most sitters in Five Points maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:

  • Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
  • Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
  • Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.

Tip: Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!

Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Five Points choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.

Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .

If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.

For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.

Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.

A Meet & Greet is a short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.

Yes, you can find sitters who have experience with handling special pet needs in Five Points. On Rover:

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

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

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