House Sitting Sleepy Hollow

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

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Over 20
pet parents in Sleepy Hollow have booked house sitting

Sleepy Hollow, 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: Alyssa V.
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Alyssa V.
Star Sitter
from
$70
per night
5.0 out of 5 stars
121 reviews
43 repeat clients
11 years of experience
Lake in the Hills, IL, 60156

Alyssa did a wonderful job house-sitting for our 2 cats! She spent a lot of time with them, stayed the nights with them, and took really great care of them! She would send us daily updates with lots of pictures and summaries of all the ways they played and what they did each day. It was such a relief during our vacation to know that our fur-babies were being well cared for while we were gone. Even our older, grumpier cat eventually warmed up to her! On top of all that, she did dishes, took out the trash, and picked up before she left. I think the house was cleaner when we got home than when we left! What a wonderful surprise to come home to! We'll definitely be using Alyssa again in the future :-D

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Jaden B.
Sitter Profile Image: Katelynn R.
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Katelynn R.
Star Sitter
from
$60
per night
4.8 out of 5 stars
17 reviews
4 repeat clients
7 years of experience
West Dundee, IL, 60118

THANK YOU so much for taking such good care of Freya! We had Katelynn stay at our house for 5 days and we got so many updates about how Freya was doing. Will ABSOLUTELY continue to book Katelynn, especially since we have a major surgery coming up for Freya and there might be days where I cannot come home and check on her during work. Thanks again!

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Devon E.
Sitter Profile Image: Jordyn L.
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Jordyn L.
Star Sitter
from
$65
per night
5.0 out of 5 stars
71 reviews
16 repeat clients
10 years of experience
Crystal Lake, IL, 60014

I help rescue and foster special needs dogs, those physically or mentally abused. While helping Sadie as a temporary foster, no one in the rescue group was willing to take care of her. So, I decided to add her to my family. I say this because I need someone that understand how to care for Sadie emotional needs. From the very first time Sadie and I met Jordyn, we knew she would be the perfect sitter when I travel for work. Jordyn gave so much love to Sadie while I was gone that I was able to focus on work and not worry about Sadie. Jordyn was amazing sending me updates and photos!! When I travel for work in the future Jordyn will be the only person I call to take care of Sadie.

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Hyman T.
Sitter Profile Image: Jenna F.
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Jenna F.
from
$50
per night
5.0 out of 5 stars
7 reviews
1 repeat client
10 years of experience
Algonquin, IL, 60102

About: I’ve had dogs and cats my whole life. Currently live with 2 dogs and 2 cats, and my family has 3 other dogs! I’ve dog-sat for many years, both staying at homes and frequently checking in. I have a natural way of connecting with animals, and I love spending time with them! During the summer, I will have availability to walk dogs, let dogs out, and care for pets during the day and evenings on weekdays. June weekdays I am available after 12, and July weekdays I am available all day. Weekend availability is not consistent throughout the summer. I live with two dogs and two cats. I walk the dogs frequently, feed them breakfast and dinner, and keep their spaces clean and safe! I monitor pets as they chew on toys, and throw away toys that could be dangerous. Managing 4 pets is a handful, but I love it!

Sitter Profile Image: Danielle E.
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Danielle E.
from
$50
per night
5.0 out of 5 stars
12 reviews
4 repeat clients
23 years of experience
Gilberts, IL, 60136

Danielle took such good care of our babies and was a responsive communicator and sent lots of pics! They love when Danielle comes to hang with them.

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Allyson C.
Sitter Profile Image: Avery L.
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Avery L.
from
$50
per night
5.0 out of 5 stars
4 reviews
2 repeat clients
5 years of experience
Gilberts, IL, 60136

We really appreciate the last minute availability as our International flight was delayed coming back. Thanks!!

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Jay K.
Sitter Profile Image: Grace G.
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Grace G.
Star Sitter
from
$65
per night
5.0 out of 5 stars
55 reviews
11 repeat clients
10 years of experience
Gilberts, IL, 60136

Cannot say enough good things about Grace's house-sitting! She was kind and patient with my weird dog, kept me updated, and left my home in great condition. Have already booked her for another stay!!

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Katherine G.
Sitter Profile Image: Valerie P.
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Valerie P.
Star Sitter
from
$75
per night
5.0 out of 5 stars
119 reviews
46 repeat clients
13 years of experience
Elgin, IL, 60123

Valerie was great on her first visit. She was very attentive to my nervous pup who wasn’t nervous at all with her. My time away was so enjoyable because of her. Will be rebooking over and over. Thank you!

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Vanessa T.
Sitter Profile Image: Marilyn P.
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Marilyn P.
from
$50
per night
5.0 out of 5 stars
37 reviews
11 repeat clients
40 years of experience
Elgin, IL, 60123

Very reliable and always punctual. Considerate of our routines and home. Gives me a peace of mind knowing my anxious girl has someone to lean on while we are gone. Appreciate that Marylin will communicate with me throughout her stay with my precious pup. She is just what my girl needs…..a calm, confident member of the pack

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Jenelle H.
Sitter Profile Image: Stephanie L.
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Stephanie L.
from
$65
per night
5.0 out of 5 stars
57 reviews
8 repeat clients
17 years of experience
Streamwood, IL, 60107

Stephanie did a fantastic job watching our four dogs. Not only did she take great care of them, but also took them out for a long walk each day. Communication skills were great, always providing us updates and videos on our pups while we were away. We highly recommend Stephanie and will definitely use her again in the future

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Joe B.
Sitter Profile Image: Catarina S.
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Catarina S.
Star Sitter
from
$65
per night
4.9 out of 5 stars
24 reviews
9 repeat clients
3 years of experience
CARPENTERSVILLE, IL, 60110

Catarina was great! Our dogs are on the more difficult side and she had such a great attitude and was very kind. Thank you Catarina!

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Guadalupe F.
Sitter Profile Image: Kimberly G.
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Kimberly G.
Star Sitter
from
$95
per night
5.0 out of 5 stars
83 reviews
36 repeat clients
30 years of experience
Batavia, IL, 60510

Kim is so sweet !!! As a dog owner I always hate having to leave my girls anywhere but Kim is such a good dog caretaker and I could have ease knowing my girls were in good hands !! Got updates as the day went on ! And she took the time to love and care for the girls !! 10/10

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Muskan M.
Sitter Profile Image: Hannah M.
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Hannah M.
Star Sitter
from
$60
per night
5.0 out of 5 stars
11 reviews
4 repeat clients
10 years of experience
University, Algonquin, IL, 60102

Hannah was outstanding. Our schedule changed slightly at last moment and Hannah changed her schedule to accommodate and arrive to our home and be with Harley soon after we had to leave. Hannah kept us up to date and posted lots of photos of our beloved Dog Harley as well as all the walks and loving she provided. We came home to Happy puppy and very clean home. Hannah was awesome and we look forward to having her sit with our dog again in the future.

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Joe B.
Sitter Profile Image: Erika G.
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Erika G.
Star Sitter
from
$80
per night
5.0 out of 5 stars
255 reviews
65 repeat clients
30 years of experience
St. Charles, IL, 60175

Erika is a sweetheart! She did a wonderful job caring for my cat while I was out of town. She left my place cleaner than she found it and kept in communication to calm an anxious cat-mom's mind. Would recommend and plan on asking her again when the time comes.

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Nina W.
Sitter Profile Image: Mark H.
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Mark H.
Star Sitter
from
$60
per night
5.0 out of 5 stars
24 reviews
7 repeat clients
22 years of experience
Holiday hills, IL, 60051

Mark is a great sitter that my family has used twice now! The animals love Mark and I'm always getting updates with pictures of them for peace of mind. Absolutely recommend for your pet sitting needs!

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Chance U.
Sitter Profile Image: Michele K.
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Michele K.
from
$50
per night
5.0 out of 5 stars
12 reviews
25 years of experience
Cary, IL, 60013

Michele did a great job watching our Livia while we were in CA. We were very comfortable knowing she was well taken care of. Michele took Livia for a morning walk daily and kept us updated with pictures and notes. She is highly recommended and we wouldn't hesitate to use her again.

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Jim B.
Sitter Profile Image: Grace S.
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Grace S.
from
$75
per night
5.0 out of 5 stars
8 reviews
1 repeat client
11 years of experience
Trout Valley, IL, 60013

Grace was excellent! She provided updates when needed and was very helpful and attentive to our requests and instructions. We came home to a happy, healthy puppy and a clean house. All we could ask for in a sitter! We will definitely be booking Grace again! Thanks, Grace!

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Meghan K.
Sitter Profile Image: Eloise L.
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Eloise L.
from
$70
per night
5.0 out of 5 stars
13 reviews
2 repeat clients
15 years of experience
Huntley, IL, 60142

Eloise is amazing. I felt very confident from the start of our interactions to the meet and greet and the eventual stay that she would take great care of Opal. I was correct! She’s super thorough yet laidback, sent updates and was easy to communicate with!

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Laura A.
Sitter Profile Image: Taylor N.
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Taylor N.
from
$52
per night
4.9 out of 5 stars
13 reviews
4 repeat clients
8 years of experience
Union, IL, 60180

Taylor was fantastic!! We were traveling to Illinois and had our young dogs and older girl with us. The two younger ones had never been boarded yet and would not have done well left in our travel trailer for an entire day while we did touristy stuff. I booked Taylor to come to our RV park and stay with the dogs in our travel trailer. It was such a relief to not have to worry about them while we were out or cut our day short to get back to them. She sent pics of them all on walks, or hanging out in the patio and kept me updated how they were doing throughout the day. She was very responsive the entire process from before booking all the way to the end. If you need someone to watch your pets, don’t hesitate to call Taylor!

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Lori M.
Sitter Profile Image: Toby J.
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Toby J.
from
$35
per night
5.0 out of 5 stars
10 reviews
2 repeat clients
4 years of experience
Lake in the Hills, IL, 60156

Toby is super punctual, dependable, kind, and caring. Toby watched my 9 week old puppy twice, and he was very loving and patient. During the time he stayed at my house, he not only watched my puppy for several hours, but also played with him and fed him per my instructions. I highly recommend Toby to take care of any pets. Toby is a spectacular pet sitter and an amazing human being.

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Paula S.
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The median cost per night for house sitting in Sleepy Hollow is $50

Pet parents share their Rover experiences - Sleepy Hollow

1 / 1
5.0 out of 5 stars

I had a wonderful experience with Jessica. She took amazing care of my three dogs and treated them like her own, which immediately put my mind at ease while I was away. She was attentive, reliable, and clearly very experienced with animals. I can tell my dogs really loved being with her. Beyond caring for the dogs, she also went above and beyond around the house, taking care of extra chores without being asked. Coming home to everything in great shape made such a difference and really showed how thoughtful and responsible she is. I would absolutely book her again and highly recommend her to anyone looking for someone trustworthy, caring, and dependable for their pets and home.

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Pauline D.
House Sitting
5.0 out of 5 stars

Kristina is the absolute best. She really gives us peace of mind that she is watching our dog and house while we are on vacation.

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Tim S.
House Sitting
5.0 out of 5 stars

Jana was great (again!). I use her every time I am away. She keeps the dogs well entertained which can be challenging and goes above and beyond with "housekeeping" to make sure my return home is stress-free. Thanks Jana!!!!!

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Kim R.
House Sitting
5.0 out of 5 stars

Karlie was great with all 3 of our dogs. This was the first time I have ever used a service to take care of my dogs. Karlie came to my house twice before our trip to get to know the dogs, etc. You could tell Karlie is a "dog person" since I could tell the dogs liked her. That really helped us enjoy our vacation so much more knowing that they were in good hands. Karlie responded to text messages quickly. Got updates on dogs and pix while I was on vacation. Now that I have gone through this process and found someone we like, we definitely will hire Karlie again.

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Heather H.
House Sitting
5.0 out of 5 stars

Katie was absolutely wonderful! She took great care of Wren and Lucy. She shared many photos and updates during our trip out of town to visit our grandchildren. Having Katie watch our dogs gave us a great piece of mind, and the dogs had a wonderful time, too! Thank you, Katie, for going above and beyond in caring for our dogs.

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Mike B.
House Sitting
5.0 out of 5 stars

Eloise was absolutely wonderful with Bella and Archie! She sent periodic updates throughout her time with them and I felt incredibly comfortable with her watching the loves of my life! I will absolutely book with Eloise again and I highly recommend her for any of your pet needs!!!

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Jamie S.
House Sitting
5.0 out of 5 stars

Iryna is awesome! Beans was so happy to have her, he didn't even miss me! Will definitely be using in the future.

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Tracie D.
House Sitting
5.0 out of 5 stars

Katelyn has been a wonderful dog sitter. She has shared great updates while we are away, and our dog always looks so content. We are so thankful for all she did for our dog while we traveled.

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Jori K.
House Sitting
5.0 out of 5 stars

Jaqueline and Uriel were (as expected) amazing while we were on vacation for a week. They kept us updated and send many pictures and videos. The house was clean when we returned and the trash was emptied. Most importantly my pets were happy and comfortable with them. Our dog is super shy and timid and he did great with them.

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Brenda A.
House Sitting
5.0 out of 5 stars

Catarina was great! Our dogs are on the more difficult side and she had such a great attitude and was very kind. Thank you Catarina!

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Guadalupe F.
House Sitting
5.0 out of 5 stars

Katy was awesome! She stayed with our dog and 2 cats for 3 nights, she was respectful of our home and kept it clean, and she let us know how our pets were doing. We would definitely have her watch our animals again!

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Amanda P.
House Sitting
4.0 out of 5 stars

Lydia sat for my 2 dogs for 8 days while I was visiting family. The dogs did just fine and seemed happy when I came home. The deal was to stay in my house where they felt safe and at home. They stayed at her house instead, not what I had planned. But they were safe and taken care of and that is what matters. I received a few photos and minimal communication. It is hard to leave our loved ones at home, but everything turned out fine.

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Katherine 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.

How Rover works

  1. 1. Search

    Browse profiles of sitters near you who offer house sitting
  2. 2. Meet & Greet

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

    It's that easy! All payments are processed through Rover's secured platform

Sitters in Sleepy Hollow average 4
repeat house sitting clients

FAQs for House Sitting - Sleepy Hollow

Frequently asked questions about Rover

The average cost for House Sitting in Sleepy Hollow on Rover is $55.5 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 4,362 sitters on Rover offering House Sitting across Sleepy Hollow. 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 Sleepy Hollow 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 Sleepy Hollow 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 Sleepy Hollow 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 Sleepy Hollow. On Rover:

  • 94% of sitters can help with special care needs
  • 96% can help with giving oral medications or injections
  • 97% 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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