House Sitting Armour Square

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Over 144
pet parents in Armour Square have booked house sitting

Armour Square, 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: Kieanji W.
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Kieanji W.
Star Sitter
from
$25
per night
4.9 out of 5 stars
28 reviews
2 repeat clients
20 years of experience
Chicago, IL, 60604

Kieanji is a great dogsitter! She was very patient with my anxious dog, asked good questions to help him feel comfortable, sent pictures, and was very responsive. Both times she dogsat my dog she arrived on time and tidied up before she left. Would definitely recommend! Kieanji!

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Jacqueline M.
Sitter Profile Image: Annie X.
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Annie X.
from
$75
per night
4.9 out of 5 stars
159 reviews
114 repeat clients
8 years of experience
Armour Square, Chicago, IL, 60616

Amazing!!! Annie is great with out shy dog and went out above to build trust with our dog. Annie was very good about communicating with us. We will definitely be using Annie as a pet sitter again!

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Angelina L.
Sitter Profile Image: Jessica S.
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Jessica S.
Star Sitter
from
$60
per night
5.0 out of 5 stars
40 reviews
15 repeat clients
5 years of experience
Near West Side, Chicago, IL, 60607

Jessica was so communicative, clean and kind!! She has a calm energy that our golden retriever was drawn to immediately. We received lots of updates and pictures while we were away and came home to a very clean apartment. Our dog seemed very satisfied with all the walks and playtime which he needed. Definitely recommend! 😊

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Rebecca M.
Sitter Profile Image: Emily N.
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Emily N.
Star Sitter
from
$68
per night
5.0 out of 5 stars
238 reviews
66 repeat clients
10 years of experience
Chicago, IL, 60605

I was very nervous as a first time Rover user and so happy I found Emily! She asked detailed questions about my dogs care and habits during our initial meet and greet which put me at ease, sent photo updates during her stay where he seemed very happy / comfortable with her and came home to a clean place. Would definitely book again!

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Shannon S.
Sitter Profile Image: Elizabeth A.
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Elizabeth A.
from
$40
per night
5.0 out of 5 stars
10 reviews
2 repeat clients
12 years of experience
Chicago, IL, 60607

Great communication and my pup loved hanging out with Elizabeth!

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Jake R.
Sitter Profile Image: Samantha E.
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Samantha E.
Star Sitter
from
$40
per night
5.0 out of 5 stars
144 reviews
62 repeat clients
13 years of experience
Loop, Chicago, IL, 60602

Samantha is amazing. She took care of my two Frenchies for 8 days in my home. She took over new training techniques for the puppy with no problem (with very little notice I might add). She took amazing care of my babes and left my apartment just as I’d left it. Love her!

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C A.
Sitter Profile Image: Tylisha J.
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Tylisha J.
from
$45
per night
4.9 out of 5 stars
41 reviews
10 repeat clients
3 years of experience
Chicago, IL, 60605

Tylisha was great! Very responsive, prompt, lots of photos shared and Airlie seemed very happy when I got home. House was clean and tidy. Highly recommend!

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Dane C.
Sitter Profile Image: Faith M.
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Faith M.
from
$60
per night
5.0 out of 5 stars
20 reviews
9 repeat clients
10 years of experience
Chicago, IL, 60622

Faith showed up for every drop in and took my babies for walks. She kept an extra close eye on Neville because he’d just had a tooth extracted and was on a soft diet with pain meds. Faith patiently soaked his kibble and proportioned his wet food to go with it and I’m so grateful for that. She was great with my fur children.

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Marissa G.
Sitter Profile Image: Eliana B.
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Eliana B.
from
$55
per night
5.0 out of 5 stars
5 reviews
3 years of experience
Lower West Side, Chicago, IL, 60608

Eliana was absolutely amazing. My partner and I have a disabled fur baby with a number of special needs, and Eliana was incredibly diligent, asked all the right questions, followed our instructions closely, and took such great care of Miss Bean and our home. We came home to a happy, healthy pup and couldn’t have been more appreciative. I will absolutely be reaching back out for future travel plans. She was a dream to have stay with our fur baby!

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William R.
Sitter Profile Image: Elizabeth C.
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Elizabeth C.
from
$75
per night
5.0 out of 5 stars
57 reviews
22 repeat clients
10 years of experience
Loop, Chicago, IL, 60601

Elizabeth was awesome! We have already booked her for an additional four stays! One of our pups isn't very trusting and tends to bark and lunge at new people. When Elizabeth came to meet them, she didn't even flinch. She remained calm and let Kona get adjusted which is exactly what Kona needed to feel comfortable. Elizabeth also sent us updates with photos of our pups while we were gone. We don't have kids, so our dogs are our kids and we, understandably, felt nervous leaving them with a new person. However, we felt so comfortable with Elizabeth and look forward to having her stay again in the future.

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Alex S.
Sitter Profile Image: Elizabeth D.
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Elizabeth D.
from
$45
per night
5.0 out of 5 stars
32 reviews
9 repeat clients
20 years of experience
Chicago, IL, 60609

Elizabeth is always so great with my dog! I really appreciate the consistent pictures and updates while I’m gone, it really puts my mind at ease. This is my second time having her house sit and both times have been amazing!

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Kennedy C.
Sitter Profile Image: Allison J.
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Allison J.
from
$85
per night
5.0 out of 5 stars
80 reviews
34 repeat clients
13 years of experience
Chicago, IL, 60608

Allison was great! She was very accommodating and communicative before the stay, and continued to be awesome throughout the stay. She sent pictures and updates throughout the weekend, which I really appreciated. We came home to a super happy pup and a very clean home! I will definitely be using Allison again and can’t recommend her enough! Thank you so much Allison!!

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Chelsea R.
Sitter Profile Image: Jorie S.
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Jorie S.
from
$70
per night
5.0 out of 5 stars
19 reviews
8 repeat clients
15 years of experience
Chicago, IL, 60605

Jorie was absolutely amazing! This was my first time using Rover for an overnight stay, and she made the entire experience so easy and comforting. We met in person for a meet-and-greet, and she was incredibly friendly and truly engaged in getting to know my pup, which meant so much to me. I left detailed instructions, and she followed everything perfectly. She also left my home exactly how she found it, which I really appreciated. Jorie kept me consistently updated with texts, photos, and messages after every walk, which gave me so much peace of mind. Leaving my puppy is always hard, and the worry is real but Jorie completely eased my anxiety. I’m so grateful for her care and would absolutely recommend her to anyone looking for someone trustworthy, attentive, and kind. ❤️

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Azure D.
Sitter Profile Image: Christina D.
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Christina D.
Star Sitter
from
$50
per night
5.0 out of 5 stars
13 reviews
5 repeat clients
13 years of experience
Oakland, Chicago, IL, 60653

Christina took excellent care of our apartment, Casey cat, and Rowdy (a recently adopted 5-month old kitten we were nervous about leaving.) We got plenty of reports and pictures, and the cats were very mellow when we got home.

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Kathleen T.
Sitter Profile Image: Nadine T.
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Nadine T.
Star Sitter
from
$70
per night
5.0 out of 5 stars
56 reviews
14 repeat clients
15 years of experience
Near South Side, Chicago, IL, 60616

Nadine house sat our 7-year-old pup during a five-day trip and took great care of her! She is great and very affectionate with dogs; my sheepadoodle instantly warmed up to her during our meet and greet. She was very communicative and sent many updates and lovely photos, which really put us at ease while away. I would definitely recommend Nadine!

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Querida Q.
Sitter Profile Image: Jozelin R.
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Jozelin R.
from
$37
per night
5.0 out of 5 stars
37 reviews
19 repeat clients
15 years of experience
Bridgeport, Chicago, IL, 60616

Jozelin took great care of our dog, Derby. She was communicative and responsive and sent us great photos of Derby while we were on vacation. I would recommend booking Jozelin to care for your pets!

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Kaylyn T.
Sitter Profile Image: Mairead M.
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Mairead M.
Star Sitter
from
$65
per night
5.0 out of 5 stars
26 reviews
4 repeat clients
5 years of experience
Lower West Side, Chicago, IL, 60616

Mairead was fantastic! She was so good with my dogs and sent me tons of pictures and updates. My dogs can be a bit anxious the first day with a new person and she handled it perfectly. She was so good about questions if something came up and letting me know how the dogs were doing each day. I never worried that my dogs were in the best hands!

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Anna M.
Sitter Profile Image: Cheyanne H.
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Cheyanne H.
Star Sitter
from
$36
per night
5.0 out of 5 stars
32 reviews
24 repeat clients
10 years of experience
Near South Side, Chicago, IL, 60616

About: • Lifelong pet owner with hands-on experience caring for dogs of all ages, breeds, and temperaments • Comfortable with feeding schedules, medication administration, and special dietary needs • Experience with crate training, basic commands, and leash manners • Knowledge of dog body language and signs of stress or illness • Confident with high-energy breeds and senior dogs alike • Able to handle multiple pets at once • Regularly walk dogs in safe, dog-friendly neighborhoods and parks • Provide both high-energy walks and relaxed strolls tailored to your dog’s needs • Keep dogs mentally stimulated through sniff walks and playtime • Familiar with using different harnesses, leashes, and walking tools • Keep your pets comfortable in their own home with regular check-ins and companionship • Maintain routines for feeding, potty breaks, and bedtime • Provide updates, photos, and videos so you always know your pet is in good hands • Water plants, bring in mail, and keep your home tidy while you’re away • Comfortable with litter box cleaning, feeding, and playtime • Experience with shy or anxious cats—patient and gentle • Can care for small pets like rabbits, hamsters, or birds I’m available any day and time that works best for you—except Sunday mornings. On Sundays, I’m free after 3:00 PM. Whether you need early morning walks, mid-day drop-ins, or evening snuggles, I’ve got you covered! When caring for pets in my client’s home, I do my best to keep their routine consistent so they feel safe and comfortable. I follow all feeding, walking, and medication instructions carefully, and make sure they get plenty of attention, playtime, and affection. I respect the home, clean up after the pets, and always keep you updated with messages and photos so you have peace of mind. If I’m caring for pets in my own home, I make sure they have a clean, cozy space to relax and feel at home. I provide regular walks, playtime, and cuddle sessions. I also pay close attention to how they’re adjusting to a new environment and take extra care to make them feel calm, loved, and secure. Whether your pet is high-energy or low-key, I adjust to their needs and treat them like family.

Sitter Profile Image: Natalie Z.
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Natalie Z.
from
$40
per night
2 years of experience
Chicago, IL, 60608

About: I am trained as a Certified Veterinary Technician that has given me the skills and knowledge to provide safe, attentive care. I’m better equipped to recognize potential health concerns, handle unexpected situations, and know when a pet may need veterinary attention. I truly love caring for animals and meeting new pets, taking the time to learn their unique personalities and needs. I’m patient, attentive, and dedicated to making every pet feel safe, comfortable, and loved while in my care. I currently work part-time at a veterinary clinic four days a week. Your pet must be okay with being alone during normal work hours, but otherwise I can provide plenty of companionship, care, and attention. I do not offer boarding in my home, but I am happy to provide house sitting in your home. I will treat your home with the same respect and care I would my own, leaving everything just as I found it.

Sitter Profile Image: Reina & Robert U.
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Reina & Robert U.
from
$55
per night
4 years of experience
Near South Side, CHICAGO, IL, 60616

About: It's summertime in Chicago and that means you get two for the price of one! I am a work from home graphic designer who loves nothing more than a fluffy companion to supervise my work. And since school is officially out for summer, your buddy will also get to hang out with my husband Rob who is a school teacher on summer break. Since having to say goodbye our precious sausage boy last winter we have lots of love to share with your furry friend. I grew up in a home bursting with feline, canine, rodent, and reptilian companions so I have plenty of experience caring for all kinds of creatures. My last dog was a very anxious rescue pup, so I am comfortable working with pets who need time and patience while adjusting to new situations and new people. I love routine and am more than happy to follow detailed instructions to ensure your pet feels as comfortable as possible while you are away. If you have any questions, or if your pet has any special needs, please feel free to send a message! I work from home and am able to set my own hours, so it is no problem for me to adjust my schedule to fit your pet's needs. I'm a major homebody and perfectly comfortable spending all day hanging out at home keeping your fluffer company. During the summer months my husband Rob will likely accompany me which means double the companionship for your buddy -- with your permission, of course. Weekdays, weekends, evenings, it's all good! The more details you can provide about your pet's preferred routine and expectations, the better. I want to make sure they and you feel comfortable so I'll probably ask a lot of questions during our meet-and-greet. At this time I am only comfortable with animals under 30 lbs. I want to make sure I am able to lift and carry them if needed. Multiple dogs are fine so long as they have good leash manners and won't try to pull me in opposite directions.

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The median cost per night for house sitting in Armour Square is $50

Pet parents share their Rover experiences - Armour Square

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5.0 out of 5 stars

Zhanna was absolutely amazing with my cat, who is an Abyssinian cat. He can definitely be a handful, he’s extremely curious, energetic, and very demanding when it comes to attention but she handled him perfectly. She was patient, attentive, and genuinely engaged with him, and I could tell he felt completely comfortable with her. I really appreciated the updates and knowing he was getting plenty of attention and affection while I was away. I felt completely at ease leaving him in her care and would absolutely book with Zhanna again!

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Iryna K.
House Sitting
5.0 out of 5 stars

Allison was absolutely wonderful with our French bulldog and two cats. As protective pet parents, this was our first time leaving all three of them in someone else’s care, so naturally we were a little apprehensive. Allison immediately put us at ease by offering two consultation visits before our trip so she could thoroughly understand our pets’ individual needs, routines, personalities, and home environment. That level of preparation and genuine care meant a lot to us. Throughout our vacation, Allison was incredibly attentive and responsive. She arrived early and kept us updated with multiple messages and plenty of photos, which gave us so much peace of mind while we were away. It was clear that she wasn’t simply checking in on our pets, but genuinely caring for them and making sure they were happy and comfortable. She even went above and beyond by offering thoughtful advice for our continued care of the pets, which we really appreciated. You can tell Allison truly loves animals and takes the responsibility of caring for them seriously. She also left the house tidy and in great shape. It was such a small gesture, but after coming home from a long trip, walking into a clean and tidy home made a bigger difference than she probably realized. We came home to three happy, well-cared-for pets and felt completely comfortable knowing they were in Allison’s hands. She helped make our vacation so much more enjoyable because we never had to worry about how things were going at home. We would absolutely recommend Allison and will definitely be using her services again. Thank you, Allison, for taking such wonderful care of our babies and allowing us to have such a relaxing vacation. We truly couldn’t have done it without you!

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Danny R.
House Sitting
5.0 out of 5 stars

Meg took great care of my dog for an extended weekend. She was super communicative all weekend which made me feel like my dog was in great hands!

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Krista M.
House Sitting
5.0 out of 5 stars

Clancy and Alice were amazing!! They made sure the pups were well taken care of and provided regular updates and pictures! We already plan to have them come again for a longer stay.

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Farnel M.
House Sitting
5.0 out of 5 stars

Elizabeth was a great sitter! She was communicative, provided consistent updates, and followed Momo’s usual routine. We would definitely use her again.

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Melissa A.
House Sitting
5.0 out of 5 stars

Stephanie was an amazing sitter. She spent a lot of time with our two cats, giving Fern her inhaler and playing with Oscar who has endless energy. She went above and beyond.

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Leigh C.
House Sitting
5.0 out of 5 stars

Eliana was absolutely amazing. My partner and I have a disabled fur baby with a number of special needs, and Eliana was incredibly diligent, asked all the right questions, followed our instructions closely, and took such great care of Miss Bean and our home. We came home to a happy, healthy pup and couldn’t have been more appreciative. I will absolutely be reaching back out for future travel plans. She was a dream to have stay with our fur baby!

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William R.
House Sitting
5.0 out of 5 stars

Elissa did an incredible job watching my Frenchie. She sent loads of pics and updates. She’s super reliable and responsive. I’ve already rebooked with her! Thank you, Elissa!

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Audrey W.
House Sitting
5.0 out of 5 stars

Nicole was great with my senior dog, Bella, while I was away for a long weekend. She sent tons of updates, was a great communicator & left my place nice and clean. I fully trusted Bella was in great hands with her and well taken care of. Highly recommend!!

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Tiffany B.
House Sitting
5.0 out of 5 stars

Danielle was amazing with my dogs! She was very patient, caring, and attentive to their needs. She kept me updated throughout their stay and sent plenty of pictures, which gave me great peace of mind. It was clear they were happy and well cared for. I highly recommend Danielle and will definitely use her again!

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Jerónimo Á.
House Sitting
5.0 out of 5 stars

McKenzie is a stellar house sitter - she sent me daily updates about my pets while I was out of town and we both cheered when my very shy cats came out of hiding for her! She also left my home in spotless condition. I will absolutely book again for future travel. Thank you McKenzie!

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Sadie K.
House Sitting
5.0 out of 5 stars

Derek was great with my two German Shepherds! I have two older, German shepherds who are rescues-one has had separation anxiety in the past and the other needs daily medications. Derek was available on short notice and came over to meet them before staying at our place for three days. He sent regular updates and photos while we were away, and was very good at communicating. I could tell my dogs were at ease with him which gave me so much peace of mind! Would definitely recommend Derek!

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Katy M.
House Sitting
5.0 out of 5 stars

Angelina took amazing care of our pup, sent lots of photos and updates, and left our house in perfect condition. Would highly recommend her as a sitter!

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Cassie W.
House Sitting
5.0 out of 5 stars

Alli is remarkable! She made our trip worry free! She bonded quickly with our Blue Heeler so quickly which doesn’t happen easily. We can’t thank her enough and will absolutely be working with her every time we go out of town!

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Colby H.
House Sitting
5.0 out of 5 stars

Dominick ROCKS! This was our first time leaving our baby for this long and she made it so easy. Clean, communicative, kind, and reliable!!!

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Hallie P.
House Sitting
5.0 out of 5 stars

Linh is incredible! She has helped me troubleshoot technical issues with my cat’s feeder and litter box. She is super communicative and makes my life easy!

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Kelsie M.
House Sitting
5.0 out of 5 stars

We trusted Ann-Marie to care for our toy fox terrier Loki in our house for over a week. She did a wonderful job! When we got home, it was clear that Loki adores her—he was happy, relaxed, and sad to see her go. Ann-Marie adjusted perfectly to Loki’s schedule and sent us photos while we were away. She even took him on walks to new places that he loved. Most of all, Ann-Marie was a calm, reliable and trustworthy presence in Loki’s life for an extended period of time. We are extremely grateful. Thank you so much!!!

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Maria M.
House Sitting
5.0 out of 5 stars

Kristine was absolutely amazing! The best dog/house sitter we have used on Rover, by far. She was attentive, punctual, and super friendly. Our dog, Daisy, was well-loved in her care. Would highly recommend her services and would definitely book her again!

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Anthony V.
House Sitting
5.0 out of 5 stars

Second time booking with Nadine and definitely won’t be my last. She takes such good care of my kitties and I can tell they are happy with her too based on how they act when I come back. Always happy and not mad at me or hiding upon my return. Thank you Nadine 💛💛💛

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Natalie M.
House Sitting
5.0 out of 5 stars

Stephanie came over for a Meet & Greet and immediately clicked with our puppy. We loved that Stephanie listened carefully to our instructions (first time leaving new puppy!) and exhibited that in her detailed periodic reports throughout the sitting period. We felt comfortable leaving our puppy with Stephanie, and will happily book her again on Rover for future sittings!

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Jamie H.
House Sitting
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