House Sitting Kenwood

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Over 133
pet parents in Kenwood have booked house sitting

Kenwood, 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: Victoria G.
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Victoria G.
Star Sitter
from
$55
per night
5.0 out of 5 stars
35 reviews
6 repeat clients
30 years of experience
Hyde Park, Chicago, IL, 60637

I had a great experience having Victoria watch my boy Ash. Her communication was excellent, she arrived on time, and took great care of Ash. I would happily have her watch him again!

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Dan L.
Sitter Profile Image: Evan P.
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Evan P.
Star Sitter
from
$50
per night
5.0 out of 5 stars
54 reviews
17 repeat clients
17 years of experience
Hyde Park, Chicago, IL, 60615

Evan was terrific - great with the dogs, good communicator, and he left the house in wonderful condition. We booked him at the last minute and would definitely book him again. Highly recommended.

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Cynthia H.
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: 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: Zoe R.
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Zoe R.
Star Sitter
from
$60
per night
5.0 out of 5 stars
16 reviews
8 repeat clients
10 years of experience
Chicago, IL, 60615

Zoe was so great with Mac and communicated well while I was away. I can’t thank her enough and would love to have her watch Mac again next time I’m out of town!

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Jackie B.
Sitter Profile Image: Lucille C.
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Lucille C.
Star Sitter
from
$35
per night
5.0 out of 5 stars
27 reviews
4 repeat clients
5 years of experience
Hyde Park, Chicago, IL, 60615

Lucille was a fantastic sitter and our dog had a blast. She was so thoughtful about making sure our dog Lea felt comfortable, and she kept us updated with great photos and videos.

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Karlos B.
Sitter Profile Image: Shakira C.
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Shakira C.
from
$75
per night
5.0 out of 5 stars
50 reviews
9 repeat clients
25 years of experience
Chicago, IL, 60619

Shakira is amazing! I feel like she's part of the family. She did an amazing job looking after my Maltipoo, Dash! She sent plenty of pictures and videos throughout the day. I really appreciate the way she made both me and Dash feel comfortable. Before she left, I had already booked her for another sitting for Dash. She's the best!

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Nicole W.
Sitter Profile Image: Jasmine P.
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Jasmine P.
from
$175
per night
5.0 out of 5 stars
99 reviews
38 repeat clients
10 years of experience
Kenwood, Chicago, IL, 60615

Jasmine was amazing yet again with my dobie, Storm. I had some last minute emergency changes to my trip and her flexibility and understanding really put me at ease during a stressful time, I'm so grateful for her support! Super communicative, Jasmine took great care of my girl and my place too. Also, Storm is reactive to other dogs and I trust Jasmine to know how to deal with that. Highly recommend.

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Michelle S.
Sitter Profile Image: Alexis W.
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Alexis W.
Star Sitter
from
$68
per night
5.0 out of 5 stars
35 reviews
10 repeat clients
5 years of experience
Chicago, IL, 60649

Alexis did such a wonderful job with our dog Murphy. Tons of video and picture updates and Murphy always seemed comfortable with her. Highly recommend!!!

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Alexis P.
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: Quinn W.
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Quinn W.
from
$50
per night
5.0 out of 5 stars
10 reviews
1 repeat client
8 years of experience
Hyde Park, Chicago, IL, 60615

Quinn was fantastic. She was very responsible, and our dog, who can be a lot of work, loved her. She stayed with our dog at our home and was very neat and responsible. I highly recommend her!

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Sara E.
Sitter Profile Image: Tabbie M.
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Tabbie M.
from
$37
per night
5.0 out of 5 stars
7 reviews
2 repeat clients
7 years of experience
Grand Crossing, Chicago, IL, 60619

Tabbie M. was on time, communicative, and professional. She worked well with sweety and sent emails, and pictures to update me. Tabbie M. is very nice and kind as well. I will definitely book her again.

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S C.
Sitter Profile Image: Claire P.
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Claire P.
from
$70
per night
5.0 out of 5 stars
10 reviews
3 repeat clients
12 years of experience
Woodlawn, Chicago, IL, 60637

Claire was fantastic. From the moment we met her, she was warm, professional, and clearly experienced with dogs. She took exceptional care of my anxious dog, Balu, and we were so relieved to come home to a relaxed, happy dog. Claire kept us updated with photos and messages throughout our trip, which gave us real peace of mind while we were away. She stayed in our home and left everything spotless. We couldn’t have asked for a better dog sitter and wouldn’t hesitate to book her again if she’s available.

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Jay N.
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: 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 great with my anxious dog Bear! She was patient, calm, and gently assertive where needed and he felt very comfortable with her. He can be reactive with strangers and she handled him well. Bear fell into his normal routine quickly, and relaxed at home during the house sit.

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Sindhu S.
Sitter Profile Image: Ashley C.
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Ashley C.
from
$80
per night
5.0 out of 5 stars
8 reviews
4 years of experience
Chicago, IL, 60653

About: I grew up taking care of family pets and have also loved sitting for friends and family over the years. I joined Rover in 2022 while in grad school because I missed having animals around and have been caring for dogs and cats since. Now I work from home and have lots of flexibility in my schedule for care! . What sets me apart? Your pet’s experience: a safe, calm, and of course, fun time. I’ll take the time to learn their quirks, shower them with plenty of love, and make them as comfortable as possible while their human is gone. I don’t have any pets and only take on one Rover client at a time so I can give your pet(s) the dedicated, individualized care they deserve. I also work from home and have lots of flexibility in my schedule. This means less stress, sticking more closely to the routine they’re used to, and no fighting for attention! . Your experience: I know how important it is to have a trustworthy sitter or walker while you’re away for peace of mind and I pride myself on being responsible, detail-oriented, and communicative. For every booking, I send plenty of photos of your pet living their best life and discuss your communication preferences ahead of time so we can be on the same page. I have a lot of flexibility in my daily schedule so I'm very happy to work with you to accommodate your needs or adjust if things change. For boarding, I live with my boyfriend in a spacious condo in Hyde Park, so there's plenty of room for your pet to play, get their zoomies out, or find a spot for some alone time. Although I'm the primary caregiver, he is also always up for a belly scratch or round of tug of war, so I consider him a nice bonus for your pet :) We live on a quiet one-way street on the top floor so there is minimal street noise and overstimulation. For house sitting, I know that your pets may be happiest in their own space, and I'm comfortable working in different environments to make sure they are safe and comfy! I will always be respectful of your space and communicative if any issues come up.

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: Brianna S.
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Brianna S.
from
$55
per night
4.9 out of 5 stars
25 reviews
12 repeat clients
4 years of experience
McKinley Park, Chicago, IL, 60609

Brianna was such an amazing sitter! She took great care of my two cats while I was out of town for a week, and sent multiple daily photo updates, making it clear she is a true animal lover. I highly recommend using her services, thank you so much Brianna!

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Samantha D.
Sitter Profile Image: Dominique F.
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Dominique F.
from
$40
per night
4.7 out of 5 stars
78 reviews
43 repeat clients
16 years of experience
South Shore, Chicago, IL, 60637

Dominique was friendly and a great sitter for my girl Millie! I was only gone for a couple days but she still sent updates throughout the weekend, letting me know what they got up to together and how Millie was doing with her meals and potty time. I appreciated her communication and flexibility as she balanced Millie’s routine with her own dog’s needs. Thank you Dominique!

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Isabel C.
Sitter Profile Image: Jasmine R.
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Jasmine R.
from
$88
per night
4.7 out of 5 stars
12 reviews
8 repeat clients
10 years of experience
Chicago, IL, 60653

About: Welcome to my care profile! Thanks so much for your consideration. My name is Jasmine 🌻 I am a plantbased artist from Chicago whose main focus is about reconnecting and interweaving ourselves with nature to cultivate vitality and a cohesive social eco environment in which every being thrives in harmony. I am an enthusiastic world traveler, animal and nature lover committed to sharing joy and my authentic glow everywhere I go. As a seasoned holistic wellness consultant, caregiver, empowerment content creator, and community herbalist I work from home and close to the earth because I love to be outside and nurturing all living creatures. My main personal values center integrity with my inner wisdom, and connecting deeply with all that there is in my environment by sharing love & compassion to every being I encounter. I believe that everyone’s presence is a gift so I take the time to be in gratitude with all living beings I encounter moment by moment. When I was younger I always had a big heart and would care deeply for everyone and everything. I grew up with a guiñea pig, a fish, making friends with trees and babysitting my younger siblings and neighborhood children. I often visited my grandmama’s house to help her play with and care for her German Shepard. As a teenager I attended a rural farming school in Vermont and volunteered on many farms near Boston where I learned how to grow produce and raise livestock namely, cows, ducks, chickens, turkeys, and goats. While In Claremont California, I obtained my BA in Environmental Analysis Africana Studies and a Minor in Studio Art, studying the intrinsic interdependence and the ultimate beauty and creative web connections that support and maintain life. Additionally, I often took care of many of my friends' dogs (chihuahua and other medium mix breeds) while away on extended trips, namely playing with pets, walks, bathing, and poop time. In my 20’s I have had various house sitting opportunities to collect packages and tend for pets, cats, fish and gardens. Currently as a full time dog walker, herbalist and land steward, I feed the local wildlife, tend to an abundant native species garden and perform other domestic duties to maintain the beauty of the home. I believe that we are one with nature so connecting with nature is how we connect with ourselves. Also as an avid world traveler, I look forward to connecting with local animals and plants of any environment. My offering: Providing Premium Care Service Diverse care experiences and utmost dedication to quality care make me the perfect candidate to care for your love one(s) and home. My goal with clients is for us to build a genuine rapport of honesty, trust, and open communication. I am attentive, loving, responsible, nurturing and flexible to fit the needs of everyone I care for. Thanks for your consideration in trusting me in such a sacred opportunity to care for your home, plants, and pets while you're away. I will provide you with the peace of mind and consistent updates to assure you everything is going well at home so you can continue to enjoy your present. What I provide: Safety trust and peace of mind while your away Caring for your all pet needs(play groom, walk, feed) 3 checkin with photos each day Emotional connection with pets Positive Energy I look forward to chatting with you. Messages is the best form of communication for me. Peace ~Goddess Jasmine I currently work virtually as an entrepreneur on part time bases generally less then 10 hrs a week. This give me flexibility and able to sure your needs with the upmost attention. Via consistent messaging, clear communication, reviewing responsibilities and providing updates, I hope to build a genuine rapport of honesty, trust, and open communication with your family 🐶

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

Pet parents share their Rover experiences - Kenwood

1 / 1
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

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

Alexis was everything that I could have asked for during a long house sitting stay with our doggo. She was great with communication for over two weeks that we had to be away. She was especially great about taking our dog on very long walks around the city. I'll definitely enlist Alexis anytime that I need to leave my dog in good hands in the future.

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Lauren S.
House Sitting
5.0 out of 5 stars

Pure gold! ⭐️ I felt super at ease with Haley watching my little pup. She was kind, flexible and extremely communicative. She sent regular updates, photos, videos and asked important questions! Would recommend & book again! Thank you Haley!

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Vanessa Castiglione
House Sitting
5.0 out of 5 stars

Victoria was so great with my dog. Mac was immediately comfortable with her during our meet and greet. Victoria was professional and communicated consistently throughout her stay. I would love to have Victoria watch Mac again!

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Jackie B.
House Sitting
5.0 out of 5 stars

Julia is amazing. She's taken our older dog on walks and she's housesat for us when we were out of town for more than a week. Our dog was so calm and happy when we came home from our trip-- it was clear that Julia made him feel so comfortable. And our house was just as we had left it. Julia meets our dog just where he is: when she saw that he didn't want to go far on walks anymore, she went at his pace and just stayed with him, showing more care and patience than we're often able to bring ourselves. She is a gentle and caring soul and we feel so lucky to have had her help!

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John 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

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.
House Sitting
5.0 out of 5 stars

We went out of town for 10 days and Zoe took care of our two whippets, Sammy and Bleu. We got updates and pictures each day, and know they got at least two long walks daily (they have Fi collars, so we can see their daily steps). Zoe also took great care of our home and left it cleaner than when she arrived! I could not recommend her enough!

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Aleisha K.
House Sitting
5.0 out of 5 stars

Danielle was fabulous! Terrific with our animals and left our home in great shape. We had a wonderful trip knowing our animals were in her calm and professional hands.

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Darcy H.
House Sitting
5.0 out of 5 stars

Jozelin was a delight. I had daily updates and photos and my apartment was clean and tidy when I returned. Will definitely book with Jozelin again!

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Kelcie B.
House Sitting
5.0 out of 5 stars

Chauntrell is a lifesaver! Our sitter backed out the day before our trip, and he was immediately available. He sent us picture updates of our sweet Lola, followed our instructions on Lola’s care, and was very communicative! You can tell he loves animals and wants to provide the best care for our furry friends. I would book Chauntrell in a heartbeat! Thank you again, Chauntrell!

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Cori W.
House Sitting
5.0 out of 5 stars

Niayla did an amazing job watching my dog while I was out of town. She sent daily photos and kept me updated throughout the sitting. Highly recommend for your pet sitting needs!

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Jommel M.
House Sitting
5.0 out of 5 stars

She's a great care taker of your dog or in my case my Son Ghost💙💙. My son enjoys hisself. She took him to the lake and some long walks. Also, my son got his chicken nuggets and went to the bank with her. I will definitely use her again. Amiyah Ghost says he loves you and thank you. He can't wait to see you again🐶🐶🐶🐶

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Lisa M.
House Sitting
5.0 out of 5 stars

Sarah helped us with our dog when we were out for a few days. She confirmed the booking at short notice, came for a meet-and-greet, and was super flexible with timings and booking modifications. I am very likely to ask Sarah to house sit and walk our dog again!

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Ramanujan S.
House Sitting
5.0 out of 5 stars

Dominique was friendly and a great sitter for my girl Millie! I was only gone for a couple days but she still sent updates throughout the weekend, letting me know what they got up to together and how Millie was doing with her meals and potty time. I appreciated her communication and flexibility as she balanced Millie’s routine with her own dog’s needs. Thank you Dominique!

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Isabel C.
House Sitting
5.0 out of 5 stars

maia was wonderful, very communicative and respectful. peanutis an anxious dog and she was nice and calm when we got home. will definitely be booking her to hang out with peanut again

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Audrey T.
House Sitting
5.0 out of 5 stars

Grace took exceptional care of our dog, Coco! She was incredibly kind, patient, and attentive, and it was clear that she genuinely cares about the pets she works with. Coco was comfortable and happy with her, which gave us so much peace of mind. Grace went above and beyond to make sure Coco was well taken care of, and her professionalism and warm personality made the entire experience wonderful. We’re so grateful for her excellent service and will definitely be requesting Grace again. Thank you for treating Coco like family!

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ketki P.
House Sitting
5.0 out of 5 stars

Ahriel was communicative, kind, and took great care of my 3 animals on short notice - including a large senior dog and a toothless cat! She asked thorough questions when interviewing her which was reassuring. Since the stay was short notice, she was unable to meet the animals before hand or get a lay of the land (confusing apartment building), but did an incredible job with everything no less. Would recommend her and will hopefully get to use her in the future!

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Madison A.
House Sitting
5.0 out of 5 stars

Mia took good care of Doby while I was away. She kept me updated with photos and she left my house clean and tidy. Knowing Doby was in such good hands made my vacation so much more relaxing. I would absolutely book Mia again for my next trip and highly recommend her to anyone looking for a caring and reliable dog sitter!

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Edie c.
House Sitting
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