House Sitting Highlands Community

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Highlands Community, 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: Anna H.
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Anna H.
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$75
per night
5.0 out of 5 stars
35 reviews
9 repeat clients
7 years of experience
Middleton, WI, 53562

Anna did a great job with our dog Oscar! Anna took him on multiple walks and was excellent with updates and sending photos. We will most definitely use Anna again!

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Don W.
Sitter Profile Image: Allegra R.
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Allegra R.
Star Sitter
from
$65
per night
5.0 out of 5 stars
133 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: Jennifer F.
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Jennifer F.
from
$41
per night
5.0 out of 5 stars
8 reviews
1 repeat client
10 years of experience
Madison, WI, 53705

Jennifer did a fantastic job taking care of Indy. Indy needed extra attention with his medications and health situation. Jennifer was very thoughtful and caring in giving attention to Indy to make him feel comfortable. We sincerely appreciate the care given by Jennifer for Indy.

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Vinoth G.
Sitter Profile Image: Brenda S.
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Brenda S.
from
$40
per night
4.9 out of 5 stars
33 reviews
11 repeat clients
9 years of experience
Waunakee, WI, 53597

⭐️⭐️⭐️⭐️⭐️ Brenda was absolutely wonderful! Her communication was great from start to finish, and she sent us pictures of our pups while we were away, which we really appreciated since we missed them so much. It gave us such peace of mind knowing they were happy and in good hands. Honestly, they weren’t even overly excited to see us when we got home — which tells me they were very well cared for and totally comfortable with Brenda! Our dogs are pretty rambunctious and full of energy, so I know she had her hands full, and we’re so grateful for the patience and care she showed them. We would 100% book with Brenda again and highly recommend her to anyone looking for a trustworthy, attentive sitter!

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Melissa W.
Sitter Profile Image: Amy U.
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Amy U.
Star Sitter
from
$65
per night
5.0 out of 5 stars
19 reviews
5 repeat clients
30 years of experience
Regent, Madison, WI, 53726

It was so nice to know we had a reliable, kind and experienced pet sitter! Amy took care of our two dogs, cat, and gecko and sent great pictures during her stay. We were lucky to have her!

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Beth R.
Sitter Profile Image: Raymar F.
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Raymar F.
Star Sitter
from
$40
per night
5.0 out of 5 stars
4 reviews
2 repeat clients
10 years of experience
Madison, WI, 53705

Ray is amazing! Any fur baby would be lucky to have her as a sitter. Our senior pup, Ralphie, fell in love with her! She lovingly cared for him and even sent us updates and photos while we were away. She was very professional and we would never hesitate leaving our dog with her again!

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Colleen Q.
Sitter Profile Image: Louisa M.
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Louisa M.
Star Sitter
from
$60
per night
5.0 out of 5 stars
89 reviews
24 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: Robert L.
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Robert L.
Star Sitter
from
$44
per night
5.0 out of 5 stars
270 reviews
52 repeat clients
40 years of experience
Capitol, Madison, WI, 53703

Robert housesat with our 2 dogs and was fantastic with the pups and as a houseguest. He worked so well with our pups and their personalities. Robert's communication is very helpful and reassuring. I was "at peace" during our entire trip away because he sent regular updates and stayed in touch during our travel days. Robert is very professional, communicative, and so good with animals. You can tell he really does this for the joy he gets taking care of your pets. You will not be sorry if you book Robert!

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Kathryn (Kate) H.
Sitter Profile Image: Julia M.
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Julia M.
from
$60
per night
5.0 out of 5 stars
3 reviews
2 repeat clients
8 years of experience
University Apartments, Madison, WI, 53705

Julia was so pleasant and professional! She asked great questions to prepare for her time with Princeton, and you could tell she really cared - Princeton warmed up to her immediately :) I highly recommend Julia and would definitely hire her again!

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Aisha B.
Sitter Profile Image: Madalyn M.
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Madalyn M.
from
$50
per night
5 years of experience
Middleton, WI, 53562

About: I enjoy caring for energetic dogs and love keeping them active through games like fetch and tug-of-war. I am a dependable and attentive pet sitter who is comfortable administering medications and providing any additional care your pet may need. I strive to build trust with every pet I care for, and I’m proud that many of my clients have chosen me as their recurring pet sitter. My goal is to ensure every pet feels safe, comfortable, and well cared for while their owners are away. I am currently available through the beginning of August and am happy to discuss scheduling to find a time that works for you. Please feel free to message me with any questions about my availability. I typically provide care in your home to help keep your pets comfortable in their familiar environment. I can also welcome your furry family members into my home for stays of up to two days, if needed. While I do not have a fenced yard, I make sure every dog gets plenty of exercise through long walks and trips to local parks. If your dog enjoys socializing with other dogs and you approve, I’d be happy to take them to a dog park for additional play and enrichment. Your pet’s safety is always my top priority. I carefully follow your care instructions and make sure every dog in my care receives plenty of love, attention, exercise, and responsible supervision. My goal is for every pet to feel safe, happy, and well cared for while you’re away.

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: Andrea P.
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Andrea P.
Star Sitter
from
$47
per night
5.0 out of 5 stars
16 reviews
4 repeat clients
1 year of experience
Sauk Creek, Madison, WI, 53717

About: I love animals and truly enjoy taking care of dogs and cats. I make sure they’re well-fed, walked, and have plenty of playtime, giving them lots of love and attention. I treat every pet as part of my family, making sure they feel comfortable, safe, and happy while under my care. I’m available to care for dogs and cats on weekends. I can provide feeding, walks, and loving companionship with care and responsibility. My available hours are from Friday at 6:00 p.m. until Sunday at 9:00 p.m. I live in an apartment with my two daughters, who are very sweet and loving with animals. We have a spacious and comfortable area where your pet can feel relaxed and happy. There are plenty of natural areas nearby where I can take your dog for walks to enjoy the outdoors and nature. I’m available on weekends, from Friday at 6:00 p.m. to Sunday at 9:00 p.m., to provide loving, responsible, and personalized care for your pet.

Sitter Profile Image: Annalesse B.
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Annalesse B.
from
$35
per night
5.0 out of 5 stars
4 reviews
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: Justine D.
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Justine D.
from
$43
per night
5.0 out of 5 stars
9 reviews
2 repeat clients
10 years of experience
Madison, WI, 53711

Justine was so great with my pups! One of my dogs has special needs and the other is anxious and shy around new people, and Justine won them both over and made sure they were well cared for while I was away. I plan on being a repeat customer!

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Erick S.
Sitter Profile Image: Annika S.
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Annika S.
from
$50
per night
5.0 out of 5 stars
4 reviews
5 years of experience
Regent, Madison, WI, 53705

Wow! Annika was an amazing and attentive pet sitter to our two very active dogs! She had no issues with giving our older dog his seizure medication and was keen on following our recommended guidelines for walking and training that we’ve been working on. Our dogs were well taken care of. We got many picture updates of our pups which also made us feel good! We will definitely be booking Annika next time we are out of town!

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Karin S.
Sitter Profile Image: Tucker S.
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Tucker S.
from
$42
per night
5.0 out of 5 stars
7 reviews
10 years of experience
Orchard Ridge Community, Madison, WI, 53711

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.
Sitter Profile Image: Sidney R.
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Sidney R.
from
$50
per night
5.0 out of 5 stars
84 reviews
33 repeat clients
20 years of experience
Middleton, WI, 53562

Sidney was great! Very attentive, patient and kept us updated the whole time! We have a very energetic pup who is still learning manners and she was patient with him. We also have an old girl who can be a little unsure of new people and she gave her the time and space to warm up to her. The dogs were in great hands! We will be using Sidney again!

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Kim and Molly J.
Sitter Profile Image: Jesse T.
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Jesse T.
Star Sitter
from
$28
per night
5.0 out of 5 stars
26 reviews
10 repeat clients
1 year of experience
Madison, WI, 53719

We had an amazing experience with Jesse! She took wonderful care of both our dog and our cat while we were away for two weeks. She was incredibly attentive, super kind with our pets, and clearly loved spending time with them. She even surprised our dog with some plush toys before she left, which meant so much to us. When we came back, both of our pets were completely relaxed and happy, which says everything about the level of care they received. On top of pet care, she was a huge help with things around the house when they came up and shared really helpful advice for managing our dog’s allergies. We truly felt supported the entire time we were away. We couldn’t be happier with her care and will absolutely be booking her again for our next trip. Highly recommend.

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

Thanks again! Briana stepped in at the last minute when we needed to leave town for a funeral. She took good care of Frankie. We’re grateful.

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Zayna T.
Sitter Profile Image: Ann A.
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Ann A.
Star Sitter
from
$82
per night
5.0 out of 5 stars
123 reviews
46 repeat clients
10 years of experience
Madison, WI, 53719

Ann did a fantastic job dog sitting our very high energy and dog-reactive pup in our home for five days! She sent so many pictures and we could tell our pup was content/happy and so well taken care of. Ann also reached out to ask clarifying questions when needed and was very responsive. I highly recommend Ann!

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Claire G.
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The median cost per night for house sitting in Highlands Community is $50

Pet parents share their Rover experiences - Highlands Community

1 / 1
5.0 out of 5 stars

Super awesome and lovely to interact with! Tube loved her and we can’t wait to book with her again 💕

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Jill T.
House Sitting
5.0 out of 5 stars

Isabel was wonderful! She sent a lot of great pictures to keep us up to date on how the cats were doing. She also took wonderful care of the house. Don't hesitate to book Isabel!

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Amy W.
House Sitting
5.0 out of 5 stars

Joel was excellent with our dogs and even made them a pillow fort when they were scared of the fireworks. We will definitely book with him again!

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Travis T.
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

Julia did an amazing job watching my dogs and I would highly recommend her. Her communication was great and she even sent me pictures of my happy dogs throughout the week.

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Sara S.
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

Helen stayed at our home and took wonderful care of our pets. She was a great communicator before, during and after her stay. We received regular updates and photos of our pets, which was really comforting. Helen was conscientious and careful about following the instructions we provided. She left our house and animals in great condition! We'd love to have her back to sit again!

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Susie M.
House Sitting
5.0 out of 5 stars

Jolie goes above and beyond to make sure my pups are doing well while I'm away. Especially appreciate her navigating July 4 with them!

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Erick S.
House Sitting
5.0 out of 5 stars

Alliyah did a great job with our furbabies while we were on a 2 week vacation. We appreciate returning to our home and knowing they were cared for. Thank you!

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Heather R.
House Sitting
5.0 out of 5 stars

Yvonne - she was very responsive friendly on-time and our dog and her got along good. She keep us Informed. She was flexible and cheerful. I do highly recommend her.

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Paula and Russell N.
House Sitting
5.0 out of 5 stars

We are so glad to have met Sophie! In addition to being a strong communicator, Sophie has a genuine desire to ensure your fur baby is well taken care of. She asks great questions, is detail-oriented, and is great about sending updates while you're away. I highly recommend Sophie and would definitely book her again!

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Aisha B.
House Sitting
5.0 out of 5 stars

Louisa did a wonderful job taking care of our two Labrador pups. She let them play in the yard, took them for a walk, gave them their evening treats, and shared some great photos for us to enjoy. It was another excellent experience, and we appreciated the care and attention she gave our dogs. We would be happy to book with Louisa again!

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Ben D.
House Sitting
5.0 out of 5 stars

Thank you for taking great care of JJ! He was so happy while his regular humans were away. We appreciate the professionalism and detail that you put into your work. Take care and see you next time!

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Katie B.
House Sitting
5.0 out of 5 stars

Aislinn was absolutely wonderful!!! She is great with communication and took the time going above and beyond to care for my pup! I’d highly recommend and hope she can help out in the future! Even my neighbor commented on how much time she spent throughout the weekend playing with Henry in the yard and making sure he was tired out before leaving :-) Thank you!

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Brenna D.
House Sitting
5.0 out of 5 stars

Taylor just finished pet and housesitting for us and she is wonderful! Responsive, easy to work with, and great with our pups (one of whom is a super needy baby). So glad we found her! Thank you, Taylor!

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Emily L.
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

Allegra was great with our dog! Very responsive, genuine care, left our dog happy and home clean and tidy. Can’t wait to have her back!

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Abbey L.
House Sitting
5.0 out of 5 stars

Ray did a great job with both our dogs, but especially with our older thunder-phobic dog during a week in which many storms were predicted and a few happened. Her willingness to communicate, and her good questions made her a great choice for our dogs. And our dogs were clearly happy, comfortable and well-cared for in our absence. We would definitely book her again.

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Karen L.
House Sitting
5.0 out of 5 stars

Josie was awesome taking care of our sweet little Brella and she even watered plants and changed sheets for us! We will definitely be booking her again in the future!!!

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Kelly R.
House Sitting
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Sitters in Highlands Community average 4
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