House Sitting Windy Hill

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

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Over 78
pet parents in Windy Hill have booked house sitting

Windy Hill, 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: Abby W.
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Abby W.
from
$45
per night
5.0 out of 5 stars
7 reviews
1 repeat client
15 years of experience
Windy Hill, Jacksonville, FL, 32246

Abby was fantastic! I have two large dogs that can be very picky about who they allow in the house. When Abby came over for the meet and greet, they quickly warmed up to her. Once it came time for her overnight stay, she was fantastic with communication. Throughout the whole stay, I felt very confident with her ability to take care of and understand my dogs’ body language. It took my dogs a whole year of knowing our previous dog sitter to jump onto the bed with her— with Abby, they jumped onto her bed for pets right away! I would absolutely recommend Abby to anyone who wants a trusting, communicative, detailed, and dog lover sitter!

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Emily W.
Sitter Profile Image: Sierra R.
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Sierra R.
from
$26
per night
5.0 out of 5 stars
7 reviews
20 years of experience
Windy Hill, Jacksonville, FL, 32246

Sierra took such good care of Sunshine! She sent pictures of him. She walked him as frequently as we requested. We will definitely be requesting her again!

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Josephine I.
Sitter Profile Image: Hannah R.
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Hannah R.
from
$40
per night
5.0 out of 5 stars
58 reviews
22 repeat clients
16 years of experience
Windy Hill, Jacksonville, FL, 32246

Hannah was absolutely amazing! We had booked her somewhat last minute for a holiday weekend but she was nothing but kind and accommodating. She kept us regularly updated with how the dogs were doing, and they seemed to have a great time playing catch and keep away! Definitely recommend booking with Hannah and we will be asking her to take care of the pups on our next vacation.

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Daniel B.
Sitter Profile Image: Alyssa B.
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Alyssa B.
from
$32
per night
5.0 out of 5 stars
6 reviews
16 years of experience
Beach Haven, Jacksonville, FL, 32224

If I could give Alyssa 100 stars, I absolutely would! I can’t even begin to explain how amazing she was as a pet sitter for my 3-month-old puppy. I was honestly so nervous about leaving my puppy because she’s still so little, but Alyssa made the entire experience so stress-free and reassuring. She was incredibly attentive, sent me updates throughout the day, and made sure my puppy felt loved and cared for. I even have a little pet camera facing my puppy’s crate, and seeing Alyssa playing with, cuddling, and spending time with her all day made me feel so much better. You can genuinely tell that she loves what she does and truly enjoys caring for animals. She went above and beyond, and I couldn’t have asked for a better person to look after my puppy. I’m so grateful for how wonderful she was, and I would 100% trust her with my puppy again. Thank you so much, Alyssa! You were absolutely amazing! 🥹🤍

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Yuliana F.
Sitter Profile Image: Heidi B.
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Heidi B.
from
$50
per night
4.9 out of 5 stars
39 reviews
9 repeat clients
20 years of experience
Deerwood, Jacksonville, FL, 32256

Heidi took fabulous care of Willis! We had to book pretty last minute and she was super accommodating with that. Looking forward to having her for future visits!

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Tegan B.
Sitter Profile Image: Katherine D.
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Katherine D.
Star Sitter
from
$70
per night
5.0 out of 5 stars
30 reviews
15 repeat clients
1 year of experience
Southsuide Estates, Jacksonville, FL, 32246

We were thrilled to meet Katherine. She was very responsive to our last minute request. We unexpectedly needed a dog sitter and she arrived in less than 2 hours. She was a perfect companion for our Shitzu “Baby” and kept her relaxed while we were away. We highly recommend Katherine!

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Lisa T.
Sitter Profile Image: Brian I.
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Brian I.
from
$50
per night
5.0 out of 5 stars
5 reviews
1 repeat client
8 years of experience
Deerwood, Jacksonville, FL, 32256

About: Ever since I was little, I have a huge heart for dogs. It wasn’t until I was 10 that I finally had a family dog, and from then on dogs have always been a part of my life. I’ve done personal dog-sitting on and off for a few years for some friends and family and I’ve always really enjoyed it. I did Rover a few years ago and loved it, but life got a bit crazy so I had to pause it. I was still able to consistently dogsit for some repeat customers these last few years, and now my wife Linsey joins me in that! Your dog can expect walks at the park or in our neighborhood and for my home to be their home. If your dog likes play dates, my Rover friends would certainly be about it! My normal job is pretty flexible on where I can work, so if your dog needs extra attention, working from home is totally doable. Between me and Linsey, at least one of us is always home. I’ve done Rover on and off for the last 8 years, and have really enjoyed it! My job is super flexible, with set hours only 2 nights a week and once during the day. I’m mostly working from home or at coffee shops, so it’s super easy to stay home with a dog. Between me and my wife, someone can pretty much always be with your pet. Our home is your dog’s home. If they want to go on the couch or follow us around, by all mean. If they like their space, I’ll give them space. Many dogs have taken a snooze on our couch, legs in the air.

Sitter Profile Image: Carter L.
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Carter L.
from
$50
per night
5.0 out of 5 stars
24 reviews
9 repeat clients
5 years of experience
Secret Cove, Jacksonville, FL, 32216

Carter is very responsive and reliable. He takes great care of our dog Tonks. Tonks doesn’t warm up to people easily, but she took to Carter right away, and we have booked Carter for many stays now.

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Lindsey M.
Sitter Profile Image: Alexandria A.
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Alexandria A.
from
$65
per night
5.0 out of 5 stars
42 reviews
14 repeat clients
20 years of experience
Sans Pareil, Jacksonville, FL, 32246

Alex was great! Freya loved her, I got daily updates 😊

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Caroline M.
Sitter Profile Image: George B.
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George B.
from
$35
per night
14 years of experience
Jacksonville, FL, 32246

About: Every animal has a unique personality. During our time together, I love discovering shared interests with your pets so we both have a genuinely fun experience. Animals are exceptionally intuitive and pick up on our energies, which is why I always bring my calmest, happiest, and most present self to every interaction. I own a pet care business called George Sits LLC in Jacksonville, and I am looking to fill my books! I would leave only to stop in on other pets nearby who may also be in my care. I have multiple years working and volunteering at boarding facilities and shelters, and I have never been petless myself. Growing up, we had dogs, chickens, snakes, guinea pigs, geckos, and so so so many cats. My Approach to Care For Dogs: Built entirely on positive reinforcement, encouragement, and active engagement. For Cats: Built on respect and consent. I understand that royalty makes the rules, and I'm happy to follow whatever boundaries your cat sets for me. Earning Your Trust I understand that handing over the keys to your home and leaving your sweet companion in someone else's hands requires immense trust. Earning and maintaining that trust is my #1 priority. That is why I offer a complimentary Meet & Greet for all new clients, giving us a chance to connect and make sure we’re a perfect fit before you book.

Sitter Profile Image: Grace G.
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Grace G.
from
$65
per night
4.2 out of 5 stars
6 reviews
2 repeat clients
6 years of experience
Jacksonville, FL, 32246

Our pets and home were fed and well cared for.

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Jason A.
Sitter Profile Image: Scott T.
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Scott T.
Star Sitter
from
$50
per night
5.0 out of 5 stars
92 reviews
25 repeat clients
12 years of experience
Deerwood Center, Jacksonville, FL, 32256

Scott was wonderful! He was very communicative, took lots of photos, followed our instructions, and left our home neat and tidy. We would not hesitate to book him again!

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Emily C.
Sitter Profile Image: Sarah F.
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Sarah F.
from
$55
per night
5.0 out of 5 stars
22 reviews
3 repeat clients
30 years of experience
Greenland, Jacksonville, FL, 32258

Sarah is our families go-to when it comes watching our two dogs. We prefer to have someone stay at our house with them and she is always willing and able as long as she’s not booked! Love her and trust her to oth our house and pups!

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Alaina R.
Sitter Profile Image: Kristin S.
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Kristin S.
from
$45
per night
4.3 out of 5 stars
12 reviews
6 repeat clients
6 years of experience
Regency, Jacksonville, FL, 32225

Kristin was awesome! Our dog loved her and she gave him took great care of him. I would absolutely recommend her to anyone looking for a polite, trustworthy sitter.

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Charitie G.
Sitter Profile Image: Jessica B.
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Jessica B.
Star Sitter
from
$50
per night
5.0 out of 5 stars
49 reviews
27 repeat clients
7 years of experience
Jacksonville, FL, 32256

So grateful to have found Jessica. She was able to fit us in with little notice, arrived on time, and dove right in to get to know our two dogs—one a very energetic puppy. They loved her (I can just tell) and we loved how she sent pics and was so personable and professional. I look forward to having her sit for us again soon.

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Heidi A.
Sitter Profile Image: Luz P.
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Luz P.
from
$25
per night
5.0 out of 5 stars
5 reviews
1 repeat client
15 years of experience
Sandalwood, Jacksonville, FL, 32246

About: I’ve been an animal lover for as long as I can remember and have years of experience caring for both dogs and cats. I also previously worked at an animal hospital, which gave me valuable hands-on experience around pets with different personalities, ages, and care needs. I understand how important it is to have someone you genuinely trust caring for your pets and entering your home. I’m patient, attentive, dependable, and will treat your pets with the same love and care I give my own. I’m comfortable with dogs of different sizes and energy levels and can provide walks, playtime, feeding, companionship, and drop-in visits while keeping your pet’s normal routine as consistent as possible. I’m also very comfortable with cats and understand that sometimes earning their trust means giving them a little extra patience and space! I’m happy to follow detailed care instructions and will always keep you updated with photos and messages so you can relax knowing your pet is safe, happy, and getting plenty of attention. 🐶🐱❤️

Sitter Profile Image: Terri V.
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Terri V.
from
$50
per night
5.0 out of 5 stars
13 reviews
2 repeat clients
14 years of experience
Greenland, Jacksonville, FL, 32258

Terri was SO wonderful!! She was flexible with a last minute booking and took such good care of my babies! I got lots of updates, and I could tell they were getting lots of love. She really thought of everything with them and left my apartment super clean and tidy. She’s absolutely the best sitter!

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Hailey S.
Sitter Profile Image: Margaret P.
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Margaret P.
Star Sitter
from
$26
per night
5.0 out of 5 stars
72 reviews
30 repeat clients
7 years of experience
Deercreek, Jacksonville, FL, 32256

Very easy going and was available for a last minute booking! Margaret even took off the sheets and washed them without being asked. Will book again!

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Olivia E.
Sitter Profile Image: Ariana C.
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Ariana C.
from
$45
per night
5.0 out of 5 stars
7 reviews
15 years of experience
Baymeadows, Jacksonville, FL, 32256

Ariana is a wonderful person and took very loving care if Buddy & Sheba. She was very accomodating although we did not book this till the last moment. We were very pleased and will certainly reach out yo her in the future

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Bipin D.
Sitter Profile Image: Kadence S.
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Kadence S.
from
$45
per night
5.0 out of 5 stars
17 reviews
8 repeat clients
10 years of experience
Jacksonville Beach, FL, 32250

⭐⭐⭐⭐⭐ Absolutely wonderful dog sitter! Reliable, caring, and treated our Willow like family. We felt completely at ease knowing she was in such great hands. Highly recommend!

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Christina S.
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The median cost per night for house sitting in Windy Hill is $50

Pet parents share their Rover experiences - Windy Hill

1 / 1
5.0 out of 5 stars

Sydney stayed at our home and took care of our two dogs. She did a fantastic job! Through the process she was very responsive and we know our dogs and house were in great hands. We would highly recommend her!

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Daniel S.
House Sitting
5.0 out of 5 stars

Ruby was amazing! She sent lots of pictures and updates, and I definitely plan to use her again in the future. Highly recommend!

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Austin E.
House Sitting
5.0 out of 5 stars

My wife and I had to be in NYC for a complex medical procedure and were gone for 16 days. Hannah stayed in our house and provided for the needs of our anxious dog and our unflappable cat. She did the same amazing job she has always done for us, just for way longer than we had ever needed before. Hannah took one worry completely off our heads during a very trying time and we will always be grateful. She can be trusted with your pets and your home.

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John B.
House Sitting
5.0 out of 5 stars

Carter is amazing! I needed someone to watch Rooney last minute and his flexibility and schedule allowed for him to be there for us when we needed a trusted sitter. He is great with Rooney and makes sure our high energy pup gets plenty of play!

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Jane B.
House Sitting
5.0 out of 5 stars

My pup ended up having stomach issue while I was away and Makayla took extra good care of my doggy. She kept me informed and followed my instruction perfectly while I was away. She sent lots of pictures and updates throughout the days I was out during my extended leave. I came back home to my pup completely relaxed and without any more stomach upset. I absolutely recommend Makayla she is extremely professional and has a great heart and natural talent with animal! I can’t thank her enough!

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Vlad C.
House Sitting
5.0 out of 5 stars

Ariana took great care of our cavapoo over Labor Day weekend. She stayed at our home, and everything looked great when we returned. Overall very happy! Would book her again in the future.

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Lauren W.
House Sitting
5.0 out of 5 stars

Heidi did a great job of house sitting for us and taking care of our 2 Boston Terriers. She was very communicative throughout and the dogs absolutely loved her. Upon arriving home, the house was in fantastic condition. Heidi said she likes to leave the house like she found it and she did exactly that. We would definitely love to have Heidi sit for us again!

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Fred B.
House Sitting
5.0 out of 5 stars

This is the third time Hannah has house/petsit my Winnchester during a vacation, and at this point I don't think I'd want anyone else. She leaves the house cleaner than when she came, and communicates and handles any pet drama with ease and professionalism.

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Jeffrey H.
House Sitting
5.0 out of 5 stars

Katherine was amazing! She was responsive, sent many pictures and videos every day, and was flexible to plans.

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Sam S.
House Sitting
5.0 out of 5 stars

Abby was fantastic! I have two large dogs that can be very picky about who they allow in the house. When Abby came over for the meet and greet, they quickly warmed up to her. Once it came time for her overnight stay, she was fantastic with communication. Throughout the whole stay, I felt very confident with her ability to take care of and understand my dogs’ body language. It took my dogs a whole year of knowing our previous dog sitter to jump onto the bed with her— with Abby, they jumped onto her bed for pets right away! I would absolutely recommend Abby to anyone who wants a trusting, communicative, detailed, and dog lover sitter!

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Emily W.
House Sitting
5.0 out of 5 stars

Alex was great with Bruce! Communicated well, was on time, very friendly and Bruce was well taken care of. Would definitely trust her again with my pup!

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Kate K.
House Sitting
5.0 out of 5 stars

We had a wonderful experience with Haleigh! She was so friendly and kind from the start, and our pets immediately felt comfortable with her. Our dog loved her right away, and even our cat—who normally hides from new people—seemed comfortable to eat his food and roam a little bit. She kept us updated throughout our trip with frequent messages and lots of pictures, which gave us so much peace of mind. When we returned home, the house was spotless, and it was clear our pets had been well cared for and loved. We couldn't have asked for a better experience. We would absolutely recommend her to anyone looking for a trustworthy, caring pet sitter, and we'll definitely be booking her again for future pet and house sitting!

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Kristina G.
House Sitting
5.0 out of 5 stars

Professional and kind. Our pets were well cared for. We recommend Grace to any of her future clients.

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Jason A.
House Sitting
5.0 out of 5 stars

Sierra is an amazing pet sitter! She took great care of my cat and my home. She i was very communicative and kind. I can tell she genuinely loves animals. Will definitely be rebooking with her!

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Caroline B.
House Sitting
5.0 out of 5 stars

Siena was amazing house sitting for me while i was out of town. She took care do my two large dogs and kept me updated throughout my time away. Couldn’t have asked for a better sitter!

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Audrey O.
House Sitting
5.0 out of 5 stars

I couldn’t be happier with the care my dogs and cat received! From the very beginning, Olivia was professional, reliable, and incredibly kind. It gave me peace of mind knowing my pets were in such loving and capable hands while i was away. I loved getting regular updates, photos, and messages that showed how happy and comfortable they were. It was obvious they were treated like family, not just “pets being watched.” When I came home, my animals were relaxed, happy, and their routines had clearly been maintained perfectly. The apartment was also spotless and well cared for. I truly appreciate the extra effort, patience, and genuine love shown to my fur babies. I highly recommend Olivia to anyone looking for a trustworthy, compassionate, and dependable pet sitter. I will absolutely be booking again!

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Julia T.
House Sitting
5.0 out of 5 stars

Emily was very responsive and flexible when my travel plans changed. She left a note with information about her time spent with my boys which I found helpful also. I would have Emily sit for my boys again.

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Rachel T.
House Sitting
5.0 out of 5 stars

Amy was great! Took great care of our two large dogs while we were gone for an extended weekend. Highly recommend!!

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Luke B.
House Sitting
5.0 out of 5 stars

Natazia is the best sitter we've ever had! Thoughtful, responsive, and ensures we know how our pets are doing.

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Johnna P.
House Sitting
5.0 out of 5 stars

Diana took very good care of the puppies while I was gone, and they looked thrilled to be with her in every picture. She left the house very clean and I would recommend her. I will definitely use her again!

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Lisa A.
House Sitting
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