House Sitting in Winston

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

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Top rated Winston house sitters

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: Megan D.
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Megan D.
from
$40
per night
5.0 out of 5 stars
3 reviews
1 repeat client
12 years of experience
Lakeland, FL, 33815

Our dog was well taken care of! We would definitely book with her again. She was caring and communicative while we were away.

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Shannon W.
Sitter Profile Image: Mattison K.
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Mattison K.
from
$40
per night
5.0 out of 5 stars
3 reviews
5 years of experience
Cleveland Heights, Lakeland, FL, 33803

Mattison was amazing with our babies! I needed someone last minute and she was available! Communicated and sent pictures! Most certainly will be using her again.

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Damaris A.
Sitter Profile Image: Elizabeth N.
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Elizabeth N.
Star Sitter
from
$40
per night
5.0 out of 5 stars
69 reviews
36 repeat clients
4 years of experience
Auburndale, FL, 33823

Elizabeth was fantastic! She sent pics and updates throughout the day while we were out! Our boy, Mav, was wiped out when we got home! He is about 3 1/2 yr old spoiled rotten Sheepadoodle! We would HIGHLY recommend her for your fur baby! She is kind and very patient - Mav took to her immediately!

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Mary Anne P.
Sitter Profile Image: Kimberly R.
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Kimberly R.
from
$50
per night
5.0 out of 5 stars
8 reviews
30 years of experience
Lakeland, FL, 33811

Kim was an amazing caretaker of our home and pets. She communicated well, exceeded all expectations and allowed us to relax while away from home. I look forward to having her come again!

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Jessica G.
Sitter Profile Image: Cathy J.
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Cathy J.
Star Sitter
from
$60
per night
5.0 out of 5 stars
67 reviews
18 repeat clients
4 years of experience
Mulberry, FL, 33860

Cathy was a great house sitter who looked after our two cats while we were traveling. She communicated really well, drove down to meet the cats before confirming the booking, and showed up on time before us leaving to get access to the building. She also did a wonderful job communicating during our travel/ her stay with the cats. She took care of the cats’ medications needs, too! What I loved most about her is how prompt she is about responding to any messages. She kept us updated with pictures and lots of other information. She has been kind to the cats and tolerated them sleeping in/ on her suitcase, ha ha. We found the cats happy and healthy. She also took care of our place, it looks great- just as we left it. She also washed the sheets and towels and overall left the place exactly as she found if not better☺️ She is a kind person, and very personable. We loved having her as a house / cat sitter and will contact her again when we need her care. Thanks much, Cathy! And see you soon ☺️

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Sohana N.
Sitter Profile Image: Mirla G.
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Mirla G.
Star Sitter
from
$33
per night
5.0 out of 5 stars
8 reviews
4 repeat clients
12 years of experience
Lakeland, FL, 33810

We couldn’t have asked for a better dog sitter! From the moment we met, it was clear how kind, reliable, and genuinely caring they are. Our dog was happy, relaxed, and clearly well-loved while we were away—which says everything. Communication was excellent, with regular updates and photos that gave us total peace of mind. We came home to a very happy pup and a tidy space, and it was obvious our dog had been treated like family. We would absolutely recommend them to anyone looking for a trustworthy, attentive, and compassionate dog sitter. We’ll definitely be booking again!

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Sammy K.
Sitter Profile Image: Pennie A.
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Pennie A.
from
$35
per night
5.0 out of 5 stars
8 reviews
1 repeat client
30 years of experience
Lakeland, FL, 33815

I absolutely adored Penny, she took great care of my animals but also knew I had a stressful day returning to my kiddos that she got the house ready for me and honestly it was amazing. I will forever only hire her for anytime I leave for another holiday.

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Mari B.
Sitter Profile Image: Vonna J.
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Vonna J.
from
$55
per night
5.0 out of 5 stars
5 reviews
3 repeat clients
5 years of experience
Plant City, FL, 33565

Vonna took care of my Minnie with love and lots of attention! She kept me updated daily on how things were going and sent photos every day of my baby 🥰 I will definitely use her again.

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Rhonda K.
Sitter Profile Image: Serenah V.
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Serenah V.
from
$50
per night
5.0 out of 5 stars
87 reviews
28 repeat clients
6 years of experience
Lakeland, FL, 33811

Serenah was amazing with communication! She sent us videos and pictures of the pups everyday! Will definitely call her again!

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Barbara F.
Sitter Profile Image: Christina G.
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Christina G.
from
$50
per night
5.0 out of 5 stars
12 reviews
12 years of experience
New Jersey Rd, Lakeland, FL, 33803

Christina was amazing with our senior dogs. One has epilepsy and the other one other health issues, so they are not that simple to take care of. She did a great job taking care of them. They were very happy with her and not stressed out. She kept me informed the entire time, was responsive, sent photos, and was able to give them their meds and vitamins. She stayed over and was respectful of our home. We recommend her and will be hiring her in the future.

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Mariela R.
Sitter Profile Image: Christian W.
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Christian W.
Star Sitter
from
$65
per night
5.0 out of 5 stars
66 reviews
28 repeat clients
10 years of experience
Lakeland, FL, 33813

Christian was amazing with our 4 dogs!!! He kept us up to date every day on how they where an that eased my mind so much!!! They dogs love playing outside with him so much an that made for good nap times an better bed time!!!

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Theresa T.
Sitter Profile Image: Maxon B.
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Maxon B.
from
$32
per night
5.0 out of 5 stars
4 reviews
1 repeat client
5 years of experience
Lake Hollingsworth, Lakeland, FL, 33803

About: I’ve been raised with a variety of pets since I was a kid. I’ve been pet sitting since college. I have experienced with younger dogs as well as senior dogs. I have a flexible summer schedule for pets that need more care. During the school year, I have a later start and am able to let pets out during lunch. I have experience working with crate trained dogs as well as high energy dogs. I have also worked with pets with special diets or medication needs.

Sitter Profile Image: Joshua G.
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Joshua G.
Star Sitter
from
$95
per night
5.0 out of 5 stars
239 reviews
48 repeat clients
15 years of experience
Lakeland, FL, 33811

Joshua is a total rockstar! He was amazing, staying with my pups & kitties. He took lots of photos and videos which definitely makes us happy to see how well they are all doing while were are away. He even scooped the litter for us without us asking. Definitely a great sitter. Trustworthy and dependable.

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Sharon & Craig A.
Sitter Profile Image: Marcy M.
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Marcy M.
from
$25
per night
4.6 out of 5 stars
8 reviews
1 repeat client
5 years of experience
Camphor, Lakeland, FL, 33803

About: Firstly, I will listen to your pet's needs that you have, and follow them accordingly. Secondly, I will play with your babies and pay attention to them, with love and affection. I will walk with them around the Lake's, and engage them, by talking to them, so that they know they are loved by me. Thirdly, I do like to play catch and engage them in different games, so their time away from you will fly by for them. Lastly, I am not trained in the Heimlich for dogs, nor CPR, but I have had to do the Heimlich on my own dog, whom was choking on food, to save her life. I look forward to playing with your babies. Thank you so very much.

Sitter Profile Image: Miranda N.
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Miranda N.
from
$70
per night
5.0 out of 5 stars
10 reviews
1 repeat client
10 years of experience
Lakeland, FL, 33809

Miranda was a godsend! I couldn’t have asked for a better pet sitter for my puppy. From the beginning, she was reliable, communicative, and clearly cared deeply about making sure my puppy felt safe, loved, and comfortable while I was away. I received regular updates and photos, which gave me so much peace of mind. When I came home, my puppy was happy, well cared for, and clearly attached to Miranda — which says everything. Miranda paid attention to routines, gave lots of playtime and affection, and treated Lola like family. It’s such a relief knowing I have someone I can completely trust with my fur baby. Highly recommend to anyone looking for a caring, dependable, and attentive pet sitter!

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Annette C.
Sitter Profile Image: Belle M.
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Belle M.
from
$65
per night
4.9 out of 5 stars
16 reviews
6 repeat clients
6 years of experience
Lakeland, FL, 33813

Belle helped us out last minute when our original sitting plans fell through. She updated with photos daily and worked through hesitation with our older dog.

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Abbigail R.
Sitter Profile Image: Zachary H.
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Zachary H.
from
$31
per night
15 years of experience
Lakeland, FL, 33811

About: I have had pets my entire life. From puppies to old dogs all shapes and sizes. Love all animals and will care for your pet like it’s my own. I am currently home for summer as a college kid. I have a dog of my own so I take care of her. Your pet will be my first priority. I will take care of the pet by following the owners instructions and knowledge from years of caring for my own pets. Making sure that they are comfortable and having fun.

Sitter Profile Image: James T.
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James T.
from
$50
per night
5.0 out of 5 stars
4 reviews
1 repeat client
37 years of experience
Lakeland, FL, 33803

About: I am a 47 year old male, whose Air Force duties were crew chief for F-22 fighter jets, serving overseas during the Iraq war. I have top secret security clearance and many missions under my belt. My passion now is animals. I am currently an SPCA foster parent to both dogs and cats. No job is too big or too small when caring for your pet. Whether they have medical needs or just need a happy face to lick, I can take care of it all. I am available day or night with total peace of mind everything will be cared for. I live in South Lakeland. I am retired and available for boarding, client home boarding and care, pet walks and visits. I'm available any day and time. I will answer all requests as soon as I see them. I live alone in a small and safe community, with little traffic, which makes it safe for walks. I have a unfenced yard but I take great care allowing the dog to have freedom in the yard while being on a leash. I have access to a fenced in dog "play" area in my community. My home is non-smoking, cozy, and quiet. I keep the home air cool to provide comfort for the animals. I maintain constant contact with your loved one to know they are safe and happy. I will provide daily texts and photos of the pet, to the owner, to show they are safe and happy.

Sitter Profile Image: Destiny R.
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Destiny R.
from
$35
per night
5.0 out of 5 stars
17 reviews
7 repeat clients
13 years of experience
Lakeland, FL, 33803

Destiny was fantastic with our 2 kitties. This was the first time we left them and she did a great job keeping us updated with texts and videos. I highly recommend her if you want someone friendly and knowledgeable.

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Angelia J.
Sitter Profile Image: Lyndsay E.
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Lyndsay E.
from
$44
per night
5.0 out of 5 stars
5 reviews
1 repeat client
7 years of experience
Mulberry, FL, 33860

Lyndsay was super communicative with me from start to finish. My flight got delayed and offered to stay a few extra hours past what we agreed upon. She sent me pics of my babies throughout the day and the entire weekend. I highly recommend her and trust her with my pups!

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Adrian C.
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Winston pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Penny did a great job. She house sat for our dog and cat and did a wonderful job. She sent us photos and kept us updated on how they were all doing. She was very respectful of our home and our pets, and we have already booked her for another much longer visit in a month.

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Jimmy K.
House Sitting
5.0 out of 5 stars

Megan was wonderful! We had a great first meeting, communication was great she was fast at responding and friendly. She sent us pictures of our pets while she was watching them and they were all happy when we got back home. I would definitely recommend her to anyone and I’d use her again.

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Kimberly K.
House Sitting
5.0 out of 5 stars

Elizabeth was fantastic with my animals! Communication was great and was very flexible with service times. 10/10

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Ashton B.
House Sitting
5.0 out of 5 stars

Sia sat for our young dog at our home for a long vacation and she was wonderful! Teddy loved her, she provided regular updates and photos . She worked with him on playing fetch and taught him “Stop” while on walks. It was comforting to know our dog and our home were well cared for while we were gone. We will definitely use her again and highly recommend anyone else to use Sia if she is available.

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patricia s.
House Sitting
5.0 out of 5 stars

Alison was great with our two large dogs. Very attentive and a kept in touch with me the whole time. She stayed with them and rarely left the whole 5 days we were gone. And kept our home neat and tidy.

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Andrea K.
House Sitting
5.0 out of 5 stars

Felicia took great care of Louie and it truly gave us peace of mind while we were away. We would definitely book with her again!

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Shannon W.
House Sitting
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Find pet care near you

How Rover works

  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

The median cost per night for house sitting in Winston is $45

Why Choose Rover?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • Reservation protection

    It doesn’t happen often, but if your house sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Sitters in Winston average 3
repeat house sitting clients

House Sitting FAQs

Frequently asked questions about Rover

House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Winston on Rover as of Jun 2026 was about $45 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.

If you’re searching for a Winston house sitter for the first time, visit the house sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a house sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 1,478 house sitters in Winston. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.

Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 86% of Winston house sitters respond in under an hour.

House sitters in Winston have an average of 13 years of experience. House sitters with repeat customers have an average of 3 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Winston.

Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Winston house sitters are great for:

  • Dogs who’d prefer to stay on their home turf
  • Cats and caged pets
  • Pet parents on a tight schedule
  • Keeping an eye on your home and plants while you’re away

Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.