Doggy Day Care in Winston

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Top rated Winston doggy day care sitters

Prices are estimates per day. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: angie a.
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angie a.
Star Sitter
from
$28
per day
5.0 out of 5 stars
48 reviews
11 repeat clients
10 years of experience
Lakeland, FL, 33811

Excellent care surrounded by a loving family. Updates were provided with photo. Fenced yard and safe surrounding.. my pup was happy. Thank you Angie. Hope to see you again.

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Darlene H.
Sitter Profile Image: Cyd Marie D.
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Cyd Marie D.
Star Sitter
from
$35
per day
5.0 out of 5 stars
81 reviews
24 repeat clients
10 years of experience
Lakeland, FL, 33810

Cyd was wonderful with KeiKi. We could have asked for someone better. Cyd communicated with us quickly and did a incredible job watching our baby.

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John R.
Sitter Profile Image: Brittanie C.
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Brittanie C.
Star Sitter
from
$25
per day
5.0 out of 5 stars
16 reviews
5 repeat clients
30 years of experience
Lakeland, FL, 33810

About: I’m a responsible, loving, and attentive pet caretaker who treats every animal like my own. Whether it’s playtime, walks, or quiet cuddle time, I make sure your pet feels safe, happy, and cared for. With experience and genuine love for animals, I’m committed to giving them the attention and affection they deserve while you're away. I also provide you with updates through texts with pictures! I am a stay at home mom with a furbaby of our own, and I have complete open availability for overnight stays and play dates! "We have a large fenced in backyard that offers plenty of space for play and relaxation, nestled in a quiet and peaceful cul-de-sac. Our friendly 2 yr old Golden Retriever, Lucy, loves to play fetch and welcomes new friends with a wagging tail. Pets are treated like family in our home-they're welcome on our oversized sectional. Fresh water is always available, along with treats (with your permission), and a variety of toys to keep them entertained and happy

Sitter Profile Image: Vely P.
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Vely P.
Star Sitter
from
$40
per day
5.0 out of 5 stars
176 reviews
43 repeat clients
15 years of experience
Lakeland, FL, 33810

Vely was awesome. We were welcomed in to see her home before leaving the dogs. We felt fully comfortable leaving our 2 pups with her. She had great communication the entire visit, with lots of pics and messages! We have already booked our next stay with her!

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Kat F.
Sitter Profile Image: Bri S.
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Bri S.
Star Sitter
from
$30
per day
5.0 out of 5 stars
57 reviews
21 repeat clients
15 years of experience
plant city, FL, 33565

Bri was amazing with our pup, Shadow! If we are ever in the area again and need a sitter, we will absolutely book with her again! 😊 Thank you, Bri!!

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Kelcie S.
Sitter Profile Image: Tracy E.
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Tracy E.
from
$40
per day
5.0 out of 5 stars
37 reviews
11 repeat clients
20 years of experience
Lakeland, FL, 33810

Tracy was great with our little guy. She kept us updated with pictures and videos thru the day. He enjoyed her big backyard. We definitely will be back

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Lester O.
Sitter Profile Image: Yusel B.
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Yusel B.
Star Sitter
from
$30
per day
5.0 out of 5 stars
80 reviews
32 repeat clients
30 years of experience
Plant city, FL, 33567

Yusel took wonderful care of my puppy and treated him like her own. Communication was great throughout, which really gave me peace of mind. My pup came back happy, comfortable, and clearly well cared for. I’d definitely trust her again and highly recommend her. My puppy will be coming back very soon !

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Alejandro P.
Sitter Profile Image: Angelica P.
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Angelica P.
Star Sitter
from
$30
per day
5.0 out of 5 stars
79 reviews
18 repeat clients
16 years of experience
North Lake Wire, Lakeland, FL, 33815

Angelica and Jose were so sweet to Cooper. She sent lots of photos and videos and even gave him a bandana, a gift bag and a thank you card. Amazing service and their home was spotless!

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Jeanna P.
Sitter Profile Image: Briana S.
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Briana S.
Star Sitter
from
$20
per day
4.9 out of 5 stars
318 reviews
122 repeat clients
11 years of experience
Lakeland, FL, 33809

Briana was amazing with Myla! I got updates and pictures, she even went out her way and clipped Myla’s nails. She responded to my booking within a few minutes of my booking (my booking was for the next day) she’s a lifesaver!

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Joyce P.
Sitter Profile Image: Randi H.
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Randi H.
from
$20
per day
5.0 out of 5 stars
70 reviews
39 repeat clients
10 years of experience
Lakeland, FL, 33810

A wonderful stay for Maggie. I would recommend to anyone. My Mags is all for me and I felt and saw how happy she was to be there. Made my day relaxing being so far from home as Randi texted me photos of Maggie in her most relaxing positions.

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Gary M.
Sitter Profile Image: Skye B.
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Skye B.
Star Sitter
from
$35
per day
5.0 out of 5 stars
392 reviews
143 repeat clients
25 years of experience
Plant City, FL, 33567

Our puppy has been going to Sky since we brought him home at 12 weeks. She has been dependable and reliable and now at just eight months old, he knows when we are pulling into her neighborhood and gets so excited to go play! She has also helped to support our training efforts and there is not anyone I could imagine trusting more with him. He gets so excited when he sees her that I never question leaving him. Plus her prices are comparable to a kennel but he’s not locked up all day! Even if I didn’t “need” to drop him off at doggy day care, I probably still would take him just for the socialization and continued training he gets when he is there.

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Jess P.
Sitter Profile Image: Shelisha F.
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Shelisha F.
Star Sitter
from
$50
per day
5.0 out of 5 stars
26 reviews
11 repeat clients
10 years of experience
Crystal Lake, Lakeland, FL, 33801

From the moment we dropped off our pup, I felt completely at ease. My dog was clearly happy, comfortable, and well cared for the entire time. She sent regular updates with photos and messages, which meant the world to me and gave me so much peace of mind. It’s obvious she genuinely loves animals and treats them like family. I will definitely be booking with her again—highly recommend!

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Hectialys H.
Sitter Profile Image: William G.
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William G.
from
$35
per day
4.8 out of 5 stars
7 reviews
1 repeat client
16 years of experience
Lakeland, FL, 33813

About: My fiancé & I have always had a deep passion for taking care of, loving on, and nurturing fur babies! I have always called her the "dog whisperer". We have always had one thing in common, and that is our LOVE for animals. My fiancé works from home and is also a FULL TIME mommy to our 3 year old{whom is ALSO an animal lover-- he got it honest😉} We have a VERY flexible schedule to accommodate your needs in someone giving the upmost CARE & LOVE for your fur baby while you are gone away and/or on vacation! You will NEVER have to worry while your furbaby is under our care, they will feel just like a part of our fam{iLy} while with us! We promise to provide the VERY BEST care and love for your furbaby♡ I am available 24/7 to care for all of your furbabies wants and needs. Available weekdays, as well as weekends. I am able to keep your pet overnight, for however many days/nights as needed. I am also very flexible and willing, IF NEEDED; to pick up AND/OR drop off and bring your fur baby to your home anytime (including EARLY PICK-UP/LATE DROP-OFF} for an additional $15.00-20.00 {depending on the distance that I would have to travel}-- if that option would be MORE CONVENIENT for you😊 I can provide references if needed! You may contact me AT ANYTIME day/night! {If you would like, we can FaceTime as well} You will receive plenty of pictures/videos, along with frequent updates on how your furbaby is doing while under our care! I have plenty of yard space for your fur baby to run around. He/she will always feel safe and loved under my care and supervision.

Sitter Profile Image: Alberto T.
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Alberto T.
from
$20
per day
5.0 out of 5 stars
9 reviews
3 repeat clients
8 years of experience
Lakeland, FL, 33805

About: I have had a big passion for animals since childhood. I grew up with many animals and always dreamed of working with animals. I graduated from university with an associate in veterinary technician. I been working for several years in veterinary medicine and doggy daycare i really have fun and enjoy all my time with them. I’m currently working 3 days per week, usually I’m off on Sunday and the rest of the time at home. My schedule rotates, I do not always have the same days off. I have an empty room only for them, small cage if needed and a porch that they can be around. I’m a pet friendly and I always walk my dog around so he can enjoy the complex.

Sitter Profile Image: James T.
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James T.
from
$30
per day
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: April R.
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April R.
from
$30
per day
5.0 out of 5 stars
82 reviews
29 repeat clients
17 years of experience
Lakeland, FL, 33810

About: I started working in the animal care industry at 15 as a kennel technician at a vets office, I went to college and became a certified veterinary technician. I have been dog sitting and pet sitting for 10 plus years. I am pending employment as a technician 4 days a wk when I am working my husband assists with walks and feeding. I try to walk pets about 4-5 times a day. I work 4 days a week and on those days my husband assists with noon walks and afternoon walks and feeding. I have a fenced yard and multi bedroom house, my pets are crate trained or have their own room to avoid exposure and stress. I do not co mingle my personal pets with other animals. A multiple acre fully fenced property, that has an automatic refilling livestock tank/doggy pool available when outside.

Sitter Profile Image: Joanne R.
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Joanne R.
Star Sitter
from
$40
per day
4.9 out of 5 stars
74 reviews
25 repeat clients
50 years of experience
Lakeland, FL, 33801

About: BEST CARE ANYWHERE! My home is calm and quiet, all dogs do great with me. My back yard is fully fenced; my back door opens into that backyard. My front doors have two barriers you can see that, in one of the photos on my profile. Customized meals for every dog. Home and dog areas sanitized daily. March 2026....10 years with Rover I have over 50 years professional experience caring for dogs, I am now retired. I have worked in the boarding, grooming, training and vet tech fields. YOUR DOG MUST BE FRIENDLY WITH OTHER DOGS NO BULLY BREEDS NO Dogs over 14yo NO drops offs or pickups after 6pm Your dog must be on flea preventive. I am retired and need to feel I am contributing to society in some small way. I love animals and they love me, so this is a good fit for me. I can care for dogs, cats, birds, horses, cattle, goats, chickens, rabbits, snakes, reptiles, raccoons and some small wildlife (depending on their needs) in their home or mine!

Sitter Profile Image: Deanna M.
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Deanna M.
from
$30
per day
5.0 out of 5 stars
34 reviews
14 repeat clients
30 years of experience
Lakeland, FL, 33810

Deanna was incredibly helpful and took amazing care of our dog, Mabel. We had a visitor in town and wanted to do some day trip-type activities, so we dropped Mabel off for daycare with Deanna a few days throughout the week. Each day, our pup came home tired, but extremely happy. You could tell she enjoyed being with Deanna and her pups. Highly recommend her care!!!

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Kristen M.
Sitter Profile Image: Elke R.
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Elke R.
Star Sitter
from
$65
per day
5.0 out of 5 stars
115 reviews
29 repeat clients
20 years of experience
Plant City, FL, 33565

My yellow lab Mazie had her 1st Rover daycare experience with Elke and it was a spectacular day for Mazie! Elke is a true dog lover and sent me a video and pictures of Mazie's great day enjoying walks, their beautiful fenced in yard, and meeting other friends! I will positively rebook Elke for Mazie's next opportunity and highly recommend her as she will do a great job taking care of your dog!

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John D.
Sitter Profile Image: Luz M.
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Luz M.
from
$30
per day
5.0 out of 5 stars
4 reviews
2 repeat clients
17 years of experience
Lakeland, FL, 33811

About: Growing up with multiple dogs, I've had the privilege of raising them from playful puppies to their senior years, witnessing their growth and providing love and care every step of the way. My oldest dog, now about 17 years old, is a testament to the dedicated care I've given throughout their lives. What Sets Me Apart: Experienced in Senior Pet Care: I have firsthand experience with aging pets, including managing age-related health issues and ensuring their comfort and happiness in their golden years. Medical Care Knowledge: I have administered medications and provided the attentive care pets need during health challenges. Loving and Compassionate Approach: Each pet is treated as part of my family, with plenty of love, patience, and understanding tailored to their individual needs. Long-Term Commitment: My experience spans a pet’s entire life cycle, ensuring that I understand the evolving needs from youth to old age. I offer a nurturing, experienced hand to care for your pets as if they were my own. As a stay-at-home mom with a 2-year-old daughter who loves animals, I have ample time to care for your pets. My flexible schedule allows me to provide consistent attention, including feeding, walks, and playtime. With my daughter by my side, your pets will receive plenty of affection, ensuring they feel loved and cared for. Whether it’s daily visits or extended care, I’m committed to meeting your pet’s needs with warmth and patience. In our nurturing home, your pets will experience the attention and love they deserve. My home is a secure, pet-friendly environment where your pets can relax and play safely, with all areas free from hazards and stocked with essentials. I supervise all interactions between pets and my daughter to ensure a gentle and safe experience. Your pet will have cozy spots to rest and designated areas for play and exercise, making them feel right at home.

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The median cost per day for doggy day care in Winston is $30

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Sitters in Winston average 4
repeat doggy day care clients

Doggy Day Care FAQs

Frequently asked questions about Rover

Sitters on Rover are free to set their rates. The median cost to hire a sitter for doggy day care in Winston on Rover as of Jun 2026 was about $30 per day, after factoring in Rover’s service fees. A sitter’s rate may also change as you customize your booking to fit your and your dog’s needs.

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

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

As of Jun 2026, 1,051 sitters provided doggy day care in Winston. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, sitters offering doggy day care joining Rover must pass a background check for you and your dog’s safety.

Rover makes it easy to reach out to multiple sitters about your booking. Typically, 87% of Winston sitters offering doggy day care respond in under an hour.

Sitters who provide doggy day care in Winston have an average of 17 years of experience. Sitters offering doggy day care with repeat customers have an average of 4 repeat clients. Experience can vary from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when you compare sitters in Winston.

Winston doggy day care sitters are happy to take care of your dog while you’re at work or unavailable for the day. Book a one-time visit, or set up a regular rhythm with your favorite Winston sitter. Drop off your dog at the sitter’s home and rest easy knowing they’ll get frequent potty breaks, plenty of playtime, and lots of love. Doggy day care is great for:

  • Puppies and high-energy dogs
  • Dogs with special needs, including seniors
  • Pet parents who work long hours
  • Dogs with separation anxiety

There are 1,051 sitters offering doggy day care in Winston on Rover, so you’re sure to find the perfect match for your dog! In Winston, 97% of sitters offer daily exercise, 98% offer medication administration, and 96% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect doggy day care sitter near you. As a reminder, sitters joining Rover must pass a background check for you and your dog’s safety.

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your doggy day care sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your 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 doggy day care 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 doggy day care service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.