Doggy Day Care in Winter Gardens

Drop off your dog at your sitter's home in the morning, and pick them up in the evening.

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Top rated Winter Gardens doggy day care sitters

Prices are estimates per day for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.

1 / 1
Sitter Profile Image: Eden L.
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Eden L.
$35
total per day
5.0 out of 5.0 stars
9 reviews
1 repeat client
14 years of experience
Santee, CA, 92071

As a mom of a toy senior fur baby who’s almost 17, it’s always worrisome when she’s not in my care with her growing list of health issues and how fragile she is. But luckily I found Eden who is amazing and has the kindest, most loving energy! Her love for dogs is apparent and shows in how she cares for both her own and mine. ❤️ She carefully asked all the appropriate questions, gave me a tour of her place (along with a separate living area perfect for small dogs; connected to a dog door and outdoor dog run) and updated me throughout the stay with pictures and quickly answered any questions I had. Thanks again Eden, you’re a lifesaver and I look forward to future bookings with you! 🐶 ❤️🫶🏻

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Jezzikah C.
Sitter Profile Image: Angela N.
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Angela N.
$28
total per day
5.0 out of 5.0 stars
18 reviews
1 repeat client
5 years of experience
El Cajon, CA, 92021

The bestest dog sitter! My girls are always so happen to see Angela and family! She takes amazing care of the doggos, has great communication skills, and makes me feel so comfortable. I couldn't ask for a better dog sitter, and her services are worth so much more! (Tip generously ;) She's worth it!)

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Janine & Michael J.
Sitter Profile Image: Chanel A.
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Chanel A.
$56
total per day
5.0 out of 5.0 stars
5 reviews
2 repeat clients
4 years of experience
El Cajon, CA, 92019

About: I’ve cared for dogs of all sizes and temperaments for over four years, including senior dogs and energetic puppies. I’m trusted by friends, family, and neighbors to walk, feed, bathe, and provide lots of love and attention. I’m comfortable administering medications, following specific routines, and reading dog body language to keep pets safe and happy. Whether it’s playtime, cuddles, or structured care, I treat every dog like my own. I’m currently don’t work, so I have plenty of time to give your pup the attention they deserve! I’m available for boarding all day every day. My flexible schedule allows me to accommodate walks, drop-ins, and extended stays with ease. I have a secure one acre fenced yard and two friendly dogs who love making new friends! Your pup will be safe, socialized, and cared for in a loving home environment. I can also crate your dog if needed and always follow the owner’s instructions for safety and comfort.

Sitter Profile Image: Daniela M.
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Daniela M.
$35
total per day
5.0 out of 5.0 stars
10 reviews
2 repeat clients
32 years of experience
El Cajon, CA, 92019

About: With 32 years of hands-on experience as a devoted dog owner, I’ve turned a lifelong love for dogs into a warm, trustworthy daycare where every pup is treated like family. Here, tails wag with joy, and your dog’s comfort and care always come first! I have plenty of free time Monday through Friday to give your dog all the love, playtime, and attention they deserve! And if you need weekend boarding, I’m here with open arms (and treats!) to make your dog feel right at home while you’re away. Welcome to a dog’s dream stay! With a spacious, fenced backyard that’s perfect for safe play and your pup will feel right at home. My pet care space is designed with love, comfort, and safety in mind giving your dog the freedom to run, explore, and relax in a secure, and happy environment. It’s not just pet care it’s a place your dog will love!

Sitter Profile Image: Ben & Luke L.
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Ben & Luke L.
$43
total per day
5.0 out of 5.0 stars
13 reviews
2 repeat clients
10 years of experience
El Cajon, CA, 92020

Ben and Luke were great with Penny and she had such a great time with them! She had a blast playing with their 4 other fur babies. We'll definitely be a returning client. Thank you Ben and Luke for taking such great care of our baby.

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Marcos F.
Sitter Profile Image: Charlie K.
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Charlie K.
$39
total per day
5.0 out of 5.0 stars
864 reviews
372 repeat clients
20 years of experience
La Mesa, CA, 91941

Our pup just had her first day with Shanna & Charlie! She came back so happy and with the cutest bandana on! Shanna kept me updated with a picture and replied back to all of my texts very quickly. I would highly recommend them. I can’t wait to book again!

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Ashley B.
Sitter Profile Image: Taylor & Andrew P.
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Taylor & Andrew P.
$56
total per day
30 years of experience
Lakeside, CA, 92040

About: I've had the pleasure of caring for all kinds of animals big and small. Seizure disorder, elderly, puppies, high-energy dogs are all welcome! I am able to administer medicine and follow any particular rules you'd like. Between my husband and I we both are home Monday thru Sunday. Always home with our pups and yours! No kids or cats live here. Just a husband and wife and 2 amazingly friendly dogs. We have a large property with a fenced yard all around. We plan to use an AirTag for increased safety for all our doggy guests.

Sitter Profile Image: Mark & Christina H.
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Mark & Christina H.
$35
total per day
5.0 out of 5.0 stars
82 reviews
26 repeat clients
25 years of experience
EL CAJON, CA, 92020

Mark, Christina, and Cody! Thank you for taking such good care of our babies. They love you so much. You're just beautiful people. I left them with you with absolutely no worries. Thank you for the daily updates and the cutest pictures! I can't say enough wonderful things about y'all. Our babies were in loving, caring hands always. I highly recommend you. And I know Sage and Noir would love to see you again!

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Veronica S.
Sitter Profile Image: Bailey S.
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Bailey S.
$35
total per day
5.0 out of 5.0 stars
73 reviews
21 repeat clients
18 years of experience
Lakeside, CA, 92040

We knew our furbabies would be well-taken care of with Bailey. She is lovely and such a caring environment. Bailey sent photos and updates through it all- We highly recommend her!

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Nanibaa B.
Sitter Profile Image: Christina G.
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Christina G.
$39
total per day
5.0 out of 5.0 stars
33 reviews
8 repeat clients
25 years of experience
El cajon, CA, 92021

I can tell our pup Mochi had a great time with Christina and her fiance, They took him out on a few walks, and gave him lots of attention! Great communication and sent us lots of pictures!

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Charles J.
Sitter Profile Image: Sean & Amy O.
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Sean & Amy O.
$43
total per day
5.0 out of 5.0 stars
140 reviews
87 repeat clients
20 years of experience
El Cajon, CA, 92020

Great family who hosted my high energy 1 yr old Weimaraner for daycare! We had a meet and greet the week before and they were really warm, friendly, and thorough which made me feel comfortable leaving my dog with them! They were able to handle his high energy well, took him out to the park and walked him. Overall great experience and would recommend! Thanks so much Sean and Amy!

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Adiva Z.
Sitter Profile Image: aspyn k.
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aspyn k.
$32
total per day
15 years of experience
Santee, CA, 92071

About: Hi, I’m Aspyn! I’ve cared for animals my whole life and currently share my home with 20 pets — dogs, cats, bunnies, reptiles, and rodents. Over the years, I’ve gained strong skills in animal behavior reading, medication administration, and creating calm environments for anxious pets. I’m experienced with special diets, cleaning enclosures, and maintaining routines for all types of animals. With patience, empathy, and years of hands-on care, I treat every pet like my own — making sure they feel loved, safe, and comfortable while you’re away. Hi, I’m Aspyn! I’m currently living in San Diego with my fiancé and our 20 pets — a mix of dogs, cats, bunnies, reptiles, and small rodents. I’ve grown up around animals my entire life, and taking care of them has become a big part of my daily routine. Between feeding schedules, walks, and playtime, there’s always something going on, but I wouldn’t have it any other way. I’m in college working toward a degree in Criminal Justice, and I’m hoping to add Psychology as well. Balancing school, life at home, and all my pets has taught me a lot about patience, organization, and consistency. When I’m not studying or spending time with my animals, I love being outdoors, relaxing with family, and enjoying quiet moments with all my pets. When it comes to caring for animals, I try to keep things as comfortable and familiar for them as possible. At my home, I have a safe, pet-friendly space with plenty of room for play, rest, and quiet time. My own pets are used to routines and socializing, so I make sure everyone feels calm and secure. I stick closely to feeding schedules, provide enrichment through toys and play, and make sure everyone gets the attention they need. When it comes to caring for animals, I treat every pet like they’re part of my own family. At my home, I already care for 20 pets, so my days naturally revolve around feeding, walking, cleaning, and spending quality time with animals. I’m used to managing routines for all kinds of pets — from dogs and cats to bunnies, reptiles, and small rodents — and making sure everyone feels safe and loved. When I’m caring for pets in a client’s home, I do my best to follow their normal routine so your pet stays comfortable and stress-free. I offer both dog walking and house sitting, whether that means taking your pup out for their daily walks, giving them exercise and attention, or staying overnight to keep them company. I always make sure their space stays clean, calm, and cared for while you’re away. No matter where I’m watching them, I focus on creating a safe, loving environment — full of routine, comfort, and plenty of affection.

Sitter Profile Image: Cheryl S.
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Cheryl S.
$44
total per day
4.9 out of 5.0 stars
135 reviews
41 repeat clients
46 years of experience
Santee, CA, 92071

Cheryl did a great job! This was my first time using Rover. She sent me pictures of my pups and let me know how they were doing! Thanks for watching our two little girls!

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Laureen T.
Sitter Profile Image: Amy S.
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Amy S.
$70
total per day
20 years of experience
El Cajon, CA, 92020

About: What sets me apart from other sitters is that I am a passionate pet lover. I provide personalized care ensuring your pets feel safe and cherished. I am an animal lover and with me they will have lots of playtime, like going to dog beach or taking a walk around Lake Murray. With me they receive empathetic companionship in a peaceful home. I am currently working part time as a yoga teacher. I have a good deal of time to pet sit. I am available to board Friday-Sunday, anytime after 1 pm. I also have availability to drive to your home Monday-Thursday for dog walks. I am a responsible, caring ,and loving pet sitter. I am dedicated to providing a safe and loving environment for your pets while ensuring their needs are met and feel comfortable and happy.

Sitter Profile Image: Shannon B.
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Shannon B.
$56
total per day
5.0 out of 5.0 stars
5 reviews
1 repeat client
8 years of experience
el cajon, CA, 92021

About: I've had a lifelong passion for working with dogs and cats, and I've spent the past eight years dedicated to the pet industry. Over the years, I've cared for dogs of all sizes and temperaments, from puppies to seniors. Whether it's feeding, potty walks, playtime, or grooming, I have extensive experience and a deep love for caring for furry friends. I’m excited to share my expertise with your pet! Pet care fits perfectly into my daily routine as I have an open schedule and am not working full-time elsewhere. This allows me to provide flexible and attentive care to your pet, ensuring they get the attention, playtime, and routine they need throughout the day! In my home, I create a comfortable, pet-friendly environment where your furry friend can feel safe and relaxed. I ensure they have plenty of space to play, rest, and enjoy their time with me. I also follow any specific instructions you provide to make sure their routine stays consistent. When caring for pets in your home, I prioritize their comfort and well-being by maintaining their usual routines, whether it’s feeding, potty breaks, or playtime. I provide plenty of attention, love, and care while ensuring your home remains safe and tidy. My goal is to offer a stress-free experience for both you and your pet!

Sitter Profile Image: Alicia A.
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Alicia A.
$39
total per day
4.9 out of 5.0 stars
42 reviews
14 repeat clients
5 years of experience
Lakeside, CA, 92040

My dog Barry is always jumping out of the car to get to her daycare. She has dogs of her own and knows how to care for them. Dogs are kept in safe fenced yards and can play throughout the day with water and food. It's a great setup and great caretaker!

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Ian E.
Sitter Profile Image: Mary C.
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Mary C.
$35
total per day
20 years of experience
El Cajon, CA, 92021

About: We are a family of 4 (humans) and 1 very sweet and playful dog Annie! We love animals and let them live in our home as any family member would. We have a large yard with turf to play and potty and I stay home to have lots of time for potty breaks and care. We love to go to the beach and parks! I am a stay at home mom and am home most hours of the day. I have watched pets for over 20 years and would love to help provide a “homey” feel stay for your pet and keep them happy and busy! Pets will stay at our home and have full access to be inside and outside throughout the day. All pets will be kept inside during the night and have access to couches or dog beds.

Sitter Profile Image: Shelby & Dalton T.
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Shelby & Dalton T.
$43
total per day
5.0 out of 5.0 stars
74 reviews
19 repeat clients
9 years of experience
El Cajon, CA, 92021

Shelby and Dalton are the best! They are so responsive and accommodating!! Literally lifesavers, I work really long hours and my husband, who usually watches our dog during the day, had to travel for work last minute. Shelby and Dalton agreed to watch my pup on one of my long days and were so understanding and flexible when I had to pick her up later in the evening - truly I don’t know what I would’ve done without them! They treated her as if she were their own and she LOVED playing with their sweet pup and cuddling with one of the cats, and I got lots of updates and pictures throughout the day. I couldn’t recommend them enough, I will definitely be taking her back to hangout and play with her new best friends!

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Jenn L.
Sitter Profile Image: Jasmine P.
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Jasmine P.
$28
total per day
3 years of experience
Lakeside, CA, 92040

About: Animals always gravitate towards me. I love how animals are like children. So innocent and sweet. I would love to help out busy families by walking or sitting for your dog. I am reliable and I overly communicate. I love taking videos and pictures of your pet and sending them to you and your loved ones . I am a mom of two girls. I have a flexible schedule and I’m willing to do whatever’s necessary to make sure your pet is taken care of. I’m a hair stylist on weekends and I love when people bring their dogs to their appointments. Rover is great way for me to play with animals, get some exercise, and make some extra income. Just message me 😊 I make sure the dog goes outside to use the bathroom . Make sure the food and water bowl is always fresh and full. Engage and play with your pet. Chill, lay down, and watch tv together. I absolutely love playing tug of war with dogs so make sure to pack that toy in their overnight bag LOL. If I were to come to your house I would let you know exactly when I enter and when I leave and give you updates on your pet .

Sitter Profile Image: Donatella O.
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Donatella O.
$70
total per day
5.0 out of 5.0 stars
18 reviews
5 repeat clients
10 years of experience
Lakeside, CA, 92040

About: Hey everyone! My name is Donatella and I grew up with animals, they are not only a part of my life but my family. I adore dogs and cats for I have 2 of each and they are a blessing. My goal is make you feel sure and safe that your companion is in safe and capable hands with me. I will provide them with all the love and care they need. I will make sure to provide exercise, play time, feeding and that they are comfortable in my home. I adore dogs and it will be such a great opportunity to be able to take care of your pets. I hope to hear from you guys soon and please know they will be in great hands.

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The median cost per day for doggy day care in Winter Gardens is $44

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