Dog Boarding Winter Gardens

Find a loving dog sitter to watch your dog overnight at your sitter's home.

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Winter Gardens, Find top rated dog boarding

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

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Sitter Profile Image: Taylor & Andrew P.
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Taylor & Andrew P.
$56
total per night
5.0 out of 5 stars
• 18 reviews
5 repeat clients
30 years of experience
Lakeside, CA, 92040

“We couldn’t have asked for better people to take care of our little Louie while we were away. Taylor and Andrew were absolutely wonderful! They sent us daily pictures and videos, which we loved receiving. It was so reassuring to see Louie happy, playing with other doggies, getting lots of cuddles and going on all kinds of fun adventures. He had the time of his life!”

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Laura G.
Sitter Profile Image: Savannah B.
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Savannah B.
$105
total per night
5.0 out of 5 stars
• 15 reviews
2 repeat clients
29 years of experience
La Mesa, CA, 91942

“20/10!! Savannah took amazing care of our pups!! Especially when it came to giving my one pup her eyedrops daily. She took the best photos and I could tell the pups had a great time! 100% recommend and would have our pups stay with her again!”

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Phylice D.
Sitter Profile Image: Cerita & Saeid A.
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Cerita & Saeid A.
$70
total per night
5.0 out of 5 stars
• 92 reviews
42 repeat clients
26 years of experience
LA MESA, CA, 91942

“Cerita is my go to dog and cat sitter. She treats all of my fur babies with so much love and makes them feel completely at home. I especially appreciate the extra care she gives my senior cat, she’s very attentive when it comes to giving him his insulin.”

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Sylvia S.
Sitter Profile Image: Eden L.
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Eden L.
$70
total per night
5.0 out of 5 stars
• 21 reviews
6 repeat clients
14 years of experience
Santee, CA, 92071

“You did a fantastic job! Eden was always quick to get back to me. She adored my pups, and they adored her too. This was my first time using Rover, and honestly, I’m giving it a perfect score with Eden. I would absolutely recommend her and would definitely go back to her.”

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Lucinda L.
Sitter Profile Image: Julia & Rory J.
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Julia & Rory J.
$38
total per night
5.0 out of 5 stars
• 7 reviews
3 repeat clients
20 years of experience
Lakeside, CA, 92040

“Julia, Rory, and family were ALL fantastic! Gussie was so comfortable being with him. It’s like, they became his second family. I really did appreciate that! Julia was great in sending photos and keeping in touch. I would recommend her to anyone in a heartbeat, to those wanting nothing but the best for their fur babies!”

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Ron M.
Sitter Profile Image: Adriana & Cameron N.
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Adriana & Cameron N.
$70
total per night
5.0 out of 5 stars
• 581 reviews
237 repeat clients
11 years of experience
Santee, CA, 92071

“This was our first time using Rover and leaving our two fur baby frenchies with someone we didn’t know. Adriana was very sweet and even met us before our booking to meet our dogs. She updated us with photos and the dogs and they had a wonderful time. We are thankful for her wonderful care of our fur babies.”

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Ruth C.
Sitter Profile Image: Ben & Luke L.
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Ben & Luke L.
$90
total per night
5.0 out of 5 stars
• 21 reviews
4 repeat clients
10 years of experience
El Cajon, CA, 92020

“So kind to our pups and made it so easy to coordinate. Super fast response times and sent lots of pics while the pups were with them. They even sent them home with cute bandanas that we will cherish always. Amazing care takers!”

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Cameron T.
Sitter Profile Image: Makayla B.
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Makayla B.
$34
total per night
5.0 out of 5 stars
• 12 reviews
3 repeat clients
1 year of experience
Santee, CA, 92071

“This was my first time using Rover in addition to having someone I didn’t know watch my dog and I have to say I had a great experience. Makayla was a dream to find, she had great communication, sent me updates and photos and genuinely cared for my Baloo. I knew as soon as I met her Baloo was going to be in good hands and you can tell how much she loves animals. I will absolutely use her again and can’t recommend enough.”

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Casey T.
Sitter Profile Image: Marissa S.
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Marissa S.
$84
total per night
4.9 out of 5 stars
• 70 reviews
23 repeat clients
3 years of experience
La Mesa, CA, 91942

“Marissa and her partner are amazing. We have used them 4 times now for week-long getaways, and they take such wonderful care of our pup! She loves the fenced outdoor space they have and gets plenty of walks and playtime. They send us regular updates and photos. We highly, highly recommend them!”

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Tori W.
Sitter Profile Image: Araceli L.
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Araceli L.
$95
total per night
5.0 out of 5 stars
• 28 reviews
7 repeat clients
30 years of experience
Balboa Park, San Diego, CA, 92104

“Araceli was amazing she took my dog on in very short notice for the holiday weekend. Very kind, clean home very dog friendly. She treated my dog as if she was her own. She gave updates which was very appreciated. I would 100% book again with her. Thank you so much Araceli.”

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Ashley K.
Sitter Profile Image: Ami R.
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Ami R.
$70
total per night
5.0 out of 5 stars
• 100 reviews
29 repeat clients
25 years of experience
Rolando, San Diego, CA, 92115

“Amy does such an amazing job. My high energy pup always comes home relaxed, happy and clean. He is always excited to see her and enjoys his stay. Highly recommend.”

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Joachia H.
Sitter Profile Image: Savanah B.
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Savanah B.
$62
total per night
5.0 out of 5 stars
• 34 reviews
7 repeat clients
17 years of experience
Lake Murray, San Diego, CA, 92119

“Savanah takes great care of Bailey! And she sends daily updates with photos, which keeps me from missing my little guy so much. I know I can trust her completely to take good care of Bailey!”

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Sharon O.
Sitter Profile Image: Adam C.
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Adam C.
$52
total per night
4.9 out of 5 stars
• 30 reviews
3 repeat clients
6 years of experience
La Mesa, CA, 91942

“Good experience. Everything went smooth, my dog came back happy and healthy. Communication was good, i received pictures of my dog along the way and i could tell that the whole family loves animals. The price was fair as well. I would book again.”

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Monique L.
Sitter Profile Image: Margaret & Kyle C.
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Margaret & Kyle C.
$66
total per night
5.0 out of 5 stars
• 107 reviews
43 repeat clients
10 years of experience
Mira Mesa, San Diego, CA, 92126

“Margaret and Kyle were so great! It worked out so perfectly to have them doggy sit Kira. Absolutely would love to have them watch after her again. I felt like I didn’t have to worry at all. Margaret would send me pics and videos to show how Kira is doing. Kira looked like she was so happy! Thanks again!”

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Elaine C.
Sitter Profile Image: Jean Pierre C.
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Jean Pierre C.
$50
total per night
5.0 out of 5 stars
• 19 reviews
1 repeat client
25 years of experience
Estlake Greens, Chula Vista, CA, 91915

“I couldn’t be happier, and neither could my goldendoodle. Jean Pierre was very responsive, answered all of my questions, and even extended my booking last minute to accommodate a change in my plans. Most importantly, my dog loved it! In fact, she probably would have been happy staying longer she had so much fun! I will definitely be taking her back to Jean Pierre in the future.”

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Liz R.
Sitter Profile Image: Luciane W.
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Luciane W.
$70
total per night
5.0 out of 5 stars
• 5 reviews
2 repeat clients
25 years of experience
Mira Mesa, San Diego, CA, 92126

“I would leave 6 stars if I could. Luciane took good care of our puppies, who were clearly very well loved during their stay. Booking was easy, communication was great, and the photos she sent were absolutely heartwarming. She had treats and toys and puzzles for the dogs... I couldn't recommend her enough. Thank you so much!”

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Dave & Cheri C.
Sitter Profile Image: Holly V.
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Holly V.
$56
total per night
5.0 out of 5 stars
• 73 reviews
34 repeat clients
11 years of experience
Rancho Penasquitos, San Diego, CA, 92129

“Holly is the best!! Her home is so welcoming and she is very communicative! She does a great job keeping the dogs occupied, safe, and well loved. She sent great updates and our pup came home so happy. We can’t recommend her enough!”

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Olivia J.
Sitter Profile Image: Mark M.
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Mark M.
$70
total per night
5.0 out of 5 stars
• 23 reviews
5 repeat clients
32 years of experience
Del Cerro, San Diego, CA, 92020

“Mark is an absolutely the best. He is so accommodating, easy to communicate with and goes above and beyond anything I couldn’t have hoped for. I had pictures everyday and my little guy was obviously at home. I felt confident and reassured that little “Stevie “ was well cared for and happy. It was all that I could have hoped for.”

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Rebecca R.
Sitter Profile Image: Kylie & Anthony W.
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Kylie & Anthony W.
$60
total per night
4.8 out of 5 stars
• 94 reviews
46 repeat clients
21 years of experience
Grantville, San Diego, CA, 92124

“Grateful for Kylie and Anthony for taking such great care of Atlas. He came home excited and happy as always. They also gave us and update while we were away”

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Trevor C.
Sitter Profile Image: Samantha G.
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Samantha G.
$84
total per night
5.0 out of 5 stars
• 11 reviews
4 repeat clients
10 years of experience
La Mesa, CA, 91942

“Samantha watched our Lab Shepherd mix, and our dog was in absolute heaven! She has a lot of anxiety, but Samantha did an amazing job following her routine and making sure she felt safe, comfortable, and loved. She sent updates and pictures throughout the day, which I really appreciated and gave me so much peace of mind. I highly recommend Samantha to anyone looking for a caring, reliable pet sitter!”

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Bryanna R.
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Dog parents share their Rover experiences - Winter Gardens

1 / 1
5.0 out of 5 stars

Julia and her family were wonderful with Louie! He felt right at home, and they treated him like one of their own. He honestly didn’t want to leave when I came to pick him up. They have a lovely, secure fenced yard where he could roam and explore, and their home was spotless and welcoming. It was such a comfort knowing he was in good hands. I can’t wait to book with them again!

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John C.
Boarding
5.0 out of 5 stars

Amber was awesome answering my concerns when we met as I have a 6 yr old rescue dog for only 4 years. We did a trial night and Tiva, my dog was excited to go..Amber sent me a couple of photos of Tiva to reassure me. I feel very comfortable leaving Tiva for a 4 day weekend now knowing she will treat my dog like her own 2 dogs.

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Drew M.
Boarding
5.0 out of 5 stars

We couldn’t have asked for better people to take care of our little Louie while we were away. Taylor and Andrew were absolutely wonderful! They sent us daily pictures and videos, which we loved receiving. It was so reassuring to see Louie happy, playing with other doggies, getting lots of cuddles and going on all kinds of fun adventures. He had the time of his life!

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Laura G.
Boarding
5.0 out of 5 stars

As always Anastazia was amazing with my babies. She sent me pictures throughout the stay and was very flexible with my schedule.

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Mayra G.
Boarding
5.0 out of 5 stars

This was our first time bringing our dog Benny to Madison and it was a fantastic experience. We appreciated the meet and greet prior since Benny can be a little much in the personality department, they answered all our questions and left us feeling nothing but sure it was the right fit for us. Benny spent his first weekend there and he did great, we received pictures and updates letting us know he was having a great time. Appreciate the knowledge and experience both Madison and Moses bring to taking care of our babies! Highly recommended and we will be sure to bring Benny back again and again!

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Maggie E.
Boarding
5.0 out of 5 stars

Jasmine was a great sitter! Sammy can be a little difficult but she took amazing care of him, would definitely book again☺️

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Victoria A.
Boarding
5.0 out of 5 stars

Christina did a great job watching Harley for a week stay! She sent a lot of pictures and messages, was extremely responsive, and flexible with pick up /drop off times. We will definitely book with her again!

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Nikki L.
Boarding
5.0 out of 5 stars

Barbra and her girls wonderful! This was our dog's first time staying overnight with them and they were so patient and understanding while he warmed up to staying in a new place. They made him feel welcome and gave him lots of love and attention. Thank you, Barbra!

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Laurie G.
Boarding
5.0 out of 5 stars

Dallas & Bri were so amazing to both me and my baby, Kojak! Given how nervous he is, they took time out of their days weeks prior to go on a small walk with us so he knew their smell and voices. They were so patient in waiting for him to open up and especially with me as the planned dates and times of sitting got wonky. It was my first time using Rover and I could not recommend them enough!

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Breslyn K.
Boarding
5.0 out of 5 stars

Bianca and her family are amazing!!! So great that I almost didn’t want to write this so I could gate-keep them!! I had to leave my guy to go out of state for a wedding and I’m usually a mess about it but I felt completely relaxed and comfortable this time. Bianca communicated well and I could tell how much they were loving on him. It allowed me to fully enjoy my trip which was priceless. He will be back, he was so comfortable with them. Such a great experience!

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Ashley V.
Boarding
5.0 out of 5 stars

would give 6 stars if able. daily updates, easy to work with, responded to last minute request. highly recommended.

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Justin
Boarding
5.0 out of 5 stars

Always amazing! Thank you! Took Koda short notice and took great care of him. She also has a sweet dog! Great communication!

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Max B.
Boarding
5.0 out of 5 stars

Terri is a true animal lover. She cared for my dog Lucy over the weekend. She took Lucy for plenty of walks and even took her to the lake a couple times. Baked her some dog treats and even sent her home with a batch. Plenty of pictures. We are very pleased.

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Kevin G.
Boarding
5.0 out of 5 stars

We love that Brandon and Mya are so close to our home and that our dog is now familiar with them. We also love the fact that they send us pictures and let us know how she is doing.It is very convenient to book, pay, drop off. Thanks again.

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Gary B.
Boarding
5.0 out of 5 stars

Angela is wonderful! She treats any dog in her care with love, gives attention, and supplies the dog owner with updates + photos. Our dogs almost don't want to leave because they are sooo happy. I highly highly recommend Angela for day care and boarding. It is such a relief to know that my dogs are loved and cared for while I'm out of town. I think she under charges, so I always give a nice tip:)

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Janine & Michael J.
Boarding
5.0 out of 5 stars

Rami was the sweetest to work with! Thank you so much rami for treating my baby with so much patience and love. I could see it in the videos and pics you were sending! I can’t wait to work with you again! I’ve never used this app before and I’m so grateful I got such a wonderful person for my first time :)

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Marielena V.
Boarding
5.0 out of 5 stars

I couldn’t have chosen a better sitter! From the moment I left my dog, she treated her like family. My dog is like one of my kids, so I truly appreciated the level of care she provided. The daily photos showed my baby looking relaxed, happy, and completely at ease, which made it easy for me to enjoy my time away without any worries. Her dogs were friendly and immediately got along with mine, creating a calm and happy environment. This was especially helpful for my dog, who is an only dog at home. The entire experience was smooth, thoughtful, and genuinely reliable. Her communication was clear, and it’s evident that she has a real gift for understanding animals and making them feel safe. I would book with her again without hesitation and highly recommend her to anyone who wants their dog to stay in a home that truly pays attention and cares.

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Amanda K.
Boarding
5.0 out of 5 stars

My baby was well taken care of by Alexis and Adam! They are professional, caring, and easy to communicate with. I would definitely use them again, and would be happy to recommend their service

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Anna H.
Boarding
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How to book dog boarding

  1. 1. Search

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FAQs for Dog Boarding - Winter Gardens

Frequently asked questions about Rover

Rover is the largest marketplace for local pet care. Whether you're looking for pet sitters, dog walkers, or house sitters who specialize in pet sitting, you can narrow your search by entering your ZIP code to find sitters within walking distance in your neighborhood.

Every sitter on Rover has their own routine. Depending on the arrangements you agree on before the stay, a sitter can follow your dog’s regular feeding schedule, provide a comfortable place to sleep, offer companionship, and support their usual exercise and play needs.

Depending on the sitter, their home environment, and your dog’s needs, daily exercise may include walks, outdoor play, indoor enrichment activities, or supervised play with compatible dogs. These activities are not automatically included with every booking, so ask the sitter what a typical day looks like.

During the Meet & Greet, discuss your dog’s usual exercise and play routine, whether they can safely interact with other dogs, and any activities or restrictions the sitter should follow. You can also ask the sitter to send photo and message updates during the stay so you can see how your dog is spending their time.

Preparing for drop-off is easy when you have a checklist! To help your dog settle into their Winter Gardens home-away-from-home, we recommend packing:

  • Health and safety essentials such as their ID tags, vaccination records, medication, and emergency vet or secondary caregiver contacts.
  • Food and gear such as harnesses, collars, food (portioned by day), and an item that smells like you.
  • Special instructions such as a list of training cues, medical administration needs, or favorite hang-out spots in your Winter Gardens.

Tip: You can upload your dog’s routine and medical info directly onto their profile so your sitter always has the details at their fingertips.

You and your Winter Gardens sitter can schedule drop-off and pick-up in a way that works best for the both of you—and your dog. Most sitters offer flexible times for drop-off and pick-up but the easiest way to confirm those times will be through in-app messaging. Confirm your arrival time the day of pick-up and drop-off can also help keep the process smooth and organized.

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the Rover Guarantee, which provides up to $25,000 in eligible veterinary care reimbursement.

Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page.

While each sitter sets their own vaccine requirements, staying up-to-date on your dog’s vaccines is the best way to be "boarding ready". Vaccinations help create a safe environment for all pets under a sitter’s care.

Many sitters in CA ask that dogs be up to date on core vaccines like the Canine Parvovirus, Canine Distemper, Canine Adenovirus, Bordetella, and Rabies.

By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.

If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your dog to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your dog is showing signs of possible illness.

For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.

Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.

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