Dog Boarding Winter Gardens

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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

“It was our first time with Taylor and Andrew and our first time leaving Buddy for vacay. While we were gone we received pics and updates everyday on how he was doing. He enjoyed his with time with his new friends Stella and Lucy. We will definitely take him back here for any upcoming travels.”

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Rosanna P.
Sitter Profile Image: Madison G.
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Madison G.
$59
total per night
5.0 out of 5 stars
• 116 reviews
52 repeat clients
7 years of experience
El Cajon, CA, 92020

“They took such great care of our Joey! He was a little nervous the first night adjusting to a new environment, but he quickly settled in and had a great week. They kept us updated with plenty of photos and were incredibly communicative throughout. We’ll definitely be using them again!”

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Michelle J.
Sitter Profile Image: Whitney G.
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Whitney G.
$70
total per night
5.0 out of 5 stars
• 531 reviews
226 repeat clients
20 years of experience
San Carlos, San Diego, CA, 92120

“Whitney and her family are absolutely wonderful! She took in our two pups last minute and took excellent care of them. Plenty of photo updates and it looked like lots of cuddles.”

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Mary C.
Sitter Profile Image: Dustin D.
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Dustin D.
$59
total per night
5.0 out of 5 stars
• 130 reviews
57 repeat clients
40 years of experience
Santee, CA, 92071

“Buddy came home happy and tired. Dustin even sent a picture of our pooch playing and having a great time with his two dogs. I will use this sitter again. ”

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Jacquelyn S.
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

“They were so great with Harriet and it seems like I missed her more than she missed me. I’ll definitively hit them up again and they also have the perfect backyard for a large baby like Harriet. I’m so incredibly grateful for their services and care!”

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Alejandra T.
Sitter Profile Image: Julia C.
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Julia C.
$56
total per night
5.0 out of 5 stars
• 53 reviews
23 repeat clients
19 years of experience
Scripps Ranch, San Diego, CA, 92131

“Julia is so wonderful with our puppy Eevee! She always has such a fun time with her dogs and is very well taken care of. We love all the pictures and videos :)”

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Sarah N.
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

“Makayla was very attentive with Teddy, sent updates and pictures, and made me feel at ease while on vacation. I will definitely book again in the future!”

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Amanda S.
Sitter Profile Image: Corinne & Christopher B.
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Corinne & Christopher B.
$63
total per night
5.0 out of 5 stars
• 37 reviews
10 repeat clients
18 years of experience
Rancho Penasquitos, San Diego, CA, 92129

“Our pup who is often overly shy with new dogsitters easily adjusted to Cori and Chris (her quickest transition so far as she was snoring on the couch within the first hour). They are both so welcoming, patient, and kind— we already have our second stay booked. Sophie gives her first stay two paws up!”

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Kimberlyn G.
Sitter Profile Image: Bailey S.
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Bailey S.
$54
total per night
5.0 out of 5 stars
• 110 reviews
30 repeat clients
18 years of experience
Lakeside, CA, 92040

“Bailey was super attentive to my diabetic old man , she sent constant updates and pictures, when my older dog didn’t feel well she handled the situation calmly with compassion and care. Definitely recommend!”

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Vivian Y.
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

“She and her partner did a great job caring for our pup when we were on an extended trip away! Our dog loved the outdoor space and we got tons of photo updates regularly. Marissa is very responsive. We will definitely use her again in the future!”

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Tori W.
Sitter Profile Image: Doug & Marisol P.
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Doug & Marisol P.
$70
total per night
5.0 out of 5 stars
• 154 reviews
53 repeat clients
26 years of experience
Alpine, CA, 91901

“OMGoodness. My Eddie will be 16 years old, can barely see and hear. Doug and Marisol took such care of him. Sent pics everyday to ease my worries. They notice Eddie wasn’t feeling well so we pick him up before we left; got him to the vet, Medication and back to Doug and Marisol in time to start of our vacation. We have canceled so many vacations because it so hard to leave him. Now we can vacation, we trust Doug and Marisol!!! Trust is huge!!”

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Cooky C.
Sitter Profile Image: Marwa M.
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Marwa M.
$66
total per night
5.0 out of 5 stars
• 26 reviews
5 repeat clients
32 years of experience
College Area, San Diego, CA, 92115

“Super grateful and happy with everything Marwa did for our cat while we were on vacation. This was our first long term trip and weren’t able to bring our cat. Marwa provided pictures and videos that comforted us while away. She went above and beyond for our kitty!”

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Eddie D.
Sitter Profile Image: May & Marc T.
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May & Marc T.
$62
total per night
5.0 out of 5 stars
• 402 reviews
226 repeat clients
30 years of experience
Carmel Valley, San Diego, CA, 92130

“May and Marc are absolutely fabulous! Winston loved his stay, and the picture updates and messages made us feel 💯 assured he was in good care. Just booked several more stays for Winston to cover our summer travel! 🐶🤗🥰”

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Kate C.
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

“We had a wonderful experience with this family! They took such great care of our dog, Junie, for two days and treated her like she was part of their own family. They kept us updated, made sure she was comfortable and well cared for, and gave me complete peace of mind while we were away. Junie came home happy, relaxed, and clearly well loved. We are so grateful for their kindness and would absolutely trust them to care for Junie again. Highly recommend!”

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Brittany C.
Sitter Profile Image: Linda Jean F.
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Linda Jean F.
$56
total per night
5.0 out of 5 stars
• 29 reviews
8 repeat clients
30 years of experience
La Mesa, CA, 91942

“Linda took amazing care of our senior dog, who has medical needs and doesn’t warm up to just anyone—but she absolutely loved Linda. She made sure she was safe, comfortable, and well cared for the entire time. We got regular updates and pictures, which gave us total peace of mind knowing she was in good hands. You can tell Linda truly cares, and we’ll definitely be booking with her again. Highly recommend!”

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Zoe S.
Sitter Profile Image: Christina G.
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Christina G.
$50
total per night
5.0 out of 5 stars
• 36 reviews
9 repeat clients
25 years of experience
El cajon, CA, 92021

“Christina was great with Punkin! As this was my first time leaving my sweet "old girl" with a sitter, I was a little apprehensive. I set up a meet & greet with Christina and in just a few minutes I could tell that Punkin was going to be well taken care of. She made herself comfy on the couch and was already getting the cuddling that she loves. Christina was great about sending pictures often of Punkin so I could see how well she was doing so I wouldn't worry. There were pictures of her playing tug-o-war with her tail wagging (it was just a blur in the picture LOL) and sleeping in her favorite "belly up" position, and out on walks. It was a great experience for both Punkin and me - I will definitely book with Christina again in the future!”

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

“Holly was an amazing sitter for Hazel. I received regular pupdates with pictures and in every single photo Hazel looked absolutely comfortable and happy with Holly, her home, and her family (including her 2 dogs). I feel 100% confident and comfortable using Holly’s services in the near future and would recommend her to anyone.”

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Mary M.
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: Cheryl S.
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Cheryl S.
$54
total per night
4.9 out of 5 stars
• 151 reviews
46 repeat clients
46 years of experience
Santee, CA, 92071

“Cheryl is Great! She sends cute photos daily showing me that my pup Sophie is happy and well taken care of. Cheryl only sits small dogs, so I don't have to worry about big dogs possibly getting too rough with my little one. :-) After time with Cheryl, Sophie comes home happy and content.”

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Betsy C.
Sitter Profile Image: Hana F.
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Hana F.
$49
total per night
5.0 out of 5 stars
• 592 reviews
145 repeat clients
25 years of experience
Tierrasanta, San Diego, CA, 92124

“Hana sent frequent videos and pictures of Casey while we were away, and he was obviously having fun. She seems to be always available, so I have come to depend on her!”

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Garrison C.
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Dog parents share their Rover experiences - Winter Gardens

1 / 1
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

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.
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

Amber and the family made Cali feel like a member of the family. From the start the technique used to introduce her dogs To Cali was great. Received daily updates and photos. Already have a couple more stays booked.

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Shirley
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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  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
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How to book dog boarding

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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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