Dog Boarding in Winter Gardens

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Top rated Winter Gardens dog boarders

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: Terri G.
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Terri G.
$84
total per night
5.0 out of 5 stars
8 reviews
2 repeat clients
40 years of experience
El Cajon, CA, 92020

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.
Sitter Profile Image: Madison G.
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Madison G.
$54
total per night
5.0 out of 5 stars
76 reviews
38 repeat clients
7 years of experience
El Cajon, CA, 92020

Madison and her husband were amazing! They were very accommodating with me when I wanted to add an additional day and additional pick up time. They made sure to send many pictures and updates. They even gave me tips on training to make sure what he was taught in those days, stuck. I'll definitely be bringing him back for future stays!

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Genny H.
Sitter Profile Image: Taylor & Andrew P.
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Taylor & Andrew P.
$43
total per night
5.0 out of 5 stars
5 reviews
1 repeat client
30 years of experience
Lakeside, CA, 92040

Taylor and Andrew spoiled Rafi! They gave her extra treats, made sure she ate, gave her run of their home and yard, took her for walks, and gave her affection. They were good about providing updates and sent photos. Rafi was with them for 2 wks., and when I picked her up I witnessed her seek attention and affection from them, she interacted well with their dogs, and had no initial interest in my return. I recommend them and will definitely use them again. I couldn’t be more pleased. Thank you!

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Karen H.
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

A Christmas gift arrived early when Dustin’s family and home boarding became available to book for the holiday! Their family accommodated an immediate introduction at their home and provided a wonderful place for 7 days! Lots of attention, pics, updates and they asked all the questions to be sure my dog’s diet, sleeping, hygiene or other habits were attended to! I couldn’t be more pleased and was totally confident my dog was happy while we enjoyed our vacation!

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Jen A.
Sitter Profile Image: Ashley M.
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Ashley M.
$70
total per night
5.0 out of 5 stars
7 reviews
2 repeat clients
15 years of experience
Lakeside, CA, 92040

While I was away, I received regular updates, photos, and messages that showed how happy and well cared my dogs were. It was obvious that my dogs felt comfortable and loved. When I returned, my dogs were relaxed, healthy, and clearly had been in great hands. If you’re looking for someone trustworthy, responsible, and truly passionate about animals, Ashley is the perfect choice. I will definitely be booking with her again!

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Luiza M.
Sitter Profile Image: Linda Jean F.
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Linda Jean F.
$56
total per night
5.0 out of 5 stars
25 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: Bailey S.
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Bailey S.
$56
total per night
5.0 out of 5 stars
92 reviews
26 repeat clients
18 years of experience
Lakeside, CA, 92040

We absolutely LOVE Bailey and her family, they are so wonderful to our Roxie when she stays. She even got to be part of the her girls birthday party this last stay. We don't trust many but Bailey and her family are always our #1 choice if we need a sitter. Thank you for always treating Roxie like part of the family when she is with you all!! ❤️❤️

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Alisha P.
Sitter Profile Image: Whitney G.
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Whitney G.
$70
total per night
5.0 out of 5 stars
505 reviews
218 repeat clients
20 years of experience
San Carlos, San Diego, CA, 92120

Whitney always takes such good care of our Bentley. He’s been boarding with Whitney for 4 years now and we do not plan on going to anyone else to take care of our baby.

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shantel j.
Sitter Profile Image: Ami R.
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Ami R.
$70
total per night
5.0 out of 5 stars
77 reviews
23 repeat clients
25 years of experience
Rolando, San Diego, CA, 92115

Ami is the greatest sitter we have ever had on Rover . Not only did she book us at the last moment her care for Stella was more than I could ever imagined. I knew Ami was kind and caring when Stella and I first met her and I am very cautious about using just any sitter. Ami kept us updated with photos and brushed her fur while sitting. Stella actually came back looking better than before I took her to Ami! She is the best and will always be my choice of sitters.

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Roger B.
Sitter Profile Image: cristina l.
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cristina l.
$56
total per night
5.0 out of 5 stars
24 reviews
8 repeat clients
10 years of experience
Sky Line, San Diego, CA, 92114

I could tell Bella was happy with Cristina. She was great with all my instructions as Bella is a senior and needs some special attention. thanks!

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Kandace Y.
Sitter Profile Image: Cerita & Saeid A.
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Cerita & Saeid A.
$70
total per night
5.0 out of 5 stars
62 reviews
28 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: Gwendolyn W.
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Gwendolyn W.
$49
total per night
5.0 out of 5 stars
53 reviews
19 repeat clients
22 years of experience
Spring Valley, CA, 91977

Gwen and her family took such great care of our boys! She sent great updates and tons of pictures. We knew they were in great hands the entire time!

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Dani D.
Sitter Profile Image: Emily H.
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Emily H.
$77
total per night
5.0 out of 5 stars
10 reviews
3 repeat clients
30 years of experience
La Mesa, CA, 91942

Emily was amazing and we will definitely have her watch Rory again!

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Jamie R.
Sitter Profile Image: Mark Z.
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Mark Z.
$77
total per night
5.0 out of 5 stars
16 reviews
6 repeat clients
35 years of experience
Lemon Grove, CA, 91945

Mark and his son were really awesome with our dog, Thor. We booked a 10 day stay, and Mark provided consistent updates on how Thor was doing. They walked him regularly and played with him often, and they have a great home with a back yard Thor could enjoy. I felt comfortable and confident leaving my fur baby with them!

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Diana R.
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

We can't say enough good things about Savanah, she took excellent care of our pup!! She was very communicative and so good at sending updates. I would highly recommend her to anyone!

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Elisa R.
Sitter Profile Image: Hana F.
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Hana F.
$49
total per night
5.0 out of 5 stars
537 reviews
134 repeat clients
25 years of experience
Tierrasanta, San Diego, CA, 92124

Casey was a little nervous at first (when I dropped him off), but he quickly adapted. Hana almost immediately sent me a video of him going for a walk, and sent copious videos after that of Casey playing with other dogs. I would certainly use her again!

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Garrison C.
Sitter Profile Image: JESSICA C.
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JESSICA C.
$56
total per night
5.0 out of 5 stars
34 reviews
5 repeat clients
7 years of experience
Bay Park, San diego, CA, 92117

Jessica was great with my dog Kodi! She was very responsive and kept me updated throughout the stay. I would absolutely want Kodi to stay with her again

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Jack R.
Sitter Profile Image: Mayank & Shruti S.
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Mayank & Shruti S.
$63
total per night
5.0 out of 5 stars
160 reviews
47 repeat clients
10 years of experience
Mira Mesa, San Diego, CA, 92126

Mayank and shruti were great sitters. Our dog Leo enjoyed his stay there. Had fun with other dogs. They kept me updated with photos and videos and I didn’t have to ask for it. We left Leo twice with them and would go to them again without doubts.

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Priyadarshini N.
Sitter Profile Image: Lori V.
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Lori V.
$84
total per night
5.0 out of 5 stars
8 reviews
3 repeat clients
25 years of experience
Northwest, Chula Vista, CA, 91910

Lori watched our dog Hana for four nights and we couldn’t be more pleased. Hana can be very anxious and temperamental, but Lori exceeded our expectations and was able to form a bond with her quickly. We usually avoid boarding Hana at larger facilities because she becomes overwhelmed and overly anxious. However, Lori was able to provide Hana with much more intimate care where she felt safer. Lori provided daily updates showing us that Hana was active and well taken care of. This made it much easier to feel at ease while we are on vacation. We will certainly be using her again.

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Monica D.
Sitter Profile Image: Doug & Marisol P.
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Doug & Marisol P.
$56
total per night
5.0 out of 5 stars
151 reviews
53 repeat clients
26 years of experience
Alpine, CA, 91901

Always such a great stay with Doug & Marisol. They are such a nice family and treat our pup like their own. Our dog always comes back happy and normal which is such a relief. Thanks as always and highly recommend!

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Brittney L.
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Winter Gardens dog parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Great experience and mindful of my dog's needs (very timid prior abused dog). My dog enjoyed the time with Stella (another doggo at the place❤️). Will book again when I need a dog sitter!

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Nataly G.
Boarding
5.0 out of 5 stars

Christina really cares for your pets as if they were her own. She sends lots of photos and gives lots of cuddles and companionship to your pet. I couldn't reccomend her more highly!

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Elizabeth D.
Boarding
5.0 out of 5 stars

Sadie always comes home happy. Madison sends pictures showing the pack and all the pups are engaged. I’m glad that I found her.

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Lynn H.
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

Anastasia I amazing my babies loved her. I received daily updates and pictures of my babies. I 100% recommend.

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Mayra 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

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

Thanks again, Barbra. It's so nice to have a loving family to leave our sweet Tillie with. She's always excited to spend time with you all!

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Nancy R.
Boarding
5.0 out of 5 stars

Cookie enjoyed the stay with Amber and her family. Amber provided daily feedback and pics. I would leave Cookie again. Thanks.

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Mahesh D.
Boarding
5.0 out of 5 stars

Shelby and Dalton were great with our Golden Retriever! They sent tons of pictures and had great updates. You could tell they showed him a lot of love!

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Adam R.
Boarding
5.0 out of 5 stars

Melissa did a great job watching my puppers while I was traveling! Was able to accept a last minute booking, and sent a bunch of pictures every day. My doggos clearly loved staying there as they didn't want to leave!

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Beth & Daniel H.
Boarding
5.0 out of 5 stars

Charles was awesome! He took great care of my two dogs. One of my dogs is anxious with new people, but he definitely knows what he’s doing and quickly earned her (and my) trust. He was very easy to work with and my dogs had a great time. I will definitely come back to him next time! Highly recommend!

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Raygan B.
Boarding
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How Rover works

  1. 1. Search

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  2. 2. Meet & Greet

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  3. 3. Book & Pay

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Why Choose Rover?

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  • Reservation protection

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

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

Dog Boarding FAQs

Frequently asked questions about Rover

If you’re searching for a Winter Gardens dog boarding 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.

Typically, dog boarding sitters on Rover respond in under an hour, so you should be matched with the perfect sitter for you and your dog in no time!

Experience can vary widely from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when comparing sitters available in Winter Gardens.

Rover makes it easy to find Winter Gardens dog boarding sitters to provide loving care from their own home. The background-checked, 5-star sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog boarding is great for:

  • Dogs of all ages and abilities, including puppies
  • Pet parents looking for a safe, loving alternative to a kennel
  • Dogs who’d love to socialize with their sitter’s pets

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog boarding 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 dog boarding 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 dog boarding service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.