Dog Boarding in Oakland, FL

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Top rated Oakland dog boarders

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

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Sitter Profile Image: Idalis L.
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Idalis L.
Star Sitter
from
$35
per night
5.0 out of 5 stars
84 reviews
29 repeat clients
10 years of experience
Clermont, FL, 34711

Idalis was amazing with our dog! She provided frequent updates and photos. Her family thoroughly enjoyed caring for him and he loved all of the attention. It's hard to find someone with such a genuine heart. The next time we need help with care for our dog, she will be the one for us. Thank you!!!

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Daniel G.
Sitter Profile Image: Mimi E.
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Mimi E.
Star Sitter
from
$30
per night
4.8 out of 5 stars
57 reviews
19 repeat clients
5 years of experience
Winter garden, FL, 34787

Mimi was so great! She sent updates and gave us reassurance that our pup was adjusting well. She goes above and beyond to make dogs and their owners feel at ease. Thanks, Mimi!

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Alyssa W.
Sitter Profile Image: Poliana D.
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Poliana D.
Star Sitter
from
$55
per night
5.0 out of 5 stars
595 reviews
157 repeat clients
15 years of experience
Windermere, FL, 34786

Our dog had a wonderful stay with Poliana! She had quick communication and sent great pictures. Our dog came home so happy and had a great time! ? We would 100% recommend.

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Lexi S.
Sitter Profile Image: Christine P.
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Christine P.
Star Sitter
from
$30
per night
5.0 out of 5 stars
58 reviews
25 repeat clients
15 years of experience
Clermont, FL, 34711

Christine took wonderful care of my Great Dane. She updated us with pictures and filled us in on Otto’s day. I didn’t realize I hadn’t given her enough of Otto’s dry food, and she went to Petco and got the same exact brand for him. Would recommend 100%.

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Brandi P.
Sitter Profile Image: Connor R.
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Connor R.
from
$35
per night
5.0 out of 5 stars
9 reviews
1 repeat client
10 years of experience
Winter Garden, FL, 34787

Connor was fantastic with Grace so much so she’s knocked out. He treated her as if she was his, he sent lots of photos and made me feel very comfortable leaving her with him. We will be returning.

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Martha F.
Sitter Profile Image: Andrew M.
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Andrew M.
from
$45
per night
5.0 out of 5 stars
315 reviews
138 repeat clients
30 years of experience
Clermont, FL, 34715

Our dogs had a great time, Andrew sent pictures every day and gave us a little update on how they were doing. This was great. We will definitely use Andrew again.

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Melanie C.
Sitter Profile Image: Wannena P.
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Wannena P.
Star Sitter
from
$39
per night
5.0 out of 5 stars
19 reviews
9 repeat clients
12 years of experience
Winter Garden, FL, 34787

My dog ​​came back happy after being at her house for almost a week. She is very attentive, always sending pictures of him doing all sorts of things, even when he's eating. I recommend her; my dog ​​loves her, and we'll definitely be back!

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Maria L.
Sitter Profile Image: Monica S.
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Monica S.
Star Sitter
from
$45
per night
5.0 out of 5 stars
33 reviews
10 repeat clients
55 years of experience
Winter Garden, FL, 34787

Monica was absolutely fantastic while caring for our dog, Willa. She was so easy to work with, dependable, and kept us updated every day with messages and photos, which gave us tremendous peace of mind while we were away. It was obvious that Willa was well cared for and receiving lots of attention and love. Monica treated Willa like one of her own, and we could tell how comfortable and happy she was in her care. We are so grateful for everything Monica did and would highly recommend her to anyone looking for a caring, trustworthy pet sitter.

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Laura M.
Sitter Profile Image: Brittany H.
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Brittany H.
Star Sitter
from
$38
per night
5.0 out of 5 stars
223 reviews
96 repeat clients
10 years of experience
Clermont, FL, 34711

Brittany was great - patient and very good with our pup. Communication was great and she was available and ready for us for both drop off and pick up.

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Rachel B.
Sitter Profile Image: Margarita N.
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Margarita N.
Star Sitter
from
$50
per night
5.0 out of 5 stars
89 reviews
23 repeat clients
22 years of experience
Clermont, FL, 34711

Margarita is an amazing dog sitter. Sends pictures & updates as requested. My dog is always excited to see her. Appreciate all the love & attention her and her husband give to my fur baby. Highly recommend

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Jacqlyn E.
Sitter Profile Image: Theresa R.
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Theresa R.
Star Sitter
from
$30
per night
5.0 out of 5 stars
32 reviews
13 repeat clients
10 years of experience
Clermont, FL, 34711

Warm and wonderful! Great communication, flexible and accommodating. We are confident our dog received top notch care while we were away! Definitely recommend and we will be back.

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Julie C.
Sitter Profile Image: Wilfredo C.
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Wilfredo C.
Star Sitter
from
$25
per night
5.0 out of 5 stars
34 reviews
11 repeat clients
30 years of experience
Clermont, FL, 34711

Wil is the best. He watched Cody for 2.5 weeks while we were out of town. I can tell Cody was comfortable and got enough exercises. Wil kept us updated by sending pictures and videos for the first week. My kids missed Cody and seeing his pictures helped. I'm glad that I found Wil and I'll consider using his service again in the future

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Latif A.
Sitter Profile Image: Kayla W.
Verified Background Check
Kayla W.
Star Sitter
from
$30
per night
4.9 out of 5 stars
167 reviews
82 repeat clients
6 years of experience
Apopka, FL, 32703

Kayla did an excellent job taking care of JR for us. She went above and beyond. She sent regular pictures and we could tell that she made him feel right at home. Her back yard was a plus for him. We were so thankful for her wonderful service and highly recommend her.

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Kathy B.
Sitter Profile Image: Jerry P.
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Jerry P.
from
$55
per night
5.0 out of 5 stars
601 reviews
305 repeat clients
15 years of experience
Windermere, FL, 34786

An amazing guy and an amazing dog dad! Forever our go to from here on out. Text and pics regularly and our pup was clearly happy and loved when we arrived to pick her back up each time.

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Jess H.
Sitter Profile Image: Pornchanok B.
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Pornchanok B.
from
$20
per night
5.0 out of 5 stars
3 reviews
20 years of experience
Ocoee, FL, 34761

Pornchanok and her husband Jim were AMAZING! This was the first time I ever left my dog with a sitter and I felt very comfortable doing so. Everyday they would send my pictures and videos updating me about my dog without even asking. I met with them before booking so they could make sure she was a good fit because we wanted to make sure both my dog and their dog got along well but also to make sure my dog was comfortable being around them. I really appreciated everything they did and would definitely book with them again in the future if needed!

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Savannah S.
Sitter Profile Image: Savannah L.
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Savannah L.
Star Sitter
from
$50
per night
5.0 out of 5 stars
138 reviews
42 repeat clients
12 years of experience
Florida Center North, Orlando, FL, 32811

Savannah helped us out in a bind as our regular sitter was on vacation. Could not have been happier! She was responsive, soft approach with our doggo, Kona took to her and her home/kids well, sent pictures regularly and updates. Felt she was well tended to even when she didn’t eat one of her meals being a picky eater, Savannah went to the lengths to try to entice her like she were her own. Thank you again and will be using her again!

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Suraj M.
Sitter Profile Image: Danielle G.
Verified Enhanced Background Check
Danielle G.
Star Sitter
from
$50
per night
5.0 out of 5 stars
8 reviews
3 repeat clients
20 years of experience
Windermere, FL, 34786

Our new puppy found a home away from home staying with Danielle! I can’t recommend her enough. The whole family (including pets!) is so welcoming, we received lots of pictures, videos, and updates while we were gone, and we could easily tell she was in good hands.

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Kaitlin L.
Sitter Profile Image: Jennifer R.
Verified Enhanced Background Check
Jennifer R.
from
$24
per night
4.9 out of 5 stars
114 reviews
38 repeat clients
35 years of experience
Groveland, FL, 34736

We have left our 2 dogs with Jennifer twice and they love staying with her. She does have several other animals and my kids enjoy saying hello to all of them when we drop off and pick up our fur-babies. She is great with communication and very kind! Definitely a lover of all animals and will treat your fur-babies the same!

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Jessica O.
Sitter Profile Image: Brooke A.
Verified Enhanced Background Check
Brooke A.
Star Sitter
from
$28
per night
5.0 out of 5 stars
256 reviews
78 repeat clients
4 years of experience
Central Business District, orlando, FL, 32801

Brooke was amazing with my 3 cats! They warmed up to her right away, and I really appreciated the pictures and updates she sent me throughout the days during their 3 day vacation. I could tell she loved them just like I do! She even sent them home with a little goodie bag with toys and treats. Will definitely book with Brooke again!

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Sarah T.
Sitter Profile Image: Marco & Mara S.
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Marco & Mara S.
Star Sitter
from
$35
per night
5.0 out of 5 stars
21 reviews
6 repeat clients
10 years of experience
Ocoee, FL, 34761

I will be using Marco & mara again such a nice couple and our lily was so happy 😊 she loved it there got her home and she just went to sleep they tired her out with all the excitement and playing they did highly recommend them

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Bridget M.
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Over 28
pet parents in Oakland have booked dog boarding

Oakland dog parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Ashley and her husband were so amazing and took such good care of our Cocoa. We were last minute too so their flexibility was so helpful!

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John M.
Boarding
5.0 out of 5 stars

Mimi was terrific and Lulu was well taken care of and happy ! She was with 3 other dogs and they all got along ! Thank you Mimi …we will see you again soon xoxo. Lulu & Victoria

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Victoria R.
Boarding
5.0 out of 5 stars

Connor was fantastic with Grace so much so she’s knocked out. He treated her as if she was his, he sent lots of photos and made me feel very comfortable leaving her with him. We will be returning.

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Martha F.
Boarding
5.0 out of 5 stars

This is our second booking with Caroline (first time boarding) and could not recommend her enough! She is phenomenal with our 1 year old lab, Sailor. We loved the video update of Sailor and her pup, Olive, running around in their yard playing!

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Kallee & Daniel C.
Boarding
5.0 out of 5 stars

5 stars! Lani was very responsive and sent a lot of pictures. She had our fur baby for over a week and he came back happy and healthy!

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Nicole G.
Boarding
5.0 out of 5 stars

Our Boston Terrier loves Julie & her family, they treat her like their own. She sends us photos everyday and follows all medication instructions. We have recommended her to others and will continue to do so.

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Leonard B.
Boarding
5.0 out of 5 stars

Chella and her boyfriend are so sweet. They watched our boy for 5 days while we were on vacation and I’d definitely use them again!

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Meagan A.
Boarding
5.0 out of 5 stars

Sara and her family took great care of our dog Baymax while we were away! She sent frequent photo updates, and gave him a weekend full of playtime and snuggles. I wouldn't hesitate to book again!

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Ashley M.
Boarding
5.0 out of 5 stars

Linda was great as always! We really appreciate her and the care she takes with our dog. She always keeps us up to date and sends a lot of pictures and videos of his stay.

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Erin B.
Boarding
5.0 out of 5 stars

Our dog Toby had the best time with this family! They were so attentive to him and good with communicating with us during the 2 week stay at their home. We will soooo be using them again when we have to go out of town.

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Jodi D.
Boarding
5.0 out of 5 stars

Buster seemed happy, almost too happy!! I received pictures frequently. I am soo happy to have found Ana and her family to care for him.

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Donna K.
Boarding
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How Rover works

  1. 1. Search

    Read verified reviews by dog parents like you and choose a boarder who’s a great match for you and your dogs
  2. 2. Meet & Greet

    Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

The median cost per night for dog boarding in Oakland is $40

Why Choose Rover?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • 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.

  • World-class support

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

Sitters in Oakland average 12
repeat dog boarding clients

Dog Boarding FAQs

Frequently asked questions about Rover

As of Jun 2026, the median cost of dog boarding in Oakland is $40 per night, including service fees. Boarding your dog for one week typically costs $280. Sitters on Rover set their own rates based on their qualifications, your dog's needs, and their space's amenities. As a result, most Oakland dog boarding rates can be found as low as $24 to as high as $48 per night.

If you’re searching for a Oakland 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.

As of Jun 2026, 2,330 sitters provided dog boarding in Oakland. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, dog boarding sitters 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, 91% of Oakland dog boarding sitters respond in under an hour.

Sitters who provide dog boarding in Oakland have an average of 18 years of experience. Dog boarding sitters with repeat customers have an average of 12 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 Oakland.

Rover makes it easy to find Oakland 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

There are 2,330 dog boarding sitters in Oakland on Rover, so you’re sure to find the perfect match for your dog! In Oakland, 96% of sitters offer daily exercise, 97% offer medication administration, and 90% 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 dog boarding 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 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.