House Sitting in Winter Haven

Find a loving dog sitter to watch your dog overnight in your home.

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Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
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Sitter Profile Image: Isabella S.
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Sitter Profile Image: Isabella S.
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1. Isabella S.

Rover 101
Pets are family too!
Davenport, FL, 33837
12.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
65 reviews
23 repeat clients
from
$50
per night

Isabella is very sweet. She was very gentle with my dogs. She sent pictures and kept me updated throughout the day. I will definitely book her again if she is available. I strongly recommend her.

Sitter Profile Image: Evan R.
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Sitter Profile Image: Evan R.
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2. Evan R.

We welcome your furry family here!
Haines City, FL, 33844
7.3 mi. away
Boarding, House Sitting, Doggy Day Care
5.0 out of 5 stars
4 reviews
1 repeat client
from
$35
per night

This was our first time booking Rover and wasn't sure what to expect. BUT Evan was wonderful.. She did exactly what was asked.. Our 2 older dogs can be a bit high maintenance with health issues.. But I can not say enough on how great she was. She stayed the entire time with them, and loved up on them as if they were her own. You can tell Evan loves what she is doing ..We have her booked for our next trip !

Sitter Profile Image: Charity A.
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Sitter Profile Image: Charity A.
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3. Charity A.

Animal Lovers Extraordinaire
Lake Alfred, FL, 33850
4.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
1 repeat client
from
$30
per night

Charity is awesome! She is very caring and kind. She was so great with our dog. He is a little apprehensive of new people and she gave him the needed space when she arrived until he warmed up to her. She gave him lots of love and attention. She took great care of him with plenty of walks and TLC. We highly recommend her.

Sitter Profile Image: Makayla K.
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Sitter Profile Image: Makayla K.
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4. Makayla K.

Animal loving future veterinarian💕
Auburndale, FL, 33823
5.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
1 repeat client
from
$40
per night

I've always been skeptical about getting a sitter for my 5 babies. but, not only Makayla reassure me that everything will be great, she exceeded my expectation when in two days my dogs were fully comfortable with her. The three out of my five babies are very cautious of new people and will start barking like crazy. But she was so patient with them that they always had their tails wagging around her and were so calm. However, nothing compares to how my pregnant dog suddenly gave birth while i was away and she was about to make sure my baby and her newborns were good as well as giving me any updates over the phone call on how she is doing. While it was nerve-racking my absent during her birth, having Makayla there every step of the way made me feel like i choose the best sitter for my babies. You will never regret choosing her!

Sitter Profile Image: Gabby B.
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Sitter Profile Image: Gabby B.
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5. Gabby B.

Experienced Animal Lover
Winter Haven, FL, 33880
4.9 mi. away
House Sitting, Dog Walking
5.0 out of 5 stars
8 reviews
2 repeat clients
from
$45
per night

Gabby was amazing with our dog Chloe! We have only left her once, and that was with family. We met Gabby and she was very nice. We were out of state for 5 days and she made it easy for us as we were nervous! Chloe did so well, we got pictures from Gabby and updates. We absolutely will use her again! Highly recommend!

Sitter Profile Image: Amberlyn B.
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Sitter Profile Image: Amberlyn B.
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6. Amberlyn B.

RoverGO
Rover 101
A tail waggin' good time!
Auburndale, FL, 33823
5.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
1 repeat client
from
$50
per night

Amberlyn hung out with our sweet boy all day and took great care of him. She write me a details update after her shift, which was appreciated!

Sitter Profile Image: Shawnee S.
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Sitter Profile Image: Shawnee S.
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7. Shawnee S.

Rover 101
I love all animals!
Auburndale, FL, 33823
6.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
from
$63
per night

Shawnee stayed with Josey while I went out of town for a night. She was very easy to work with and took good care of my baby. She sent pictures and communicated well.

Sitter Profile Image: Bradley L.
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Sitter Profile Image: Bradley L.
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8. Bradley L.

Rover 101
All dogs big and small!
Bartow, FL, 33830
4.9 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
165 reviews
55 repeat clients
from
$32
per night

Bradley is the best! He is our go to sitter, I wouldn't trust my babies with anyone else. I have peace of mind knowing Bradley will give my dog his medicine every night. He handles my giant rambunctious dog and my little, skittish Westie with loving care and attention. Even my people hating cat likes Bradley! He is very professional and more importantly, my babies are happy and safe under his care.

Sitter Profile Image: Brianna K.
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Sitter Profile Image: Brianna K.
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9. Brianna K.

Hello I love love love animals!
Winter Haven, FL, 33880
1.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
8 reviews
3 repeat clients
from
$30
per night

Brianna is just amazing!!! She has stayed over with my dogs while I was out of town, and the dogs just love her!! She has become another family member to our dogs.

Sitter Profile Image: Javid G.
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Sitter Profile Image: Javid G.
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10. Javid G.

Let’s have a PAW date 😊
Winter Haven, FL, 33881
5.5 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
2 reviews
1 repeat client
from
$35
per night

About: I’ve been taking care of animals as far as I can remember. such as dogs, cats, birds and fish lol. So trust me when I says your fur babies are in great hands. I have a German Shepard/lab dog so taking care of your fur baby will blend right in with our daily walk sessions when the weather allows us to do so. Your for baby will be an excellent hands with the help of our dog Jacob. We have a huge backyard which is more than enough room for the babies to play. Not to worry they are never left unattended

Sitter Profile Image: Morgan V.
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Sitter Profile Image: Morgan V.
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11. Morgan V.

Pet Caretaker Extraordinaire
Winter Haven, FL, 33880
1.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
2 reviews
from
$30
per night

Morgan has watched my dog and cat multiple times. She’s a very trustworthy person and one of the only ones I trust to stay at my house and care for my animals. Highly recommend for any walks, check-ins, and overnight stays.

Sitter Profile Image: Gabriella P.
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Sitter Profile Image: Gabriella P.
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12. Gabriella P.

Dedicated to providing the best!
Winter Haven, FL, 33881
3.0 mi. away
House Sitting, Drop-In Visits
1 review
from
$30
per night

Loves and cares for all the dogs in her care, very good and attentive. She’s always eager to entertain the animals, and often goes above and beyond.

Sitter Profile Image: Katelyn M.
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Sitter Profile Image: Katelyn M.
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13. Katelyn M.

Let me take care of your family
Winter Haven, FL, 33880
4.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
16 years of experience
from
$35
per night

About: I have had my personal animals my entire life, this includes dogs, cats, and horses. I also have experience with small animals and cows. I have been taking care of neighbors and friends pets for about a year and have been very successful in building a relationship with these animals and giving them the best care possible. I am a full time student so I am in the school building from 7am to 2 pm, Monday through Friday. During the summer I am free all the time and I am always free on weekends. I will stay over night in your home to give your pet comfort, and will also feed and walk them as much as you would like.

Sitter Profile Image: Josselin G.
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Sitter Profile Image: Josselin G.
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14. Josselin G.

Pet Lover
Winter Haven, FL, 33880
1.1 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
14 reviews
2 repeat clients
from
$33
per night

Josselin was a perfect match for my pups! She followed my care sheet perfectly and with care. One of my dogs is very skiddish around people and Josselin made sure to be slow and gentle with her. Josselin was also very communicative with giving me updates and having questions. She also was very considerate with keeping my house clean! 100% definitely booking in the future!

Sitter Profile Image: Cat R.
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Sitter Profile Image: Cat R.
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15. Cat R.

I love pets <3
Winter Haven, FL, 33880
1.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
1 repeat client
from
$37
per night

Cat did great on our meet and greet! Very kind and our dog loved her. She is not easily overwhelmed by special need asks. We are excited for our pup to spend the day with her tomorrow!

Sitter Profile Image: Christy M.
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Sitter Profile Image: Christy M.
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16. Christy M.

Animals are better than some people
Winter Haven, FL, 33880
1.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
10 reviews
2 repeat clients
from
$45
per night

Christy would be excellent with any pet. She loves animals. She has even gone to the local shelter to help out with their animals. She is very responsible and trustworthy.

Sitter Profile Image: Heather S.
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Sitter Profile Image: Heather S.
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17. Heather S.

Because pets are people too 🐾
Winter Haven, FL, 33881
1.1 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
30 years of experience
from
$40
per night

About: I have plenty of time, patience and love to give to your babies. I am extremely attentive, love the outdoors, dog parks, walking, hiking, or just snuggling in PJ’s catching up on True Crime documentaries! Whichever your pet requires, I can shape shift to fit their individual needs 🤍 Currently I am a stay at home daughter taking care of the worlds best mother 🫶🏼 I am home all day and take frequent trips to nature parks, ice cream shops (for a pup cup of course) and dog friendly beach trips. We both love animals ridiculously and treat them like we do our own children. I also have two children ages 10 & 13 who are also HUGE animal advocates and often find all of our animals piled up on their beds at night. Our youngest boy is also the neighborhood dog walker. You can trust that your pets would be in not only a kind and loving environment, but our home is also very well kept, clean, in a beautiful neighborhood with a mile long walking track directly across the street from our home. We have pool for those water bugs and a gate around it for those who aren’t 😊 You can trust your pet will always be safe and in case of an unlikely event, I am CPR/First aid/Life support certified for that extra boost of confidence in your pets care.

Sitter Profile Image: Sonia G.
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Sitter Profile Image: Sonia G.
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18. Sonia G.

The doggy whisperer :)
Winter haven, FL, 33880
1.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
24 reviews
7 repeat clients
from
$32
per night

About: Hi my name is Sonia. I am 25 years old and have been caring for pets for a little over 20 years. Growing up I have always had dogs, cats and birds. I have lots of experience in caring for all animals, whether on a farm or a house pet. You name it! I recently got out of the ARMY and I am currently in school working on my degree to become a Veterinarian. In the years prior to the ARMY I volunteered at a local animal hospital caring for the animals who had extended stays. I also have volunteer time with local animal shelters doing dog walks and dropping off items that are needed. I would love to be considered on your dog walking or boarding journey :)

Sitter Profile Image: Raechelle K.
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Sitter Profile Image: Raechelle K.
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19. Raechelle K.

Animals are my passion
Winter Haven, FL
1.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
8 reviews
1 repeat client
from
$30
per night

Raechelle is amazing ! She took great care of my Great Dane for a week and my house was clean when I returned home. I will definitely be calling her again.

Sitter Profile Image: Dante B.
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Sitter Profile Image: Dante B.
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20. Dante B.

Im a loving dog person!!
Winter Haven, FL, 33881
2.1 mi. away
House Sitting, Dog Walking
3.0 out of 5 stars
3 reviews
from
$35
per night

Dante is a very trustworthy and caring person. He has a special love for dogs. He takes excellent care of dogs and is always willing to help out. Dante is what I would call a dog whisperer. Every dog big or small loves playing with him. I would 100 percent recommend letting Dante take care of your pets.

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Winter Haven House Sitting ratings

Overall Rating:
4.8 out of 5 stars

House sitters in Winter Haven are rated on average 4.8 out of 5 stars based on 81 reviews.

Rover also offers House Sitting in:

Rover also offers other services in Winter Haven:

Never beg a friend to watch your house again. With Rover, you can find the perfect house sitter in seconds. Rover sitters are pet lovers, who will be happy to sit dogs, cats, caged pets, and even horses while they take care of your home. By removing common pet care obstacles, Rover ensures dogs nationwide are happy and well-cared for even when their human is away, and empowers pet lovers to live happy and fulfilling lives. Founded on the belief that everyone should have the opportunity to experience the unconditional love of a pet, Rover makes it easy for you to reach trusted house sitters who can provide the care your pet needs, when they need it.

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