Dog Sitting Osteen

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Over 56
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Osteen, Find top rated dog sitting

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

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Sitter Profile Image: Leslie & James S.
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Leslie & James S.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
• 25 reviews
5 repeat clients
40 years of experience
Orange City, FL, 32763

About: Between my husband and I we have taken care of dogs for over 40 years between our own dogs or a friend's. We have a lot of experience with the care of senior dogs in addition to caring for puppies. Over the years between the two have us we have had our own dogs of whom we have loved and had the pleasure of taking care of. We have a fenced backyard and a doggie door plus tons of doggy toys and snacks so your pup will feel very comfortable with us! I am semi-retired and my husband is fully retired so we are home most of the day almost everyday. We have plenty of time to care for your pup.We have a fully fenced backyard, doggy beds, toys, treats, and a doggy door for convenience. We have a fully fenced yard plus a doggie door that leads out to the backyard. We do not have any dogs right now (our last just passed:( but we will be able to give the utmost attention to your pup!

Sitter Profile Image: Jeffrey B.
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Jeffrey B.
from
$24
per visit
5.0 out of 5 stars
• 4 reviews
1 repeat client
15 years of experience
Sanford, FL, 32773

“Jeffrey took amazing care of Ryla including great walks, fun play time and leaving with Ryla being tired, happy and ready for his return! Will hire again and again.”

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Nancy C.
Sitter Profile Image: Lauryn M.
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Lauryn M.
from
$25
per visit
1 repeat client
25 years of experience
Sanford, FL, 32771

About: I've had animals all my life and I have to say I like them more than most people!! I'm here to offer your family member a home away from home! A second family of their very own! I can help out with special request weather it be extra play time, walks, baths, learning new tricks or just some extra love while mom / dad are away on vacation or work trips!! No more worrying about leaving part of the family behind alone! Family #2 is here to save the day!! Weather it be just for the weekend or a 2 month summer vacation! Family #2 is here! If anything special is needed for your furry friend please let me know and I'll do my best to help!!

Sitter Profile Image: Brianne H.
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Brianne H.
from
$35
per visit
4.7 out of 5 stars
• 21 reviews
2 repeat clients
18 years of experience
Deltona, FL, 32725

About: While attending the University of Florida, I boarded dogs through Rover. I missed my family’s dogs and needed to pay my electric bill & groceries. I loved it, so I continue to offer pet care services now that I’ve graduated and moved back home! I am pursuing another degree online and I work part time remotely, so my schedule is flexible and I am able to spend lots of time with your pets. I’d love to come over and take care of your home! My schedule is very flexible, so I can cater to your pets’ individual needs. I do part time freelance work online, so I can complete it from anywhere. While you are away, you can rest assured that your home is well taken care of. I put everything away in its proper place, and lock all doors when entering/leaving a residence. I only enter common or approved areas, and do not bring anyone else into the home. I do not drink, smoke, vape, etc. Upon your return, you will find your home in the same or better condition than you left it in! All bookings include taking in mail/packages, watering plants, and light housekeeping.

Sitter Profile Image: Ryan W.
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Ryan W.
from
$15
per visit
1 year of experience
Sanford, FL, 32773

About: I am an experienced pet walker and sitter with knowledge in dogs and cats, especially senior dogs. No matter what, I believe that all animals deserve respect and care, in any circumstance. I currently have open availability. I would gladly go take care of any pet. Any day or time. I am also happy to do holidays. I like to keep pets I'm looking after close enough to me that I can readily get to them. Just in case they need help.

Sitter Profile Image: Juan V.
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Juan V.
Star Sitter
from
$66
per visit
4.9 out of 5 stars
• 100 reviews
45 repeat clients
5 years of experience
Sanford, FL, 32771

“Our dogs were very well taken care of and enjoyed a walk with each drop in! We appreciated Juan’s attention to detail and felt so relieved to have our dogs in good hands.”

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Emily M.
Sitter Profile Image: Jadyn S.
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Jadyn S.
from
$13
per visit
5.0 out of 5 stars
• 4 reviews
3 years of experience
Winter Springs, FL, 32708

“Jayden was very friendly with the dogs and attentive and receptive to learning about puppy training so she can help keep consistency.”

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Ralph C.
Sitter Profile Image: Daniel A.
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Daniel A.
from
$30
per visit
4.9 out of 5 stars
• 11 reviews
6 repeat clients
20 years of experience
Sanford, FL, 32771

About: Hello there! I'm thrilled to introduce myself as your experienced and dedicated pet sitter with over 20 years of expertise in caring for dogs. Throughout my extensive career, I've had the pleasure of nurturing countless furry friends, providing them with top-notch care, love, and attention. When it comes to your beloved pooch, rest assured they're in capable hands. Whether it's administering medications with precision or helping with basic training exercises, I'm here to ensure your furry companion receives the best care possible. With years of experience under my belt, I understand the individual needs and quirks of each dog, tailoring my approach to suit their unique personalities and preferences. From daily walks to playtime sessions, I prioritize your dog's physical and mental well-being, keeping them happy, healthy, and engaged throughout their time in my care. Plus, I'm more than happy to provide regular updates and photos, so you can have peace of mind knowing your furry friend is in good hands while you're away. So, whether you're planning a weekend getaway or an extended vacation, you can count on me to provide reliable and compassionate pet sitting services that exceed your expectations. Let's ensure your dog's tail keeps wagging even when you're not around! While I do work full-time, I want to reassure you that your pup won't be left alone for extended periods. My partner works from home, providing an extra layer of care and attention throughout the day. They're just as experienced and knowledgeable in caring for dogs as I am, ensuring that your furry friend receives constant companionship and supervision. With both of us available to tend to your dog's needs, whether it's feeding, playtime, or simply providing comfort, your pup will be in excellent hands around the clock. We're committed to making sure your dog feels loved, happy, and well-cared for throughout their stay with us. Absolutely! Your dog's safety is my top priority, and I'm delighted to assure you that they'll be in a secure and comfortable environment while in my care. My home is equipped with a 6-foot fence in the back and a picket fence in the front, providing a safe and enclosed space for your furry friend to roam and play freely. With these measures in place, you can have peace of mind knowing that your dog will be well-protected during their stay. If you have any specific concerns or questions about their safety, please don't hesitate to let me know—I'm here to ensure both you and your dog feel completely at ease.

Sitter Profile Image: Calvin C.
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Calvin C.
from
$40
per visit
5.0 out of 5 stars
• 15 reviews
3 repeat clients
10 years of experience
Deltona, FL, 32738

About: I care for pets like family. Whether it’s extra playtime for puppies, gentle walks for seniors, or just cuddles for comfort, I give each pet the love and attention they deserve. My goal is to make them feel safe and happy while giving you total peace of mind. I love staying active with my own dog, so walks, play sessions, and exercise are already part of my daily routine. Adding more furry friends into that mix just makes it even better! Caring for pets is something I genuinely enjoy, and I’m happy to make it part of every day. I make every pet feel safe, happy, and loved, just like I do for my own dog. In my home, pets enjoy walks, playtime, and plenty of attention. In a client’s home, I follow their routines closely, provide care and companionship, and send updates so owners can feel confident their pets are well cared for.

Sitter Profile Image: Stephanie P.
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Stephanie P.
from
$20
per visit
5.0 out of 5 stars
• 33 reviews
7 repeat clients
7 years of experience
Lake Mary, FL, 32746

“Stephanie is fantastic! She is reliable and has such a love for dogs. Highly recommend!”

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Brittany S.
Sitter Profile Image: Annette R.
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Annette R.
from
$25
per visit
5.0 out of 5 stars
• 4 reviews
1 repeat client
35 years of experience
Lake Mary, FL, 32746

About: I have always treated every pet with love and kindness. I have administered medication for all illness, even seizures. I constantly speak to pets as if they are human, they answer in their pet language🙂 I am available to care for your pet. I can work out the schedule to accommodate your needs. I look forward to taking care of your pet. I have a fenced in small yard; however, I do have an area within my area where your dog will love to run and play.

Sitter Profile Image: Jasmynne B.
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Jasmynne B.
from
$10
per visit
4 years of experience
Oviedo, FL, 32765

About: Growing up in Mississippi really familiarized me with animals. I took care of animals as big as giant dogs to animals as fragile as a cat my entire life. I’ve also dog-sat for many people from my community during my high school years, before moving to Florida for college. I’ve job shadowed at the vet clinic as well throughout the years so I know a little when it comes to their health as well. I’m also very familiar with administering medications, as I had to do it multiple times for my family’s dogs. I just want to show your dog love and support! I’m a student full time at UCF, but i’m online for this semester because of the need to travel home occasionally! So, i’m available the entire week for any service, minus the weekend (which would only be dog walking or cat sitting). I really have a flexible schedule! When it comes to my own home, I want not only the client to trust me with their pet but I want the pet to feel comfortable as well. I have no pets with me and the environment is kept very clean and organized. As for my clients home, I would say it’s relatively the same. I would do as they asked and maintain a clean and safe environment. Anything to make them feel comfortable with trusting me with their fur baby!

Sitter Profile Image: Brooke C.
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Brooke C.
from
$20
per visit
10 years of experience
Casselberry, FL, 32707

About: As a dog lover I have always had dogs in my life! I’m a responsible, caring, and attentive pet sitter who will treat your pets like they’re my own. I’m comfortable with walks, playtime, feeding routines, cuddles, and making sure your pets feel safe and comfortable while you’re away. I am a business owner and make my own schedule! I have flexible availability throughout the week and weekends — open to come to you or have your doggies stay with us! I have a fenced in yard as well as two friendly dogs who love other doggies! I am also able to come to your home and watch your dogs!

Sitter Profile Image: Eva M.
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Eva M.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
• 10 reviews
4 repeat clients
8 years of experience
Longwood, FL, 32750

About: I've taken care of everything from pitties to kitties! I love animals and dream of having my own mini menagerie someday. I've been petsitting reptiles, cats, and dogs since I was 13 years old, and have never run into any issues. I can render any service from medication to enrichment. I currently work part-time, so I'll have plenty of time to spend with your pet. I have no trouble taking a day off from work if the situation calls for it, and can work around medication schedules even on work days. When taking pets out for walks, leashes are a must! Additionally, any potentially dangerous foods or substances will be put safely out of reach of the pet. I set alarms and reminders for feeding, medication, and appointments to make sure everything is done at the proper time.

Sitter Profile Image: Cynthia W.
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Cynthia W.
from
$18
per visit
5.0 out of 5 stars
• 23 reviews
3 repeat clients
65 years of experience
Edgewater, FL, 32141

“Cynthia is awesome!! She arrived early and was very patient and friendly with my 2 shy cats. I would highly recommend her to any of my friends and family! There’s no one else I would trust ❤️”

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Anasemon W.
Sitter Profile Image: Kamryn B.
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Kamryn B.
from
$20
per visit
10 years of experience
Chuluota, FL, 32766

About: I’ve had a variety of animals my entire life. This includes dogs, cats, reptiles, saltwater fish, and birds. I am skilled in training and working with animals of all ages. I am also able to administer medication if needed. I currently am a college student and I have a part-time job at a saltwater aquarium store. Thursdays is normally my only available day to pet work, but that can change. I am able to make several visits a day and I will provide a safe and clean environment for the animals. If there is a schedule I will make sure to stick to that so that their routine is consistent.

Sitter Profile Image: Ashland B.
Verified Enhanced Background Check
Ashland B.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
• 71 reviews
15 repeat clients
26 years of experience
Casselberry, FL, 32707

“Ashland is absolutely the best care giver for pets! We are beyond grateful for finding her! She is incredibly sweet and her love for animals is amazing. Thank you for sharing all the photos and information from your visits.”

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Brittany C.
Sitter Profile Image: Kalee J.
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Kalee J.
from
$13
per visit
6 years of experience
Longwood, FL, 32750

About: -walking pets -bathing pets -scooping litter -giving meds -playing with pets -senior pet care -special needs pet care -small pets care -trim nails -food accommodations I'm a college student and my life basically revolves around pets. I like to be organized with my schedule so that all the pets I care for get everything the need without fail, I can br flexible though if something needs to be adjusted. I have quite a few pets of my own and I love all pets just like I love my own! I'm willing to have small pets stay over at my house, I have experience with guinea pigs, gerbils, and hermit crabs. Pets such as dogs and cats I will come over to your house. I can walk them, stick to a feeding schedule, play with them, groom them, and give them all the attention they need!

Sitter Profile Image: Emma G.
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Emma G.
from
$20
per visit
5.0 out of 5 stars
• 4 reviews
14 years of experience
Lake Helen, FL, 32744

“Emma was the so attentive & caring for my boys! She really made an effort to understand them & show them lots of love while we were away.”

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Mia C.
Sitter Profile Image: Alexis J.
Verified Enhanced Background Check
Alexis J.
from
$20
per visit
10 years of experience
New Smyrna Beach, FL, 32168

About: I’ve been caring for animals for many years and have always had a passion for pets. I’ve owned two dogs and currently have two cats, so I understand the love, patience, and responsibility that come with caring for animals every day. Friends, family, and neighbors have trusted me to care for their pets by feeding them, giving fresh water, taking dogs on walks, cleaning litter boxes, playing with them, and making sure they feel safe and comfortable while their owners are away. I know that every pet has a different personality, and I enjoy taking the time to make them feel happy and cared for. Whether your pet loves to play, go on walks, or just wants someone to keep them company, I’ll treat them like they’re my own. My goal is to give you peace of mind knowing your pet is in loving, dependable hands. I’m currently a student at the University of Central Florida and attend classes in person two days a week. I also work remotely, which gives me a flexible schedule and allows me to care for pets throughout the day. I live in New Smyrna Beach and can provide reliable drop-in visits, walks, and overnight care while making sure your pet gets plenty of attention, exercise, and companionship. Your pet’s safety and comfort are always my top priorities. I take the time to learn each pet’s routine and follow your care instructions carefully, including feeding schedules, medications, exercise, and any special needs. I’ll treat your home with respect and your pet like one of my own. I’m happy to provide regular updates and photos so you can have peace of mind while you’re away.

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The median cost per visit for dog sitting in Osteen is $20

Dog parents share their Rover experiences - Osteen

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5.0 out of 5 stars

Absolutely enjoyed having Shealeaha come and visit with our boys! She sent me updates throughout the time she came to visit and we used her multiple times the week we were in town. When we come back she will be our first contact!

Profile image
Heather J.
Drop-In Visits
5.0 out of 5 stars

Shea was absolutely amazing! Our dogs loved her and she put us at ease while we were away. It was nice seeing the photos while we were away. I will be using her again!

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Geniva W.
Drop-In Visits
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How to book dog sitting

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Popular requests for dog sitting - Osteen

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Sitters in Osteen average 6
repeat dog sitting clients

FAQs for Dog Sitting - Osteen

Frequently asked questions about Rover

The average cost of Dog Sitting in Osteen is $20 per visit as of November 2026. Most bookings cost between $15 and $28 per visit. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of November 2026, there are 4,090 sitters on Rover offering Dog Sitting across Osteen. Enter your ZIP code to see which available sitters are closest to your home.

You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.

Before booking, confirm:

  • the timing, length, and frequency of visits;
  • the care instructions the sitter should follow;
  • which parts of your pet’s usual routine should be prioritized;
  • how often you would like to receive messages, photos, or other updates.

Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.

Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Osteen choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!

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.

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.

A Meet & Greet is a casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.

Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet or the new environment.

During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first Meet & Greet.

While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.

To find sitters in Osteen with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.

Yes, you can find sitters who have experience with handling special pet needs in Osteen. On Rover:

  • 89% of sitters can help with special care needs
  • 94% can help with giving oral medications or injections
  • 96% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

sitters on Rover set their own cancellation policy, which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.

Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.

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