Dog Sitting Osteen
Book a Osteen dog sitter to watch your dog in your sitter’s home or yours.
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.
“Love Caryna! She sent me photos everyday of my dogs while I was away! She loves my dogs and they love her... I wouldn’t want anyone else to watch my dogs when me and my fiancé are away”
About: Grew up with dogs and cats and have extensive experience caring for them. Pet sitter for the last 7 years, I have experience with all kinds of animals, from rodents to reptiles and all sorts of furry friends. I would love to look after your loved one. I am currently on summer break from college. I have pretty open availability throughout the summer and would love to take care of your furry family member. I have a big fenced in yard with a pool, a screened in porch, and a lot of area to run around and explore the yard with lots of shade.
“Laurie stepped in for us last minute and was both prompt and efficient. She kept us updated throughout and sent plenty of photos of our pups while we were out of town, which we really appreciated.”
About: I have 3 years experience working in pet stores as an animal care expert, 2 years as a dog bather, and 1 year as a kennel technician. I have 3 cats and a hound dog currently and have grown up caring for animals! I am a stay at home mom and my husband works from home. This gives me the freedom to leave my house when needed and care for your babies! I am very passionate about proper animal care. I have 4 pets that I adore, and I will treat your baby as if they were my own! I will ensure that any rules or instructions are followed to a T.
“Emillie and Brittney are very attentive with both of my dogs. They are also very informative and helpful if anything is off. I really appreciate them taking the time to have met my dogs first and let them warm up to Brittney and Emillie before jumping into everything.”
“Becca is warm and responsible and very, very professional. It has been an absolute pleasure to work with her and I’m really grateful that we connected on Rover. Thank you, Becca, for taking such good care of our little one!”
About: I have always taken care of my own dogs and I occasionally help my roommates with their cats and dog whenever they travel. Or if they randomly ask me. Love animals. I currently work full time as an RBT. My schedule consists of 8 hour shifts. 8am-4pm. Monday-Friday. If you need more details about my schedule, you can contact me personally! :) Your pet’s safety and comfort come first. I treat every dog like my own, with reliable care, secure walks, and respect for your home. Trust, communication, and a calm environment are part of every visit.
“My animals love Serena. They don’t even notice when I’m gone thanks to this lovely lady! It’s made seeing family and traveling for work a breeze! I always get amazing pictures and updates of my babies during Serena’s visits and it’s a huge help and pleasure to have her every time!”
“Katie was great with our girl Zoey! She kept in touch, sent pictures, and even brought her a toy after Zoey annihilated all of hers. Will definitely request to use Katie again on our next trip!”
“Hannah (Casey) is fantastic with my year old kittens Maple and Holly. Shes affectionate with them and spends time giving them the attention they need at play time. When I get home everything is taken care of as requested and she's gone above and beyond with little extras like refilling their treat and dry food dispensers, grabbing a delivery of their food, and hiding their catnip when they discovered they could jump on the counter :'D Her photos are also the cutest :)”
“Just knowing that Jamie is checking on our pets, let’s us relax and enjoy our vacation. Whether it’s several nights with Faith and Dolby or check ins when it’s just the cat, we can count on her. Thank you!!!”
“Halee is kind, communicative, attentive and great with our furry crew of one pup and three cats. She listens to our needs for our feeding routine and is just a joy to be around.”
“Kelly was on time for her playtime with Mosley and Molly. She tuckered them out while playing in the backyard. I look forward to having her back so Mosley and Molly can get to know her. I want Kelly and the dogs to become fast friends before we leave on our vacation. Look forward to our next playtime.”
“Stacy does a great job taking care of my two Boston Terrier puppies. She spends good amount of time with the dogs. She takes great photos and she does good check ins.”
About: I’ve had dogs and cats almost all my life, young and old! Im currently a Valencia student doing my two years in hope of one day becoming a veterinarian. I promise to treat every animal I care for as if it was my own. I’ll always make sure your furry friend’s happy and taken care of! I’m currently a student at Valencia college my class load is not very big. I only have to be in class Monday, Wednesday and Friday for about an hour or two midday. I can always be there for your pet even on short notice! I’ll always make sure to clean up after your pets an anything else you need! If there’s anything specific just ask and I’ll make sure it’s ready for when you return home.
“Above and beyond! 2nd time using her service and I always come back to happy dogs. She does things like close the blinds which I totally forgot. Brought packages in without me asking nor expecting. Robin puts back on the dog diapers. It’s the little things that make coming home so easy!”
The median cost per visit for dog sitting in Osteen is $20
Dog parents share their Rover experiences - Osteen
Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.
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 sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
How Rover works
1. Search
Browse profiles of sitters near you who offer dog sitting
2. Meet & Greet
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests near you
Select a filter and find qualifying Osteen sitters!Sitters in Osteen average 6 repeat dog sitting clients
FAQs for Drop-In Visits - Osteen
Frequently asked questions about Rover
As of June 2026, there are 4,147 sitters on Rover offering Dog Sitting across Osteen. Enter your ZIP code to see which available sitters are closest to your home.
A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.
Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Osteen stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.
Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.
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 short introductory meeting between you, your dog, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter 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. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.
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:
- 90% of sitters can help with special care needs
- 97% can help with giving oral medications or injections
- 98% 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 calendar availability.
Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.
Connect anywhere with the Rover app
