Dog Sitting Osprey
Book a Osprey dog sitter to watch your dog in your sitter’s home or yours.

Osprey, 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.
About: I’ve been taking care of animals since I was about 11 and have always been the go-to pet helper in my neighborhood. I grew up loving nature thanks to my mom we were always visiting zoos and wildlife reserves, so being around animals has just always felt natural to me. My family has had both dogs and cats my whole life, and I truly adore them all. Your furry loved one will be treated like family with me and cared for with lots of love and attention 🐾💛 My schedule is fully open at the moment! Would love to take your dog for a walk early morning/late afternoon so it’s not too hot!!! I can also do drop in visits! I am very respectful of your space and treat your home just like it’s my own. I always clean up after myself and your pet, and I make sure everything is left exactly how I found it. Your pet’s safety and comfort are my top priorities. I’m also happy to host pets in my home, where they’ll receive lots of attention and care.

About: Hello! My name is Skylar Kerr and I am an Elementary Music teacher in Sarasota. I LOVE dogs, and being in a place where I can’t have a dog of my own yet has been hard. I am excited to get to love your dogs and play with them now too. Pet sitting is something I've done for many years and have grown up with 5 dogs of my own. I also have experience with dogs of all ages. From house sitting a 1 year old for two weeks, as well as helping to take care of my own 15 year old pup who I had to help go in and out to use the restroom and wake to make sure he eats. I love going for walks and know that some dogs need more patience than others, and some need more energy than others(LOTS MORE). I am excited and look forward to getting to play and bond with your puppies!! I am currently working full time so during the week I am available in the morning and afternoons to check in on your pups. And on the weekends have all the time to give them the love and activity they would need while you’re away! I live in a ground floor condo giving easy access for pups of all ages, as well as a large community area to walk around with lots of grass and open space. I can happily crate your dog if needed or give them the living room to lounge in while gone for short periods of time. And will happily continue whatever care your pets are used to in your own home!
About: I’m a huge animal lover, I have 2 dogs and 2 cats. Neighbors, family and friends have all relied on me, numerous times to take care of their fur babies! I love animals of all kinds. I’m available all day, through out week, including weekends. I have no restrictions on times or days to come take care and play with your pet/s. I have a fenced in yard, 2 super friendly dogs, I also have a safe space for my dogs or yours to explore if any pets get uncomfortable. I have no problem taking long walks, or playing fetch, whatever your pet may enjoy.
About: Hi, I’m Hannah — a lifelong lover of animals big or small, furry or feathered, shy or spirited! I have a B.S. in Zoology from Michigan State University and years of hands-on experience caring for animals in a multitude of environments. I gained experience at home with two beloved family dogs before working as a pet sitter, walker, and trainer around my neighborhood. From there, I volunteered to care for both cats and dogs at Help From My Friends Pet Crisis Center in Michigan and at Crazy Horse Rescue Ranch in California. So whether it’s feeding, cleaning, or just providing a little extra love, I’m comfortable with pets of all ages, sizes, needs, and temperaments. Now in Sarasota, I’m excited to offer attentive pet care services to local families and community members. I’m here to treat your pet like one of my own be it a daily walk, check-in, or overnight care. I am currently working part-time as a barista, so I have flexible availability starting in the afternoon to check-in, feed, and exercise your pets every day. When I care for pets in a client’s home, I prioritize routine, safety, and comfort. I follow your instructions closely from feeding schedules to medications to walks or quiet time so your pet feels secure and at ease. I’m mindful of your home and always make sure doors, gates, and leashes are secure. I also keep things clean and organized and love to send updates and photos so that you know your pet is doing well while you’re away.
“This was our first experience using Rover in Florida and Katie did a great job taking care of our cat Cami. She kept us informed with pictures and put our mind at ease. We will definitely use her in the future.”

About: I’ve had dogs my whole life and just got a new puppy, who I’m currently training! Caring for dogs comes naturally to me. I’m a newer sitter on here, but I’m not new to giving caring love to my own pets and bringing that same level of care to every pet I meet, canine or feline. I’m in school getting ready to go into my junior year in 2026 at USF, so my schedule is flexible! I’m available most days. Let me know what works for you! Due to my own dogs that I need to walk and feed before heading out, I’m not available for walks or drop-ins earlier than 8:00 AM. My oldest dog takes medication nightly and I’m currently house training my puppy, so I understand its importance. I follow routines, keep pets safe, and ensure they feel loved and comfortable while you’re away.
About: I have had a dog my entire life and I have dog sat for many families either for daily care or long term care (i.e. vacation purposes). I am very thoughtful in how I care for your fur babies and would love to work with you! I just moved to the sarasota area for nursing school and I am walking dogs with all of my free time. I am available most days/times, so don’t hesitate to reach out or shoot me a schedule! I currently have no pets of my own as I just moved from out of state into an apartment here. I am willing take care of your animals in their own space or take them for a walk in your neighborhood!
About: I've had dogs my whole life, love them all. My kids are now in college and I have more time to spend doing things that I love! I have 2 dogs of my own at home. I have fostered for Florida Boxer Rescue before and rescued my current dogs from Satchels Last Resort. I currently work part time from home so my schedule is super flexible! I live in Osprey and love to get out of the house so I'm not on the computer all day! I want your pets to feel comfortable in their own home so I'll gladly come by on a schedule that you prefer! I know my dogs feel better being at home vs a kennel or other strange place!
About: I am the go-to person within my workplace for all dog sitting needs. I’ve had dogs come to my place and I’ve also stayed at others homes. I enjoy playing with dogs and taking them on walks. There is no doubt that any dog will go unloved or cared for during the time their owner is gone. I’m a big puppy cuddler!! I work at a coffee shop downtown, and don’t work more than 6 hours a day. I have a lot of free time on my hands! If I am caring for an animal at the clients home, I will bring whatever I need to the home that way I can give my full attention to the pets and not have to go back and forth between my place and the home. I’m very flexible as well! If the animal is staying at my place, I’ve had ppl bring all of their pets essentials and I dnt mind if they lay on my couch or bed! As long as they are comfortable!

“Gretchen is responsive and dependable. She genuinely loves dogs and always sends a sweet picture of my pup. I appreciate her and would recommend her. I have booked her several times.”

About: Hi! I’m Allie. I grew up with four golden retrievers and have cared for others’ pets since I was a little girl. I have experience with puppies, seniors, anxious dogs, hyper dogs, slow dogs, sick dogs, and everything in between. I treat all dogs like my own - with love, humility, and respect. I am new to Chicago and was recently laid off, so I have all the time in the world to care for your pup. I have a very flexible schedule. My building allows dogs under 25 lbs. I am in a small space on a quiet street near lots of grass outside. I am attentive, intuitive, and caring.

About: I've had dogs and cats my whole life so I have a lot of experience caring for them. They become my family and I love them dearly. I treat them better than most people treat their children. I would do anything for them, and I would treat any other pet the exact same way, as if they were my own. I live in a house with a fenced in backyard, great for running and playing. I live in a safe neighborhood with large sidewalks that are great for afternoon walks. I have a standard poodle and a mini-poodle who love to run and play together, they would make your pet feel welcomed and right at home. I also have two cats that are very friendly and loves the dogs. Pet care is a natural part of my daily routine. I plan my schedule around visits, ensuring, consistent, reliable care, timely walks, feedings, and regular updates. I follow each pets routine closely, including feeding, walks, medications, and playtime. I maintain a clean, safe environment and provide regular updates for peace of mind.

About: Dogs have always been a huge part of my life, especially senior dogs. I foster older pups for dog rescues here in Florida, and when I’m not fostering, I offer pet sitting services. I’m patient, attentive, and truly enjoy getting to know each dog’s personality and needs. Whether your pet is young or in their golden years, they’ll be loved and well cared for with me. When I’m not fostering, I pet sit and structure my days around the needs of the pets in my care to make sure they receive consistent, reliable, and loving attention. I am currently home enough to provide regular check-ins and make sure pets feel safe, relaxed, and well cared for. I would follow all the directions provided to me by the pet parent and treat the pet with the caution and care that I would my own.
About: I recently relocated to Sarasota, FL from Boston after many years of caring for pets back home. I’ve grown up with animals my whole life and have had my own pets for over 20 years, giving me a deep understanding of their needs and behaviors. I currently share my home with two cats and a dog, so I’m familiar with the daily joys and responsibilities of pet care. Over the years, I’ve also pet-sat for friends, neighbors, family, and colleagues, caring for their cats and dogs with the same love and attention I give my own. I specialize in thoughtful, loving care for pets of all ages and personalities—from playful puppies to senior dogs, and curious kittens to shy adult cats. I also volunteer as a cat socializer at a local animal shelter, helping nervous or anxious cats gain trust and confidence. ****While I’m new to Rover as a sitter, I’ve been a trusted pet caregiver outside the app for years and can provide references if needed. I’ve also used Rover myself as a pet parent, so I understand how important clear communication, respecting routines, and truly connecting with your pets are.**** Whether it’s a dog who loves long walks or a cat who needs a calm presence, I bring reliability, patience, and a deep love for animals to every booking. I have a very open and flexible schedule, which lets me give pets the time and attention they truly deserve. Working remotely throughout the day means I can easily accommodate pets who need extra companionship, custom routines, or even last-minute bookings. My dog and two cats keep me on a regular pet care rhythm—walks, meals, playtime, and plenty of interaction are already part of my daily life! I believe pets thrive when they can stay in their familiar environment, so I’m happy to care for them right in their home where they feel safest. I’m very respectful of each pet’s existing routine—whether that’s specific feeding times, walks, medication, or bedtime rituals- I do my best to keep everything consistent and stress-free. I offer both drop-in visits and overnight stays, depending on your pet’s needs. Whether it’s a quick check-in for a midday walk or staying overnight for full-time companionship, I make sure your pet feels loved, comfortable, and cared for while you’re away. I also keep pet parents updated with photos and messages, so you can feel connected and confident every step of the way!!
About: I’m a counselor during the school year and have side jobs to supplement my income. Kids and animals love me as I love them even more! ;) For the pets that I fall in love with, I will maintain those services throughout the entire year. I have a therapy dog that works along side me. I’ve given medicine, bathe them, love them and be their fill in mommy until you return. ;) I’m also open to discussing the costs. ***Currently I don’t have any pets of my own so I have a lot of flexibility. The therapy dog is a volunteer. I have a lot of flexibility as this is my only job at the moment. I am off during the summers so I enjoy working with animals. During the school year I’m a school counselor. I feed them, provide love, walks, and play with them. I am happy to have your kennel here for them to feel comfortable in their little home.
About: I have grown up with dogs my whole life , from small to large and have been entrusted by family, friends and word of mouth for pet sitting. I am reliable and very conscientious about pet family members. I have a part time job working with special needs children and have many days off including holidays, summers and various other days. Weekends are always flexible and I am off all weekend. Currently we don't have any pets. We have a pool with a fence around it almost and an acre yard and a park at the end of our street. I would be available to walk pets in their home, feed and be a companion for visits or watch a dog that is house trained or crate trained in my home.
About: I have three dogs at home currently but have had and cared for dogs as well as cats my entire life. I am an animal person, passionate about the welfare and well-being of all animals. I work full time with my work schedule changing weekly. Let me know your pet's needs and I can make sure to create a schedule that will meet their needs. I typically work 8 hours at a time, 5 days a week. When I am not home I hardly leave the house so I can stay with your pup or kitty every other hour of the day. I am willing to do whatever will make your pet the most comfortable. If your pet just needs their basic needs met and isn't huge on strangers, I can give them their space. If they need to cuddle up to me in bed to sleep comfortably, I welcome that!
The median cost per visit for dog sitting in Osprey is $22
Dog parents share their Rover experiences - Osprey
Dot was wonderful with my Goldendoodle, Charlie. From our first conversation throughout Charlie’s visit with Dot, her communication and the comfort she provided was exceptional. Great attention to detail, promptness and follow through with instructions. Dot has a kind and loving personality. That was a perfect match for my fur baby. I will be hiring her again.
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 Osprey sitters!Sitters in Osprey average 5 repeat dog sitting clients
FAQs for Drop-In Visits - Osprey
Frequently asked questions about Rover
As of June 2026, there are 1,707 sitters on Rover offering Dog Sitting across Osprey. 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 Osprey 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 Osprey 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 Osprey 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 Osprey. On Rover:
- 94% of sitters can help with special care needs
- 95% 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.








