Dog Sitting Winter Park

Book a Winter Park dog sitter to watch your dog in your sitter’s home or yours.

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Over 693
pet parents in Winter Park have booked dog sitting

Winter Park, 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: Carolina S.
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Carolina S.
from
$30
per visit
5.0 out of 5 stars
36 reviews
19 repeat clients
25 years of experience
North Orange, Winter Park, FL, 32789

Carolina did a wonderful job with Levi for his drop in visit! She kept me well informed and made sure my little guy was feeling relaxed before leaving him, and overall exceeded expectations. Would highly recommend her!

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Erika W.
Sitter Profile Image: Glacie D.
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Glacie D.
from
$17
per visit
5.0 out of 5 stars
56 reviews
20 repeat clients
7 years of experience
Winter Park, FL, 32792

We just moved into the area and was able to schedule Glacie for a drop in visit for our pups. She did an excellent job and will definitely schedule her again.

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Ken K.
Sitter Profile Image: Patama B.
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Patama B.
from
$18
per visit
4.0 out of 5 stars
3 reviews
1 repeat client
20 years of experience
Winter Park, FL, 32789

About: Hi! I’ve always been an animal lover — I’ve grown up with dogs for my whole life. I treat every dog like my own. walks, cuddles, and lots of playtime! My daily routine already includes lots of pet time! I work from home, so it’s easy for me to give attention, walks, and love throughout the day. Having furry friends around just makes everything better I have a sweet dog at home, so your pup will have a little friend to hang out with! I make sure they feel comfy, get walks, playtime, and lots of love — just like they’re part of the family.

Sitter Profile Image: Mackenzie W.
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Mackenzie W.
from
$13
per visit
4 years of experience
Winter Park, FL, 32789

About: I’m new to Rover, but not new to pets. I’ve spent years dog and cat sitting for family, friends, and people from my church while they travel so I’ve basically already been doing this, just without the app. Boarding is where I’m strongest. Whatever you’re away for a weekend trip, a long workweek, a stretch out of town your pet gets a quiet, pet free home and someone who’s actually paying attention to them, not just checking a box. It’s just me and my roommate here, no kids, no chaos, no other pets running around unless we’re talking about yours LOL. But if boarding isn’t what you need, I also do drop in visits and walks. A midday or evening walk for your dog, or a quick morning/night stop to feed and check on your cat while you’re out. My schedule’s flexible (I work fulltime but it’s not a rigid 9-5), so I can usually make mornings, evenings, weekends, whenever your pet needs me. I’m not the type to drop them off with food and a bowl and disappear for the day. I want to actually know their personality by the time you pick them up. I’ve taken care of dogs and cats of pretty much every age and energy level, from the zoomies at 6am crowd to older pets who just want someone patient around and a quiet spot to nap. Routines matter to me too if your pet eats at a certain time, walks a certain route, or has a little quirk, I want to know about it and stick to it. I’ll keep you in the loop while I’m with them. Feeding on schedule, medication if they need it, litter box scooped, fresh water, the whole routine handled the way you’d do it yourself. Photo updates too, so you’re never left wondering how things are going. Can’t wait to meet you both and hear what your pet’s routine looks like. My schedule is flexible, so I’m available mornings, evenings, weekends, and throughout the week as needed. I take the time to learn your pet’s personality, preferences, and routine so they can feel as comfortable as possible. I know how hard it can be to leave your pet with someone else, so I do my best to make them feel safe, comfortable, and loved while you’re away. Whether they’re staying in my home or I’m stopping by yours, I follow their routine as closely as possible, including feeding schedules, potty breaks, walks, medications, and any special instructions you provide. I provide a calm, pet free home for boarding and make sure every pet gets plenty of attention and care. I also send photo updates throughout their stay because I’d want the same thing if it were my pet. My goal is for you to enjoy your time away knowing your pet is in good hands

Sitter Profile Image: Maya C.
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Maya C.
from
$18
per visit
4.6 out of 5 stars
14 reviews
5 repeat clients
4 years of experience
Winter Park, FL, 32792

Maya was very accommodating and quick to respond to any questions or concerns. I'd happily rebook with her!

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Ariana M.
Sitter Profile Image: Hannah M.
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Hannah M.
from
$20
per visit
5.0 out of 5 stars
39 reviews
12 repeat clients
12 years of experience
Altamonte Springs, FL, 32701

Hannah always does a great job with our three dogs and two cats when we travel! I highly recommend her 😁

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Christopher B.
Sitter Profile Image: Tatiana M.
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Tatiana M.
Star Sitter
from
$26
per visit
5.0 out of 5 stars
185 reviews
88 repeat clients
10 years of experience
Casselberry, FL, 32707

Tatiana replaced our smoke alarm battery when it died while we were away because it kept beeping and she was concerned for Molly. This is not a sitter who goes through the motions (although she is thorough with photos and check-ins) but rather she cares about your home and your pet.

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Patricia J.
Sitter Profile Image: Meghan W.
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Meghan W.
from
$20
per visit
5.0 out of 5 stars
17 reviews
7 repeat clients
25 years of experience
Winter Park, FL, 32792

Meghan was excellent! I get anxious leaving our babies, but made me feel confident that our doggos were in good hands. She sent lots of pics and updates.

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Melissa R.
Sitter Profile Image: Emilee P.
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Emilee P.
from
$15
per visit
5.0 out of 5 stars
5 reviews
2 repeat clients
8 years of experience
Orlando, FL, 32803

My Mia always looks so happy to see her in the pictures!

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Emily P.
Sitter Profile Image: Narghess M.
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Narghess M.
from
$20
per visit
9 years of experience
Winter Park, FL, 32789

About: Animals have been part of my life for as long as I can remember. I currently have a senior dog who I’ve cared for since I was 13, so I understand how to be patient and attentive with older pets. I also help take care of my neighbors’ and family friends’ dogs regularly. I’m a full-time student who also works, but pet sitting is something I genuinely enjoy. Spending time with dogs is a peaceful escape for me, and I treat every pet with the same love and care I give my own. My experience with pets of all ages and my genuine passion for animals is what sets me apart from other sitters. I currently work part-time, which gives me the flexibility to prioritize pet care throughout my week. I’m completely available on weekends and can care for your pet after 4 PM on weekdays. Whether it’s drop-in visits, walks, or overnight stays, I genuinely enjoy making time for animals and giving them the attention they deserve. When caring for pets in my home, I make sure they have a safe, clean, and comfortable space with plenty of love, playtime, and attention. I follow any feeding or medication instructions carefully and keep their routine as consistent as possible. In a client’s home, I respect their space and always make sure pets feel relaxed and secure in their familiar environment. I provide regular walks, play, and updates, and I’m attentive to each pet’s unique personality and needs.

Sitter Profile Image: Brittney R.
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Brittney R.
from
$17
per visit
5.0 out of 5 stars
8 reviews
3 repeat clients
8 years of experience
Maitland, FL, 32751

Incredibly helpful and quick to assist in a pinch. Adapted to my dogs’ usual schedules for a few visits while we were out of town. We’ll definitely reach back out (with more of a heads up next time)!

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Adam L.
Sitter Profile Image: Evan R.
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Evan R.
from
$14
per visit
5.0 out of 5 stars
19 reviews
2 repeat clients
8 years of experience
Colonicaltown North, Orlando, FL, 32803

About: I am a passionate about pet care with eight years of experience in providing exceptional care for dogs and cats. I am committed to building a strong bond with pet(s). I prioritize health, happiness, and well-being in every interaction. Daily routines include feeding, exercising, and TLC. Each morning I feed my two dogs and take them for a walk. We then come home and get treats before letting them enjoy playtime. We then go on an afternoon walk with the same feeding and exercise routine at night. Your pet is my priority. If they have a routing they need to follow then that is the schedule we will set. My animals are my children, so I understand what it’s like to make sure they enjoy their time.

Sitter Profile Image: Veronica S.
Verified Background Check
Veronica S.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
29 reviews
6 repeat clients
24 years of experience
Orlando, FL, 32804

Excellent pet care and service! Veronica was very detailed oriented and went above and beyond to take care of my sweet cat. I’m very thankful and will use her services again!

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David K.
Sitter Profile Image: Samuel C.
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Samuel C.
from
$20
per visit
4.9 out of 5 stars
11 reviews
5 repeat clients
10 years of experience
Winter Park, FL, 32789

Buttercup was super happy when she came back from her walk! Samuel had inastant rapport with her and great communication with me. Definitely would recommend!!!

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Deborah S.
Sitter Profile Image: Amber P.
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Amber P.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
21 reviews
4 repeat clients
10 years of experience
Winter Park, FL, 32789

About: Pet parents love leaving their dogs in my care because they know they don’t have to worry. I take the time to learn your dog’s routine, send regular updates with quality photos, and provide a cozy home sanctuary where your pup will be loved and cared for like my own. I’m an artist working out of my home studio, allowing plenty of flexibility throughout the week to offer hands-on care. I’m also available most weekends for boarding. Your dog will spend the day in a calm, loving home with a large, fully fenced yard — perfect for play, sunbathing, and safe exploration. Inside, pets enjoy a relaxed environment with cozy rest areas and plenty of attention. We will enjoy multiple walks per day in a quiet and safe neighborhood.

Sitter Profile Image: Christopher Q.
Verified Enhanced Background Check
Christopher Q.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
24 reviews
5 repeat clients
6 years of experience
Orlando, FL, 32817

Christopher was fantastic with my animals and took great care of them ! He was timely and sent plenty of photos

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Robert H.
Sitter Profile Image: Altynai G.
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Altynai G.
from
$17
per visit
4.9 out of 5 stars
162 reviews
53 repeat clients
10 years of experience
Maitland, FL, 32751

Aly is so wonderful to work with. When our old pet sitter moved we were devastated. Our girls are precious to us and we were worried we wouldn’t be able to find another sitter that would have the same compassion for them that we could trust. All of my fears went away when we met Aly. She came over for a meet and greet and immediately her calm energy eased all my worries. Our cats are pretty shy with strangers, but when Aly came in and went to greet them they met her with interest and curiosity (and didn’t run away!) They sat calm next to Aly and she patiently let them sniff her until they were comfortable. Talking with Aly, it was clear her love for animals and this type of work. I immediately booked her when we said our goodbyes. During her check ins, Aly is prompt, detailed, and so loving to our girls. I’m so surprised that our shy girl, Pepper, has come out so much for her! She was born right before the covid outbreak and didn’t get much interaction with strangers in our home. Despite that, Aly had some play sessions with Pepper and she even wanted some pets! It makes my little cat mom heart swell with happiness. Needless to say, we’ve found our new favorite pet sitter in Orlando. We can’t wait to become Aly’s regulars. Thank you so much Aly! ☺️💛

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Melanie S.
Sitter Profile Image: Sherry c.
Verified Enhanced Background Check
Sherry c.
Star Sitter
from
$14
per visit
5.0 out of 5 stars
5 reviews
2 repeat clients
40 years of experience
Winter Park, FL, 32792

Sherry went above and beyond!! I came home to two happy cats and tidy litter boxes. She even fixed the annoying automatic feeder with no complaints. She’s bright and cheerful, it was lovely! Thank you Sherry!

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Sherree L.
Sitter Profile Image: Jazzlyn S.
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Jazzlyn S.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
7 reviews
5 repeat clients
15 years of experience
Orlando, FL, 32807

Jazzlyn is super communicative and responsive, and she took great care of my two kitties, including my high needs senior cat who needed medication twice daily. She fearlessly administered it for him, which is exactly what he needed. She even spent extra time with him so he wouldn’t feel so lonely. I highly recommend!

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Leanna A.
Sitter Profile Image: Noelle R.
Verified Enhanced Background Check
Noelle R.
Star Sitter
from
$13
per visit
5.0 out of 5 stars
8 reviews
6 repeat clients
4 years of experience
Rosemont, Orlando, FL, 32808

Super friendly and accommodating with the pups. Great feedback from her visits!

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Adam L.
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The median cost per visit for dog sitting in Winter Park is $20

Dog parents share their Rover experiences - Winter Park

1 / 1
5.0 out of 5 stars

Autumn is one amazing lady. She is kind, communicative, and very thorough. 10/10 would highly recommend!

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Summer B.
Drop-In Visits
5.0 out of 5 stars

First time Rover family and so thankful for reviews we read for Nina. She responded right away to our booking request. Loved the photos of my girls and knowing they were being loved on. Highly recommend Nina!

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Jennifer B.
Drop-In Visits
5.0 out of 5 stars

Thank you again Isabella for the peace of mind you give me whenever I leave my pet children. Your love and care are appreciated. Highly recommend.

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Maria H.
Drop-In Visits
5.0 out of 5 stars

Marin was great w my 11 month old puppy!! She was very communicative and even stopped by before for a meet and greet. You can tell she’s truly passionate about caring for your pets, and goes above and beyond to show that. Thank you Marin!

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Jill M.
Drop-In Visits
5.0 out of 5 stars

Natalie was fantastic to work with. We have three cats and a dog. She is communicative, kind, and took good care of our crew. I felt very comfortable and at ease working with Natalie and would request future bookings. Thanks!

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Jessica B.
Drop-In Visits
5.0 out of 5 stars

Natalie came into a crazy first time working with me and 7 of my pets. One of the ferrets had neglected to get in the cage at the appropriate time and so she had to corral her. All while trying to give the appropriate attention to the cats and the dogs. She did a phenomenal job! all the Pets and the house were good to go and ready for me when I got home. Definitely recommend and will rebook.

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Linda L.
Drop-In Visits
5.0 out of 5 stars

Thank you Rebecca! Stevie seems more compliant and not jumping as much. Thanks for working with her.

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John G.
Drop-In Visits
5.0 out of 5 stars

Anna has been wonderful with our puppy! She’s kind, reliable, and always keeps us updated with photos and messages after her visits. We’re very grateful for her help and would highly recommend her to anyone looking for a caring and trustworthy pet sitter or dog walker.

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Deborah M.
Drop-In Visits
5.0 out of 5 stars

Awesome! I’m very picky when it comes to my dogs and Sarah was absolutely amazing with them and they loved her visits!!! Highly recommended

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Russell H.
Drop-In Visits
5.0 out of 5 stars

Cheyenne is attentive, flexible and took great care of our boys. She even adjusted her schedule when a medical issue came up for one of our dogs during her visit. 12/10 recommend her!!!

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A&B M.
Drop-In Visits
5.0 out of 5 stars

Yesenia did a wonderful job dropping in on Cookie & Rajah over the weekend. She kept us updated on everything & sent pics everyday which was really nice. If we weren’t moving we’d book with her again, the girls loved her. Thank you so much Yesenia!!

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Teeya B.
Drop-In Visits
5.0 out of 5 stars

Sage was very happy with his new paw friend 🐾 great communication and updates, Bailey did not skip a beat! Always on time! She’s everything you want and need as a pet sitter!

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Wanda D.
Drop-In Visits
5.0 out of 5 stars

Leah is an absolute darling and both my pups fell in love with her instantly. They felt so comfortable with her and she is incredibly knowledgeable and caring. I could focus on my work and meetings knowing Leah is there taking care of my fur babies. We are all thrilled (my pups and I) that we found Leah! I will definitely rebook very soon.

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Lorena W.
Drop-In Visits
5.0 out of 5 stars

Jazzlyn was amazing and both of my fur babies fell in love with her the moment they met her. So much so that when I took them for a walk and returned home they both went looking for her in all the rooms hoping to find her. Jazzlyn is knowledgeable and gentle and I couldn’t be more happy knowing that when I am not home with my pups Jazzlyn is there taking care of them. I will definitely re-book with the amazing Jazzlyn.

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Lorena W.
Drop-In Visits
5.0 out of 5 stars

Bluey was well taken care of by Susan while we were away. Nice to have the peace of mind knowing our girl was in good hands!

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Tiffany M.
Drop-In Visits
5.0 out of 5 stars

Caitlin came over at the last minute over the atto take care of my dog. She was on time and communicating with her was easy. I totally recommend her services, asked all the important questions to make sure my baby was safe and happy.

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Kendel p.
Drop-In Visits
5.0 out of 5 stars

Kendall did twice-daily drop-in visits for my boys and was great! She was dependable, kind, and kept me updated. I came home to happy pups and couldn’t ask for more, will definitely book with her again!

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Elaine M.
Drop-In Visits
5.0 out of 5 stars

Reyna does an excellent job with Kira and is super responsive even for last minute requests which is so appreciated!

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Sarah B.
Drop-In Visits
5.0 out of 5 stars

I feel so lucky to have connected with Carolina on my first use of Rover! I have a senior French Bulldog who can't be alone all day. Carolina did a meet and greet with us and then two drop in visits while I was gone all day. My dog, who can be pretty grouchy and protective, has been won over! We will hire Carolina again.

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Sara D.
Drop-In Visits
5.0 out of 5 stars

Sam is amazing with my 10 week old puppy and has been a rock star helping me walk him mid morning while I'm at work, before I can take him out during my late afternoon lunch 😊😊 Benito loves him & he's been amazing!

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Lidyamar C.
Drop-In Visits
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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. 1. Search

    Browse profiles of sitters near you who offer dog sitting
  2. 2. Meet & Greet

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform

Sitters in Winter Park average 6
repeat dog sitting clients

FAQs for Drop-In Visits - Winter Park

Frequently asked questions about Rover

The average cost for Dog Sitting in Winter Park on Rover is $19.98 per visit (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Dog Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Sitting. For more information on service fees, click here .

As of July 2026, there are 5,332 sitters on Rover offering Dog Sitting across Winter Park. 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 Winter Park 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 Winter Park 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 Winter Park 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 Winter Park. On Rover:

  • 91% 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.

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