Dog Sitting Windermere

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

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Over 448
pet parents in Windermere have booked dog sitting

Windermere, 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: Karen R.
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Karen R.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
342 reviews
94 repeat clients
30 years of experience
Winter Garden, FL, 34787

Karen took amazing care of our cats while we were away on a cruise. She left detailed rover cards for us that made us smile everyday. Thank you!

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Sara H.
Sitter Profile Image: Yelena L.
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Yelena L.
Star Sitter
from
$24
per visit
5.0 out of 5 stars
27 reviews
5 repeat clients
40 years of experience
Gotha, FL, 34734

Yelena provided outstanding care for my Giant Schnauzer, Jager. From the moment we met her, it was clear that she genuinely loves animals and takes her responsibilities seriously. She kept us updated, was attentive to Jager’s needs, and made sure he was comfortable and well cared for throughout his stay. Jager came home happy, relaxed, and clearly enjoyed the time he spent with her. Knowing that he was in such caring and trustworthy hands gave us complete peace of mind. I highly recommend Yelena to anyone looking for a reliable, compassionate, and professional dog sitter. Thank you, Yelena, for taking such wonderful care of Jager. We would gladly trust you with him again!

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Cesar T.
Sitter Profile Image: Samantha D.
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Samantha D.
from
$20
per visit
5.0 out of 5 stars
15 reviews
4 repeat clients
10 years of experience
Winter Garden, FL, 34787

About: I long for the day I can have a pet of my own, but in the mean time I will treat your fur baby like family! I work full-time in the healthcare field however I am available before and/or after shifts as well as on the weekends! My schedule is relatively consistent. My current living situation has space constraints, therefore I would be better suited to maintain the environment your pet is already accustomed to! This offers a level of heightened convenience and comfort to you and your pet.

Sitter Profile Image: Taylor A.
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Taylor A.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
17 reviews
6 repeat clients
20 years of experience
Lake Copeland, Winter Garden, FL, 34787

First time using Taylor and we are very happy with her communication and how she treated our cat-Koko. We will definitely book her again during our upcoming trips. Thanks!

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Milivette M.
Sitter Profile Image: Jessie P.
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Jessie P.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
32 reviews
9 repeat clients
7 years of experience
Metro West, Orlando, FL, 32835

Jessie was truly the best cat sitter I could have ever asked for. My cat Marvin is special needs due to his diabetes and she was extremely thorough, attentive, and truly cared about Marvin’s wellbeing. Jessie was also super flexible in being able to see Marvin still when I had a last minute change in my plans. She sends lots and lots of pictures and detailed updates as well which I so so appreciate being so far away from him. I will absolutely be requesting Jessie again and can confidently say she would do the same for your pet!

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Alexy B.
Sitter Profile Image: Sarah H.
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Sarah H.
Star Sitter
from
$32
per visit
4.9 out of 5 stars
179 reviews
74 repeat clients
12 years of experience
Windermere, FL, 34786

The best! Sarah sent pics of our kitty, who was so happy to have her attention. She’s attentive and caring - I’ll definitely be recommending and using her in the future!

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Karen G.
Sitter Profile Image: Cassia V.
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Cassia V.
Star Sitter
from
$28
per visit
5.0 out of 5 stars
123 reviews
21 repeat clients
27 years of experience
Windermere, FL, 34786

We are so glad to have met Cassia She took great care of our cat whiskey while we went on vacation for a week. We received messages and photos after each check in. She also helped bring in mail and boxes which was greatly appreciated. We will definitely book with Cassia again.

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Ashley L.
Sitter Profile Image: Mariana S.
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Mariana S.
from
$10
per visit
18 years of experience
Ocoee, FL, 34761

About: I have taken care of dogs since I was a little kid. My godmother used to own five dogs and seven cats back in Brazil. Every time that I would come over to her place I would love to take care of her pets. The best memories I have are from feeding, playing, and having sleepovers with these animals every night. After my godmother passed away, I adopted one of her dogs named Liza. I brought Liza here to the United States with my family and she lived an eighteen year long and happy life! Towards the end of her life, she had vestibular disease. I made sure we were on top of all vet visits, meds and rehab care. She was very important to me so I wanted make sure we gave her the best care. Since then, I have been there for my family and friends to watch their beloved pets. I have experience from cat sitting, dog sitting, and dog walking! I make sure to send my friends and family updates on their fur baby as I know going on vacation can make you miss your pets. So excited for future fur buddies to meet! Hi guys, I am new here!! I work part time and I have full time availability at my day job, but I decided to reserve some time to take care of pets which has always been a dream of mine! I am trying to make this app work and will change my availability on a week to week basis depending on my scheduling at work, but I will be as flexible and as convenient as I can to fit into your schedule! I know how important it is for your pet's happiness to take their daily walks, so during their daily walk I will make sure that they exercise, have enrichment and also have fun with the scenery! If I am doing check ins I will make sure that your pup is happy and also that they have everything that they may need such as food, water and most importantly, are happy!

Sitter Profile Image: Heather J.
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Heather J.
from
$15
per visit
5.0 out of 5 stars
2 reviews
1 repeat client
30 years of experience
Windermere, FL, 34786

About: Drop In Availability: Morning: 6a-9a; Evening: 6p-10p Dog Walk Availability: Morning: 6a-9a; Evening: 6p-9p I grew up with two Mastiffs, so I understand the importance of structure, patience, and making pets feel loved. I truly thought of Brutus and Khan (my mastiffs) like my brothers. Brutus and Khan were afraid of the thunderstorms so I learned from a young age how to comfort them. Over the years, I’ve cared for dogs, cats, a reptile and some farm animals. I truly enjoy getting to know each pet and animal’s personality. I’m comfortable administering medications, including pills, powders, and injections, and I always follow care instructions closely to keep your pet’s routine consistent. As someone who works remotely, I’m reliable, communicative, and able to give your pet the time and attention they need. I treat every pet like they’re my own, creating a calm, loving environment so you can feel completely at ease while you’re away. I work remotely, which allows me to be flexible and present throughout the day. I’m able to schedule drop-ins, feedings, playtime, and check-ins around my work, so pets receive consistent attention. At home, I schedule myself around a “Pomodoro Method” and include 5-10 minutes of playtime with my cat when I need a break. When I’m caring for pets in your home, my goal is to make everything feel as normal and comforting as possible for them. I stick closely to their usual routine so they feel safe and at ease in their own home. I also treat your home with the same respect I would my own, keeping things clean and giving you regular updates. At home, I keep a calm, cozy environment for my own cat. I never use the “big light” and the TV is always kept on a quiet level for her. I will turn on the CatTV when I get busy with my work as well.

Sitter Profile Image: Stephen N.
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Stephen N.
from
$18
per visit
15 years of experience
Orlando, FL, 32819

About: I have been surrounded by animals throughout my life and understand that every pet has its own personality, routine, and comfort level. I was raised with a red-nose Pit Bull, an XL Bully, and two English Bulldogs, so I am comfortable caring for strong, large-breed dogs as well as smaller pets. My family also cares for a flock of chickens, African geese, ducks, and a turkey. This experience has taught me to be patient, observant, dependable, and respectful of animals with very different needs and temperaments. I can help with feeding, fresh water, walks, playtime, litter-box or pet-area cleanup, companionship, and following your pet’s normal routine. I will carefully follow your instructions and provide photos and updates so you can feel confident that your pet is safe, comfortable, and receiving attentive care while you are away. Pet care fits well into my daily schedule. I have a flexible routine and can make time to feed, walk, play with, and care for animals consistently. I’m dependable, punctual, and able to adjust my schedule to meet the needs of the pets I’m responsible for. I care for pets by following their routine as closely as possible. I make sure they have fresh food and water, get plenty of exercise and playtime, and receive lots of attention and affection. I also keep their living area clean, watch for any signs that they may not be feeling well, and follow any instructions the owner provides, including administering medication if needed and I’m trained to do so. My goal is to make every pet feel safe, comfortable, and cared for while their owner is away.

Sitter Profile Image: Jocelyn D.
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Jocelyn D.
from
$20
per visit
4.9 out of 5 stars
61 reviews
25 repeat clients
11 years of experience
Orlando, FL, 32819

Jocelyn took great care of our two dogs, dropping in during the day to check on them. She was very communicative, provided great photos during her visits, and was great with our needy dogs. We will be happily booking her for our future dog care needs!

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Whitney R.
Sitter Profile Image: Yanran L.
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Yanran L.
from
$18
per visit
5.0 out of 5 stars
21 reviews
7 repeat clients
5 years of experience
Windermere, FL, 34786

About: I stand out because I truly treat every pet like family. I have hands-on experience volunteering at animal shelters, where I cared for dogs of all breeds, sizes, and temperaments—including nervous rescues and high-energy pups. I’m patient, gentle, and quick to adapt to each pet’s unique needs. Whether it’s walking, feeding, playtime, or just providing comfort, I bring calm, consistency, and affection. I also understand the importance of routines and know how to care for senior dogs who need a little extra love and attention. I’m comfortable administering oral medications and following detailed care instructions. Your pet’s happiness and safety are my top priorities—and I’ll always keep you updated with photos and notes while you're away! Pet care is something I genuinely enjoy and make time for throughout my week. Whether it’s morning walks, afternoon play sessions, or cozy evening check-ins, I build my schedule around giving pets the attention and care they need. I’m naturally active and love being outside, so walking dogs or visiting pets is a part of my regular routine that never feels like work. Because I’ve volunteered at shelters, I’m used to working with different pet personalities and needs—from energetic puppies to older dogs who move at a slower pace. I’m flexible, dependable, and always happy to adjust my day to fit your pet’s routine so they feel safe and cared for even when you’re not home. In a client’s home, I prioritize keeping your pet comfortable by sticking closely to their usual routine—whether that means feeding schedules, walk times, or favorite spots to nap and play. I always make sure they feel safe and cared for by giving them lots of affection, positive attention, and a calm presence. I also keep your space tidy and treat your home with respect. If caring for pets in my own home, I create a peaceful, pet-friendly environment with cozy spots for rest, safe areas for play, and lots of attention throughout the day. I make sure they have everything they need—fresh water, clean feeding areas, bathroom breaks, and companionship. I send regular photo updates so you know your pet is happy and well cared for. Whether I’m in your home or welcoming your pet into mine, I focus on creating a loving, stress-free experience that feels just like home.

Sitter Profile Image: Jenn H.
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Jenn H.
Star Sitter
from
$23
per visit
5.0 out of 5 stars
123 reviews
47 repeat clients
10 years of experience
Orlando, FL, 32835

Great experience!! She was great at communicating and my pups loved her. She stopped by to do a meet and greet before the drop in visit which I greatly appreciated. I will definitely be using this rover walker again!

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Rachel M.
Sitter Profile Image: Samantha Y.
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Samantha Y.
Star Sitter
from
$21
per visit
4.9 out of 5 stars
83 reviews
29 repeat clients
7 years of experience
Orlando, FL, 32836

Samantha was a hit with Mulder when they first met! I saw how he immediately accepted Samantha. It gave me peace of mind while we were away for an extended period of time. We have your number Samantha and we will call you again when needed. Thank you!

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Betsy M.
Sitter Profile Image: Darryl W.
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Darryl W.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
38 reviews
11 repeat clients
20 years of experience
Winter Garden, FL, 34787

Darryl was so great! took great care of Monchi and took the cutest pics of him 🥹 made me feel easy and safe trusting my boy to Darryl, even took out the trash and brought in all my packages while I was gone. Would definitely love to have Darryl take care of Monch again 💗

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Amelia J.
Sitter Profile Image: Katherine F.
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Katherine F.
from
$17
per visit
5.0 out of 5 stars
18 reviews
5 repeat clients
12 years of experience
Windermere, FL, 34786

Katherine is absolutely wonderful! She was very responsive and reliable. I also appreciate that she would grab our packages if we had any sitting and bring them in. I will absolutely schedule care with Katherine again in the future!

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Jessica M.
Sitter Profile Image: Jennifer L.
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Jennifer L.
from
$15
per visit
5.0 out of 5 stars
6 reviews
1 repeat client
20 years of experience
Orlando, FL, 32835

About: My family has had several dogs, currently a German Shepherd puppy rescue who is fully of energy. I’ve cat and dog sit in addition to helping raise my own dogs. I enjoy daily walks and snuggling before bed. I work remotely so I’m available to visit your home and walk / play / feed your pet and stay a while with my laptop (providing you have internet 😊) or I can house sit and entertain your pet while working and staying in your home. I like to get up in the mornings and go for a walk. I work from home so I’ll be around most of the time. I can check in on your pets as needed. If desired I can go on an evening walk as well. I enjoy play with pets and having them around.

Sitter Profile Image: Anna K.
Verified Enhanced Background Check
Anna K.
from
$18
per visit
17 years of experience
Orlando, FL, 32835

About: I’ve been around animals my entire life and grew up with both cats and dogs. Caring for pets has always been a natural part of who I am. Today, I’m a proud cat parent to two senior cats, ages 12 and 13, who have taught me patience, responsibility, and the importance of personalized care. I understand that every pet has its own personality, routine, and needs. Whether it’s playtime, walks, feeding, medication, or simply providing companionship, I treat every pet as if they were my own. My goal is to make sure your furry family member feels safe, comfortable, and loved while you’re away. I look forward to meeting you and your pets! 🐾❤️ I’m not working at the moment, so I have full availability and a flexible schedule to care for pets. This allows me to give them plenty of attention, stick to their regular routines, and make sure they feel comfortable, safe, and loved while their owners are away. I can also accommodate last-minute bookings whenever possible. When caring for pets in their own home, my priority is to keep their routine as normal as possible. I’ll make sure they’re fed on schedule, have fresh water, get plenty of exercise and playtime, and receive lots of love and attention. I’ll also keep your home tidy, follow all care instructions carefully, and send regular photo updates so you can relax knowing your pet is happy, safe, and well cared for. 🐾❤️

Sitter Profile Image: Matthew L.
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Matthew L.
from
$13
per visit
5 years of experience
Windermere, FL, 34786

About: I grew up with plenty of pets and am well experienced on what it takes to care for animals. I’ve worked as a pet sitter and dog walker on the past. I also have my own Goldendoodle named Luna, she keeps me well trained 😂 I work from home and can work anywhere with WiFi/cell reception. My schedule is very flexible, So I can easily work pet care into my schedule without issue. I have a friendly, well acclimated Goldendoodle for play dates, I am experienced with animals that are both crate trained and non crate pets, so happy to follow clients preferences.

Sitter Profile Image: Alexis T.
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Alexis T.
from
$20
per visit
5.0 out of 5 stars
19 reviews
12 repeat clients
7 years of experience
Winter Garden, FL, 34787

Alexis was a tremendous help with checking in on our kitties while we were out of town for two weeks. She was timely, shared updates and photos with me, and took great care to maintain the cats food, water, and litter during her check-ins. I would recommend Alexis to any cat parent!

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Cheyanna J.
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The median cost per visit for dog sitting in Windermere is $20

Dog parents share their Rover experiences - Windermere

1 / 1
5.0 out of 5 stars

Gina was able to help us out last minute and was punctual and had great communication, will definitely book her again!

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Harman K.
Drop-In Visits
5.0 out of 5 stars

Today was our first time leaving our puppy while we were at work and school. Cassia stopped in for a day visit where she stayed an hour feeding, walking and training our little Billie boo (mini Dashund). I received over 40 photos of the visit and a detailed explanation of her visit! We will be booking with cassia in the future. ❤️ 🐶

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

Amazing experience with Lindsay. She was always on time, very sweet with my pet, excellent communication and very accomodating.

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Alexander T.
Drop-In Visits
5.0 out of 5 stars

Watched our dogs for a week with two check ins each day. Took them on walks, provided timely updates and pictures every day. Dogs did great with her! Would definitely book again.

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Chris E.
Drop-In Visits
5.0 out of 5 stars

Alexis was amazing - my pets (dog & cat) immediately warmed up to her and were comfortable with her. Will definitely utilize her services again and recommend her to neighbors.

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Elizabeth R.
Drop-In Visits
5.0 out of 5 stars

Thanks again for giving so much TLC to all our fur babies. Never once did I have any anxiety! Thanya is one of the best. I hope she continues to pet sit in her new career as a veterinarian.

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

I highly recommend Elizabeth’s dog sitting services! She has excellent communication. Also, she’s friendly and dependable. My puppy had a great time!

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Brittany I.
Drop-In Visits
5.0 out of 5 stars

Jamie was so wonderful. She came at the last minute when I was in trouble. She was wonderful with the dogs. They loved her so much. I definitely have her watch my dogs from now on.

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

The pets were well taken care of and it was much better than leaving them at a boarding place. Will definitely be using Katherine again!

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

Taylor was excellent with our dog, flexible, listened to what he needed when he got too tired and gave him a lot of love an attention. We’ll definitely be using Taylor again.

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

My dog babies and I had a wonderful experience with Georgiana, my babies loved her immediately. Thank you

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

Chris is fantastic! He cares for our dogs and always goes the extra mile!! I trust him without any hesitation!

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CANDIDO V.
Drop-In Visits
5.0 out of 5 stars

Michael did a great job taking care of my dogs! He was on time for each visit and very respectful of the house. He sent many photos and videos of the dogs which we appreciated very much. Would definitely hire Michael again to watch our dogs!

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Mario C.
Drop-In Visits
5.0 out of 5 stars

Reece was great! Jock really took a liking to her immediately. She was on time and very communicative. A definite rebooking on my next need

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

Thank you, I’ll totally recommend you to anyone. Responsible and charming with our dogs. Hope to see you soon.

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Gloria C.
Drop-In Visits
5.0 out of 5 stars

Maddie is absolutely amazing with my nervous pup! Callie looks so forward to seeing Ms. Maddie!! We are thankful we found her!!

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

Samantha was amazing! We were so fortunate to have Haze in her care. I have a 3 year old German Shepherd with a lot of energy, and she handled him so well. Samantha was attentive, communicative, and took great care of him. I really appreciated the frequent updates and photos too! Would definitely book with her again. Highly recommend! 🐾

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Bri Lauren i.
Drop-In Visits
5.0 out of 5 stars

Hailey was super helpful to us last minute! She shared great info and photos about our dog and was very responsive.

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Caroline P.
Drop-In Visits
5.0 out of 5 stars

Thank you Jessica for taking such good care of our babies! We will definitely call on you in the future 😊

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Janet R.
Drop-In Visits
5.0 out of 5 stars

Wonderful and caring. Entertained our pups and made sure they had fun while we were out. Definitely will be calling on Nathan again.

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Shannon A.
Drop-In Visits
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Sitters in Windermere average 6
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FAQs for Drop-In Visits - Windermere

Frequently asked questions about Rover

The average cost for Dog Sitting in Windermere on Rover is $22.2 per visit (as of August 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 August 2026, there are 5,142 sitters on Rover offering Dog Sitting across Windermere. 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 Windermere 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 Windermere 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 Windermere 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 Windermere. On Rover:

  • 90% of sitters can help with special care needs
  • 96% 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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