Dog Walking Winter Gardens

Book a dog walker to give your dog a 30-minute walk around your neighborhood.

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Over 30
pet parents in Winter Gardens have booked dog walking

Winter Gardens, Find top rated dog walking

Prices are estimates per walk for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.

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Sitter Profile Image: Frida A.
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Frida A.
$23
total per walk
5.0 out of 5 stars
6 reviews
2 repeat clients
13 years of experience
Lakeside, CA, 92040

She’s really great with my dog and he came home so happy!

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Yuki M.
Sitter Profile Image: Audrey P.
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Audrey P.
$16
total per walk
5.0 out of 5 stars
12 reviews
3 repeat clients
5 years of experience
Santee, CA, 92071

Audrey has been walking and caring for our little JRT, Fio. She is very flexible with our schedule and willing to take on more days at a moment's notice.

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Laney S.
Sitter Profile Image: Kathy H.
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Kathy H.
$23
total per walk
5.0 out of 5 stars
4 reviews
1 repeat client
5 years of experience
San Diego, CA, 92101

About: Rescued my current 5 year old dog from being abandoned in Tijuana. Spent every day with her since, I have so much love for animals especially dogs. I’m currently working part time and am looking for a side hustle that can help others and something that I love at the same time. I have 1 medium sized dog and 3 cats, I know how they both can be, I’ve seen the good and the bad and know how to handle situations.

Sitter Profile Image: Christina G.
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Christina G.
$23
total per walk
5.0 out of 5 stars
36 reviews
8 repeat clients
25 years of experience
El cajon, CA, 92021

About: My name is Christina, i was born & raised in San Diego. Grew up in Normal Heights area. But now reside in El cajon area. I am currently a SAHM, so I would be with your dog all day. Living with me are my husband and 2 beautiful baby girls who are 5 and 3 I've always had a love & passion for animals. Growing up i had rabbits, lizards, beta/ gold fish, and dogs. I have experience in dog walking as i use to dog walk, via a ad i had on Craigslist about 4 yrs or so ago. Ive also attented and graduated from the veterinary assistant program from PIMA medical institute in Chula Vista. So i have some experience in the medical side of pet care. I can give meds if needed such as pills or even insulin. I hope i get the chance to watch your four legged baby for you and put a smile on yours & your pets face. 😊 I am a stay at home mom. So I have time to ensure your dog is taken care of through out the day. Walks, feedings, and of course play time. I care for them just like I would my own pets. With the utmost love and care. Lots of Love and snuggles. And plenty of .

Sitter Profile Image: Jennifer H.
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Jennifer H.
$20
total per walk
20 years of experience
Santee, CA, 92071

About: I’ve had animals all of my life and I love meeting new fuzzy friends! I’ve had experience with all types of animals! I have two cats of my own and take care of them dog my sisters two cats and our family dog! I work for a senior care company but because it’s not super reliable in terms of a set schedule I’m looking to help pet parents whenever I can! I’m very reliable! My regular job is a in-home healthcare for seniors so I’m always in their homes cleaning their houses and stuff like that, as well as as if they have pets taken care of those as well. I care for all of my pet clients just like I with them. I respect the houses that I work in like they are my own!

Sitter Profile Image: Loren C.
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Loren C.
$37
total per walk
5.0 out of 5 stars
165 reviews
52 repeat clients
20 years of experience
El Cajon, CA, 92021

Loren is an amazing and responsive dog walker. She's really caring of our dog's needs and is devoted to her job. We are really happy with Loren and I'm sure our dog Bruno is as well! Highly recommend.

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Anne L.
Sitter Profile Image: Karyn D.
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Karyn D.
$22
total per walk
4 years of experience
El Cajon, CA, 92021

About: I am not a professional dog sitter or walker but I do have a dog of my own as of 2021. One of the best decisions of my life. My little furball, Jayla. Many friends and family have dogs from small to big that’ll let me care for them as if they were one of my children. They are fur babies after all! Walking, playing, feedings, and bathroom time become a pawsitive routine in my care and I’m here to help when or wherever needed. I work a part-time schedule, which gives me flexibility to fit pet care into my day. I’m able to work around my job and other responsibilities while still providing reliable and attentive care. I’m happy to coordinate with clients to find times that work well for both of us. When it comes to walking your dogs, or dropping in on your cats, I always make sure to bring their leash, some treats if allowed, poop bags and to be SAFE, we will cross from other animals, children or adults. You have to be prepared! Exploring the routes is a great way to bond and keep them active! I will definitely know the signs of your furbaby wanting relax or be given space. If you have a set feeding schedule, you would like me use before or after walks I will provide that service.

Sitter Profile Image: Alexis & Adam B.
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Alexis & Adam B.
$24
total per walk
5.0 out of 5 stars
21 reviews
7 repeat clients
20 years of experience
Santee, CA, 92071

My family and I highly recommend Alexis and Adam as dog walkers! They walked my two German Shepherd mixes early in the morning for 16 consecutive days for an hour each while we were on vacation. Always on time, always submitting report cards with photos and the route they walked. On top of that, my dogs, who are rescues with shyness or aggression toward strangers AND severe dog reactivity on walks, LOVED Lex and Adam! As a professional dog trainer and walker myself, I’m extremely careful with people who interact with my dogs, and Lex and Adam exceeded my expectations! It’s clear to me that they take caring for their clients’ dogs seriously and both are extremely nice and personable. Thank you Lex and Adam!!

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Swetlana F.
Sitter Profile Image: Jasmine P.
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Jasmine P.
$43
total per walk
5.0 out of 5 stars
6 reviews
1 repeat client
10 years of experience
Lakeside, CA, 92040

About: Hi! I'm new to the Rover app, but I'm not new to caring for animals. I've always had a natural connection with animals and they seem to gravitate toward me wherever I go. I’m a stay at home mom of a 3 and 5 year old so I am always home and always active and my fiance is home while I run errands. We have a decent size fenced yard where your animal can get some energy out while staying safe. I truly believe animals are family, and I care for every pet as if they were my own child. I'm highly communicative, reliable, and genuinely empathetic. I pay close attention to each pet's unique personality and needs, making sure they feel safe, loved, and comfortable while you're away. Whether your dog enjoys long walks, playtime, or just having a calm companion, I'll make sure they receive the care and attention they deserve. I understand how important it is to trust the person caring for your furry family member. That's why I'll keep you updated with plenty of photos, videos, and messages throughout each visit, so you always know how your pet is doing and can enjoy those special moments even while you're apart. If you're a busy family looking for a dependable dog walker or pet sitter who will treat your pet with patience, kindness, and lots of love, I'd be honored to help. I can't wait to meet you and your best friend! I am a mom of two girls. I have a flexible schedule and I’m willing to do whatever’s necessary to make sure your pet is taken care of. I’m a hair stylist on weekends and I love when people bring their dogs to their appointments. Rover is great way for me to play with animals, get some exercise, and make some extra income. Just message me 😊 I make sure the dog goes outside to use the bathroom . Make sure the food and water bowl is always fresh and full. Engage and play with your pet. Chill, lay down, and watch tv together. I absolutely love playing tug of war with dogs so make sure to pack that toy in their overnight bag LOL. If I were to come to your house I would let you know exactly when I enter and when I leave and give you updates on your pet .

Sitter Profile Image: Angel S.
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Angel S.
$28
total per walk
8 years of experience
El Cajon, CA, 92021

About: I’ve had a guinea pig, a bunny, and 2 dogs. I’ve always been an animal person. And I help my friends out by taking care of there pets. It depends on the my work day sense I do freelance contracting for production work. But I would have to what day you would want to book me for and times. It depends on how friendly the animal is and how many days I am pet sitting for. But I will feed, bathe, play and be around to watch what they do.

Sitter Profile Image: María E.
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María E.
$35
total per walk
5.0 out of 5 stars
148 reviews
27 repeat clients
10 years of experience
LA MESA, CA, 91942

Maria is the sweetest lady and my dog really loves spending time with her. Dogs can sense a friendly soul. I highly recommend Maria. She is the best!

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Alan And Sandy P.
Sitter Profile Image: Tahniiyah S.
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Tahniiyah S.
$28
total per walk
5.0 out of 5 stars
4 reviews
1 repeat client
3 years of experience
Mountain View, El Cajon, CA, 92021

About: I have hands-on experience caring for pets through personal and family settings, including feeding, walking, basic grooming, playtime, and providing companionship. I am attentive, patient, and mindful of each pet’s unique needs and routines. I understand the importance of safety, consistency, and trust when caring for animals. What sets me apart is my empathy, reliability, and genuine love for animals. I take the time to observe behavior, respond calmly to challenges, and ensure pets feel comfortable and cared for. I am highly adaptable, organized, and committed to following instructions closely while maintaining clear communication with pet owners. I treat every pet with the same care and respect I would give my own. I feel I can fit pet care into my weekly/daily routine because I’m free most of the time and Ive been looking for something productive too do that I’d actually enjoy I treat every pet with patience, kindness, and respect, whether they are in my home or a client’s home. I focus on creating a safe, calm, and comfortable environment by following routines, paying close attention to each pet’s needs, and ensuring they feel secure and cared for. I handle pets gently, maintain cleanliness, and prioritize their well-being, happiness, and safety at all times.

Sitter Profile Image: Remy H.
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Remy H.
$24
total per walk
5.0 out of 5 stars
20 reviews
6 repeat clients
20 years of experience
Lakeside, CA, 92040

About: Hi there! I’ve had my own dogs and cats my whole life and have done pet sitting for over 10 years. I am also well-versed in dog training and have worked extensively with cats at a pet resort. They call me the animal whisperer. 😋 I am a freelance photographer so my schedule is very flexible. I am available on weekdays and weekends and you can guarantee you’ll get some nice photos of your furry friend while you’re away. I have a senior cat at home so I don’t allow other pets at my home but I’m available for drop ins and walk dates no problem.

Sitter Profile Image: Chelsea F.
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Chelsea F.
$28
total per walk
5.0 out of 5 stars
6 reviews
2 repeat clients
25 years of experience
El Cajon, CA, 92021

About: I have worked as a veterinarian technician for 4 years. I currently have one dog, but have had almost every pet you can think of. I am willing to care for pets of all ages and kinds. I can’t wait to meet yours! I am currently free most times to walk or check on your babies! Let me know what time and I’m sure I can accommodate for you. I would love to play, feed, dog walk or check in and provide any needs for pets of all kinds. I can house sit as well! I will keep you updated and can send you pictures of how they are doing.

Sitter Profile Image: Nickie J.
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Nickie J.
$56
total per walk
5.0 out of 5 stars
20 reviews
7 repeat clients
10 years of experience
El Cajon, CA, 92021

About: Being raised in the rural parts of El Cajon, with my mom being apart of the AKC- American Kennel Club, I spent a lot of time around animals. Learning at a young age how to properly interact with dogs. I have walked up to three small dogs at the same time that belonged to my land-lord of 5 years. Even though these three dogs were considered aggressive toward other people, they loved and trusted me and I loved them back. I enjoy being around small animals and spending quality time with them. I am retired from the County of San Diego where I worked for 16 years. I am very flexible, reliable and punctual. I am looking forward to meeting you and your fur babies.

Sitter Profile Image: Megan H.
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Megan H.
$56
total per walk
5.0 out of 5 stars
3 reviews
7 years of experience
Santee, CA, 92071

About: I have worked at two dog daycares for several years. I have also petsit friends animals. I have had my own animals throughout the years. I am also a dog groomer. I’ve done all you could think of, feeding, giving water, administering meds, bathing, desheds, trims, shaves, nails, walking. I am a dog groomer full time in Santee. However I can work around my work schedule to help care for pets around the times I’m available 🐾 Feel free to reach out with any questions and we can work out if it I’m available for the times you need. I am offering my services to the areas of Santee, Lakeside, some parts of El Cajon. Safety & trust is my number one priority. I will always make sure all environments are safe for all of the pets and I. With your trust in me to care for your pets i will always make sure i do everything to keep them safe and happy. I will ask necessary questions of pets needs to help ensure safety.

Sitter Profile Image: Margarita N.
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Margarita N.
$28
total per walk
4 years of experience
El Cajon, CA, 92019

About: I personally have 3 dogs so I know how to deal with multiples in families. I used to walk for WAG before I got an office job, very experienced in drop-ins and Housesitting. Available whenever you need me! I work flexible part-time so this is a fun way for me and your pup(s) to stay active! I’ll follow your directions and if you have preferences of where to walk your pup(s) those will be followed as well. sticking to their routine will keep them comfortable if i’m meeting them for the 1st time

Sitter Profile Image: Lilliana R.
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Lilliana R.
$50
total per walk
5.0 out of 5 stars
21 reviews
4 repeat clients
20 years of experience
El Cajon, CA, 92021

About: I have always loved animals since I was a child. I have taken care of all sorts of animals large and small. I have experience with caring for puppies all the way to senior dogs, cats, birds and reptiles. It brings me joy to make sure your pets are happy, healthy and had a great time!. I have a flexible availability to Care for your pet. It would be a perfect fit while the pet parents handle their business, I am more than happy to care for them. I have a Veterinary Assistant Diploma and many years of experience with different species and breeds of dogs and cats. If you have any questions, i am happy to answer them with best of my knowledge. I also reply within less than 2 to 3 minutes. NOTE: Due to my dog oso i have adopted. I can no longer provide boarding service. I can provide walks, drop ins and house sitting any time!. MY SERVICES: 1. Dog walking/Cat adventures 2. House Sitting 3. Drop in Visits 4. Grooming MY CERTIFICATIONS: 1. Medication (oral or injection) 2. CPR certified 3. Fear Free certified Description of Rover Fees: Rover takes a 25% fee from a sitters earnings per booking and the separate 11% service fee is charged to the pet parent, not deducted from the sitters pay. Msg, txt, call im here for you and your beloved fur babie(s). I have plenty of time on hand unless booked already. Any day is a good day for me to spend time with any loving animal. Note: If booking me and requested but no longer wish to book, please cancel on your behalf if not i will not show as available on the entire Rover app. Which means other pet parents cannot book me for any services. Thank You kindly. :) I have a patio we can hang out in to sun bathe and relax after a fun day at the dog park, beach or home. Everything is clean and organized. Nothing they can chew on unless it’s their toys, no choking hazards. I am a veterinary assistant i am cpr certified fear free certified and can administer medications. Will always ask in regards to any allergies and behaviours and other medical conditions.

Sitter Profile Image: Alexis P.
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Alexis P.
$43
total per walk
5.0 out of 5 stars
97 reviews
31 repeat clients
13 years of experience
Santee, CA, 92071

Alexis was awesome and very responsive as I contacted her the day before. She took great pictures of Mika and will ask for her. This is my first time using Rover and overall experience was great. Will be using her in the future again!

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Marshall M.
Sitter Profile Image: Sunrise P.
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Sunrise P.
$43
total per walk
5.0 out of 5 stars
2 reviews
1 repeat client
11 years of experience
Lakeside, CA, 92040

About: Ive taken care of dogs and cats since I was very young! I grew up fostering animals and taking care of our own. I am great with dogs of all sizes and breeds, but have a special love for big breeds as ive had akitas most of my life! I worked at petsmart for 2 years, so I got to work with dogs, cats, and exotics nearly every day! I also have a variety of animals of my own, including a rabbit, a gecko, and some tree frogs! I have a very fun home🏡☺️ I also have some light experience with grooming and lots of bathing experience! I currently work as a respite care worker for individuals with disabilities, so my schedule is very variable!😊 I schedule week by week so please feel free to send me a request! Best days to reach out ahead of time for me are Sundays and Mondays as I usually don’t have my week fully scheduled out yet by then. 😊 I will always aim to provide a fun, safe, and enriching environment for your pet whether it’s a pop in visit, a walk or whatever your personal pet needs are!

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The median cost per walk for dog walking in Winter Gardens is $23

Dog parents share their Rover experiences - Winter Gardens

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5.0 out of 5 stars

Frida is very good with my timid dog, Xochitl. 😊 Xochi doesn’t open up to everyone but she comforts Xochi quickly. She loves walking with her now!

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Yuki M.
Dog Walking
5.0 out of 5 stars

I will definitely use Claudia again! She was very attentive to my dog and was very responsive to my messages.

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Giovanni L.
Dog Walking
5.0 out of 5 stars

Audrey has been walking and caring for our little JRT, Fio. She is very flexible with our schedule and willing to take on more days at a moment's notice.

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Laney S.
Dog Walking
5.0 out of 5 stars

This sitter was amazing! Charlie was very communicative, caring, and attentive the entire time. You can tell charlie truly love dogs and knows how to work with them. My babies were happy, well cared for, and I felt safe and confident leaving them in charlie’s care. Thank you for taking such great care of my pups—I would definitely book again!

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Rosalia F.
Dog Walking
5.0 out of 5 stars

Loren is an amazing and responsive dog walker. She's really caring of our dog's needs and is devoted to her job. We are really happy with Loren and I'm sure our dog Bruno is as well! Highly recommend.

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Anne L.
Dog Walking
5.0 out of 5 stars

Laura was reliable, communicative and I was confident that she could handle our big guy! Will be booking with her again!

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Andrea & Tim B.
Dog Walking
5.0 out of 5 stars

We’ve been regulars with Jane for a while now and so thankful to find someone who shows she truly cares about the pups. Great communication and attention to detail always.

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Andreea B.
Dog Walking
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  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
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Why Choose Rover?

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Meet local walkers who will treat your dogs like family

  1. 1. Search

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Popular requests for dog walking - Winter Gardens

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Sitters in Winter Gardens average 3
repeat dog walking clients

FAQs for Dog Walking - Winter Gardens

Frequently asked questions about Rover

The average cost for Dog Walking in Winter Gardens on Rover is $21.4 per walk (as of September 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Dog Walking 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 Walking. For more information on service fees, click here .

As of September 2026, there are 9,227 sitters on Rover offering Dog Walking across Winter Gardens. Enter your ZIP code to see which available sitters are closest to your home.

Whether you want a solo or group walk depends on your dog's personality. Solo walks can be beneficial for dog parents with reactive dogs, puppies, or dogs who are anxious around unfamiliar animals. Many dog walkers on Rover offer private, one-on-one walking services.

Group walks are a good fit for social dogs who enjoy structured walks. If your dog prefers the energy of a group stroll, ask your dog walker about group walks in your Winter Gardens. Since all dog walkers are local, they may have a neighborhood dog who is a good walking companion to yours.

For dog walking services, you can request a report card update with specifics about your dog’s walk. Report cards require photos and can include a map of the walking route , total walk time, poop and pee breaks, and distance traveled, so you know exactly where your dog has been walking in Winter Gardens.

Got specific details you'd like the dog walker to include? Message them in the app before your dog’s walk begins.

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.

Every walker 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 .

Yes, you can find walkers who have experience with handling special pet needs in Winter Gardens. On Rover:

  • 92% of walkers 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.

A Meet & Greet is a short introductory meeting between you, your dog, and a walker. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your walker 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 walker questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and walkers 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.

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 walker.

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