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: Jaidy M.
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Jaidy M.
$16
total per walk
8 years of experience
El Cajon, CA, 92021

About: I bring over 8 years of hands-on experience from owning my own dog, which has taught me everything from daily care and routines to reading a dog’s body language and understanding their needs. Along with that, I’ve also cared for friends’ pets, giving me experience with different breeds, personalities, and temperaments. I’m patient, reliable, and treat every dog like my own. Because I already care for my own dogs, pet care is a regular part of my day. I’m used to morning walks, meal times, and keeping pets on a steady routine. I’m flexible and easily make room in my weekly schedule to give each pet the time and attention they need. Whether pets stay in my home or I care for them in yours, I keep their routine consistent so they feel secure. I stick to their feeding schedule, provide regular walks, and give plenty of playtime and attention. I focus on creating a clean, safe, and loving environment and always stay in touch with updates and photos.

Sitter Profile Image: Trinity W.
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Trinity W.
$17
total per walk
5.0 out of 5 stars
• 34 reviews
10 repeat clients
4 years of experience
El Cajon, CA, 92019

“Trinity is amazing with dogs! She walked both my dogs, two very different walkers, and they were giving her doggie kisses before she left. Would highly recommend!”

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Jade S.
Sitter Profile Image: Valerie G.
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Valerie G.
$20
total per walk
20 years of experience
El Cajon, CA, 92021

About: I've had pets of all ages my entire life! Cats, dogs, rabbits, turtles, lizards, and fish 😊 I feel comfortable caring for them and know they feel comfortable with me. I enjoy playing, being active and walking with them. Please reach out and I'll help you feel comfortable with your pets needs. I'm retired and have a very flexible schedule. Reach out and I will do my best to accomadate your needs for your fur baby's care ☺️ I will provide care for your pet in your home, so they're schedule and comfort is not disrupted. I work for you, so you tell me what works best for you!

Sitter Profile Image: Audrey P.
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Audrey P.
$16
total per walk
5.0 out of 5 stars
• 12 reviews
4 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: Loren C.
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Loren C.
$37
total per walk
5.0 out of 5 stars
• 166 reviews
52 repeat clients
20 years of experience
El Cajon, CA, 92021

“I’ve booked Loren for a few walks and a game of fetch for my dog. She has great communication and is very responsive. I appreciate her professionalism and reliability. She has shown that I can count on her. Kona has a blast! Thanks Loren!”

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Camtu P.
Sitter Profile Image: Frida A.
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Frida A.
$23
total per walk
5.0 out of 5 stars
• 10 reviews
3 repeat clients
13 years of experience
Lakeside, CA, 92040

“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.
Sitter Profile Image: Elizabeth M.
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Elizabeth M.
$29
total per walk
5.0 out of 5 stars
• 115 reviews
46 repeat clients
20 years of experience
Lakeside, CA, 92040

“Liz is fabulous. She is getting to know Shasta slowly, coming over for walks and just to hang out. We are building up to Liz staying overnight while we leave town and leave Shasta alone for the first time ever (7 years!). Liz is amazingly patient with this process knowing that Shasta is a fairly damaged rescue dog. We are extremely grateful to her for being so patient and understanding. Shasta will be in good hands.”

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Dana F.
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: Christina G.
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Christina G.
$23
total per walk
5.0 out of 5 stars
• 36 reviews
9 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
5.0 out of 5 stars
• 4 reviews
1 repeat client
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: 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: 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: Saddaf Y.
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Saddaf Y.
$33
total per walk
5.0 out of 5 stars
• 6 reviews
1 repeat client
14 years of experience
El Cajon, CA, 92020

About: For the past 14 years, my world revolved around my dog, Zuri. Sadly, she passed away in April, and while I’m not ready to welcome another dog into my life just yet, I realized how much I miss spending time with them. Caring for dogs has never felt like work to me. I’m naturally attentive, patient, and deeply attuned to animals. I tend to notice the little things; when a dog needs a slower pace, extra reassurance, more water, a sniff break, or simply someone calm to help them feel safe. Zuri taught me that every walk is the highlight of a dog’s day, not just another task to check off a list. Whether your dog is energetic, shy, anxious, or a senior who needs a gentler pace, I’ll care for them with the same love, presence, and respect I gave my own. I know how much trust it takes to leave your best friend in someone else’s care, and I don’t take that responsibility lightly. My goal is for you to feel completely at ease, knowing your dog is safe, understood, and genuinely loved while we’re together. I’m also available for boarding and overnight care, either in my home or yours. I’m home throughout the day, so your dog will have plenty of companionship and attention. I have experience caring for senior dogs, administering medications when needed, and understanding that every dog has their own personality, pace, and emotional needs. I have a flexible schedule and genuinely enjoy being active, so dog walks fit naturally into my daily routine. Walking has been an important part of my own life for years, and after losing my beloved dog of 14 years a few months ago, spending time with dogs has become something that brings me joy and healing. I’m reliable, communicative, and committed to making sure your dog gets the exercise, enrichment, and attention they deserve. I understand that trusting someone with your dog is a big decision because I know what it’s feels like to love a dog like family. I always prioritize safety by following your dog’s routine, using secure leash handling, paying close attention to their body language, and adapting to their individual personality and energy level. Whether your dog is playful, shy, anxious, or a senior who needs a slower pace, I’ll care for them with patience, kindness, and respect. I’ll also keep you updated with photos and messages so you can feel confident they’re in good hands.

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: Aaliyah T.
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Aaliyah T.
$32
total per walk
6 years of experience
El Cajon, CA, 92021

About: CNA and longtime dog owner with 6 years of experience providing dependable, compassionate care. I prioritize safety, comfort, and each pet's need when needed. My schedule is flexible, and I do my best to accommodate both planned and last-minute bookings whenever possible. As a healthcare professional, I understand the importance of reliability, communication, and showing up on time. Wether your pup needs a walk, a drop-in visit, or some extra love while you're away, I'll make sure they receive the same care and attention I'd give my own dog. I look forward to meeting you and your furry family member <3. Safety and trust are extremely important to me. I treat every pet as if they were my own by following each owner's routine and instructions carefully. I'm committed to providing dependable, attentive care and making sure every walk and visit is a safe, positive experience of for your pet.

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

“María has been really patient with my girls. Tessa gets very anxious and barks and María met with us twice to allow her time to warm up. María is excellent with updates and we look forward to having her stay with the girls overnight.”

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Kristi V.
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: Jasmine P.
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Jasmine P.
$43
total per walk
5.0 out of 5 stars
• 7 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: Margarita N.
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Margarita N.
$35
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.

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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

1 / 1
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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    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

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 of Dog Walking in Winter Gardens on Rover is $21 per walk as of October 2026. Most bookings cost between $21 and $22 per walk. walkers set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of October 2026, there are 9,255 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 bookings, your dog walker can send a Rover Card with details about your dog’s walk. Rover Cards require at least one photo and may include a map of the walking route , the total walk time and distance, and any pee or poop breaks recorded by the walker.

The route map lets you review where your dog was walked in Winter Gardens after the booking. It is not live GPS tracking.

Have specific details you would like included? Message your dog walker in the app before the 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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.

Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your walker interacts with your pet 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. Meet & Greets are a great way to prepare your pet and walker for longer stays or first-time bookings. Read our tips for your first Meet & Greet .

walkers on Rover set their own cancellation policy , which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.

Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement walker.

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