Dog Walking Highland Beach

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Over 25
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Sitter Profile Image: Hannah C.
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Hannah C.
from
$15
per walk
20 years of experience
Annapolis, MD, 21403

About: Hi, I’m Hannah! I’ve grown up with dogs my whole life and can’t remember a time when I didn’t have a furry companion by my side. Since my teenage years, I’ve been the go-to pet sitter for friends and family, and I still love helping out whenever I can. I also foster dogs, so I’m experienced with pups of all sizes, temperaments, and needs. Your dog will be in caring, capable hands with me! I am currently working remotely, so I am free most of the day to care for your dog and be there as a friend and make sure they are not left alone. I have a fenced in backyard that your pup can run around in. I also have two sweet and loving dogs of my own that will keep your pup company! If coming to your house, I will respect your space, and let you tell me how to manage your pet and home.

Sitter Profile Image: Elizabeth G.
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Elizabeth G.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
50 reviews
22 repeat clients
10 years of experience
Annapolis, MD, 21403

Thank you Elizabeth for taking great care of both dogs for us! We appreciate Elizabeth being patient as one of our dogs was hiding, afraid in a closet and she helped to get him out and comfortable on a walk.

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Brooke T.
Sitter Profile Image: Stephanie M.
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Stephanie M.
from
$20
per walk
5.0 out of 5 stars
4 reviews
2 repeat clients
7 years of experience
Annapolis, MD, 21403

Mae is very reliable, punctual and takes great care of our dog Cannon on their daily walks. She is a great communicator and genuinely loves caring for our dog. I would highly recommend Mae for your dog walking/sitting needs.

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Sadie S.
Sitter Profile Image: Beth W.
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Beth W.
Star Sitter
from
$35
per walk
5.0 out of 5 stars
78 reviews
34 repeat clients
25 years of experience
Annapolis, MD, 21403

Beth was so helpful, caring, and just generally great with my pup! I will definitely book again in the future!

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Caitlin I.
Sitter Profile Image: Laura D.
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Laura D.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
63 reviews
20 repeat clients
35 years of experience
Annapolis, MD, 21403

Laura has been excellent for us. Our dog can be a handful around other dogs and Laura shows her expertise in keeping things calm during walks. Communication has been great and we’ve never had any scheduling issues. Laura’s rover cards are excellent and we get plenty of pictures! We’re really grateful we found Laura and that she had the availability for us. Highly recommend to anyone who is looking for a kind, reliable, trustworthy dog walker.

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John S.
Sitter Profile Image: Andrew P.
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Andrew P.
Star Sitter
from
$19
per walk
5.0 out of 5 stars
67 reviews
19 repeat clients
15 years of experience
Annapolis, MD, 21403

Andrew did a great job this weekend! He walked my very large Labradoodle and St Bernadoodle and made sure both dogs and my 3 cats were fed and had water. He followed the care instructions, was extremely communicative and arrived promptly at the booking time. I will absolutely be using Andrew for future bookings, highly recommended!!

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Megan M.
Sitter Profile Image: Thomas R.
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Thomas R.
Star Sitter
from
$30
per walk
5.0 out of 5 stars
89 reviews
20 repeat clients
7 years of experience
Annapolis, MD, 21403

Thomas is so good working with our 14 1/2 year old black lab with some serious arthritis. He helps her up the stairs and competently gets her on and off the boat. When Thomas is here, we don’t worry about her while we are away. He goes above and beyond for our old girl with a smile and kind words.

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Dottie L.
Sitter Profile Image: Blinne F.
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Blinne F.
from
$18
per walk
5.0 out of 5 stars
20 reviews
6 repeat clients
20 years of experience
Annapolis, MD, 21403

Blinne was fabulous with my highly energetic pup and offered great feedback as to Kali’s behaviors after every walk. Kali would wait excitedly at the door each day for Blinne’s arrival. I will definitely reach out to Blinne again!

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Alison W.
Sitter Profile Image: Allison M.
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Allison M.
from
$30
per walk
5.0 out of 5 stars
74 reviews
21 repeat clients
27 years of experience
Annapolis, MD, 21403

Allison has been amazing for us! She has been available and more than happy to take our dog on walks (even when I contact her last minute) Finn is getting much needed exercise and love during the day while we are working. We are so, so thankful for her!!

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Elizabeth U.
Sitter Profile Image: Alexis H.
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Alexis H.
from
$25
per walk
5.0 out of 5 stars
7 reviews
2 repeat clients
13 years of experience
Annapolis, MD, 21403

About: I’ve been around animals my entire life and grew up caring for 3 dogs, 2 cats, birds, lizards, hermit crabs, fish, and rabbits. Taking care of pets has always come naturally to me. Since I was around 10 years old, I’ve helped walk my neighbors’ dogs and puppies, as well as pet sit their dogs and cats while they were away on vacation. I’m very patient, attentive, and love making pets feel safe, comfortable, and cared for like they’re part of the family. 🐾 Pet care fits naturally into my daily routine as a stay-at-home mom, which gives me a very flexible schedule and allows me to be home throughout the day for walks, feedings, playtime, check-ins, and lots of attention. My 5-month-old daughter and I spend a lot of time at home, so I’m able to provide consistent care, companionship, and updates for pet owners. I enjoy having animals as part of our daily routine and make sure every pet feels comfortable, safe, and cared for. In my home, pets are treated like family and are welcome on the furniture for comfort and companionship. I create a calm, loving environment where animals can feel safe and relaxed while away from their owners. My cats have access to food and water throughout the day, with their setup safely placed out of reach from dogs when needed. I do not crate animals unless specifically requested by the owner, as I prefer pets to feel comfortable and free in the home. I pay close attention to each pet’s routine, personality, and comfort level to make sure they receive individualized care, attention, and plenty of love.

Sitter Profile Image: Jessica B.
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Jessica B.
from
$25
per walk
5.0 out of 5 stars
12 reviews
5 repeat clients
12 years of experience
Edgewater, MD, 21037

Jessica has been wonderful! I needed help on short notice for my energetic Staffy/Lab mix while I worked overnight shifts, and she exceeded my expectations. She was great with my dog from the very first meet and greet, and clearly has experience handling larger, high-energy dogs. She provided a full 30 minute walk, updates with photos, notes about the visit, and even tracked potty breaks and checked her water. Knowing my dog was getting exercise and attention in the middle of my 12 hour shift made a huge difference and greatly reduced my stress. Jessica has been reliable, professional, communicative, and caring. My dog absolutely loves her, and I feel completely comfortable having her care for my pet. I highly recommend her to anyone looking for a trustworthy and experienced dog walker!

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Francesca S.
Sitter Profile Image: Carly B.
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Carly B.
from
$30
per walk
35 years of experience
Annapolis, MD, 21403

About: Hello! I'm a former VP at a real estate non-profit, transitioning to a new job. I'm available in August and September for drop-in visits, walks, and overnight care. As a resident of Arundel on the Bay neighborhood, I'm available to AOTB, Annapolis Cove, Bay Ridge, and Thomas Point neighborhoods within a 5-7 minute drive. I have no kids, so dogs have always been my 4-legged fur babies. I'm an active volunteer and puppy raiser with Warrior Canine Connections, an organization who trains service and therapy dogs for veterans with visible and non-visible injuries. I currently have 2 dogs of my own. Sookie, a 6 year old pointer mix, and Penny, a 6 year old lab/retriever mix. Both about 70 lbs! Sookie is a handful and I've participated in a few different training programs with her. I've become well versed in many types of dog behaviors, reactivity, fear aggression, and more. I'm calm, patient, warm, and well-versed in managing dogs with different personalities. I've also raised two special needs English Bulldogs, and understand the care required for dogs with medical issues. If you hate the idea of boarding your dog at a strange place when you're away, or have heard bad stories about injuries or neglect at doggy daycares, I'm looking forward to caring for your furry friend in your home! I will make sure your dog gets physical activity, potty breaks, or nap times in the sun. I will be happy to send you pictures, videos, and updates, and will work with you to make sure your dog and/or cat is cared for in a way that makes you and the pet happy! I look forward to meeting you and your furry friend! Most importantly, you can feel safe and secure with me in your home. I'm a former VP at a real estate non-profit, transitioning to a new job. I'm available in August and September for drop-in visits, walks, and overnight care. As a resident of Arundel on the Bay neighborhood, I'm available to AOTB, Annapolis Cove, Bay Ridge, and Thomas Point neighborhoods within a 5-7 minute drive. I have no kids, so dogs have always been my 4-legged fur babies. I'm an active volunteer and puppy raiser with Warrior Canine Connections, an organization who trains service and therapy dogs for veterans with visible and non-visible injuries. I currently have 2 dogs of my own. Sookie, a 6 year old pointer mix, and Penny, a 6 year old lab/retriever mix. Both about 70 lbs! Sookie is a handful and I've participated in a few different training programs with her. I've become well versed in many types of dog behaviors, reactivity, fear aggression, and more. I'm calm, patient, warm, and well-versed in managing dogs with different personalities. I've also raised two special needs English Bulldogs, and understand the care required for dogs with medical issues. If you hate the idea of boarding your dog at a strange place when your away, or have heard the bad stories about injuries or neglect at doggy daycares, I'm looking forward to caring for your furry friend in your home! I I will make sure your dog gets physical activity, potty breaks, or nap times in the sun. I will be happy to send you pictures and videos and updates, and will work with you to make sure your dog and/or cat is cared for in a way that makes you and the pet happy! I look forward to meeting you and your furry friend! I want to make sure you and your pet feel most comfortable. What is their normal routine that will make their time away from their owner more enjoyable? Any tips or tricks to making your pet more comfortable with me, or any special needs, words you use, or special requirements? Do they have any fears, reactivity, dog-aggressions, resource guarding, or other behaviors I should be aware of? I am familiar and well-versed in those behaviors, but the more I know in advance, the better! If you are a new client, I request a complimentary meetup for us to get acquainted.

Sitter Profile Image: Ellie H.
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Ellie H.
from
$17
per walk
5.0 out of 5 stars
11 reviews
3 repeat clients
10 years of experience
Annapolis, MD, 21403

Ellie was great! She’s flexible and communicates well which makes it easy to trust her! She also did an outstanding job with my husky lab, Malibu. Would definitely recommend booking!

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Kaitlin N.
Sitter Profile Image: Margriet M.
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Margriet M.
from
$30
per walk
5.0 out of 5 stars
9 reviews
1 repeat client
17 years of experience
Annapolis, MD, 21403

Totally awesome. Coop tried to drag me up the sidewalk to her house on our walk this morning, so I guess he's a fan too! So happy that we found Margriet.

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Michael B.
Sitter Profile Image: Megan T.
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Megan T.
from
$15
per walk
5.0 out of 5 stars
12 reviews
1 repeat client
10 years of experience
Annapolis, MD, 21403

About: Hi! I'm a lifelong dog lover who grew up with 3 dogs, and regularly pet sit for friends and family before deciding to make it official. Friends often call me an animal whisperer because even shy or nervous pets tend to warm up to me quickly. I work remotely, and am very active, so I have a flexible schedule and can give your pet plenty of attention (and activity)! I work remotely and have very flexible hours, so your pet will have plenty of time, walking, snuggling, and being active. I also attend run clubs where pets are allowed, so if your fur baby is social, I’ll happily take them! I have a backyard, and live in a community with plenty areas to walk and sniff. Pets are welcome to be on furniture and in bed! I’m an excellent communicator, and will work collaboratively with you to determine the best care plan for your pet.

Sitter Profile Image: Campbell S.
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Campbell S.
from
$20
per walk
1 year of experience
Annapolis, MD, 21403

About: I grew up around big dogs and cats, so I’m familiar with reading animal behavior. Dog walker and cat socialization volunteer at local animal shelter near college. I’m currently taking a class that meets Tuesdays and Thursdays, but other than that (and studying) my days are free! I do also work at an organic farm in the mornings on weekends, but my afternoons and evenings are free! I’m looking to help out whenever and wherever I can. Able to wear them out with loads of play time or to just give them a good belly rub. Whatever is needed! I’m used to playing with a high energy German Shepard/Akita mix and a one year old Black Mouth Cur. Needless to say, I can hold my own against big dogs zoomies.

Sitter Profile Image: Ella M.
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Ella M.
from
$22
per walk
5.0 out of 5 stars
1 review
2 years of experience
Annapolis, MD, 21401

About: As a dedicated dog walker and in-home pet sitter with over two years of experience, I know how important it is to find someone you can truly trust with your pet. I care for every dog (and cat!) as if they were my own — with patience, love, and attention to their unique needs and routines. What You Can Expect: ✅ Safe, fun, and tailored walks ✅ Home visits that follow your pet’s schedule ✅ Clean water, food, meds (if needed), and lots of affection ✅ Daily photo updates and messages so you never have to wonder how things are going ✅ Respect for your home and your pet’s space I’m trained in basic pet first aid and always check collars, leashes, and gates before heading out. Whether it’s a quiet walk or an energy-burning play session, your pet's safety and happiness are always my top priority. Let’s schedule a meet-and-greet! I’d love to learn more about your pet and how I can help make your time away stress-free for both of you. 🐶🐾 Pet care fits naturally into my daily routine because of how flexible and rewarding it is. Since I set my own schedule, I can book pet care clients around my part-time job shifts and study blocks, which helps me stay balanced and productive. Walking dogs gives me a much-needed mental reset from screen time and studying, and it keeps me active throughout the day. It’s also a great way to supplement my income without taking on another traditional job. Most of all, spending time with animals brings me a lot of joy and motivation — it breaks up long study days and reminds me why I love what I do Whether you’re at work or away for a few days, I provide reliable, in-home care that keeps your pets safe, happy, and stress-free in their familiar environment. From daily walks to feeding, playtime, and medication routines, I tailor every visit to your pet’s unique needs. 🔐 Safety & Professionalism Equipped for pet first aid always carrying a kit Detailed home-entry and security protocols Leash and harness checks before every walk Weather-conscious and always alert to potential hazards Respectful of your home, your pets, and your time 📸 Peace of Mind After each visit, you’ll receive a photo and short update so you know how your furry friend is doing — because trust is built on communication

Sitter Profile Image: Elaine S.
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Elaine S.
from
$20
per walk
5.0 out of 5 stars
69 reviews
37 repeat clients
20 years of experience
Annapolis, MD, 21403

About: I get a lot of pleasure assisting busy professionals with their pet sitting needs. I provide a nurturing and loving environment for your special pets in a very tranquil setting. Your pets will be treated as if they were my own. My husband and I will treat your pet with the utmost care and attention. References available upon request.

Sitter Profile Image: Mark D.
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Mark D.
from
$20
per walk
5.0 out of 5 stars
3 reviews
2 repeat clients
30 years of experience
Annapolis, MD, 21403

Mark did a fantastic job with our new dog Teddy! We are long-time dog owners as is Mark, and his years of experience and bed-side manner was certainly evident and provided great peace of mind while we were away from our new pup. We will be relying on Mark in the future and strongly recommend him to others!

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Terry J.
Sitter Profile Image: Tiffany B.
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Tiffany B.
from
$25
per walk
15 years of experience
Annapolis, MD, 21403

About: Hi, I’m Tiffany! I’m a lifelong animal lover and the former owner of Jazz Pet Care, a full-time pet sitting and dog walking company that I built from the ground up during college. Through Jazz and growing up with 11 (yes… eleven) cats I gained countless experience helping care for your pets. While I took a break from professionally providing pet care, I’m excited to be back doing what I love through Rover! My goal today with pet care is to help pay back my student loans. Whether it’s feeding, medications, playtime, potty breaks, or extra cuddles, I’ll follow your pet’s routine closely and keep you updated with photos and messages so you always have peace of mind. Happy to be a friendly neighbor to you and your pets :) My schedule changes a bit each week, but luckily I have a flexible full-time job! I’m usually available for morning visits before work, lunch-time drop-ins, evening walks, and later evening check-ins. My weekends are flexible too. I occasionally work local events, but I’m almost always nearby and can easily fit visits in before or after. Feel free to reach out, even if your schedule is a little unique! I know how important it is to trust someone with both your pet and your home. During each drop-in, I stick closely to your pet’s normal routine to help them feel comfortable and stress-free. Whether that means feeding, potty breaks, playtime, cuddles, medications, or just keeping them company, I’m happy to tailor each visit to their needs. Before I leave, I always make sure your home is secure and send plenty of photos and an update so you know exactly how your furry family member is doing.

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The median cost per walk for dog walking in Highland Beach is $20

Dog parents share their Rover experiences - Highland Beach

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5.0 out of 5 stars

Carly was great, quick response and good communication with taking care of our Pawley - he was happy and content when we came home!

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Maureen K.
Dog Walking
5.0 out of 5 stars

Leigh Ann is wonderful. She is so kind and loving to our senior girl Lola. Leigh Ann communicates well and will rebook more walks with her soon!

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Kalei K.
Dog Walking
5.0 out of 5 stars

Ali took our pup for a long walk and then fed him while we were out! She was timely and communicative and we’d happy to continue to book her!

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Sam K.
Dog Walking
5.0 out of 5 stars

He showed up on time, was very communicative, and dedicated almost the whole time to walking my dog.

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Anill M.
Dog Walking
5.0 out of 5 stars

Mae is very reliable, punctual and takes great care of our dog Cannon on their daily walks. She is a great communicator and genuinely loves caring for our dog. I would highly recommend Mae for your dog walking/sitting needs.

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Sadie S.
Dog Walking
5.0 out of 5 stars

Beth was so helpful, caring, and just generally great with my pup! I will definitely book again in the future!

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Caitlin I.
Dog Walking
5.0 out of 5 stars

Bridgette was on time, attentive and kept me up to date on how my pup was doing. Thanks for all the detailed messages, Missy would love to see you again!

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Aarti C.
Dog Walking
5.0 out of 5 stars

Harrison is always on time and keeps me up to date on how my pet is doing! I know I can count on him!

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Aarti C.
Dog Walking
5.0 out of 5 stars

We can’t recommend Kayla highly enough. Throughout the last year of our elderly dog’s life, her anxiety increased as her physical capabilities and comfort decreased. Kayla was always responsible, gentle, and kind with our sweet old girl. She was also a great communicator during planning and if anything unusual came up during walks/visits (like the time we had to get her to go room to room in our house because the dog was too spooked by a recent thunderstorm to come to the door when Kayla arrived — Kayla found treats and coaxed her out from under the bed!)

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Katy L.
Dog Walking
5.0 out of 5 stars

Megan was prompt, communicative, and sent lots of cute photos of Baker! Look forward to having her take care of our pets again.

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Alexa E.
Dog Walking
5.0 out of 5 stars

Ella has been an excellent dog walker for Cannon. She is extremely reliable and a great communicator. We would highly recommend her to care for your pets!

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Sadie S.
Dog Walking
5.0 out of 5 stars

Blinne was fabulous with my highly energetic pup and offered great feedback as to Kali’s behaviors after every walk. Kali would wait excitedly at the door each day for Blinne’s arrival. I will definitely reach out to Blinne again!

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Alison W.
Dog Walking
5.0 out of 5 stars

Thomas was so thoughtful and caring with our geriatric dog. He went above and beyond for us (and him). It gave us a peace of mind we really needed to be able to go away. We couldn’t recommend Thomas more!

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Lauren H.
Dog Walking
5.0 out of 5 stars

Lauren is the best! I would highly recommend her to anyone. She is really patient and kind with my pups, takes them on good walks, and gives them lots of treats to keep them happy. Shes very punctual, responsive, and reliable!

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Megan M.
Dog Walking
5.0 out of 5 stars

Ellie was great with my dog. She stayed in close communication and was both trustworthy and very sweet. I would hire her again.

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Mary R.
Dog Walking
5.0 out of 5 stars

Camilla came over for a meet and greet yesterday with my two senior Pyrenees. They loved her! We look forward to working with her more in the future!!

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Christina K.
Dog Walking
5.0 out of 5 stars

I really appreciate MaKayla she is always on time and keeps me posted on what is going on. I feel like we make a great team for Cooper.

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Debbie E.
Dog Walking
5.0 out of 5 stars

Totally awesome. Coop tried to drag me up the sidewalk to her house on our walk this morning, so I guess he's a fan too! So happy that we found Margriet.

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Michael B.
Dog Walking
5.0 out of 5 stars

Arem was reliable and great with Lexi. He consistently did an excellent job and I’d absolutely use him again.

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Elsie V.
Dog Walking
5.0 out of 5 stars

Kristine is our go to dog walker in the Annapolis area. She is reliable and we feel confident that our dog is getting great exercise and being well cared for when she comes.

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Devon D.
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
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

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Meet local walkers who will treat your dogs like family

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Popular requests for dog walking - Highland Beach

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Sitters in Highland Beach average 4
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FAQs for Dog Walking - Highland Beach

Frequently asked questions about Rover

The average cost for Dog Walking in Highland Beach on Rover is $27.75 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 12,882 sitters on Rover offering Dog Walking across Highland Beach. 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 Highland Beach. 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 Highland Beach.

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 Highland Beach. On Rover:

  • 90% of walkers can help with special care needs
  • 96% can help with giving oral medications or injections
  • 96% 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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