Dog Walking Highland Beach

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

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Over 25
pet parents in Highland Beach have booked dog walking

Highland Beach, Find top rated dog walking

Prices are estimates per walk. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Allison M.
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Allison M.
from
$25
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: 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 was great! I made a mistake on the booking date, and she was kind enough to still go by and make sure my babies were taken care of despite my mistake. I will absolutely be working with her again. Highly recommend.”

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Catie K.
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

“Elizabeth is so reliable and so caring! She will care for your pet as her own. We are so grateful to have found someone to help with our fur baby and someone who loves our pup as much as we do!”

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Brittany S.
Sitter Profile Image: Andrew R.
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Andrew R.
from
$15
per walk
5.0 out of 5 stars
• 6 reviews
20 years of experience
Annapolis, MD, 21403

“I cannot recommend Andrew enough! I booked him for a whole week while I was on vacation, and my at-home dog sitter was unable to walk my dog, Champ. My sitter said that Champ got so excited every time he saw Andrew, and came home happy and tired after every walk with him. Andrew was extremely communicative, hardworking, and professional. He really listened to all my concerns about Champ, and made sure he prepared accordingly. He even walked in a torrential downpour to ensure Champ got his full amount of exercise! You won’t regret hiring Andrew for anything your dog may need.”

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Erin S.
Sitter Profile Image: Stephanie M.
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Stephanie M.
from
$20
per walk
5.0 out of 5 stars
• 5 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: Lauren W.
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Lauren W.
from
$25
per walk
5.0 out of 5 stars
• 16 reviews
7 repeat clients
27 years of experience
Annapolis, MD, 21403

“Lauren is the best! Could not recommend her enough. She loved our pup like it was her own! We are so thankful for her!”

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Caroline A.
Sitter Profile Image: Patrick L.
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Patrick L.
from
$30
per walk
5.0 out of 5 stars
• 4 reviews
20 years of experience
Annapolis, MD, 21401

About: I have been walking and sitting dogs for over 20 years, starting at age 11 when I realized dogs just made sense to me. I have owned hounds my whole life and currently share my home with a spirited beagle/jack russell mix named Tate who keeps me well-practiced with high-energy breeds. I recently lost our beloved 11-year-old foxhound mix Juniper, a gentle 70-pound soul who reminded me daily why this work matters. I am a firm believer in Cesar Millan's calm, assertive approach to dog handling. Dogs respond to confident, consistent leadership, and I bring that to every walk and every stay. I am comfortable with all breeds, large and small, and experienced administering medications and hands-on therapy when needed. I work from home in central Annapolis, which means flexible scheduling and plenty of attention for your dog during the day. Your pup is a member of your family and I always treat them like a member of my own. I own a design firm that I run out of my home. My work varies as a creative from video work to graphic design and more but it all comes from my home office located right next to my dog's food and water bowls (my hound dog Tate is currently asleep at my feet- exactly where he loves to be, and right where I love to have him). My workdays typically start around 7am and I work through the early afternoon, occasionally in the evenings. Though I have a full office setup, I also have a laptop that travels with me during house/dog sitting sessions if I need to be away for an extended period of time. As my work is on the creative spectrum, I can always adapt my schedule to fit around yours (and your pup's). Whether it's daily walks or stays with your dog, you can rest assured that they will be looked after with love, care, and the attention they deserve. I live in an apartment in Annapolis so we don't have a fenced in yard. Instead, I take my boy out in the neighborhood on short and extended walks and in the community dog park. Sniff spots and local trails are always on our schedule as our dog is high-energy so he thrives on long walks with lots of smells. Depending on your dog's needs and routine, I'm happy to take them on long walks in and around your neighborhood and parks they're comfortable with, or just playing with them in your own backyard. I'm also open to taking them further out to nature hikes and trails as long as you're comfortable with that. I tend to have Blue Buffalo, Newman's Own, and Charlee Bear treats at the ready (but of course that's up to your discretion) for good dogs and I always adhere to any diet or medication requirements to ensure a happy and healthy experience. I treat your dog like I treat my own and I've always had a great experience with every breed and personality.

Sitter Profile Image: Laurie H.
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Laurie H.
from
$20
per walk
45 years of experience
Annapolis, MD, 21401

About: I truly adore cats and their unique personalities. I'm a retired empty nester, who is flexible, attentive, patient, affectionate, and I believe great cat care includes a fresh, spotless litter box every day. Your cat will get plenty of love, attention, and a comfortable environment giving you a peace of mind while you're away. Being retired gives me a flexible schedule and plenty of time to devote to your pets, providing attentive, dependable care without rushing or juggling another job. Whether in my home or yours, I follow each pet's normal routine, providing plenty of love, attention, exercise, fresh water, clean spaces, play time and personalized care.

Sitter Profile Image: Courtney A.
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Courtney A.
Star Sitter
from
$27
per walk
5.0 out of 5 stars
• 20 reviews
14 repeat clients
15 years of experience

About: Hi! I’m Courtney — a true dog lover, experienced pet caregiver, and someone who treats every pet like family. As a dog mom myself, I understand how important it is to trust the person caring for your pet. Whether your dog loves long walks, playtime, couch snuggles, or just a calm and reassuring presence, my goal is to make them feel safe, comfortable, and loved while you’re away. I have extensive experience caring for dogs with a wide range of personalities, energy levels, and care needs, and I pride myself on being dependable, communicative, and attentive to details. For house sitting, my standard rate includes typical care such as feeding, walks/potty breaks, companionship, overnight care, and lots of love. If your pet requires additional support — including senior care, medication administration, frequent potty breaks (every few hours), mobility assistance, separation anxiety management, or near-constant supervision — please let me know before booking, as these higher-needs situations may require custom pricing to ensure I can provide the level of care your pet deserves. Please be as detailed as possible about your pet’s routine, behaviors, and care needs so I can make sure we’re the right fit. Looking forward to meeting your furry family member!

Sitter Profile Image: Savannah P.
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Savannah P.
from
$20
per walk
4 years of experience
Edgewater, MD, 21037

About: I have 4 years of pet experience. I have a 4 year old Maltese and have helped my family with their dogs for many years when they go on vacation. I walk the dogs, feed them, play with them, I do take them on car rides etc to make sure they’re happy and healthy. Dogs say I have a good sense of humor they really warm up to me. I’m currently working as a babysitter part-time so I have lots of time on my hands to help watch the little and big dogs and play with them and watch them for families who are going away. I go to many peoples homes to babysit who have dogs and I treat them like my own. I have have a dog myself and will treat the dog as if it was my own and take it on lots of walks and make sure the water is filled and the food is filled as well and make sure everything is done for their routine.

Sitter Profile Image: Chasity P.
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Chasity P.
from
$25
per walk
5.0 out of 5 stars
• 2 reviews
2 repeat clients
8 years of experience
Shady Side, MD, 20764

About: I'm a very energetic person so I will always play with the pets and I'm always making sure they are well looked after. I have taken care of plenty of pets aging from young puppies and kittens to older. When taking care of cats I have plenty of toys and things for them to climb on. I have also taken care of pets that have special needs. Like diabetics and other things. I know how to give medications oral and in shot form. Special skills would be probably that I can keep up with any animal and I love all of them. They put a smile on my face. And I love seeing owners with the same smiles. It warms my heart every day. ? I'm usually free most of the day and love cuddles and walking with the pups and kitties. So scheduling will be easy and always available. I have a fenced in yard and a dog and cat that love others. We can play and go for walks. Also tons of activities to do.

Sitter Profile Image: Sarah M.
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Sarah M.
from
$20
per walk
5.0 out of 5 stars
• 2 reviews
1 repeat client
22 years of experience
Davidsonville, MD, 21035

About: I have always been a big animal lover. I got my first dog when I turned 2 years old and did everything I could to help take care of her. I got another dog a couple of years later who became my best friend. Before I left for college he would come everywhere with me. I am now the happy and proud owner of a 6 and 12 year old cat and want to continue growing my pet family. In addition to growing up taking care of my own pets I had the responsibility of pet sitting for a lot of different families in my neighborhood. I have worked as a client service representative and now as a veterinary assistant at an animal hospital and have been able to gain knowledge and experience about pet healthcare and wellbeing beyond the general scope. I will always do my absolute best to make sure your animals are happy and healthy. I love pets of every kind and would be happy to help you take care of yours if the need ever arises! I am currently a full time employee at an animal hospital. I would be available to do drop ins before and after work and am happy to do overnight visits as long as the owner is aware I will have to leave for around 8 hours to work. Establishing trust with a pet is the most important thing you can do to ensure they are happy and healthy. I will be sure to provide individualized care for your pet depending on their needs and temperament to ensure they are as mentally and physically comfortable as possible.

Sitter Profile Image: Hannah P.
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Hannah P.
from
$25
per walk
1 repeat client
10 years of experience
Annapolis, MD, 21409

About: Hi!! I work from home and am looking to make a little extra money. I am 27 years old and have been a pet owner my whole life. I currently have two dogs and one cat. I have a lot of experience with pet sitting and am comfortable with all animals! My work schedule varies but it does allow me to be pretty flexible, especially during typical working hours. I am also an early riser so anytime in the mornings is great for me! I am extremely reliable and responsible and can assure that your pets and your home will be in good hands. I have been entrusted to house sit many times and can provide references.

Sitter Profile Image: Rachel S.
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Rachel S.
Star Sitter
from
$45
per walk
5.0 out of 5 stars
• 47 reviews
17 repeat clients
33 years of experience
Arnold, MD, 21012

About: I enjoy taking care of animals! I’ve been around dogs my entire life and helped my mom breed labradors growing up. I enjoy pet sitting because I get to enjoy that extra love from dogs/cats and the opportunity to play with them and go for walks! I have been pet sitting for about 10 years now and enjoy having them in my home and treating them like family. Pets bring so much joy to myself and my children that we love to have them around all the time! I do spoil them by letting them lay on the bed/couch in my home and I always have extra treats! We have a nice park in my neighborhood and love to go on long walks! Thank you!

Sitter Profile Image: Ella O.
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Ella O.
from
$25
per walk
5.0 out of 5 stars
• 2 reviews
2 repeat clients
7 years of experience
Severna Park, MD, 21146

About: I’ve been caring for dogs of all sizes and personalities since I was young. I grew up with dogs in my home and currently have two dogs of my own, so I know how much our pets mean to us and how important it is to find someone you can trust with them. I love getting to know each pet’s unique personality and making sure they feel safe, comfortable, and loved while their owners are away. I truly love all fur babies and would be so excited to care for yours! 🐾❤️ I am currently a part time student at Anne Arundel community college. I also have a part time job. My weekends are available. Weekdays I have a lot of free time during the day between classes before I head to work at 2:30-5:30 (usual hours). Safety is my top priority when caring for your pets. I will always make sure they are supervised, secure, and comfortable, whether we are out on a walk, during a drop-in visit, or staying overnight. I follow each pet’s routine and any instructions you provide, including feeding schedules, medications, walks, and anything else that helps them feel at home.

Sitter Profile Image: Amanda F.
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Amanda F.
from
$15
per walk
5.0 out of 5 stars
• 13 reviews
6 repeat clients
11 years of experience
Crofton, MD, 21114

About: I have had a dog of every age at some point in my life and they brought me so much joy. I no longer have pets of my own but I would love the chance to care for yours. I am not currently in school so I will have plenty of time to give your pets (or pets) all the love and attention needed. I have a small fenced yard if the service will be done in my home, and will follow the pet parents routine if the service is at your home.

Sitter Profile Image: Tristen G.
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Tristen G.
from
$35
per walk
15 years of experience
Annapolis, MD, 21409

About: I have a lot of experience with different breeds of dogs. From Jack Russell’s and shepards, golden doodles, and labs. I will treat your fur babies like my own and make sure they get as many belly as they desire I currently work part time, mainly in the mornings, so I have plenty of time in the evenings to take care of your fur babies. I have experience with a lot of different types pet care. Whether you need me to bathe, brush, give medicine, feed them, clean litter boxes, cut nails, give belly rubs, and anything you need me to do as a fur baby guardian.

Sitter Profile Image: Alexandra A.
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Alexandra A.
from
$18
per walk
5 years of experience
Gambrills, MD, 21054

About: Hi everyone! I’m a vet tech by day and have been in for about 7 years. I love all fur babies and would love to meet your babies. I’m currently working at a veterinary radiation clinic in Annapolis. I have worked at an Emergency Room for animals in Columbia. I do work from 8am to 1pm but am sometime off early. I will take care of your babies as if they were my own. I understand that our fur babies mean a lot to us and that they are family.

Sitter Profile Image: Michael P.
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Michael P.
from
$35
per walk
5.0 out of 5 stars
• 75 reviews
38 repeat clients
10 years of experience
Arnold, MD, 21012

“Michael is a great dog walker! He responded to my last minute request and is very flexible. He has walked my dog twice and has been punctual and notified me when my poop bags were empty. I would definitely recommend!”

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Kiersten W.
Sitter Profile Image: Michaela E.
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Michaela E.
from
$10
per walk
5.0 out of 5 stars
• 1 review
7 years of experience
Odenton, MD, 21113

About: Hi, I am excited to meet your pet and give them the most greatest time of there lives ! I believe in taking proper care for your pet and making sure they have a good person to take care of them! I have had multiple experiences with dogs and I love working with them! It may be winter time but I am still able to walk and feed your dog! Being able to watch your dog would truly be an honor and I will do everything I can to supply everything your dog needs. Let me know if your dog has any allergies and I can also buy them treats and goodies for them. Please set up a time with me and I am flexible with you! Thanks and I can't wait to meet your pet!

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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

Ali walked our Husky Hazel several times. We received a photos and a report card detailing the visit. On a rainy day Ali took the time to dry Hazel and make sure she was comfortable. We appreciate the thoughtfulness!

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Melissa G.
Dog Walking
5.0 out of 5 stars

Hannah is the best! She is reliable and cares about my dog. She does a great job walking her and I would recommend her highly.

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Audrey A.
Dog Walking
5.0 out of 5 stars

Leigh Ann has been walking Lola for 3 weeks now. Lola loves walking with her; I can tell by how happy she is in all the pictures we receive during their walks together. Highly recommended!

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Kalei K.
Dog Walking
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

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

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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How to book dog walking

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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 of Dog Walking in Highland Beach is $28 per walk as of October 2026. Most bookings cost between $23 and $34 per walk. On Rover, 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 12,784 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 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 , 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 Highland Beach 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 , 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 .

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

  • 85% of walkers can help with special care needs
  • 90% can help with giving oral medications or injections
  • 95% 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 .

walkers on Rover set their own , 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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