House Sitting in Highland Beach, MD

Find a loving dog sitter to watch your dog overnight in your home.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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1. Harold

They won't want you to come home.

Annapolis, MD, 21403

House Sitting, Drop-In Visits, Dog Walking

"Scotty - Was amazing!!!!! Gave me updates on the dogs all the time. Was quick to respond to my messages. I had to add on a couple of days to the original ... (more)"

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2. Bronte

I love animals & I’m very flexible!

Annapolis, MD, 21401

House Sitting, Drop-In Visits, Dog Walking

"Very responsive and flexible! (more)"

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3. Katelyn

Can’t wait to work with your dog!

Annapolis, MD, 21403

House Sitting, Drop-In Visits, Dog Walking

"Last minute, we needed a sitter for our pup, Mazie. Katelyn met with me last minute and was so accommodating. She watched them during the day, sent us update... (more)"

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4. Stephanie

Insured, Annapolis based pet sitter

Annapolis, MD, 21403

House Sitting, Drop-In Visits, Dog Walking

"Stephanie provided excellent care for our girls and daily updates along with photos. Her care with our girls was extremely comforting as we had a last minut... (more)"

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5. Leah

I love dogs and long dog walks!

Annapolis, MD, 21403

House Sitting, Drop-In Visits, Dog Walking

"Leah is AWESOMELY!!! She house sat for us. I feel very comfortable having her in my home. Leah is loving and patient with our puppy. He still has accidents ... (more)"

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6. Stephen

They call me the animal whisperer.

Edgewater, MD, 21037

House Sitting, Drop-In Visits, Dog Walking

"This is he first time we have used Stephen. Our little shy rescue seemed to take to him quickly and Stephen definitely understands special needs dogs. He k... (more)"

Confirmed availability
This weekend
7. Sarah

Takes time to show your dog love

Annapolis, MD, 21401

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

"Sarah was wonderful...she house sat for me and my husband and took care of our two very energetic dogs while we were away on a long weekend...she came to mee... (more)"

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8. Lindsey

Eastport dog walker/cat snuggler :)

Annapolis, MD, 21403

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: I am a lifelong animal lover. I work full time at a no kill animal shelter and walk/sit dogs in my free time. I am comfortable handling any size do... (more)

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9. Haley

Dogs Are My Kind Of People :)

Annapolis, MD, 21403

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Haley was great with our 2 dogs. She visited with us prior to house sitting and was very good with our dogs: 10 year old Lenore and 6 year old Teri. I was v... (more)"

Confirmed availability
This weekend
10. Abigail

Working from home-love walking dogs

Annapolis, MD, 21401

House Sitting, Drop-In Visits, Dog Walking

"We just started working with Abigail and she's great! We're self-proclaimed helicopter dog parents, and we feel confident that our pack is in good hands with... (more)"

Confirmed availability
Christmas and New Year
11. Mark

Your dog is my top priority!

Edgewater, MD, 21037

House Sitting, Drop-In Visits, Dog Walking

"Mark did a fantastic jon with our 3 dogs & 1 cat. A family friend referred me and I am definitely glad they did. He was reliable and very responsive! I got a... (more)"

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12. Maggie

Dog Loving Dog Walker

Annapolis, MD, 21403

House Sitting, Drop-In Visits, Dog Walking

"Maggie was absolutely amazing! She came to house/dog sit for us when we had to leave town on short notice. We can’t wait to use her again in a few weeks! (more)"

Confirmed availability
Christmas and New Year
13. Lauren

I also beg at the dinner table

Annapolis, MD, 21401

House Sitting, Drop-In Visits, Dog Walking

"Lauren is communicative, punctual, and professional, and she loves dogs! What more could you ask for? Your dog will be in good hands with her. (more)"

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14. Joelle

Animal Lover

Annapolis, MD, 21403

House Sitting, Drop-In Visits, Dog Walking

"Joelle is such a kind and caring person! She is about to be a nurse soon, and her experience with taking care or others will follow through in how she will t... (more)"

Confirmed availability
Christmas and New Year
15. Allie

Home on Fridays, will jog with dogs

Annapolis, MD, 21403

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: I have been a dog owner for over 6 years and have countless experiences caring for pets of family, friends, and clients! I am available once a day ... (more)

Confirmed availability
Christmas and New Year
16. Stephanie

Dog lover extraordinaire

Annapolis, MD, 21403

House Sitting, Drop-In Visits, Dog Walking

"Steph has watched my dog a few times the past few years and has been very flexible, available and accommodating to my pup and my schedule. She is responds qu... (more)"

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17. Alexa

Love all dogs & like being active

Annapolis, MD, 21403

House Sitting, Drop-In Visits

"This is a young lady who loves animals, so much so, she’s a vegan. she volunteers at the SPCA and falls in love with those in their charge looking for their ... (more)"

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18. Sydney

Owner and Lover of dogs

Annapolis, MD, 21403

House Sitting, Drop-In Visits, Dog Walking

"We are so lucky to have had Sydney with our fur baby while we were out of the country! She was so attentive and caring, like he was her own. She’s already bo... (more)"

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19. Casey

Dogs Love Me - Let's Play!

Annapolis, MD, 21403

House Sitting, Drop-In Visits, Dog Walking

"Casey petsat for me on a few occasions. My pup loved her, and I’d highly recommend her to take care of your pets. She’s got years of experience wotking with ... (more)"

20. Julia

I will love your dog like you do!!!

annapolis, MD, 21403

House Sitting, Drop-In Visits, Dog Walking

"Julia was a fantastic sitter. Made things very easy, was very responsive and came home to a very happy pup! Thanks Julia for taking great care of Juno! (more)"


Rover offers the perfect alternative to dog kennels. The next time you head out of town and need someone to take care of your dog — and your home — turn to Rover for your Highland Beach house sitting needs. On Rover, it's easy to find a loving dog sitter in Highland Beach who'll give your dog one-on-one attention while you're away, and your dog can enjoy a sweet staycation, right at home. Search from hundreds of trusted Highland Beach house sitters near you, read sitter profiles, and reach out to sitters who seem like a good fit for you and your dog. We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your dog's stay all through Rover — it's easy, safe, and cashless. You get free premium insurance, a team of safety experts available 24/7, and cute photo updates throughout the stay. It's the easiest way to find trustworthy house sitters in Highland Beach for your dog — people who'll treat him like family.