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. Gabrielle

Exercise and Dogs? Heaven on Earth.

Annapolis, MD, 21412

House Sitting, Drop-In Visits, Dog Walking

About: I'm a busy, passionate, energetic, and focused college student. Currently studying physics at the United States Naval Academy. I am a junior, part ... (more)

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2. Mollie

Haven’t met a dog I don’t like!

Annapolis, MD, 21403

House Sitting, Drop-In Visits, Dog Walking

"Mollie has loved animals since we can remember. She is kind caring and very tuned in to their needs. She has cared for animals for 15 years or more. She is e... (more)"

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3. Jennifer

Annapolis Dog Walker & House Sitter

Annapolis, MD, 21401

House Sitting, Drop-In Visits, Dog Walking

"This was a repeat visit for Jennifer with our two small dogs—couldn’t have been happier with the service and with Jennifer personally—she exhibits caring and... (more)"

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4. 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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5. 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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6. Haley

Dogs Are My Kind Of People :)

Annapolis, MD, 21403

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

"Haley is incredibly generous and loving, both to people and pets. She is sensitive and intuitive about pets' needs. She adores her own two dogs, and she is t... (more)"

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7. Sydney

Owner and Lover of dogs

Annapolis, MD, 21403

House Sitting, Drop-In Visits, Dog Walking

"Sydney did a fantastic job taking care of our Penelope while we were away! She listened to our special requests, responds promptly and sends pictures and upd... (more)"

8. Christie

Love dogs Personal love & attenti

Edgewater, MD, 21037

House Sitting, Drop-In Visits, Dog Walking

"Awesome, attention to detail, kept in touch. Wonderful peace of mind while we were away! (more)"

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9. Anne

I’ll make your dog tired and happy

Annapolis, MD, 21401

House Sitting, Drop-In Visits, Dog Walking

"Anne is such an amazing friend to my husband and I with our dog. She was visiting once and my husband had a car emergency that I had to go pick him up from. ... (more)"

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10. Sarah

Takes time to show your dog love

Annapolis, MD, 21401

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

"Sarah was willing to house sit and watch my dog for a week on very short notice. She asked questions to make sure that my dog was very. She made sure to sen... (more)"

11. Julia

I will love your dog like you do!!!

annapolis, MD, 21403

House Sitting, Drop-In Visits, Dog Walking

"Julia did a great job of house/dog sitting for our two dogs. Very pleasant and mature young lady. (more)"

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12. Colleen

I love to run walk play with dogs.

Annapolis, MD, 21403

House Sitting, Drop-In Visits, Dog Walking

"Colleen has been living with dogs since the day she was home from the hospital as a newborn. She grew up with dogs, and has owned her own since she moved out... (more)"

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13. Alexa

Love all dogs & like being active

Annapolis, MD, 21403

House Sitting, Drop-In Visits

"Alexa is an AVID animal lover ergo why she’s vegan. She had a pet dog for over 17 years of her life when he passed. (more)"

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14. Georgie

Long-time dog owner and foster!

Annapolis, MD, 21401

House Sitting, Drop-In Visits, Dog Walking

"Georgie Jones has been a dog sitter for my three dogs many many times throughout the years. She has always taken excellent care of my dogs, and they truly en... (more)"

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15. Logan

I’ll run your dog very fast.

Annapolis, MD, 21041

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

"Logan has always had a soft spot in his heart for dogs. He is a huge animal lover but dogs Hold a special place. His patience and love of running are a great... (more)"

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16. Natalie

Flexible, energetic, loving!

Annapolis, MD, 21403

House Sitting, Drop-In Visits, Dog Walking

"Natalie is the best! My mini dog is a handful: whiny, scared, and needs 2 shots a day. But he loved her as soon as she walked in! Always sent pics and always... (more)"

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17. Abigail

Working from home-love walking dogs

Annapolis, MD, 21401

House Sitting, Drop-In Visits, Dog Walking

"Abby was a great dog sitter and house sitter. She has watched our house and our pets six times, and is excellent. She is tidy, responsible, and great with pe... (more)"

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18. Erin

We love dogs as much as people!

Annapolis, MD, 21401

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

"I used Erin Adams for pet sitting every time I needed one. Pretty much the only person I would trust to watch my cat, Bill, or my dogs, Coalie and Igor. I kn... (more)"

19. David

Home with your pup

Annapolis, MD, 21402

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

"David is a natural with dogs! He has owned and helped take care of a wide variety of sizes, breeds, and temperaments. He has certainly helped me when I neede... (more)"

20. April

I dog sit for fun

Annapolis, MD, 21403

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

"April is a dog lover to her core. She'll treat your dog like her own baby. I can't imagine she's ever encountered a dog she didn't want to immediately love a... (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.