House Sitting in Highland Beach

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

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
Which dates do you need?
What size are your dogs (lbs)?

Search Results

Sitter Profile Image: Ava M.
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Sitter Profile Image: Ava M.
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1. Ava M.

Star Sitter
Animal Lover & Former Vet Tech
Annapolis, MD, 21401
5.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
46 reviews
10 repeat clients
from
$75
per night
Profile image

Ava took such great care of our 3 dogs overnight. We were confident that our pups were in great hands and received many pictures/uodates throughout the days. We will definitely have Ava watch our dogs again!

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Sitter Profile Image: Andrew P.
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Sitter Profile Image: Andrew P.
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2. Andrew P.

Star Sitter
Caring, animal-loving PA
Annapolis, MD, 21401
5.4 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
46 reviews
14 repeat clients
from
$45
per night
Profile image

Andrew provided incredible care to my pup brutus. He was very proactive with sending updates and pictures, and my dog looked so happy in every one he sent. Could not recommend his sitting services enough!!

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Sitter Profile Image: Pam J.
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Sitter Profile Image: Pam J.
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3. Pam J.

Star Sitter
Every pet client is #1 to me!
Annapolis, MD, 21401
5.8 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
57 reviews
25 repeat clients
from
$75
per night
Profile image

Pam was absolutely amazing and an angel when taking care of our animals. Our animals even had stomach issues and she was super caring and communicative with us. I would highly recommend her to anyone and we will be using her again!

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Sitter Profile Image: Jamie P.
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Sitter Profile Image: Jamie P.
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4. Jamie P.

Best Buddy for the Furry Royalty
Annapolis, MD, 21403
2.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
91 reviews
37 repeat clients
from
$45
per night
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Jamie is great. She took such good care of our dog and the house for a week. We have already booked her for a weekend in May. The pictures she took of our pup and the welcome home banner were a sweet surprise!

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Sitter Profile Image: Summerlyn S.
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Sitter Profile Image: Summerlyn S.
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5. Summerlyn S.

Reliable pet lover & owner 💓🐾
Edgewater, MD, 21037
4.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
4 reviews
1 repeat client
from
$40
per night

Summerlyn is great with animals of all sorts. I trust her to take care of my mini farm when I go away. I have 6 chickens, 3 ducks and 11 outside bunnies. 1 garage chicken that is let out every morning and put to bed every night (lowest on pecking order). Also have 2 dogs, a cat, parrot, tortoise and a bearded dragon. She also waters all of my plants inside and outside. I definitely recommend Summerlyn to care for your pets no matter what your pet might be!

Sitter Profile Image: Madison A.
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Sitter Profile Image: Madison A.
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6. Madison A.

A mini vacay for your fur children
Annapolis, MD, 21401
5.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
4 reviews
1 repeat client
from
$40
per night
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Madison was great with Gordie, took him on field trips, gave him lots of cuddles, and left our house cleaner than we’d left it! Will definitely hire again!

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Sitter Profile Image: Michael P.
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Sitter Profile Image: Michael P.
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7. Michael P.

Rover 101
Compassionate, Reliable, Fun Loving
Annapolis, MD, 21409
6.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
56 reviews
29 repeat clients
from
$75
per night
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Michael was great; did a meet and greet first to make sure Cobbler was comfortable with him, and he took immaculate care of her and my house. Would recommend!

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Sitter Profile Image: Angela M.
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Sitter Profile Image: Angela M.
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8. Angela M.

Striving to be a great pet sitter
Annapolis, MD, 21401
6.3 mi. away
House Sitting, Drop-In Visits
5.0 out of 5 stars
5 reviews
from
$50
per night
Profile image

Angela was very prompt, responsible, and communicative. I booked her a few weeks in advance, she came over once to meet my dog and get an idea of her routine. She then came back the day before my trip for a refresher. She took care of my dog exactly as we had discussed and sent regular pictures and updates while I was gone. My home was exactly as I left it when I got back. Would definitely use Angela again!

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Sitter Profile Image: Susan S.
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Sitter Profile Image: Susan S.
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9. Susan S.

Star Sitter
Dr. Dolittle- talks,walks, cuddles
Annapolis, MD, 21401
3.5 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
33 reviews
15 repeat clients
from
$80
per night
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It was a pleasure having Susan watch our dog! She was so nice during our meet & greet and our dog took to her right away. She was very responsive and sent us photos during her stay.

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Sitter Profile Image: Charlotte S.
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Sitter Profile Image: Charlotte S.
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10. Charlotte S.

Friendly, Trustworthy,Animal Lover!
Annapolis, MD, 21403
3.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
34 reviews
8 repeat clients
from
$52
per night
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Charlotte was amazing! We asked for a last minute sit and she was able to accommodate. She communicated very well and took care of our little girl! We could not have asked for better! Will definitely book her again!

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Sitter Profile Image: Debbie B.
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Sitter Profile Image: Debbie B.
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11. Debbie B.

Star Sitter
Pets are people too;)
Annapolis, MD, 21403
0.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
22 reviews
5 repeat clients
from
$75
per night
Profile image

Debbie was SO WONDERFUL with my nervous pup! Bailey got comfortable with her quickly and they had good walks. Debbie was great about juggling her schedule and Bailey's needs. I will be working with Debbie again!

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Sitter Profile Image: Andy & Lydia M.
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Sitter Profile Image: Andy & Lydia M.
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12. Andy & Lydia M.

Dog Lover, proud veteran, sailor
Annapolis, MD, 21403
2.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care
5.0 out of 5 stars
4 reviews
1 repeat client
from
$52
per night

Leaving your pet with someone else is like trusting them to take care of your beating heart. So you want someone like Andy, who is kind and careful and who will treat your dog as if it is his own. A walk around his fenced-in yard, though modest in size, proves his dedication to helping things thrive -- the birdfeeders are always full, the birdbaths are clean, the trees and plants are healthy and lush. The yard is tidy and welcoming. It is a wonderful respite where your dog can run and play. His home is completely dog-friendly, with soft places to rest for a nap or a good night's sleep. And you can relax when necessity takes you away from home, knowing your dog is in good hands.

Sitter Profile Image: Lindsay M.
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Sitter Profile Image: Lindsay M.
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13. Lindsay M.

Star Sitter
Will Treat Your Pets Like My Own!
Annapolis, MD, 21402
4.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
11 reviews
3 repeat clients
from
$50
per night
Profile image

Lindsay was a lifesaver. We had some issues while we were on our trip with a different sitter and Lindsay stepped in and looked after our two dogs. She immediately connected with our pups and they absolutely loved her. I would highly recommend to anyone looking for a sitter!

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Sitter Profile Image: Gabriella F.
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Sitter Profile Image: Gabriella F.
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14. Gabriella F.

Attentive and gentle
Annapolis, MD, 21403
1.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
1 review
from
$50
per night

I have known Gabby for years. She has such a kind heart and absolutely adores animals. She has always been there to help me with pets I watch if I cannot make certain dates. The animals always tend to love her.

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Sitter Profile Image: Grayce M.
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Sitter Profile Image: Grayce M.
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15. Grayce M.

Dog owner & lover!
Annapolis, MD, 21411
3.7 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
2 reviews
from
$50
per night

Grayce has cared for our dogs like they were her own! She is incredibly responsible and loving with them, spending time to play and make sure they are walked, fed, and anything else when needed. We love having Grayce around to help make sure Scout (and previously our dog Riggins) get the attention they deserve when we're not available. Plus, they loved playing with her dog Luna who couldn't be sweeter! Thanks for everything Grayce!

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Sitter Profile Image: siara p.
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Sitter Profile Image: siara p.
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16. siara p.

Star Sitter
Flexible schedule, responsible
Annapolis, MD, 21403
1.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
18 reviews
6 repeat clients
from
$27
per night

Siara is great with my dog Shep! She’s so friendly and has the best energy when it comes to taking care of my dog for me.

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Sitter Profile Image: Patty P.
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Sitter Profile Image: Patty P.
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17. Patty P.

I'll take your dog on hikes!
Annapolis, MD, 21401
3.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
1 repeat client
from
$50
per night
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Patty was great! I felt great going away knowing I was leaving my pup in good hands. She was super responsive during my time away and made everything easy.

Sitter Profile Image: Hayden H.
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Sitter Profile Image: Hayden H.
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18. Hayden H.

Only the best for our furry friends
Annapolis, MD, 21403
2.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5 reviews
1 repeat client
from
$30
per night

Hayden excels as a pet sitter due to his deep love for animals and pure happiness while being around them. Hayden is very responsible and reliable will will go above and beyond to ensure that the pets are happy and treated with a lot of love. With Hayden, pet owners can trust their pets are in caring and capable hands.

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Sitter Profile Image: Liam K.
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Sitter Profile Image: Liam K.
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19. Liam K.

Dog Sitter Extraordinaire
Annapolis, MD, 21403
1.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
1 repeat client
from
$40
per night
Profile image

Very responsive and you can tell Liam loves pets!

Sitter Profile Image: Sammy S.
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Sitter Profile Image: Sammy S.
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20. Sammy S.

I love all animals!
Annapolis, MD, 21403
0.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
1 review
from
$40
per night

Sammy is an animal lover. She never misses an opportunity to stop and pet a dog or take her own dog Chelsea the husky for a walk or dog park. She is patient and sweet. Sammy would love to meet some new furry friends and would be an awesome rover.

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Rover also offers other services in Highland Beach:


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.

House Sitting