House Sitting in Highland Beach

Find a loving house sitter to watch over your pets and your home.

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Top rated Highland Beach house sitters

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

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Sitter Profile Image: Leigh Ann E.
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Leigh Ann E.
from
$31
per night
5.0 out of 5 stars
6 reviews
3 repeat clients
37 years of experience
Annapolis, MD, 21403

Leigh Ann was amazing taking care of our dogs and cat while we were on vacation. She sent us regular updates of time spent with our pets. Her attention and care was as if they were her own dogs.

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Lisa M.
Sitter Profile Image: Jamie P.
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Jamie P.
Star Sitter
from
$50
per night
5.0 out of 5 stars
121 reviews
48 repeat clients
45 years of experience
Annapolis, MD, 21403

Jamie is so great with my dogs! She reached out a few days before her stay to confirm details and showed up as promised and sent pictures and updates each day. She even made me a welcome home banner from the dogs, that was a sweet treat! I'm glad she is taking care of my babies for my next couple of trips and hope she is available for anymore that I may have. She truly is a gem!!

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Glenda L.
Sitter Profile Image: Stella N.
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Stella N.
from
$30
per night
5.0 out of 5 stars
14 reviews
3 repeat clients
7 years of experience
Annapolis, MD, 21403

About: I'm the kind of person who stops to pet every single dog I see on my walks—I simply can't resist their precious, furry faces. I've been obsessed with animals for as long as I can remember, and that love naturally led me to start pet sitting as soon as anyone would let me. Over the years, I've cared for animals belonging to friends, family, neighbors—just about anyone who asked! I truly love giving pets the care and attention they deserve, because to me, they are one of the greatest gifts in the world. I promise to care for your animals as if they were my own and can't wait to spend some time with them! I'm a part-time worker, so I have plenty of time. I love getting out and taking walks, but my dog is getting old and doesn't like to walk as much, so I'm looking for more pups to give her a break and walk with. I have a fenced-in yard in a neighborhood with lots of trails to walk on. I have a very friendly and old dog at home, but she loves company. I love spending time with animals, playing fetch, petting them, and especially going on walks. I can feed and entertain the animals.

Sitter Profile Image: Emica M.
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Emica M.
from
$50
per night
5.0 out of 5 stars
7 reviews
20 years of experience
Annapolis, MD, 21401

Emica was a wonderful dog sitter for our pups. She gave great updates and took good care of them. I would not hesitate to book her again and can recommend her highly!

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Francesca S.
Sitter Profile Image: Halsey C.
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Halsey C.
from
$50
per night
5.0 out of 5 stars
6 reviews
1 repeat client
4 years of experience
Annapolis, MD, 21403

Halsey was so caring, sent photos, went the extra mile to make sure both of our dogs were well loved while we were away!

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Kathy W.
Sitter Profile Image: Karen R.
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Karen R.
from
$50
per night
5.0 out of 5 stars
10 reviews
3 repeat clients
15 years of experience
Annapolis, MD, 21401

Karen took wonderful care of our dogs, Sam and Tito, for a full week while we were on vacation. She was incredibly responsive, always sending updates and photos when we asked, which gave us so much peace of mind. It was clear our boys were happy, comfortable, and well cared for the entire time. She also left our home in perfect condition, which we really appreciated. We would absolutely book with Karen again and highly recommend her to anyone looking for a reliable, thoughtful sitter!

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Julie G.
Sitter Profile Image: Courtney A.
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Courtney A.
Star Sitter
from
$75
per night
5.0 out of 5 stars
9 reviews
3 repeat clients
15 years of experience
Parole, MD

Courtney was great! We felt very comfortable being away knowing that our pets were getting so much love and attention. We had clear and frequent communications and a plenty of pictures confirming all the good things happening. We'd (and our critters) would be very happy to see Courtney again.

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Joanne B.
Sitter Profile Image: Samantha C.
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Samantha C.
from
$30
per night
5.0 out of 5 stars
24 reviews
8 repeat clients
6 years of experience
Annapolis, MD, 21401

Samantha was wonderful with my 2 elderly and high maintenance dogs. She sent pictures and checked in just enough while my family was away for a week. We came home to happy dogs and the house looks like we just left it. We look forward to using her again in the future!

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Erin W.
Sitter Profile Image: Jerad B.
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Jerad B.
Star Sitter
from
$50
per night
5.0 out of 5 stars
9 reviews
4 repeat clients
15 years of experience
Annapolis, MD, 21401

Jerad did an awesome job with Samson. Followed the instructions perfectly and was a great friend to our little guy. Took him on walks and sent lots of updates. Would definitely recommend!

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Clay K.
Sitter Profile Image: Ava M.
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Ava M.
Star Sitter
from
$90
per night
4.9 out of 5 stars
115 reviews
33 repeat clients
18 years of experience
Annapolis, MD, 21401

Ava is always great with our pup Haze! He's a handful and she is a pro. She also handled a household emergency for us while we were away and we couldn't be more grateful!

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Liza M.
Sitter Profile Image: Alaina G.
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Alaina G.
from
$50
per night
9 years of experience
Edgewater, MD, 21037

About: I’ve been surrounded by animals my whole life and have years of hands-on experience caring for dogs of all ages and sizes. My family has also fostered puppies for the past 5–6 years, which has given me experience with young dogs, routines, patience, and providing a safe, loving environment. Friends and family have always trusted me to walk, feed, play with, and care for their pets like they’re my own. I currently have a very flexible schedule and plenty of free time to dedicate to your pets before starting my full-time role in July. Once I begin, I’ll only be in office two days a week, so I’ll still have lots of availability. I’m available on both weekdays and weekends, and I’m happy to accommodate a variety of schedules and care needs. Your pet’s safety and comfort are my top priorities. I have a fenced yard and one friendly small dog who loves making new friends. Whether caring for your dog in my home or yours, I’ll make sure they feel loved, safe, active, and comfortable. I enjoy long walks, playtime, and giving pets lots of attention and care while you’re away.

Sitter Profile Image: Ellie H.
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Ellie H.
from
$40
per night
5.0 out of 5 stars
10 reviews
2 repeat clients
10 years of experience
Annapolis, MD, 21403

Ellie did a wonderful job of watching our dog, Camden! She was incredibly communicative and kind and treated him just like we would have if we were there. It is clear that Ellie has a passion for animals and that her responsible nature and kind disposition will make her a staple for watching our sweet boy in the future. Ellie really did go above and beyond in caring for Camden and watching our home while we were away, she really has a way with pets, even large and very playful dogs like ours. We are so glad we've found a great option for care for future needs with Ellie.

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Lisa I.
Sitter Profile Image: Carmella F.
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Carmella F.
from
$30
per night
5.0 out of 5 stars
2 reviews
1 repeat client
15 years of experience
Annapolis, MD, 21403

About: I’ve spent my 24 years of life surrounded by dogs and cats as I grew up with a mother who worked in animal rescue. I’ve been around all temperaments and know how to handle the easygoing and the most reactive. I also have experience with puppies and plenty of experience with senior pets as most of my own dogs are seniors. I currently live with my 3 cats and 1 chinchilla! I currently work full time however besides those 8 hours a day I am free to care for and look after your pets! I’m available everyday of the week including weekends and am committed to prioritizing your pets. When it comes to caring for pets, safety is always my top priority. In your home, I follow your pet’s established routine as closely as possible. I’m vigilant about locking doors, securing gates, and following any specific safety instructions you provide. I also monitor your pet’s behavior to ensure they’re healthy and comfortable. During drop-ins, I check on your pet, refill water and food as needed, and give them attention and playtime. I make sure doors and windows are locked when I leave and always follow any safety guidelines specific to your home, such as alarm codes or gate instructions.

Sitter Profile Image: Amber T.
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Amber T.
from
$45
per night
6 years of experience
Annapolis, MD, 21403

About: I have three dogs, ages 3, 6, and 14, as well as a 3-year-old cat. I’m passionate about animal care and have dedicated time to helping my community by working around my neighborhood and volunteered at the local shelter, where I walked the dogs. I’m so excited to offer my help and look after your animals! I am a college student on summer vacation! I am looking to help out with anything that is needed and have a great time. My schedule is currently very free so I am excited to meet you and your pet! I have a fenced yard, so I like to run around with my dogs. I also take them on walks around the neighborhood. Whatever you need for your dog, I can help with!

Sitter Profile Image: Alexandra R.
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Alexandra R.
from
$40
per night
10 years of experience
Annapolis, MD, 21403

About: I’ve owned 5 dogs through my life & have always loved caring for others’ pets as well. Being around animals is my happy place 🥰 I work part time on a charter boat & would love something besides gardening to keep me busy during the week. Also trying to save up for an Rv to travel I’ve been around all types of different kinds of dogs and know how to deal with different personalities and needs ❤️ from weeks old to golden days I love them all

Sitter Profile Image: Emilee A.
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Emilee A.
from
$50
per night
15 years of experience
Annapolis, MD, 21401

About: I’ve taken care of dogs of multiple sizes and ages. I grew up with dogs, cats, hamsters, a bunny, you name it. I’m the go to family member for when it comes to pet sitting! I work full time between M-F 8:30am to 5:30pm I can always find time on my lunch break or after work or weekends to help out! I can help out with whatever is needed. It doesn’t matter if they need a leash or can free roam. I will take care of them just like you would!

Sitter Profile Image: Ella L.
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Ella L.
from
$50
per night
6 years of experience
Annapolis, MD, 21403

About: I’m a reliable pet sitter who treats every pet like my own! I’m comfortable caring for puppies and have lots of experience taking care of neighbors dogs, as well as my own. I currently work part-time, which gives me flexibility to provide dependable pet care throughout the week. I’m able to make time for walks, feeding, playtime, and giving pets the attention and care they need. I provide loving and reliable care in your pet’s familiar home environment, helping them stay comfortable and stress-free while you’re away. I follow your pet’s routine closely and make sure they get plenty of attention, playtime, exercise, and care.

Sitter Profile Image: Leticia S.
Verified Enhanced Background Check
Leticia S.
from
$50
per night
5.0 out of 5 stars
2 reviews
3 repeat clients
2 years of experience
Annapolis, MD, 21401

Leticia was great with our young puppy!

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Alyssa D.
Sitter Profile Image: Vanessa R.
Verified Enhanced Background Check
Vanessa R.
from
$105
per night
5.0 out of 5 stars
13 reviews
5 repeat clients
30 years of experience
Annapolis, MD, 21403

Vanessa was fantastic to work with. She arrived promptly, kept me updated on my pup Morgan with pics and notes. I’m felt very comfortable having Vanessa house/dog sit. Would highly recommend here. Patty

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Patricia J.
Sitter Profile Image: Andrew R.
Verified Enhanced Background Check
Andrew R.
from
$31
per night
5.0 out of 5 stars
6 reviews
20 years of experience
Annapolis, MD, 21403

About: I have taken care of dogs since I was a kid. Had two dogs and I currently have a pit-bull mix, Delaney. I will consider boarding in the home My schedule is pretty open for the next few months . Let me know when you need dog services and I will be there :) While in your home, I will follow your rules and make sure the house is secure when leaving. I will take care of your dog with love and careful hand.

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Highland Beach pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Leigh Ann was great with my 2 newly adopted dogs. They were very comfortable with her right away. She is very knowledgeable, works at a veterinary hospital, and has much experience with animals. She listens carefully and gave a detailed report after our evening out. I would not hesitate to book her services again!

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Lois B.
House Sitting
5.0 out of 5 stars

Ellie did a wonderful job of watching our dog, Camden! She was incredibly communicative and kind and treated him just like we would have if we were there. It is clear that Ellie has a passion for animals and that her responsible nature and kind disposition will make her a staple for watching our sweet boy in the future. Ellie really did go above and beyond in caring for Camden and watching our home while we were away, she really has a way with pets, even large and very playful dogs like ours. We are so glad we've found a great option for care for future needs with Ellie.

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Lisa I.
House Sitting
5.0 out of 5 stars

Jamie watched our chocolate lab Winston and sister-in-laws dog Leah while we were in Annapolis for my son's wedding. I knew she was the best choice the minute my lab met her a few days prior. Winston was so excite to meet Jamie! It was like he was seeing one of our friends he has known for years! Jamie, was wonderful with her communication and pictures while she was sitting with the dogs. She watched them for an evening event we needed to attend, and then for the entire day of wedding events. I would highly recommend Jamie!! We have only ever had a friend or family member watch Winston. We are very picky!! Wish Jamie lived closer to where we live, I would always choose her to watch Winston!

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Jacqueline S.
House Sitting
5.0 out of 5 stars

Catherine was great with our dog. They went on long walks together. The house was perfect when we returned. Will definitely use Catherine again.

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Virginia R.
House Sitting
5.0 out of 5 stars

I just took a quick long weekend and Makayla made it so seamless for me. Cooper felt so loved in his own environment with her and the updates and pictures allowed me to enjoy my time. Makayla is fantastic, I almost don’t want to share how good she is because she will get to busy!!

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Debbie E.
House Sitting
5.0 out of 5 stars

Julia was amazing with Barker! She was really quick to respond to our request, she communicated clearly and was very punctual. She sent updates regularly during her stay in our home which gave me so much peace of mind, she took care of Barker following all our detailed instructions and we came back to a very happy pup. I’ll definitely work with her again!

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Celia C.
House Sitting
5.0 out of 5 stars

Halsey was so caring, sent photos, went the extra mile to make sure both of our dogs were well loved while we were away!

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Kathy W.
House Sitting
5.0 out of 5 stars

Camilla was an outstanding dog sitter for us and our two dogs! She was extremely caring, detail oriented, and responsible, and proactively provided us with updates and photos. We wouldn't hesitate to use Camilla again, she is the best!

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Lauren N.
House Sitting
5.0 out of 5 stars

Blinne did a great job taking care of our dog and cat. She was very communicative and sent photo updates. We would definitely use Blinne again!

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Jill P.
House Sitting
5.0 out of 5 stars

Kevin, who provided house sitting services for a little over a week, was accommodating when I requested an in-person meet and greet before finalizing the booking. My dog responded positively to Kevin. He maintained constant communication throughout the service and responded promptly. When I returned home, my dog appeared quite relaxed, which is always a positive sign of his comfort. I highly recommend Kevin and would definitely hire his services again.

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Jireh A.
House Sitting
5.0 out of 5 stars

Tirzah took really good care of my high energy pup. She was a great house guest as well and very thoughtful. Thanks, Tirzah!

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Caroline L.
House Sitting
5.0 out of 5 stars

Jenna helped us out last minute when our travel plans changed. She always takes such good care of Chibs and Opie!

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Lindsey G.
House Sitting
5.0 out of 5 stars

Gabriella housesat our dog when we went on a vacation. She is very dedicated and attentive. she took care of our pet like she was her own. She is a natural pet-sitter who takes her job very seriously. She is very caring. She sent us pictures and updates regularly, and replied to our questions promptly. We will certainly use her services again. We highly recommend her! Also we came back to a clean house. Thank you Gabriella.

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Rupali T.
House Sitting
5.0 out of 5 stars

Carmel was great! She adapted well to my dog’s needs and was very good at keeping us up to date. She took our dog on great long walks, which she loved! Would definitely book again!

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Katarina H.
House Sitting
5.0 out of 5 stars

Haley is seriously the best. This was the second time she watched on my Bea girl and she goes above and beyond taking care of Bea. I was also surprised to see that she unloaded my dishwasher. Haley is a great house sitter on top of dog sitting.

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Caroline L.
House Sitting
5.0 out of 5 stars

Pam was amazing! She stayed with our two dogs and cat. She could not have taken better care of our pets. They went for long walks, to the park, even to the coffee shop! She was very communicative and sent us lots of photos. It's so nice to go away and not worry about our fur babies! Thanks a bunch, Pam!

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Melissa Z.
House Sitting
5.0 out of 5 stars

Amazing sitter! She kept me up to date about how our little guy was doing!! I would highly recommend and would book again!

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Brian T.
House Sitting
5.0 out of 5 stars

Alex stepped in to house sit for us after a previous sitter needed to cancel last minute. From the start, there was clear communication that put us at ease. From the first time meeting Alex, we could tell our pup was comfortable and would be well cared for. We came home to our house looking better than we left it, and our dog, fish and plants looking like they had amazing care. Thank you, Alex!

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Cassi H.
House Sitting
5.0 out of 5 stars

Brittany helped us out so much this weekend while we attended a family wedding. It was so great to be able to trust her to care for our puppies while we were away. She sent us some adorable pictures and graciously allowed me to leave a third dog with her unexpectedly. I definitely recommend Brittanny to anyone!

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Caroline J.
House Sitting
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How Rover works

  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

The median cost per night for house sitting in Highland Beach is $50

Why Choose Rover?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • Reservation protection

    It doesn’t happen often, but if your house sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Sitters in Highland Beach average 4
repeat house sitting clients

House Sitting FAQs

Frequently asked questions about Rover

House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Highland Beach on Rover as of Jun 2026 was about $50 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.

If you’re searching for a Highland Beach house sitter for the first time, visit the house sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a house sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 2,071 house sitters in Highland Beach. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.

Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 87% of Highland Beach house sitters respond in under an hour.

House sitters in Highland Beach have an average of 14 years of experience. House sitters with repeat customers have an average of 4 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Highland Beach.

Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Highland Beach house sitters are great for:

  • Dogs who’d prefer to stay on their home turf
  • Cats and caged pets
  • Pet parents on a tight schedule
  • Keeping an eye on your home and plants while you’re away

Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.