House Sitting Highland Beach

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Over 25
pet parents in Highland Beach have booked house sitting

Highland Beach, Find top rated house sitting

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

1 / 1
Sitter Profile Image: Leigh Ann E.
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Leigh Ann E.
Star Sitter
from
$31
per night
5.0 out of 5 stars
21 reviews
9 repeat clients
37 years of experience
Annapolis, MD, 21403

Leigh Anne did a great job house sitting my dog, Bea. She sent updates each day with photos of them playing in the yard. She treated my house with respect and was very tidy. I will definitely rebook!

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Caroline L.
Sitter Profile Image: Jamie P.
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Jamie P.
Star Sitter
from
$50
per night
5.0 out of 5 stars
127 reviews
49 repeat clients
45 years of experience
Annapolis, MD, 21403

Jamie was so wonderful with our dog which has very special needs. She took great care of her and gave us real peace of mind while we were gone. We’ve already booked Jamie for another upcoming trip!

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Bradley W.
Sitter Profile Image: Ava M.
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Ava M.
Star Sitter
from
$90
per night
4.9 out of 5 stars
121 reviews
35 repeat clients
18 years of experience
Annapolis, MD, 21401

Ava is consistently wonderful with our cat snd our anxious, senior dog. She’s super communicative, and puts us at ease. We never worry about leaving town if Ava is with our pets!

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Kelsey C.
Sitter Profile Image: Courtney A.
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Courtney A.
Star Sitter
from
$85
per night
5.0 out of 5 stars
19 reviews
8 repeat clients
15 years of experience
Edgewater, MD, 21037

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: Carly B.
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Carly B.
from
$85
per night
35 years of experience
Annapolis, MD, 21403

About: Hello! I'm a former VP at a real estate non-profit, transitioning to a new job. I'm available in August and September for drop-in visits, walks, and overnight care. As a resident of Arundel on the Bay neighborhood, I'm available to AOTB, Annapolis Cove, Bay Ridge, and Thomas Point neighborhoods within a 5-7 minute drive. I have no kids, so dogs have always been my 4-legged fur babies. I'm an active volunteer and puppy raiser with Warrior Canine Connections, an organization who trains service and therapy dogs for veterans with visible and non-visible injuries. I currently have 2 dogs of my own. Sookie, a 6 year old pointer mix, and Penny, a 6 year old lab/retriever mix. Both about 70 lbs! Sookie is a handful and I've participated in a few different training programs with her. I've become well versed in many types of dog behaviors, reactivity, fear aggression, and more. I'm calm, patient, warm, and well-versed in managing dogs with different personalities. I've also raised two special needs English Bulldogs, and understand the care required for dogs with medical issues. If you hate the idea of boarding your dog at a strange place when you're away, or have heard bad stories about injuries or neglect at doggy daycares, I'm looking forward to caring for your furry friend in your home! I will make sure your dog gets physical activity, potty breaks, or nap times in the sun. I will be happy to send you pictures, videos, and updates, and will work with you to make sure your dog and/or cat is cared for in a way that makes you and the pet happy! I look forward to meeting you and your furry friend! Most importantly, you can feel safe and secure with me in your home. I'm a former VP at a real estate non-profit, transitioning to a new job. I'm available in August and September for drop-in visits, walks, and overnight care. As a resident of Arundel on the Bay neighborhood, I'm available to AOTB, Annapolis Cove, Bay Ridge, and Thomas Point neighborhoods within a 5-7 minute drive. I have no kids, so dogs have always been my 4-legged fur babies. I'm an active volunteer and puppy raiser with Warrior Canine Connections, an organization who trains service and therapy dogs for veterans with visible and non-visible injuries. I currently have 2 dogs of my own. Sookie, a 6 year old pointer mix, and Penny, a 6 year old lab/retriever mix. Both about 70 lbs! Sookie is a handful and I've participated in a few different training programs with her. I've become well versed in many types of dog behaviors, reactivity, fear aggression, and more. I'm calm, patient, warm, and well-versed in managing dogs with different personalities. I've also raised two special needs English Bulldogs, and understand the care required for dogs with medical issues. If you hate the idea of boarding your dog at a strange place when your away, or have heard the bad stories about injuries or neglect at doggy daycares, I'm looking forward to caring for your furry friend in your home! I I will make sure your dog gets physical activity, potty breaks, or nap times in the sun. I will be happy to send you pictures and videos and updates, and will work with you to make sure your dog and/or cat is cared for in a way that makes you and the pet happy! I look forward to meeting you and your furry friend! I want to make sure you and your pet feel most comfortable. What is their normal routine that will make their time away from their owner more enjoyable? Any tips or tricks to making your pet more comfortable with me, or any special needs, words you use, or special requirements? Do they have any fears, reactivity, dog-aggressions, resource guarding, or other behaviors I should be aware of? I am familiar and well-versed in those behaviors, but the more I know in advance, the better! If you are a new client, I request a complimentary meetup for us to get acquainted.

Sitter Profile Image: Ella M.
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Ella M.
from
$55
per night
5.0 out of 5 stars
1 review
2 years of experience
Annapolis, MD, 21401

Simply the best!!! Very communicative, my Karma loved their walks!! Thank you for taking care of our baby!!!!

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Christa G.
Sitter Profile Image: Jessica B.
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Jessica B.
from
$70
per night
5.0 out of 5 stars
12 reviews
5 repeat clients
12 years of experience
Edgewater, MD, 21037

Jess is wonderful. She was so patient and gentle with our dog, Ellie. She is officially our “go-to”! Highly recommend!

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Nicole J.
Sitter Profile Image: Vanessa R.
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Vanessa R.
from
$110
per night
5.0 out of 5 stars
13 reviews
5 repeat clients
40 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: Marla H.
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Marla H.
from
$50
per night
10 years of experience
Annapolis, MD, 21401

About: What sets me apart is the hands-on experience I bring with animals at every stage of life. I’ve bottle-fed newborns, cared for senior dogs with patience and love, and have extensive experience giving medicine to pets of all kinds. Beyond dogs and cats, I’ve also cared for guinea pigs and reptiles,so I understand that every animal has unique needs. With me, you can trust that your pet will be treated like family, whether that means playtime, specialized care, or extra snuggles. Pet care fits seamlessly into my routine. I plan my schedule to prioritize feeding times, walks, and any special care instructions so that pets always receive consistent attention. I’m organized, dependable, and detail-oriented, which allows me to maintain each pet’s routine reliable,whether it’s daily exercise, administering medicine, or simply giving them the reassurance they need while you’re away. In my home, pets are welcomed into a safe and supervised environment where I treat them like family. I’m experienced with bottle-feeding young animals, administering medications, and providing gentle care for senior pets. I also have hands-on experience with small animals like guinea pigs and reptiles, so I understand how to meet a variety of unique needs. In a client’s home, I follow feeding, exercise, and care routines exactly as directed, while adding the patience and attentiveness that comes with my experience. Whether it’s giving medicine on schedule, offering extra support to older pets, or ensuring younger animals burn off energy in healthy ways, I provide reliable and compassionate care.

Sitter Profile Image: Ryan L.
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Ryan L.
Star Sitter
from
$90
per night
5.0 out of 5 stars
11 reviews
3 repeat clients
25 years of experience
Annapolis, MD, 21409

Ryan was absolutely great! He pinch-hit for a Rover cancellation at the last minute, and was able to come for a meet & greet the day before sitting for our dog. He and Rory hit it off immediately and pics confirmed how much fun they had. Ryan takes his job seriously and asks lots of questions about routine, food, etc. We would not hesitate to use Ryan's services again. Two thumbs way up!

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Lois B.
Sitter Profile Image: Tiffany D.
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Tiffany D.
from
$55
per night
8 years of experience
Annapolis, MD, 21403

About: All my life, I’ve owned and cared for dogs, cats, rabbits, and hamsters, so I’m comfortable with pets of different sizes, personalities, energy levels and routines. I have experience in handling reactive dogs of all sizes as well as couch potatos. You can count on me to follow any specific feeding routines and dietary needs, as well as administering medications. Pups, kitties, bunnies, and everything in between are welcome! I'm currently working a flexible part-time schedule which gives me plenty of time to walk your reactive pup, play with your crazy cats, or sit (and crochet) while keeping your pets company! Most pets don't want strangers in their space! I pay close attention to body language, and let them set the pace so each visit feels as safe and comfortable as possible. When staying in your home, I follow your pet’s routine closely, including feeding, waste cleanup, playtime, medications, and as many walks as requested. I keep your home secure, never invite guests over, follow household instructions, and always clean up after myself.

Sitter Profile Image: Margriet M.
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Margriet M.
from
$100
per night
5.0 out of 5 stars
7 reviews
1 repeat client
17 years of experience
Annapolis, MD, 21403

Margriet was a wonderful dog sitter. Rory took to her immediately (and she to him). We were able to go on vacation knowing that he would be fed, walked, cuddled, and let outside to run around in the backyard. Rory was not completely house trained when we left, but Margriet finished the job for us. Margriet also brought in packages from Amazon, and left the house clean and sheets laundered. We highly recommend Margriet for all dog sitting needs.

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Lois B.
Sitter Profile Image: Catherine N.
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Catherine N.
from
$73
per night
5.0 out of 5 stars
16 reviews
2 repeat clients
30 years of experience
Annapolis, MD, 21403

We were in town for a wedding and Catherine took such great care of our pups Baggins! Stayed with him and took him on a great hike. A real life saver for us!!!

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Heather Z.
Sitter Profile Image: Lisa H.
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Lisa H.
from
$50
per night
5.0 out of 5 stars
3 reviews
5 years of experience
Arnold, MD, 21012

About: I've been taking care of family and friends dogs for over 5 years. And used to have dogs and cats of my own. I have many fur-nieces and fur-nephews and love them as my own. Because I work remotely, I can take my work anywhere. So, I will be able to stay with your pet for the duration you are gone. I work from home. And have the ability to work from anywhere. I will bring my laptop and be able to work and keep your baby company. Taking care of them in familiar surroundings.

Sitter Profile Image: Marley D.
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Marley D.
Star Sitter
from
$65
per night
5.0 out of 5 stars
53 reviews
20 repeat clients
15 years of experience
Annapolis, MD, 21401

Marley is so sweet and reliable with my dog. Highly recommend!

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Courtney R.
Sitter Profile Image: Megan H.
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Megan H.
Star Sitter
from
$40
per night
4.9 out of 5 stars
56 reviews
17 repeat clients
10 years of experience
Crownsville, MD, 21032

Megan was wonderful. She took great care of our pup and was excellent with her communication with us. We highly recommend her.

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Abbie E.
Sitter Profile Image: Hannah B.
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Hannah B.
Star Sitter
from
$60
per night
5.0 out of 5 stars
27 reviews
10 repeat clients
15 years of experience
Annapolis, MD, 21403

Hannah was very responsive and flexible! Willing to go the extra mile to make us and our dog comfortable. Would definitely book with her again!

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Winston C.
Sitter Profile Image: Rachel J.
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Rachel J.
from
$70
per night
5.0 out of 5 stars
22 reviews
7 repeat clients
20 years of experience
Annapolis, MD, 21401

Rachel stayed with Daisy for 5 nights and had great communication! She sent lots of photos and updates and Daisy obviously loves spending time with her! Highly recommend booking with Rachel and we will definitely be booking with her again!

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Jessica & Matthew O.
Sitter Profile Image: Brittanny A.
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Brittanny A.
from
$55
per night
4.2 out of 5 stars
8 reviews
2 repeat clients
12 years of experience
Annapolis, MD, 21401

Brittanny was great with our two dogs - they really loved her. She spent so much time with them and stuck to their normal schedule. We will definitely be booking Brittanny again!

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Macey W.
Sitter Profile Image: Megan T.
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Megan T.
from
$31
per night
5.0 out of 5 stars
11 reviews
1 repeat client
10 years of experience
Annapolis, MD, 21403

About: Hi! I'm a lifelong dog lover who grew up with 3 dogs, and regularly pet sit for friends and family before deciding to make it official. Friends often call me an animal whisperer because even shy or nervous pets tend to warm up to me quickly. I work remotely, and am very active, so I have a flexible schedule and can give your pet plenty of attention (and activity)! I work remotely and have very flexible hours, so your pet will have plenty of time, walking, snuggling, and being active. I also attend run clubs where pets are allowed, so if your fur baby is social, I’ll happily take them! I have a backyard, and live in a community with plenty areas to walk and sniff. Pets are welcome to be on furniture and in bed! I’m an excellent communicator, and will work collaboratively with you to determine the best care plan for your pet.

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

Pet parents share their Rover experiences - Highland Beach

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5.0 out of 5 stars

Ali came through for us in a pinch, and our dog who had separation anxiety was very relaxed and chill with Ali's company. We would definitely call upon Ali's help again.

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Barbara C.
House Sitting
5.0 out of 5 stars

This was the first time that Leigh-Ann took care of my two dogs. She is fabulous. Came when she said she would, asked questions to clarify my instructions, spent quality time with the dogs (they love her!) and left the house in great condition. I have already booked her again and am so happy I found her. Thanks Leigh-Ann!

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Susan S.
House Sitting
5.0 out of 5 stars

Margriet was a Godsend for us! We have two pups, one which suffers from separation anxiety that results in digestive issues (stress colitis). We were so worried that he would get sick while we were away from being depressed and stressed. When we returned, he was in such great spirits and not sick at all. Margriet kept us updated throughout our trip- she sent us pictures of the pups on walks, sitting in our backyard happily in the sun, and snoozing comfortably next to her on the couch. She really gave them love while we were away which resulted in very happy pups. We can tell she truly loves dogs. She also was good with handling our own anxieties about leaving a distressed pup – she went the extra mile to do two home visits prior to our departure. We (us and the pups) are so happy we found Margriet. It was a perfect match! Anyone would be lucky to have her pup-sit at their home! We have finally found our person who we can trust to stay in our home and give our dogs the love they need while we’re away! Thank you, Margriet!

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Ivonne K.
House Sitting
5.0 out of 5 stars

Lucille was fantastic!! She kept us informed on their day and the administration of his medications. When she was concerned about something she called us and gave us updates every day. She also took care of the house by removing the trash etc! It was also so obvious that she loves animals. I will definitely book her again!! Thanks Lucille for making my trip so much more enjoyable knowing that my dog was in such good hands!!

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Nancy C.
House Sitting
5.0 out of 5 stars

Jamie once again did great with the fur babies. I felt so comfortable leaving my reactive cattle dog. She also watched my cat and watered the plants. There was a big storm the night before we came back and a neighbors tree fell in our yard and she sent pictures and told us about the situation. We will use Jamie again in the future!!!

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Erin L.
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

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
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  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
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Popular requests for house sitting - Highland Beach

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Sitters in Highland Beach average 4
repeat house sitting clients

FAQs for House Sitting - Highland Beach

Frequently asked questions about Rover

The average cost for House Sitting in Highland Beach on Rover is $93.21 per night (as of September 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of House Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for House Sitting. For more information on service fees, click here .

As of September 2026, there are 8,402 sitters on Rover offering House Sitting across Highland Beach. Enter your ZIP code to see which available sitters are closest to your home.

Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:

  • Mail & deliveries: Collecting letters and packages so they don't pile up.
  • Plant care: Keeping your indoor or outdoor garden hydrated.
  • Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
  • Home security: Sitters can stay overnight to keep your home occupied.

The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Highland Beach walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.

It’s helpful to think of house sitting as a "home base" service. Most sitters in Highland Beach maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:

  • Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
  • Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
  • Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.

Tip: Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!

Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Highland Beach choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!

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 Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.

Every sitter 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 Rover's Trust & Safety page .

If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.

For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.

Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.

A Meet & Greet is a short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter 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 sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.

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

  • 92% of sitters can help with special care needs
  • 96% can help with giving oral medications or injections
  • 96% 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.

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