House Sitting in Trails Of Countryside, Clearwater, FL

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Top rated Trails Of Countryside 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: Alyssa S.
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Alyssa S.
from
$40
per night
5.0 out of 5 stars
12 reviews
1 repeat client
2 years of experience
Palm Harbor, FL, 34684

Alyssa was absolutely amazing beyond expectations. She cared for our 2 pups and our cat. Great communication and true care for our babies. Would highly recommend and when needed Will definitely ask for help again. A+++

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Todd I.
Sitter Profile Image: Mary W.
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Mary W.
from
$45
per night
5.0 out of 5 stars
15 reviews
5 repeat clients
33 years of experience
Ozona, FL, 34660

Mary was wonderful house sitting for my dogs. She was very communicative and kept my pups in a safe environment keeping me informed throughout her stay. Thank you so much!!

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Amanda H.
Sitter Profile Image: Peyton S.
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Peyton S.
from
$70
per night
5.0 out of 5 stars
55 reviews
21 repeat clients
10 years of experience
Clearwater, FL, 33761

Peyton was really good with Ginger, sent at least 1 photo daily, kept in contact with us about Gingers care and anything that seemed a little off. Ginger seemed happy with her.

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Brad V.
Sitter Profile Image: Maureen T.
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Maureen T.
Star Sitter
from
$50
per night
5.0 out of 5 stars
40 reviews
14 repeat clients
35 years of experience
Oldsmar, FL, 34677

Five stars! Thanks for your flexibility and prompt communication, Maureen. I highly recommend working with Maureen for all your pet sitting needs!

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Sara & Corbitt O.
Sitter Profile Image: Brooke H.
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Brooke H.
Star Sitter
from
$75
per night
5.0 out of 5 stars
53 reviews
24 repeat clients
1 year of experience
Dunedin, FL, 34698

Brooke was very kind, positive, and communicated well with texts and photos, which allowed us to enjoy our vacation with peace of mind. The pets were well taken care of.

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Douglas B.
Sitter Profile Image: Douglas W.
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Douglas W.
from
$32
per night
5.0 out of 5 stars
4 reviews
1 repeat client
14 years of experience
Palm Harbor, FL, 34684

Doug is such a caring person. He took amazing care of our dog and house for more than a week. Our dog absolutely loved him. Moreover he took care of our plants and fish. He also did a very beautiful sketch of our dog. He is so talented! We are highly recommending him!

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Lavinia W.
Sitter Profile Image: Barbara B.
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Barbara B.
from
$80
per night
5.0 out of 5 stars
50 reviews
18 repeat clients
30 years of experience
Oldsmar, FL, 34677

Our dog, Kugel, absolutely loved Barbara! Barbara spent lots of quality time with him, took him on nice long walks, and sent a bunch of updates and cute pictures to me while I was gone. She was very prompt, professional, and attentive in all of our conversations and always took time to answer any questions and concerns. I highly recommend Barbara for any dog walking/sitting needs!

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Elana B.
Sitter Profile Image: Lydia & Emmitt J.
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Lydia & Emmitt J.
Star Sitter
from
$50
per night
5.0 out of 5 stars
332 reviews
50 repeat clients
6 years of experience
Palm Harbor, FL, 34684

Lydia and Emmitt took such good care of my little guy! They provided pictures and daily updates. They reiterated how they provided meals, walks, and medications in their communications. They put me at ease and allowed me to focus on work. I came home to a clean home and happy dog! I highly recommend (unless it's when I need them again!) Lol!

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Sherri D.
Sitter Profile Image: Stephanie A.
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Stephanie A.
Star Sitter
from
$44
per night
4.9 out of 5 stars
42 reviews
15 repeat clients
10 years of experience
Dunedin, FL, 34698

10/10 for another stay with Stephanie! I got so many updates and pictures of my sweet babies while away! She went above and beyond! Always made sure they had fresh food and water and ample love!! Even did laundry before she left! Cannot recommend Stephanie enough! If you are looking for someone to not only care for your animals but also your home - book with Stephanie!

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Michelle D.
Sitter Profile Image: Janelle M.
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Janelle M.
from
$70
per night
5.0 out of 5 stars
22 reviews
5 repeat clients
15 years of experience
Winding Wood, Clearwater, FL, 33761

Janelle is great!

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Denise C.
Sitter Profile Image: MaCailey M.
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MaCailey M.
from
$35
per night
5.0 out of 5 stars
2 reviews
10 years of experience
Palm Harbor, FL, 34684

MaCailey was excellent with all my animals. She was very caring and met their needs. They all seem happy and healthy. We will definitely request her again in the near future.

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Wendy L.
Sitter Profile Image: Courtney F.
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Courtney F.
from
$85
per night
4.9 out of 5 stars
34 reviews
9 repeat clients
5 years of experience
Palm Harbor, FL, 34684

Archie LOVES Courtney. Courtney showed up on short notice, with limited direction, and stole Archie's heart within seconds of arriving. I would give Courtney the highest recommendation, without reservation.

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Christopher C.
Sitter Profile Image: Stephanie W.
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Stephanie W.
Star Sitter
from
$65
per night
5.0 out of 5 stars
61 reviews
23 repeat clients
28 years of experience
Oldsmar, FL, 34677

Stephanie did an incredible job with our two golden retrievers. She sent me lots of pictures while we were gone and i could tell the dogs were having a great time. She left our house immaculate - it looked better than before we left! She was a pleasure to work with and we will definitely be using her again in the future!

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Maureen C.
Sitter Profile Image: Megan S.
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Megan S.
Star Sitter
from
$65
per night
5.0 out of 5 stars
205 reviews
58 repeat clients
17 years of experience
Palm Harbor, FL, 34683

Another great experience with Megan! She took excellent care of our two kitties and pup while we were away on our cruise. We didn't worry about our babies well being at all. She made sure to constantly update us and send us photos. Our pets looked so happy in every picture. Megan even got our shy kitty to come out and feel comfortable without us there. We love Megan's care! We will definitely be booking with her from now on :)

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Elizabeth S.
Sitter Profile Image: Isabella W.
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Isabella W.
from
$40
per night
5.0 out of 5 stars
6 reviews
5 years of experience
Palm Harbor, FL, 34683

About: I’ve been pet sitting since I was 14, big and small animals. I’m also experienced at giving medicine to elderly and young animals. The most I’ve ever cared for at one time was 8 cats and 2 dogs! I’m a college student so it fits well with my class schedule. As well as I miss my puppies back home in Tennessee! So watching other peoples animals can fill that space. I have a fenced in yard. Plenty of space in the house, couch is never off limits. I can provide potty breaks every two hours.

Sitter Profile Image: Margot O.
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Margot O.
Star Sitter
from
$75
per night
5.0 out of 5 stars
428 reviews
147 repeat clients
34 years of experience
Palm Harbor, FL, 34684

Margot is amazing! We would give her 6 stars if we could. She is so good with the boys and she sends us pictures everyday while we are gone. We hope Margot is available every time we go out of town.

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Karen C.
Sitter Profile Image: Samouila S.
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Samouila S.
from
$40
per night
5.0 out of 5 stars
27 reviews
8 repeat clients
15 years of experience
PALM HARBOR, FL, 34684

I immediately felt at ease when I met Samouila. It’s difficult to find someone you’re comfortable taking care of your dogs, nevermind staying in your home! But I left feeling completely confident that my dogs and my home was safe. Highly recommended!!

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Lisa P.
Sitter Profile Image: David L.
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David L.
Star Sitter
from
$45
per night
5.0 out of 5 stars
43 reviews
12 repeat clients
10 years of experience
Clearwater, FL, 33764

It was a pleasure meeting David. We felt very comfortable leaving our somewhat high energy young german shepherd with him. He's not a super friendly dog with people but David was cool with that and won him over. Highly recommended!

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Elizabeth D.
Sitter Profile Image: Alexandra M.
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Alexandra M.
Star Sitter
from
$94
per night
5.0 out of 5 stars
110 reviews
19 repeat clients
20 years of experience
Palm Harbor, FL, 34683

About: Hi, I’m Alex! I’ve been caring for ALL types of animals since I was a kid, and it’s something I truly love! I have 2 cats of my own, regularly dogsit German Shepherds for a close friend, and occasionally volunteer with the Humane Society of Pinellas. Having worked with pets of all ages, from bottle babies to seniors with special needs, my best approach is to calmly match energy. Patience is more than key, and I will always respect each animal’s unique personality and nonverbal boundaries. Pet care is my full-time job! Working with animals and supporting my community are truly my passions. I’m very savvy with time management and love keeping my schedule steady, reliable, and flexible for my clients. Unless we discuss otherwise, I typically spend 30–40 minutes at each drop-in to give your pets proper attention and care without ever rushing. Weekends, holidays, and last-minute requests are always welcome! Even if my calendar shows I’m booked, still feel free to reach out. Further distances and specific circumstances may incur additional fees, which will always be disclosed before confirming. Caring for pets in their own home helps them feel safe and secure in a familiar space. With my own animals at home, this setup also works best for me! I focus on maintaining your pet’s usual routines and paying close attention to their comfort, body language, and any changes in behavior. A calm, familiar environment is essential for building an organic, trusting relationship between new human and pet!

Sitter Profile Image: Taylor B.
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Taylor B.
Star Sitter
from
$55
per night
5.0 out of 5 stars
28 reviews
7 repeat clients
18 years of experience
Clearwater, FL, 33755

Taylor was very good with Hunter. He had a couple of skin infections and she was on top of it! He had a trip to the vet and a trip to the ER. She made sure he had his medicine, daily exercise, food and water, and made sure he wore the dreaded cone. Taylor took very good care of him. Taylor gave us daily updates and pictures of Hunter. If she had a question, she asked. Taylor also stayed at our house. She treated it as her own. Everything was in order when we came home. Bedding (ours and Hunters) was washed. We were very pleased with the care Taylor gave Hunter and our home.

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Mary G.
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Trails Of Countryside pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

I have booked with Jessica several times with my pups. I always have confidence they are in good hands.

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Jeanine C.
House Sitting
5.0 out of 5 stars

MaCailey was amazing with my girls. She took great care of them and my house while I was on a work trip. I will be hiring her again.

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Amy K.
House Sitting
5.0 out of 5 stars

Always happy to book with Maureen. She takes great care of my mini Goldendoodle and is very trustworthy!

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Sara & Corbitt O.
House Sitting
5.0 out of 5 stars

Patrick was caring, thoughtful and our dog appeared happy! He sent photos each day and notes of new behaviors (flipping for a belly rub, etc.). Our dog was immediately comfortable with Patrick. Since we picked her up, if we mention Patrick’s name, she starts wagging her tail.

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Barbara M.
House Sitting
5.0 out of 5 stars

Doug was great! On time and very responsive. Sent pics and the dogs loved him. Will book with him again.

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Adam B.
House Sitting
5.0 out of 5 stars

Debra is a 5+ sitter! My dogs enjoyed their time with her. Debra took great care of them and I am so grateful for her attention towards them! Debra is very professional, very knowledgeable about caring for dogs, attentive to details as to how to make the doggies happy and feel safe, and extremely considerate as a house guest. I would highly recommend Debra! Luna and Kaia send you a big doggie hug!

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Maria P.
House Sitting
5.0 out of 5 stars

This was our 2nd time using Allyson to house sit our dog and she was wonderful! Constant updates, pictures, and spent quality time with our big guy while we were away!

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Baron H.
House Sitting
5.0 out of 5 stars

Once again, Megan kept our two Shih Tzus for us. It was such a relief to know she was caring for them. She sent pictures and updates over the weekend. We know they are in good hands when Megan is there.

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Sydeana D.
House Sitting
5.0 out of 5 stars

I can’t say enough good things about Mason and how well he cared for the house and dogs. Showed up on time faithfully. Gave the greatest updates and pics of our pooches. Highly recommend and will be using him again and again.

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Kelli R.
House Sitting
5.0 out of 5 stars

Stephanie is one of the most conscientious and compassionate sitters I have had!! Her communication skills are spot on and her care is the best. Thank you, Stephanie.

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Bonnie S.
House Sitting
5.0 out of 5 stars

Stephanie did an incredible job with our two golden retrievers. She sent me lots of pictures while we were gone and i could tell the dogs were having a great time. She left our house immaculate - it looked better than before we left! She was a pleasure to work with and we will definitely be using her again in the future!

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Maureen C.
House Sitting
5.0 out of 5 stars

We cannot rave enough about Lydia & Emmitt. This was our first experience using dog/house sitters and we were very nervous about the well-being of our pups especially with one being older. It’s obvious that they love animals and take great pride in their work. They followed every instruction exactly with regards to feeding/schedules/medication. But more importantly, they were very affectionate with our pups and provided enrichment. Our home was also left immaculate. They were very respectful and responsive throughout and will definitely be booking them again.

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Niguel A.
House Sitting
5.0 out of 5 stars

Peyton was amazing! This was our first time using Rover and we couldn’t be happier. Our dog Charlie is over 15 and blind, so requires some extra attention and someone to stay at our house. Peyton took great care of both Charlie and our home. She provided multiple updates and photos throughout each day which we really appreciated. Highly recommended!

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Kevin P.
House Sitting
5.0 out of 5 stars

I couldn’t be happier or more impressed with Sophia. She is awesome! she took wonderful care of our baby and treated her life her own I saw this with the many updates (not just pictures but videos)of their time together I could see how loved Lulu was by their interaction this was our first time leaving our little girl alone for so long and using the service so of course we were a little nervous. When we arrived home our place was left in the same condition we left it I was really great being able to keep Lulu in her comfortable space. Sophia is kind,compassionate, respectful and a wonderful caregiver. We completely trust her and she relieved our stress and anxiety and about leaving so we were able to enjoy our trip to the fullest knowing she was well taken care Lulu has a new Auntie lol! We will be requesting Sophia every time from now on, I would highly recommend her to anyone who wants to feel secure and worry free about their pet care💕

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Autumn B.
House Sitting
5.0 out of 5 stars

Cortney did a wonderful job! She was great with my German Shepherd - her experience and knowledge came in very handy with my willful dog. She was easy to get a hold of and kept me well informed and I could tell my pup was happy in all the pics.

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Paul F.
House Sitting
5.0 out of 5 stars

So happy with Margot house sitting our "girls!" My dog and cat were stress free when we returned from our trip. Will definitely reach out to her again! I highly recommend her. Margot- I can't thank you enough for taking care of our girls!

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Penny L.
House Sitting
5.0 out of 5 stars

Mackenzie was the best sitter Peanut has had! She took great care of him and provided excellent communication with me! I highly recommend using Mackenzie when ever you need a sitter!

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Sean R.
House Sitting
5.0 out of 5 stars

Christine did a wonderful job caring for our two dogs. She took them for lots of walks and sent lots of great updates throughout the day. Would recommend to anyone looking for a great dog sitter.

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Melinda J.
House Sitting
5.0 out of 5 stars

I know my dog Pickles is in great hands when Richi comes to pet sit for him. Pickles loves lots of attention and love and Richi is so caring and always sends me photos to enjoy. I highly recommend these two pet lovers for times we need to be away from our fur babies.

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Laura P.
House Sitting
5.0 out of 5 stars

Gabriela was great! Kept me updated and sent photos. My pups were very well taken care of. Easy booking and great communication with her as well especially for a last minute request.

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Ann W.
House Sitting
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House Sitting FAQs

Frequently asked questions about Rover

If you’re searching for a Trails Of Countryside 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.

Rover makes it easy to reach out to multiple house sitters about your booking. Typically, house sitters on Rover respond in under an hour.

Experience can vary widely from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when comparing house sitters available in Trails Of Countryside.

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. Trails Of Countryside 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.