Dog Boarding in Winding Wood, Clearwater, FL

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Top rated Winding Wood dog boarders

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Sitter Profile Image: Jennifer b.
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Jennifer b.
from
$45
per night
5 out of 4.8 stars
67 reviews
20 repeat clients
20 years of experience
Keystone Manor, Clearwater, FL, 33755

This was my first time using Rover and Jennifer was absolutely amazing! She messaged me everyday with updates and pictures/videos of how Chloe was doing. I couldn’t ask for a better experience! Jennifer truly cares for animals and goes above and beyond to make sure your pet is well taken care of! I highly recommend her and will be using her again in the future!

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Kelsey G.
Sitter Profile Image: Heather D.
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Heather D.
Star Sitter
from
$26
per night
5 out of 5.0 stars
50 reviews
12 repeat clients
25 years of experience
Dunedin, FL, 34698

Heather took the best of care of our little old man and even went out of her way to help us with drop off and met us at a convenient location! She kept us up to date with pictures and updates. We will definitely have her watch our pup again!

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Alicia P.
Sitter Profile Image: Matthew & Nicole P.
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Matthew & Nicole P.
Star Sitter
from
$40
per night
5 out of 5.0 stars
17 reviews
11 repeat clients
20 years of experience
Palm Harbor, FL, 34685

Matthew and Nicole took great care of my Doberman. They were able to keep up with his high energy level and quirks. Thank you both again for taking care of my Kane and I will definitely use you in the future.

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Ciara R.
Sitter Profile Image: Athena & Richi E.
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Athena & Richi E.
Star Sitter
from
$45
per night
5 out of 5.0 stars
275 reviews
71 repeat clients
18 years of experience
Dunedin, FL, 34698

Athena and Richi are incredible dog sitters! They took great care of Oscar, providing daily updates a few times a day and ensuring daily exercise. Oscar was so calm, happy, and energetic when we picked him up. This shows how well Athena and Richi cared for him. Thank you so much!

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Liza G.
Sitter Profile Image: Marisa & Robert C.
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Marisa & Robert C.
Star Sitter
from
$38
per night
5 out of 4.9 stars
48 reviews
18 repeat clients
15 years of experience
Tampa, FL, 33635

Marisa and Robert were great! I will definitely use there services again. They gave me so many pictures and updates. I never had to worry about my Coco. I felt she was in good hands. And Goldie was a bonus for her to play with!!!!

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Tiesha B.
Sitter Profile Image: Ashleigh Y.
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Ashleigh Y.
Star Sitter
from
$45
per night
5 out of 5.0 stars
261 reviews
96 repeat clients
20 years of experience
Keystone Manor, Clearwater, FL, 33755

Ziggy and Waylon had a blast at Ashleigh’s! She provided great care and updates on the dogs and was very accommodating as she was able to take them last minute. Would definitely book with Ashleigh again!

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Amanda C.
Sitter Profile Image: Stephen R.
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Stephen R.
from
$39
per night
5 out of 5.0 stars
51 reviews
14 repeat clients
24 years of experience
Clearwater, FL, 33755

My pups had a longer stay this round and they came home safe and happy! Can’t recommend Stephen enough. He does a great job making us feel comfortable leaving our them with him. Hence we tip him well when we pick up the pooches!

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Anthony C.
Sitter Profile Image: Debbie T.
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Debbie T.
Star Sitter
from
$38
per night
5 out of 5.0 stars
26 reviews
6 repeat clients
45 years of experience
Dunedin, FL, 34698

Debbie is wonderful.Peyton loved the attention she received and I felt very grateful to have someone so kind to watch over my girl. She sent me photos daily keeping me updated.

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Kimberly R.
Sitter Profile Image: Jessica & Colin M.
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Jessica & Colin M.
from
$34
per night
5 out of 5.0 stars
31 reviews
3 repeat clients
30 years of experience
Clearwater, FL, 33759

Jessica and Colin watched our pup, Hazel, recently and did a great job! Hazel had a great time at their home with their adorable family. Jessica was quick to respond every time I texted , and was very flexible. We will definitely be using Jessica and Colin again if they are available. They are trustworthy, responsible and reliable . Hazel can’t wait to go back! 🐾

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Kathleen C.
Sitter Profile Image: Norma H.
Verified Background Check
Norma H.
Star Sitter
from
$49
per night
5 out of 5.0 stars
123 reviews
60 repeat clients
20 years of experience
Dunedin, FL, 34698

Norma was extremely nice and responded promptly to questions. She is very organized and strives to care for your pet keeping to as much as their normal routine as possible at her home. My boston terrier, Capt Nemo had so much fun playing with another dog who was visiting and Norma provided pictures and updates everyday. We have already booked our next stay with Norma and I am quite confident that Capt Nemo will be safe and well taken care of.

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Karen A.
Sitter Profile Image: Isabella & Richard L.
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Isabella & Richard L.
Star Sitter
from
$48
per night
5 out of 5.0 stars
27 reviews
6 repeat clients
15 years of experience
Dunedin, FL, 34698

Tucker had the best time this weekend! They took such good care of him, and he loved playing with their dog. They were super friendly and always quick to respond. I felt totally at ease knowing he was in great hands. Highly recommend!

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Ashley C.
Sitter Profile Image: Leslie A.
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Leslie A.
Star Sitter
from
$32
per night
5 out of 5.0 stars
10 reviews
3 repeat clients
10 years of experience
Clearwater, FL, 33755

Left my kitten Leo over a holiday weekend with her on short notice. She was accomindating, friendly, and gave good updates/photos so I did not have to worry. Leo came back healthy and happy. Good experience.

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William R.
Sitter Profile Image: Kate W.
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Kate W.
from
$49
per night
5 out of 5.0 stars
15 reviews
5 repeat clients
55 years of experience
On Top Of The World, Clearwater, FL, 33763

Kate did a great job with our sweet girl, Honey! Honey was missing us and Kate gave her extra love and attention. She was well cared for and got to go on lots of walks. Thank you, Kate!

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Elizabeth H.
Sitter Profile Image: LAVINIA C.
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LAVINIA C.
from
$35
per night
5 out of 5.0 stars
10 reviews
1 repeat client
5 years of experience
Valencia Park, Clearwater, FL, 33763

Great experience for both my dog and me. Lavinia's personality and experience made me feel confident in leaving my dog in her care. My dog quickly made herself right at home. I would definitely recommend her!

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Nora G.
Sitter Profile Image: Marissa H.
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Marissa H.
Star Sitter
from
$42
per night
5 out of 5.0 stars
50 reviews
13 repeat clients
9 years of experience
Greenbriar Club, Clearwater, FL, 33763

Marissa was awesome! Gus had a great stay! Marisa was also accommodating to arrange a meet and greet beforehand. I got great updates throughout the stay and cute “vacation” pics of Gus.

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Shannon H.
Sitter Profile Image: Leslie P.
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Leslie P.
from
$45
per night
5 out of 5.0 stars
5 reviews
2 repeat clients
20 years of experience
Dunedin, FL, 34685

Leslie, Willa & company did an absolutely fantastic job caring for our Benny. She sent us regular photos and updates and he came home healthy, happy and relaxed. She has a relaxed yet attentive manner which fits perfectly with our boy’s personality. Her girl Willa welcomed Benny and both set their boundaries maturely, quickly and fairly. A+ for Willa too! Always a treasure to find someone who takes such great care of our little man. We’ll definitely rebook with Leslie in the future. Highly recommend!

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Linda C.
Sitter Profile Image: JD & Magdalena D.
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JD & Magdalena D.
Star Sitter
from
$40
per night
5 out of 5.0 stars
24 reviews
8 repeat clients
7 years of experience
Clearwater, FL, 33759

My little fur all had a blast! I got constant updates and photos on how she was doing! I will definitely be coming back to them to watch her again!

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Michael M.
Sitter Profile Image: Martha & Brett B.
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Martha & Brett B.
Star Sitter
from
$45
per night
5 out of 5.0 stars
190 reviews
82 repeat clients
20 years of experience
clearwater, FL, 33761

I was so pleased with the care Floppy received at Martha and Brett's home. She is older and has some special needs and while she was stressed when I left her, when I picked her up she was happy and calm. The photo updates assured me she was doing well while we were gone. Will definitely use them again!

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Deb K.
Sitter Profile Image: Tuany L.
Verified Background Check
Tuany L.
from
$39
per night
5 out of 5.0 stars
9 reviews
1 repeat client
16 years of experience
Winding Wood, Clearwater, FL, 33761

Great Pet Sitter! Grateful to Tuany for caring for our little daschund mix while we traveled. Tuany only takes one pet at a time, which allowed her to give Lucy plenty of attention in a quiet setting. When we picked up Lucy, she was relaxed and happy, consistent with an excellent stay. One could tell that Lucy had developed a real affection for Tuany and her little boy. Tuany was great about communicating with me by text. She provided an occasional photo and update while we were away, just as I had requested. Tuany is an excellent pet sitter and genuinely lovely person.

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Jackie C.
Sitter Profile Image: Jace W.
Verified Enhanced Background Check
Jace W.
Star Sitter
from
$30
per night
5 out of 5.0 stars
14 reviews
4 repeat clients
4 years of experience
Clearwater, FL, 33761

Jace was very kind and accommodating. I felt at ease leaving my dog with her for the first time. She sent us pics and updates daily. I will definitely be using her again!

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Janet W.
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Sitter Profile Image: Jennifer b.
Verified Background Check
Sitter Profile Image: Jennifer b.
Verified Background Check

Jennifer b.

🐾Boujee Bullies🐾
Keystone Manor, Clearwater, FL, 33755
4.4 mi. away
Boarding, Dog Walking
from
$45
per night
5 out of 4.8 stars
67 reviews
20 repeat clients
Profile image

This was my first time using Rover and Jennifer was absolutely amazing! She messaged me everyday with updates and pictures/videos of how Chloe was doing. I couldn’t ask for a better experience! Jennifer truly cares for animals and goes above and beyond to make sure your pet is well taken care of! I highly recommend her and will be using her again in the future!

Availability updated yesterday
Sitter Profile Image: Heather D.
Verified Enhanced Background Check
Sitter Profile Image: Heather D.
Verified Enhanced Background Check

Heather D.
Star Sitter

Family of animal lovers
Dunedin, FL, 34698
3.4 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$26
per night
5 out of 5.0 stars
50 reviews
12 repeat clients
Profile image

Heather took the best of care of our little old man and even went out of her way to help us with drop off and met us at a convenient location! She kept us up to date with pictures and updates. We will definitely have her watch our pup again!

Availability updated 26 days ago
Sitter Profile Image: Matthew & Nicole P.
Verified Enhanced Background Check
Sitter Profile Image: Matthew & Nicole P.
Verified Enhanced Background Check

Matthew & Nicole P.
Star Sitter

Furry Friend's Next Best Friend
Palm Harbor, FL, 34685
5.9 mi. away
Boarding
from
$40
per night
5 out of 5.0 stars
17 reviews
11 repeat clients
Profile image

Matthew and Nicole took great care of my Doberman. They were able to keep up with his high energy level and quirks. Thank you both again for taking care of my Kane and I will definitely use you in the future.

Availability updated 8 days ago
Sitter Profile Image: Athena & Richi E.
Verified Enhanced Background Check
Sitter Profile Image: Athena & Richi E.
Verified Enhanced Background Check

Athena & Richi E.
Rover 101
Star Sitter

CPR/First Aid Certified ❤️24/7 Care
Dunedin, FL, 34698
1.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$45
per night
5 out of 5.0 stars
275 reviews
71 repeat clients
Profile image

Athena and Richi are incredible dog sitters! They took great care of Oscar, providing daily updates a few times a day and ensuring daily exercise. Oscar was so calm, happy, and energetic when we picked him up. This shows how well Athena and Richi cared for him. Thank you so much!

Availability updated today
Sitter Profile Image: Marisa & Robert C.
Verified Enhanced Background Check
Sitter Profile Image: Marisa & Robert C.
Verified Enhanced Background Check

Marisa & Robert C.
Star Sitter

Dog Owner Loves Dogs OF All kinds
Tampa, FL, 33635
7.1 mi. away
Boarding
from
$38
per night
5 out of 4.9 stars
48 reviews
18 repeat clients
Profile image

Marisa and Robert were great! I will definitely use there services again. They gave me so many pictures and updates. I never had to worry about my Coco. I felt she was in good hands. And Goldie was a bonus for her to play with!!!!

Availability updated 25 days ago
Sitter Profile Image: Ashleigh Y.
Verified Background Check
Sitter Profile Image: Ashleigh Y.
Verified Background Check

Ashleigh Y.
Star Sitter

Ashleigh+Reptar Full Care Services
Keystone Manor, Clearwater, FL, 33755
4.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care
from
$45
per night
5 out of 5.0 stars
261 reviews
96 repeat clients
Profile image

Ziggy and Waylon had a blast at Ashleigh’s! She provided great care and updates on the dogs and was very accommodating as she was able to take them last minute. Would definitely book with Ashleigh again!

Availability updated yesterday
Sitter Profile Image: Stephen R.
Verified Enhanced Background Check
Sitter Profile Image: Stephen R.
Verified Enhanced Background Check

Stephen R.
Rover 101

Your Pup will NEVER be left ALONE!
Clearwater, FL, 33755
3.3 mi. away
Boarding
from
$39
per night
5 out of 5.0 stars
51 reviews
14 repeat clients
Profile image

My pups had a longer stay this round and they came home safe and happy! Can’t recommend Stephen enough. He does a great job making us feel comfortable leaving our them with him. Hence we tip him well when we pick up the pooches!

Availability updated today
Sitter Profile Image: Debbie T.
Verified Enhanced Background Check
Sitter Profile Image: Debbie T.
Verified Enhanced Background Check

Debbie T.
Star Sitter

Work from home - loving sitter 🐶🐾
Dunedin, FL, 34698
3.5 mi. away
Boarding, Drop-In Visits, Doggy Day Care
from
$38
per night
5 out of 5.0 stars
26 reviews
6 repeat clients
Profile image

Debbie is wonderful.Peyton loved the attention she received and I felt very grateful to have someone so kind to watch over my girl. She sent me photos daily keeping me updated.

Availability updated 2 days ago
Sitter Profile Image: Jessica & Colin M.
Verified Enhanced Background Check
Sitter Profile Image: Jessica & Colin M.
Verified Enhanced Background Check

Jessica & Colin M.

Pets are family - I'll love yours!
Clearwater, FL, 33759
2.5 mi. away
Boarding, Doggy Day Care
from
$34
per night
5 out of 5.0 stars
31 reviews
3 repeat clients
Profile image

Jessica and Colin watched our pup, Hazel, recently and did a great job! Hazel had a great time at their home with their adorable family. Jessica was quick to respond every time I texted , and was very flexible. We will definitely be using Jessica and Colin again if they are available. They are trustworthy, responsible and reliable . Hazel can’t wait to go back! 🐾

Availability updated 9 days ago
Sitter Profile Image: Norma H.
Verified Background Check
Sitter Profile Image: Norma H.
Verified Background Check

Norma H.
Star Sitter

Happy Happy Secure Home ❤ 🐾😊 🐶
Dunedin, FL, 34698
2.6 mi. away
Boarding, Doggy Day Care
from
$49
per night
5 out of 5.0 stars
123 reviews
60 repeat clients
Profile image

Norma was extremely nice and responded promptly to questions. She is very organized and strives to care for your pet keeping to as much as their normal routine as possible at her home. My boston terrier, Capt Nemo had so much fun playing with another dog who was visiting and Norma provided pictures and updates everyday. We have already booked our next stay with Norma and I am quite confident that Capt Nemo will be safe and well taken care of.

Availability updated 25 days ago
Sitter Profile Image: Isabella & Richard L.
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Sitter Profile Image: Isabella & Richard L.
Verified Enhanced Background Check

Isabella & Richard L.
Star Sitter

Dog obsessed & work from home!
Dunedin, FL, 34698
1.9 mi. away
Boarding, Drop-In Visits, Doggy Day Care
from
$48
per night
5 out of 5.0 stars
27 reviews
6 repeat clients
Profile image

Tucker had the best time this weekend! They took such good care of him, and he loved playing with their dog. They were super friendly and always quick to respond. I felt totally at ease knowing he was in great hands. Highly recommend!

Availability updated today
Sitter Profile Image: Leslie A.
Verified Enhanced Background Check
Sitter Profile Image: Leslie A.
Verified Enhanced Background Check

Leslie A.
Star Sitter

Cozy safe home for your pet friends
Clearwater, FL, 33755
4.5 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$32
per night
5 out of 5.0 stars
10 reviews
3 repeat clients
Profile image

Left my kitten Leo over a holiday weekend with her on short notice. She was accomindating, friendly, and gave good updates/photos so I did not have to worry. Leo came back healthy and happy. Good experience.

Availability updated yesterday
Sitter Profile Image: Kate W.
Verified Enhanced Background Check
Sitter Profile Image: Kate W.
Verified Enhanced Background Check

Kate W.

Loving Dog Mom here 💗💗
On Top Of The World, Clearwater, FL, 33763
1.6 mi. away
Boarding
from
$49
per night
5 out of 5.0 stars
15 reviews
5 repeat clients
Profile image

Kate did a great job with our sweet girl, Honey! Honey was missing us and Kate gave her extra love and attention. She was well cared for and got to go on lots of walks. Thank you, Kate!

Availability updated 2 days ago
Sitter Profile Image: LAVINIA C.
Verified Enhanced Background Check
Sitter Profile Image: LAVINIA C.
Verified Enhanced Background Check

LAVINIA C.

Loving and caring fur baby care
Valencia Park, Clearwater, FL, 33763
2.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care
from
$35
per night
5 out of 5.0 stars
10 reviews
1 repeat client
Profile image

Great experience for both my dog and me. Lavinia's personality and experience made me feel confident in leaving my dog in her care. My dog quickly made herself right at home. I would definitely recommend her!

Availability updated 5 days ago
Sitter Profile Image: Marissa H.
Verified Enhanced Background Check
Sitter Profile Image: Marissa H.
Verified Enhanced Background Check

Marissa H.
Star Sitter

Loving dog mom offering loving help
Greenbriar Club, Clearwater, FL, 33763
1.3 mi. away
Boarding, Doggy Day Care
from
$42
per night
5 out of 5.0 stars
50 reviews
13 repeat clients
Profile image

Marissa was awesome! Gus had a great stay! Marisa was also accommodating to arrange a meet and greet beforehand. I got great updates throughout the stay and cute “vacation” pics of Gus.

Availability updated today
Sitter Profile Image: Leslie P.
Verified Enhanced Background Check
Sitter Profile Image: Leslie P.
Verified Enhanced Background Check

Leslie P.

Your baby’s Home Away From Home
Dunedin, FL, 34685
2.2 mi. away
Boarding
from
$45
per night
5 out of 5.0 stars
5 reviews
2 repeat clients
Profile image

Leslie, Willa & company did an absolutely fantastic job caring for our Benny. She sent us regular photos and updates and he came home healthy, happy and relaxed. She has a relaxed yet attentive manner which fits perfectly with our boy’s personality. Her girl Willa welcomed Benny and both set their boundaries maturely, quickly and fairly. A+ for Willa too! Always a treasure to find someone who takes such great care of our little man. We’ll definitely rebook with Leslie in the future. Highly recommend!

Availability updated 10 days ago
Sitter Profile Image: JD & Magdalena D.
Verified Enhanced Background Check
Sitter Profile Image: JD & Magdalena D.
Verified Enhanced Background Check

JD & Magdalena D.
Star Sitter

We will love your pet like ours!!
Clearwater, FL, 33759
2.4 mi. away
Boarding, Doggy Day Care
from
$40
per night
5 out of 5.0 stars
24 reviews
8 repeat clients
Profile image

My little fur all had a blast! I got constant updates and photos on how she was doing! I will definitely be coming back to them to watch her again!

Availability updated 21 days ago
Sitter Profile Image: Martha & Brett B.
Verified Background Check
Sitter Profile Image: Martha & Brett B.
Verified Background Check

Martha & Brett B.
Rover 101
Star Sitter

Work from Home-Large Fenced in Yard
clearwater, FL, 33761
1.6 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$45
per night
5 out of 5.0 stars
190 reviews
82 repeat clients
Profile image

I was so pleased with the care Floppy received at Martha and Brett's home. She is older and has some special needs and while she was stressed when I left her, when I picked her up she was happy and calm. The photo updates assured me she was doing well while we were gone. Will definitely use them again!

Availability updated 7 days ago
Sitter Profile Image: Tuany L.
Verified Background Check
Sitter Profile Image: Tuany L.
Verified Background Check

Tuany L.

Care of your dog like it’s my own
Winding Wood, Clearwater, FL, 33761
0.1 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$39
per night
5 out of 5.0 stars
9 reviews
1 repeat client
Profile image

Great Pet Sitter! Grateful to Tuany for caring for our little daschund mix while we traveled. Tuany only takes one pet at a time, which allowed her to give Lucy plenty of attention in a quiet setting. When we picked up Lucy, she was relaxed and happy, consistent with an excellent stay. One could tell that Lucy had developed a real affection for Tuany and her little boy. Tuany was great about communicating with me by text. She provided an occasional photo and update while we were away, just as I had requested. Tuany is an excellent pet sitter and genuinely lovely person.

Availability updated yesterday
Sitter Profile Image: Jace W.
Verified Enhanced Background Check
Sitter Profile Image: Jace W.
Verified Enhanced Background Check

Jace W.
Star Sitter

Ask About My Tiny Dog Discount!
Clearwater, FL, 33761
0.7 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$30
per night
5 out of 5.0 stars
14 reviews
4 repeat clients
Profile image

Jace was very kind and accommodating. I felt at ease leaving my dog with her for the first time. She sent us pics and updates daily. I will definitely be using her again!

Availability updated yesterday

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