House Sitting in Winter Springs

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

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Top rated Winter Springs house sitters

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: Peter B.
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Peter B.
Star Sitter
from
$50
per night
5.0 out of 5 stars
107 reviews
56 repeat clients
3 years of experience
Casselberry, FL, 32707

Peter did a great job… he was very caring for our dog and house. He has been open to our comments that allow him to fully understand what we look for in a dog/house sitter.

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Mark L.
Sitter Profile Image: Jordan C.
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Jordan C.
Star Sitter
from
$50
per night
5.0 out of 5 stars
7 reviews
2 repeat clients
10 years of experience
Winter Springs, FL, 32708

Jordan took great care of Lollipop while we were out of town. I can be a bit over the top when it comes to my dog. She accommodated my request with kindness.

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Lindsey F.
Sitter Profile Image: Ashland B.
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Ashland B.
Star Sitter
from
$70
per night
5.0 out of 5 stars
64 reviews
14 repeat clients
26 years of experience
Casselberry, FL, 32707

Neo LOVES Ashland, just mention her name and he starts looking around..ears are perked up. He definitely glad when she comes over. Neo has never been away from us , so we were not sure how it would be. Trust me once Ashland is here he doesnt care if we leave. He has even done an overnight with no issue. Numerous booking so far, and definitely lots more in the future.

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Sharon S.
Sitter Profile Image: Zachary A.
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Zachary A.
Star Sitter
from
$74
per night
5.0 out of 5 stars
179 reviews
74 repeat clients
12 years of experience
Longwood, FL, 32750

Zach was amazing and we will absolutely be using his services again. Our Great Dane, Kallie, is sweet as can be and very easy to manage. However our other dog, Captain, suffers from some pretty significant anxiety and it can be quite difficult to get him to trust new people. Zach was calm, thorough, and patient with him. Captain completely fell in love!! Zach sent us multiple updates and pictures over the 3 days that he house/dog sat for us and was extremely detailed in his questions beforehand. He even got Captain to go for a walk with him!!! We truly can’t recommend him enough and have no doubt that WHEN he comes back to care for our home and babies they will all be well loved and cared for!! Thanks Z, we really appreciate you!

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Kylie C.
Sitter Profile Image: Anastasia E.
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Anastasia E.
from
$40
per night
5.0 out of 5 stars
73 reviews
13 repeat clients
8 years of experience
Sanford, FL, 32773

Anastasia always does a great job taking care of Tomi. Tomi is very stubborn but Anastasia is very patient with her. She also communicates well with me while I’m away.

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Kati K.
Sitter Profile Image: Alicia K.
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Alicia K.
Star Sitter
from
$86
per night
5.0 out of 5 stars
34 reviews
9 repeat clients
30 years of experience
Winter Park, FL, 32707

Alicia stayed at our home for the weekend and took care of our 2 small dogs. They can be barky but they seemed to relax around her pretty quickly. She sent several pix -our doxie was snuggling up to her the same night we left and our nervous chihuahua was in out in the yard wagging away the next day. The house was the same as we left it. We would definitely book Alicia again 😀

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Julie T.
Sitter Profile Image: Gaby B.
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Gaby B.
from
$30
per night
5.0 out of 5 stars
7 reviews
1 repeat client
10 years of experience
Winter Springs, FL, 32708

Gaby took wonderful care of my 3 cats when we were gone for 5 days. She fed them their special diets, kept their litter boxes scooped, gave them fresh water, and made sure their water fountain stayed full. She played with all the cats, especially the very active kitten. She was respectful of our home as well. Would definitely use again and would recommend to anyone who needs a responsible person to take care of their pets while they are away.

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Jennifer T.
Sitter Profile Image: Sara M.
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Sara M.
from
$40
per night
5.0 out of 5 stars
7 reviews
1 repeat client
10 years of experience
Winter Park, FL, 32707

About: What sets me apart as a pet sitter is my lifelong experience and genuine love for animals. Growing up, I cared for a dog, cat, and even a turtle, which gave me a deep understanding of different personalities and needs. For four years, I volunteered at a wildlife sanctuary, where I was trusted with important responsibilities like cleaning enclosures and feeding a variety of animals. Today, I’m a proud cat mom to Oliver, who is truly my heart and soul. I bring that same care, attentiveness, and love to every pet I watch. Being observant and detail-oriented means I notice the little things—whether it’s changes in behavior, eating habits, or comfort—that make all the difference in keeping pets safe, happy, and cared for. I currently work a full-time job 8:30 AM to 5 PM Monday- Friday. If you need me to housesit I can do so as long as walking times are flexible as I work out of downtown Orlando and I don’t usually do lunch walks (12-1 PM) due to traffic. It is easier for me to drop in/ walk before 8 AM and after 5:30 PM Monday- Friday. Weekends/ Holidays are good anytime, please refer to my calendar for updates. Reliability and communication are important to me, so you can always count on updates and peace of mind while you’re away. I do not board at this time, but can house sit or drop in! Please schedule a meeting with me before booking as I would like to meet your pet and you! Instructions on feeding and medications are required upon booking. Playtime and pets always included!

Sitter Profile Image: Isabella O.
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Isabella O.
Star Sitter
from
$50
per night
4.9 out of 5 stars
32 reviews
9 repeat clients
7 years of experience
Ventura, Winter Park, FL, 32792

Isabella was Great with our puppy! She made sure to send pictures everyday and update us throughout the day. She took amazing care of our dog and even went the extra mile for him! 10/10 would recommend her!

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Justyn S.
Sitter Profile Image: Valery S.
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Valery S.
Star Sitter
from
$65
per night
5.0 out of 5 stars
54 reviews
18 repeat clients
15 years of experience
Winter springs, FL, 32708

Valery is AWESOME!!! She has done drop in visits for our 5 1/2 month old puppy as well as has taken care of her for a weekend in her own home. We would definitely hire Valery again. She's reliable and takes amazing care of our baby!

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Lynne C.
Sitter Profile Image: Jennifer M.
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Jennifer M.
from
$45
per night
5.0 out of 5 stars
18 reviews
6 repeat clients
25 years of experience
Sanford, FL, 32771

Jennifer was excellent - she connected with all 3 of our dogs and kept us constantly updated with photos and videos! As a first time Rover client , I was definitely apprehensive but can honestly say that I am more the comfortable now and would definitely use Jennifer again !

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Patrick P.
Sitter Profile Image: Alexa A.
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Alexa A.
from
$35
per night
5.0 out of 5 stars
10 reviews
1 repeat client
3 years of experience
Altamonte Springs, FL, 32701

Alexa was great with housesitting my 2 dogs! She is responsible and friendly, arrived on time, and kept me updated throughout her stay with messages and photos. I would definitely trust her to watch my doggos again!

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Kelsey M.
Sitter Profile Image: Alayna N.
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Alayna N.
from
$27
per night
1 repeat client
3 years of experience
Casselberry, FL, 32707

About: I have experience caring for a diverse array of dogs, from Poodles to Bernese Mountain Dogs. While I was a student I was trusted by several families for recurring dog and child-sitting, and I also provided reliable house sitting services during their vacations. I have a flexible schedule that aligns perfectly with my remote work arrangement. I’m available for dog care and companionship on Mondays, Wednesdays, Fridays, and over weekends, ensuring that your furry friend receives constant attention and care. Your pet’s safety and well-being are my top priorities. I offer a secure and loving environment for dogs of all sizes. You can feel confident that your furry friend is in experienced and caring hands.

Sitter Profile Image: Raechel C.
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Raechel C.
from
$40
per night
4.8 out of 5 stars
10 reviews
1 repeat client
15 years of experience
Casselberry, FL, 32707

Raechel was great! This was my first time using the app and I was in a bit of a time crunch and this was also the first time I needed a house sitter for my animals. I have 2 dogs and 2 cats so the job was large and Raechel did not blink an eye to it! Her communication is fabulous as I was sent multiple pictures each day of the crew. Even my most reclusive cat seemed to love her new sitter which totally surprised me! Overall the dogs and cats seemed to love their new friend for the week and I felt completely confident in Raechel while I was gone.

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Kristen G.
Sitter Profile Image: Keonna M.
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Keonna M.
from
$27
per night
10 years of experience
Winter Springs, FL, 32708

About: I’ve been around animals for most of my life and grew up with smaller dogs in my home while developing a love for dogs of all breeds and sizes. I currently care for my cat, Teddy, and our new kitten, Minnie, which has given me daily experience with feeding schedules, playtime, litter box maintenance, and providing plenty of love and attention. As someone who works remotely and attends school online, I have a flexible schedule that allows me to provide attentive care, companionship, walks, and potty breaks throughout the day. I promise to treat your pets with the same care and patience that I give my own! I currently work remotely as an online fitness coach while also attending school online, which gives me a very flexible schedule. Because I work from home, I can provide frequent potty breaks, walks, playtime, companionship, and regular check ins throughout the day. I genuinely enjoy spending time with animals and have the flexibility to adapt to your pet’s routine and needs! I care for pets in their own home where they are most comfortable and can maintain their normal routine. I understand the importance of following feeding schedules, exercise routines, medication instructions, and household rules exactly as requested. As a pet owner myself, I prioritize safety, patience, and building trust with every animal in my care. I’m also willing to provide regular updates and photos so you can feel confident that your pet is safe, happy, and well cared for while you’re away!

Sitter Profile Image: Kailey D.
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Kailey D.
from
$40
per night
5.0 out of 5 stars
5 reviews
1 repeat client
10 years of experience
Winter park, FL, 32792

Kailey is awesome! She cared for my senior dog and cat while I was out of town. My animals loved her.

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John G.
Sitter Profile Image: Gina K.
Verified Enhanced Background Check
Gina K.
from
$40
per night
5.0 out of 5 stars
5 reviews
1 repeat client
7 years of experience
Winter Springs, FL, 32708

Gina arrived early, which was great and very nice to do prompt courteous prepared by watching videos and being ready for the given the dog insulin and I will be using Gina in the future and I recommend her to other persons

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Cindy M.
Sitter Profile Image: Brent W.
Verified Enhanced Background Check
Brent W.
from
$60
per night
5.0 out of 5 stars
14 reviews
1 repeat client
3 years of experience
Lake Mary, FL, 32746

Brent was incredible with our dog. He was super detailed and attentive. Also very clean and organized. I really appreciated how Brent sent multiple photos and videos each day. We knew our puppy and our home were well cared for.

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Jennifer R.
Sitter Profile Image: Caryna P.
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Caryna P.
from
$50
per night
5.0 out of 5 stars
16 reviews
3 repeat clients
15 years of experience
Sanford, FL, 32773

Caryna is amazing. Professional, sweet, caring. Our dogs loved her. We will be using her again in the future. Thank you for loving our fur babies Caryna.

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Karen S.
Sitter Profile Image: Kelsey M.
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Kelsey M.
from
$45
per night
4.8 out of 5 stars
14 reviews
1 repeat client
35 years of experience
Winter Springs, FL, 32708

Kelsey is always AMAZING with our pups. She is now our go-to dog sitter anytime we need someone to watch the girls!

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Vivian B.
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Over 234
pet parents in Winter Springs have booked house sitting

Winter Springs pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Raechel was awesome! she took care of our 3 boxers and corgi. Had absolutely no issues and the pups loved her! Would definitely recommend her

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Katlin S.
House Sitting
5.0 out of 5 stars

Gaby took wonderful care of my 3 cats when we were gone for 5 days. She fed them their special diets, kept their litter boxes scooped, gave them fresh water, and made sure their water fountain stayed full. She played with all the cats, especially the very active kitten. She was respectful of our home as well. Would definitely use again and would recommend to anyone who needs a responsible person to take care of their pets while they are away.

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Jennifer T.
House Sitting
5.0 out of 5 stars

Brent was a great communicator and so thoughtful in updating us with pictures and videos throughout his stay at our home with our two dogs. Everyone seemed happy and healthy when we returned -- even our very high energy Springer Spaniel!

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Claire M.
House Sitting
5.0 out of 5 stars

Thank you for taking such good care of our girls! They love when you come stay with them! We have such a great vacation knowing Bailey and Willow are having a good time too with Joyce!

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Diana M.
House Sitting
5.0 out of 5 stars

Here’s a smoother and more polished version that keeps your warmth and sincerity: I want to thank Brandee for taking such great care of Burton during his time with her! She was easy to communicate with, attentive to every detail I asked for, and made me feel completely comfortable leaving him in her care. Burton absolutely loved her, and he can be very selective about people. This was the longest time I’ve ever been away from him, and all of the pictures and check-ins gave me such a sense of peace while I was gone. I’m so grateful for the care and attention she gave him!

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Kaisor M.
House Sitting
5.0 out of 5 stars

Nicole was very kind and caring to my baby champ. She showed up when expected and sent pictures throughout her time. My dog seemed very calm and happy upon our return home.

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Andrea F.
House Sitting
5.0 out of 5 stars

Annalise took great care of our 3 cats, two of which are diabetic! We appreciated the pictures and the care in which she gave our babies! 10/10 would recommend and will book again! Thank you!

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Christian L.
House Sitting
5.0 out of 5 stars

Gina arrived early, which was great and very nice to do prompt courteous prepared by watching videos and being ready for the given the dog insulin and I will be using Gina in the future and I recommend her to other persons

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Cindy M.
House Sitting
5.0 out of 5 stars

Peter was able to accommodate two last-minute bookings to watch my dog really early in the morning. I am extremely grateful! He was on time and communicative. I would have him watch my dogs again in the future.

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Alexis B.
House Sitting
5.0 out of 5 stars

Kaylee took great care of our dogs and home while we were traveling. She’s an excellent communicator sending updates and photos. Our home was left clean and we returned to happy pups! Thanks so much!

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Kayla S.
House Sitting
5.0 out of 5 stars

Jordan took great care of Lollipop while we were out of town. I can be a bit over the top when it comes to my dog. She accommodated my request with kindness.

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Lindsey F.
House Sitting
5.0 out of 5 stars

Ashland was AMAZING with my 16 month old Great Dane named George. I was so nervous as this was the first time we left him. Ashland was on time, reassuring and just so great with my pup! He is a bed dog and that was A ok with Ashland. He actually went and looked for her the next morning. Highly recommend Ashland!!

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Debbie A.
House Sitting
5.0 out of 5 stars

Eva was an amazing house sitter for our dog, Kaiya! She took great care of her, kept us updated, and made us feel completely at ease while we were away. We truly appreciate her kindness and reliability—highly recommend!

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Leslie R.
House Sitting
5.0 out of 5 stars

Nina is a wonderful sitter. We felt confident that our fur baby was well cared for as well as our home.

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Susie B.
House Sitting
5.0 out of 5 stars

Madison made our anxious senior Chihuahua feel safe and secure. I think Madison has a new BFF. Thank you.

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William S.
House Sitting
5.0 out of 5 stars

Katelyn did a great job staying with Ginger while we were on vacation. Our dog is a little particular and set in her ways so nativgating that can take a little time but Ginger has warmed up to her and we are so happy to have her as an option to know Ginger can stay at home and have the care she needs while we are away.

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Erica H.
House Sitting
5.0 out of 5 stars

Makenzie is a very sweet girl. She took great care of my tiny dog. She kept me updated with texts and pictures and she stayed overnight at my house. Will definitely use her again!

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Salvina W.
House Sitting
5.0 out of 5 stars

Gina was great! She followed all instructions and took EXCELLENT care of my boys. She send regular updates and I was able to enjoy my trip knowing they were in great hands. Thanks Gina!

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Donna O.
House Sitting
5.0 out of 5 stars

I'm so excited to have met Jennifer .. She did a great job and I don't think my dog cared that I was home ... He was very well taken care of and I highly recommend her ... ❣️❣️

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Kristy A.
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 Winter Springs is $45

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 Winter Springs 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 Winter Springs on Rover as of Jun 2026 was about $45 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 Winter Springs 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 2,623 house sitters in Winter Springs. 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, 86% of Winter Springs house sitters respond in under an hour.

House sitters in Winter Springs have an average of 15 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 Winter Springs.

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. Winter Springs 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.