House Sitting in Winter Park

Find a loving dog sitter to watch your dog overnight in your home.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
Confirmed availability: Memorial day
Pam C.
1.
Pam 
Verified Background Check
Come & Play & Have a Blast!!!!!Winter Park, FL, 32789
House Sitting, Drop-In Visits

Pam was the most exceptional dog sitter for our 12 year old golden retriever. She was communicative the entire time we were away with fun/sweet updates. She als… (more)

from
$30
per night
Confirmed availability: Memorial day
Emmanuel D.
I'll treat your dog like family.Winter w, FL, 32792
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Emmanuel was the perfect person to watch my dogs when I need it the most. He sent me pictures and videos of my pets daily as he cares for them. He is trustworth… (more)

from
$30
per night
Calendar Recently Updated
Lindsay C.
Animal Lover and Student!Altamonte Springs, FL, 32714
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Our dog and home were well taken care of, thank you Lindsay!? (more)

from
$30
per night
Calendar Recently Updated
Joyce R.
4.
Purr..fessional Pet SitterCasselberry, FL, 32707
House Sitting, Drop-In Visits, Dog Walking

We recently needed a sitter for our dogs while we were gone for thanksgiving and I got to say that I felt my babies were very safe with Joyce. She communicated … (more)

from
$30
per night
Calendar Recently Updated
Francesca L.
I’ll make sure your pet feels lovedCasselberry, FL, 32707
House Sitting, Drop-In Visits, Dog Walking

Francesca did a great job with both my boys. I had a whole list written of what they needed and she was able to do it all no questions asked. My older pup also … (more)

from
$65
per night
Calendar Recently Updated
6.
Im here to care for your fur babiesWinter springs, FL, 32708
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Valery went above and beyond for us while we were away. She sent tons of photos, communicated quickly, and really cared for our beloved puppy. I would highly re… (more)

from
$35
per night
Confirmed availability: Memorial day
7.
Always home - Large fenced yardColonicaltown North, Orlando, FL, 32803
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Jacob did a wonderful job taking care of Hershey and sent me wonderful pictures with updates quite frequently. A+, would highly recommend! (more)

from
$60
per night
Calendar Recently Updated
Walk/sit, play, train. I do it all!Altamonte Springs, FL, 32701
Dog Boarding, House Sitting, Doggy Day Care, Dog Walking

I have booked with Brittany twice now and both times she has done a wonderful job! She send pics to check in and is easy to get in touch with while away. Will c… (more)

from
$40
per night
Calendar Recently Updated
9.
Loving & Responsible Pet CareOrlando, FL, 32817
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Nancy did a great job taking care of our dog while we were gone. She was communicative and friendly and we would highly recommend her to anyone. (more)

from
$35
per night
Calendar Recently Updated
10.
Trusty adult with lifelong pup loveBaldwin Park, Winter Park, FL, 32792
House Sitting, Drop-In Visits, Dog Walking

We are very pleased having Abigail housesit for us while we were away for a long weekend. We knew our two pups would be in good hands as she was attentive to th… (more)

from
$25
per night
Reliable and Doting Dog Lover!Dover Shores East, Orlando, FL, 32807
House Sitting, Drop-In Visits, Dog Walking

Alexandra fit us in at the last minute and our puppy was well taken care of. Jordan did not want her to leave after their time together. I was very happy that… (more)

from
$50
per night
Calendar Recently Updated
12.
Dog kisses make every day better!Colonial Town Center, Orlando, FL, 32803
House Sitting, Drop-In Visits, Dog Walking

Austin is the best dog sitter! He has been dog sitting my fur babies for four years and I always feel at ease leaving them with him. Typically, I come home and … (more)

from
$45
per night
Confirmed availability: Memorial day
13.
Animals are my biggest passion!MAITLAND, FL, 32751
House Sitting, Drop-In Visits, Dog Walking

I very highly recommend Candace for all your pet care needs! Her quiet manner, extensive experience, and generous heart make Candace my ONLY trusted provider f… (more)

from
$60
per night
Calendar Recently Updated
Dog and cat mom & animal loverWINTER PARK, FL, 32792
House Sitting, Drop-In Visits, Dog Walking

About: I have taken care of dogs and cat ever since I could remember! Family and friends always rely on me to care for their pets. I currently work full ti… (more)

from
$30
per night
Calendar Recently Updated
15.
Check meowt!Winter Park, FL, 32789
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Let me start off by saying that I highly recommend Heather for any of your pet related needs! We had a trip planned prior to knowing we'd have a little pup in o… (more)

from
$37
per night
Calendar Recently Updated
16.
Your Pup Is My Priority!Orlando, FL, 32807
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

We felt so at ease having Ruby stay with our sweet Lawrence. She sent us regular updates, and was kind and respectful in all of her interactions. When our trip … (more)

from
$30
per night
Calendar Recently Updated
17.
I can’t wait to meet your fluff 🌻Colonicaltown North, Orlando, FL, 32803
House Sitting, Drop-In Visits, Dog Walking

Mary is the best! She watched our dogs for a week and we couldn’t be happier. 2 Danes can be a handful at times (especially one that can get anxious) but Mary k… (more)

from
$65
per night
Calendar Recently Updated
18.
Full-Time Dog Sitter 🐾Winter Park, FL, 32792
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care

Emma was fabulous! She brought her little pup so my little girl has a new BFF! Emma sent lots of pictures and kept us up to date on what was going on. I high… (more)

from
$35
per night
Confirmed availability: Memorial day
19.
Need a friendly pet sitter?!Winter Park, FL, 32789
Dog Boarding, House Sitting, Dog Walking

Lyndsey is an amazing pet sitter. She is the most responsible,Hardworking and animal loving person out there! She has always had a love for dogs especially! She… (more)

from
$40
per night
20.
Elite Pet SittingWinter Park, FL, 32789
House Sitting, Dog Walking

Oriana did a wonderful job. She was very professional and for along with our dog very well. I would definitely use her again when we need a pet sitter. (more)

from
$45
per night

Rover also offers House Sitting in:

Rover.com is the simple, savvy way to find and book house sitting. It's easy to find the perfect house sitter - many sitters on Rover have a long history of house and pet sitting, and 95% of reviewed stays have received a perfect five-star rating. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Every pet sitter on Rover has the option to complete a free background check, so look for their badge that says they've had the check done. Pet and house sitters are booked on Rover every minute of every day, and 92% of the population lives within a short drive of one of the more 40,000 sitters who've listed their services on Rover, so you're sure to find the perfect house sitter on Rover. When you book with one of our trusted house sitters on Rover you get peace of mind that your home and pets are in loving hands.