House Sitting Windermere

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

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Over 75
pet parents in Windermere have booked house sitting

Windermere, 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.

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Sitter Profile Image: Karen D.
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Karen D.
Star Sitter
from
$30
per night
5.0 out of 5 stars
29 reviews
7 repeat clients
6 years of experience
Orlando, FL, 32819

Karen was the perfect dog sitter for Otis! She was so playful and spoiled him with long walks and play time. Her updates made me comfortable on my trip and allowed me to truly enjoy my time knowing Otis was happy and cared for. HIGHLY recommend!

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Jordan F.
Sitter Profile Image: Shelley R.
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Shelley R.
Star Sitter
from
$35
per night
5.0 out of 5 stars
39 reviews
12 repeat clients
3 years of experience
Windermere, FL, 34786

Shelley was very communicative with us about what was going on with our dogs. Pics were daily and it was nice to know they were well taken care of.

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Lynne T.
Sitter Profile Image: Alyson F.
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Alyson F.
Star Sitter
from
$50
per night
4.9 out of 5 stars
73 reviews
22 repeat clients
30 years of experience
Windermere, FL, 34786

Alyson has gone out of her way to make sure our girl is well taken care of! We appreciate all she has done and will continue to book with her knowing that Gracie is in good hands 💕

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Katie F.
Sitter Profile Image: Tiffany P.
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Tiffany P.
Star Sitter
from
$50
per night
5.0 out of 5 stars
7 reviews
3 repeat clients
20 years of experience
Metro West, Orlando, FL, 32835

Tiffany was so great! She arrived as promised and even took our dog out one extra time for us since we were returning late. The dog was happy and well- cared for, left the house in great shape. Will definitely use Tiffany again and highly recommend!

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Darla S.
Sitter Profile Image: Sarah H.
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Sarah H.
Star Sitter
from
$70
per night
4.9 out of 5 stars
179 reviews
74 repeat clients
12 years of experience
Windermere, FL, 34786

Sarah took care of Mora while we were in Puerto Rico for 6 days. She kept us up to date with how Mora was doing and sent us lots of pictures. We love that she was able to stay here at our home, so Mora did not have to deal with the stress of being in an unfamiliar place.

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Marie O.
Sitter Profile Image: Sarah V.
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Sarah V.
from
$40
per night
5.0 out of 5 stars
2 reviews
3 repeat clients
15 years of experience
Windermere, FL, 34786

About: For over 15 years, I have provided comprehensive, high-quality care for both dogs and cats. My experience ranges from high-energy playtime to specialized senior care and positive reinforcement training. I pride myself on creating a safe, structured, and joyful environment for every pet. What I Offer- Medical & Senior Care: Confident in administering oral medications and skin topicals, as well as managing specialized routines for aging pets. Positive Training: Skilled in teaching basic manners, tricks, and reinforcing good behavior using force-free methods. Play & Enrichment: Expert at reading animal body language to deliver the perfect balance of physical exercise and mental stimulation. Feline Expertise: Experienced in managing cat behavior, specialized diets, and giving space to timid or anxious felines. Whether your pet needs basic puppy training, gentle elder care, or just a fun day of structured play, I adapt my approach to their unique personality. Because my work schedule varies week-to-week, I am highly adaptable and can often accommodate non-traditional times, last-minute requests, and mid-day visits that standard 9-to-5 sitters cannot. I manage my calendar tightly to ensure that when your pet is booked, they get my 100% undivided attention, medical care, and training focus. As a seasoned pet professional specializing in medical administration and behavioral training, I look at safety through a clinical and preventative lens. I do not just watch your pet; I actively monitor their health, behavior, and physical surroundings to prevent accidents before they happen. You can travel with total peace of mind knowing an expert is at the helm.

Sitter Profile Image: Yelena L.
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Yelena L.
Star Sitter
from
$57
per night
5.0 out of 5 stars
27 reviews
5 repeat clients
40 years of experience
Gotha, FL, 34734

Under unexpected and difficult circumstances during her stay, Yelena cared for my dogs in an extraordinarily special manner…an effort I won’t forget and remain thankful for

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Kyle S.
Sitter Profile Image: Elizabeth D.
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Elizabeth D.
Star Sitter
from
$45
per night
5.0 out of 5 stars
19 reviews
4 repeat clients
10 years of experience
Windermere, FL, 34786

Elizabeth was great with my three very different personality dogs. They are little with big personalities! She managed them all so well, no accidents in the house, and gave them love as if they were her own. I’m happy to have found someone reliable and patient to be with our pups when we go out of town:)

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Kathryn A.
Sitter Profile Image: Jasmine G.
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Jasmine G.
from
$35
per night
5.0 out of 5 stars
36 reviews
9 repeat clients
15 years of experience
Orlando, FL, 32819

About: I’ve adored animals my entire life and have taken care of many different types of pets for the last 15 years ranging from my neighbors cats and dogs, to my friends reptiles, and my many pets over the years. Consisting of walking, playing, feeding, bathing, and occasionally overnight stays with their animals. I’ve owned many fish, hamsters, a bunny, duck, and 6 dogs over the course of my life. For the past 8 years I’ve been raising my two beautiful female Rottweilers who are giant teddy bears, full of energy and love. I’m currently working around my full-time job. If you’re looking for care outside of my availability, send me a message and I’ll do my best to accommodate you. Availability: Sunday after 7pm Monday after 5pm Tuesday before noon Wednesday ALL DAY Thursday after 5pm Friday after 3pm Saturday ALL DAY As of now, I offer both dog walking and day visits at your home, and will eventually be offering dog boarding services. I am physically fit to keep up with your dogs no matter their energy level and will give them plenty of exercise during walks throughout your neighborhood or a nearby park. I am well organized and a clean person who will treat your home like my own!

Sitter Profile Image: Jonathan W.
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Jonathan W.
from
$75
per night
5.0 out of 5 stars
42 reviews
18 repeat clients
13 years of experience
Orlando, FL, 32819

Jonathan has a clear love for animals and he did a tremendous job with our dog and cat. Great updates, very timely and house was spotless. Would highly recommend, in fact, we are already hiring him for a second job in a few weeks!!!!

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Jim E.
Sitter Profile Image: Steffanie D.
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Steffanie D.
from
$50
per night
5.0 out of 5 stars
26 reviews
7 repeat clients
40 years of experience
Winter Garden, FL, 34787

Absolutely the best dog, cat and house sitter we've ever had. Wonderful with our sensitive rescue dog. Continued with the training we had started. Took her for long walks. Extra caring for our very old cat and even monitored his weight for us. Found a problem with our jacuzzi that the pool people missed and got them to correct it. Ended up drying all of our bedding and towels at her own home as there was a problem with our dryer on her last day. Left the house spotless and watered the plants. Sent wonderful photos and updates. Excellent communicator and problem solver. Made 9 days of our trip much more enjoyable knowing she was there. Highly recommend.

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Lora F.
Sitter Profile Image: Mariana S.
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Mariana S.
from
$27
per night
18 years of experience
Ocoee, FL, 34761

About: I have taken care of dogs since I was a little kid. My godmother used to own five dogs and seven cats back in Brazil. Every time that I would come over to her place I would love to take care of her pets. The best memories I have are from feeding, playing, and having sleepovers with these animals every night. After my godmother passed away, I adopted one of her dogs named Liza. I brought Liza here to the United States with my family and she lived an eighteen year long and happy life! Towards the end of her life, she had vestibular disease. I made sure we were on top of all vet visits, meds and rehab care. She was very important to me so I wanted make sure we gave her the best care. Since then, I have been there for my family and friends to watch their beloved pets. I have experience from cat sitting, dog sitting, and dog walking! I make sure to send my friends and family updates on their fur baby as I know going on vacation can make you miss your pets. So excited for future fur buddies to meet! Hi guys, I am new here!! I work part time and I have full time availability at my day job, but I decided to reserve some time to take care of pets which has always been a dream of mine! I am trying to make this app work and will change my availability on a week to week basis depending on my scheduling at work, but I will be as flexible and as convenient as I can to fit into your schedule! I know how important it is for your pet's happiness to take their daily walks, so during their daily walk I will make sure that they exercise, have enrichment and also have fun with the scenery! If I am doing check ins I will make sure that your pup is happy and also that they have everything that they may need such as food, water and most importantly, are happy!

Sitter Profile Image: Taylor A.
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Taylor A.
Star Sitter
from
$45
per night
5.0 out of 5 stars
17 reviews
6 repeat clients
20 years of experience
Lake Copeland, Winter Garden, FL, 34787

Taylor took excellent care of our dog and cat! We have quite a few "special" requirements for our senior four-legged family members and Taylor was up for the task. She stayed in our home and fit in like a champ! In fact, we've booked Taylor for another (longer) visit. Thank you, Taylor!

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Steve E.
Sitter Profile Image: Nathan B.
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Nathan B.
Star Sitter
from
$105
per night
5.0 out of 5 stars
80 reviews
33 repeat clients
9 years of experience
Windermere, FL, 34786

We were able to go on vacation without worry because our animals were in good hands. Nathan took excellent care of them. When our dog became ill, he knew just what to do. It was a comfort to know our Charlie was taken care of.

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Jessica B.
Sitter Profile Image: Alexis T.
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Alexis T.
from
$50
per night
5.0 out of 5 stars
19 reviews
12 repeat clients
7 years of experience
Winter Garden, FL, 34787

Alexis took great care of our two senior cats while housesitting — including caring for my houseplants. Our cats are very affectionate and can be very needy, so we were happy to receive regular updates with photos showing them being loved on. I highly recommend her services and we will be happy to book her again for our future travel.

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Lindsey L.
Sitter Profile Image: Ariella P.
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Ariella P.
from
$115
per night
5.0 out of 5 stars
32 reviews
11 repeat clients
9 years of experience
Windermere, FL, 34786

Ariella did an amazing job! Our dog had a stomach issue while we were gone and Ariella took such great care of her, even offering to take her to the vet. She went above and beyond, washing blankets and sheets, handling a dog that threw up every night she was here. We are so grateful Ariella was with our dog when this happened.

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Ginny H.
Sitter Profile Image: Stephen N.
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Stephen N.
from
$38
per night
15 years of experience
Orlando, FL, 32819

About: I have been surrounded by animals throughout my life and understand that every pet has its own personality, routine, and comfort level. I was raised with a red-nose Pit Bull, an XL Bully, and two English Bulldogs, so I am comfortable caring for strong, large-breed dogs as well as smaller pets. My family also cares for a flock of chickens, African geese, ducks, and a turkey. This experience has taught me to be patient, observant, dependable, and respectful of animals with very different needs and temperaments. I can help with feeding, fresh water, walks, playtime, litter-box or pet-area cleanup, companionship, and following your pet’s normal routine. I will carefully follow your instructions and provide photos and updates so you can feel confident that your pet is safe, comfortable, and receiving attentive care while you are away. Pet care fits well into my daily schedule. I have a flexible routine and can make time to feed, walk, play with, and care for animals consistently. I’m dependable, punctual, and able to adjust my schedule to meet the needs of the pets I’m responsible for. I care for pets by following their routine as closely as possible. I make sure they have fresh food and water, get plenty of exercise and playtime, and receive lots of attention and affection. I also keep their living area clean, watch for any signs that they may not be feeling well, and follow any instructions the owner provides, including administering medication if needed and I’m trained to do so. My goal is to make every pet feel safe, comfortable, and cared for while their owner is away.

Sitter Profile Image: Paula L.
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Paula L.
Star Sitter
from
$23
per night
5.0 out of 5 stars
6 reviews
3 repeat clients
10 years of experience
Orlando, FL, 32835

About: Hi! I’m a true animal lover with a big heart for both dogs and cats. I understand that pets are family, and I treat every animal in my care with the same love, patience, and attention I would give my own. Whether your pup needs long walks and playtime or your cat prefers quiet companionship and gentle care, I’m happy to match their unique personality and routine. I currently work part-time and have a flexible schedule, which allows me to accommodate drop-in visits and pet sitting in your home. Whether your puppy needs patience, playtime, and consistency, or your senior dog needs a slower pace and extra TLC, I have experience providing attentive, compassionate care for both. I’m happy to follow your pet’s routine closely, provide regular updates and photos, and make sure they feel safe, comfortable, and loved while you’re away. My goal is to give you peace of mind and keep your furry family members happy in their own familiar environment.

Sitter Profile Image: Nickolas J.
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Nickolas J.
Star Sitter
from
$50
per night
5.0 out of 5 stars
256 reviews
60 repeat clients
25 years of experience
Florida Center North, Orlando, FL, 32811

Nick was the absolute perfect sitter for our pup. This was our first time using Rover and we were a little worried about the process and he put our mind at ease. Now that we are home, our pup keeps going into our guest room to look for Nick, so our pup must have had a great time! Will definitely use again for our next trip!

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Colton B.
Sitter Profile Image: Jennifer L.
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Jennifer L.
from
$30
per night
5.0 out of 5 stars
6 reviews
1 repeat client
20 years of experience
Orlando, FL, 32835

Jennifer is the Best. She is very responsible. She stayed at my house and sat with my older Great Dane and no one could have done a better job.

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susan j.
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The median cost per night for house sitting in Windermere is $45

Pet parents share their Rover experiences - Windermere

1 / 1
5.0 out of 5 stars

Thanya went beyond expectations staying at our home and caring for our dog Bogy! She sent many photos, tried many options to get Bogy to take his Meds, my house was well kept! It look just as I left it !!! What a pleasure to come home to ! I highly recommend Thanya and plan on booking with her again!

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Jane B.
House Sitting
5.0 out of 5 stars

Hailey is the best! She came and house sat for us while watching our little Pomeranian for 4 nights while we took a little trip up to GA. She always communicated with us, sent us pictures, kept us updated, and went above and beyond. If you’re looking for someone to treat your fur baby like their own, Hailey is the one!

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Kevin S.
House Sitting
5.0 out of 5 stars

Elizabeth is incredible!! She is so caring and took amazing care of our dog and cat. She sent lots of pictures and updates and answered any questions we had very quickly. What I loved most was that you can tell our boys got lots of love and we came home to two happy pets!

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Kylee W.
House Sitting
5.0 out of 5 stars

Taylor was great with my dogs! She kept me updated on them and sent great pictures showing how the dogs were content! I would highly recommend Taylor to watch your pets/home.

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Jeffrey S.
House Sitting
5.0 out of 5 stars

Love love love Lillian! She is flexible, a problem solver, and super accommodating to our needs. She is our go-to dog sitter without question. Already have her booked for another weekend!

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Dylan M.
House Sitting
5.0 out of 5 stars

Yanran cared for my four cats and one dog and we were very pleased with her care. I got photos and updates daily, the pets were all happy when we returned, she let the dog sleep in bed with her as he was obviously missing his family, and the house was clean when we returned. We greatly appreciated her care and will be booking her again soon!

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Julie K.
House Sitting
5.0 out of 5 stars

Nathan took such great care of our pup Winston! He communicated frequently with pictures and updates. Winston seemed very happy and at ease with him. I definitely recommend Nathan!

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Natasha L.
House Sitting
5.0 out of 5 stars

Miranda did a great job. She sent pictures and my 4 dogs were well taken care of. I would recommend Miranda for pet sitting! Lisa

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Lisa S.
House Sitting
5.0 out of 5 stars

Alexis is an amazing sitter! She truly cares about all the animals we have. My old dog had an accident and she cleaned it up before we got home. Sorry I know what was gross.

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Randy M.
House Sitting
5.0 out of 5 stars

Laura was amazing. On time and sent tons of photos. Our dog loved her and was so comfortable with her from the moment we met her. Extremely respectful of our house and a great communicator. We look forward to having her sit for us again!

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Daniel G.
House Sitting
5.0 out of 5 stars

Handled some complicated medicine for elderly dog well. Also managed some oddball behaviors for both of them without issues.

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Julie G.
House Sitting
5.0 out of 5 stars

Aries was wonderful with my two large dogs. She sent photos daily to make the stay away less stressful. I highly recommend her!!

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Dani C.
House Sitting
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Book with peace of mind

  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

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 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.

Meet local sitters who will treat your pets like family

  1. 1. Search

    Browse profiles of sitters near you who offer house sitting
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit
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Popular requests for house sitting - Windermere

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Sitters in Windermere average 4
repeat house sitting clients

FAQs for House Sitting - Windermere

Frequently asked questions about Rover

The average cost for House Sitting in Windermere on Rover is $55.5 per night (as of August 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 August 2026, there are 3,056 sitters on Rover offering House Sitting across Windermere. 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 Windermere 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 Windermere 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 Windermere 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 Windermere. On Rover:

  • 90% of sitters can help with special care needs
  • 94% can help with giving oral medications or injections
  • 95% 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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