Windsor Poolside Escape with Stunning Pool View-Perfect for Families!
Relax in a luxurious poolside condo with breathtaking views in the heart of Windsor Hills. Just minutes from Disney, our space offers a serene retreat with resort-style amenities, a private balcony, and a beautiful view of the pool. Perfect for families or couples seeking comfort, convenience, and a little magic during their Orlando adventure.
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The host requires you to complete the following before checking out:
Load and start the dishwasher
Gather used towels
Remove personal items, remove leftover food and drinks and take out the rubbish
Turn off the lights and lock the doors
Failure to complete these may result in a negative review from the host.
Important information
You need to know
Property # 4196468vb
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Kissimmee
Located in Windsor Hills, a neighbourhood in Kissimmee, this condo is near theme parks and near a water park. Mystic Dunes Golf Club and Reunion Resort Golf Course are worth checking out if an activity is on the agenda, while those wishing to experience the area's popular attractions can visit Walt Disney World® Resort and Old Town. Travelling with kids? Don't miss Disney's Animal Kingdom® Theme Park and Disney's Hollywood Studios®. Kayaking offers a great chance to get out on the surrounding water, or you can seek out an adventure with cycling nearby.
Kissimmee, FL
What's nearby
Bonanza Golf & Gifts - 3 min drive - 2.4 km
Walt Disney World® Resort - 6 min drive - 4.4 km
Disney's Animal Kingdom® Theme Park - 7 min drive - 4.2 km
Disney Springs™ - 11 min drive - 13.4 km
Magic Kingdom® Park - 14 min drive - 15.0 km
Getting around
Brightline Orlando Station - 29 min drive
Kissimmee, FL (ISM-Kissimmee Gateway) - 30 min drive
Restaurants
McDonald's - 3 min drive
Starbucks - 2 min drive
Del Taco - 3 min drive
Osaka Bay Buffet - 3 min drive
Sickies Garage Burgers & Brews - 3 min drive
Frequently asked questions
Does Windsor Poolside Escape with Stunning Pool View-Perfect for Families! have a pool?
Yes, this property has an outdoor pool.
How much does it cost to stay at Windsor Poolside Escape with Stunning Pool View-Perfect for Families!?
As of 9 May 2026, prices found for a 1-night stay for 2 adults at Windsor Poolside Escape with Stunning Pool View-Perfect for Families! on 3 Sept 2026 start from AU$385, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is Windsor Poolside Escape with Stunning Pool View-Perfect for Families! pet-friendly?
No, pets are not allowed at this property.
How much is parking at Windsor Poolside Escape with Stunning Pool View-Perfect for Families!?
On-site parking is available at the property.
What time is check-in at Windsor Poolside Escape with Stunning Pool View-Perfect for Families!?
Check-in begins at 4:00 PM.
What time is check-out at Windsor Poolside Escape with Stunning Pool View-Perfect for Families!?
Checkout is at 10:00 AM.
Where is Windsor Poolside Escape with Stunning Pool View-Perfect for Families! located?
This family-friendly Kissimmee condo building is located in Windsor Hills, within 3 mi (5 km) of Mystic Dunes Golf Club and Walt Disney World® Resort. Island H2O Live! is 2.6 mi (4.1 km) away.
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Beautiful condo with a great location. Kitchen is very well stocked. Jennifer is very responsive to any questions/concerns we had.
Denise K.
Stayed 28 nights in Feb 2026
Response from VrboOwner on 23 Mar 2026
Denise, thank you so much for coming back and staying with us again it really means a lot. You were an absolute pleasure as always and I truly appreciate how easy everything was with your stay. Would love to have you back anytime 😊
Verified
10/10 Excellent
Kim P.
24 Apr 2026
Liked: Location
The condo was great and had everything we needed for a comfortable stay. The kitchen was well stocked with a coffee maker and more, which made it really convenient for our family. The beds were very comfortable, and we appreciated the extra blankets and pillows.We enjoyed the pool view from the balcony, especially in the mornings and evenings. The girls loved the pool, and having the Xbox was a big hit for the boys!The location was perfect for visiting the parks, and communication with Jennifer was easy—she was responsive throughout our stay.If you’re looking for a place that combines comfort, convenience, and a little bit of magic, this is it. We would absolutely stay here again and recommend it to anyone visiting the Orlando area!
Kim P.
Stayed 7 nights in Apr 2026
Response from VrboOwner on 24 Apr 2026
Thank you so much for taking the time to leave this. It really means a lot to me.
I’m so happy your family felt comfortable and had everything you needed during your stay. Hearing that everyone was able to relax and enjoy their time is exactly what I hope for with every guest.
It sounds like the kids had a great time between the pool and some downtime inside which is always a win 😊 And I agree that view never gets old especially early in the day or when things wind down at night.
I’m also really glad everything felt smooth and easy from start to finish. That is always important to me.
You were wonderful guests and I would love to host you again anytime
The entire condo was amazing! From a well stocked kitchen with a coffee pot, the espresso machine, an air fryer, a George Forman and many other items! Our kids loved all of the stuffed animals spread through out the condo! The beds were very comfortable, with extra blankets and pillows. A great view of the pool area! There are so many great things that can be said! Communication was great and easy with Jennifer. Close to many food venues. My older son was ecstatic when he saw the Xbox. Would love to stay here again if we are in the area!
My family had a wonderful stay! The communication with the owner was great. The location was convenient to the Disney parks, and the pool and hot tub areas were relaxing after a long day. The property was clean and outfitted with everything we needed. Loved using the coffee bar and sitting out on the screened deck overlooking the pool in the morning. Would definitely stay here again.
Very nice property located near shopping and other amenities. The host was very helpful in answering questions and quickly responded to a minor issue we reached out about. I would recommend this unit for families, friends, or a couple who just want to get away.
Just as in the pictures. Great location. Comfortable rooms and beds. Communication with host was excellent. Had a wonderful vacation.
Jared S.
Stayed 7 nights in Jan 2026
Response from VrboOwner on 16 Jan 2026
Thank you so much for the kind review! We’re so happy to hear everything was just as expected and that you had a wonderful vacation. It was a pleasure hosting you, and we’d love to welcome you back anytime! 😊
Property was wonderful with all the little touches that help make for a magical disney trip. Beds were extremely comfortable and the provided coffee options were the best I've ever experienced.
Josh F.
Stayed 2 nights in Nov 2025
Response from VrboOwner on 2 Dec 2025
Thank you so much! I’m really happy you enjoyed the condo and all the little touches. I’m big on making sure everything feels special for your Disney trip ✨
So glad the beds were comfy and you loved the coffee setup (I’m obsessed with good coffee options so I’m happy it came through! ☕️).
Would love to have you back anytime for another magical stay! 🏰💫
Our stay was great. The communication leading up to our stay was great. Any questions we had were answered promptly. The place was in great condition, Very clean and comfortable. All the little things were covered. The pictures and the room themes were fabulous. The best part was the numerous Disney characters setup throughout the rooms including some dinner guests. :). Highly recommend!
We loved our stay! The condo was clean, comfortable, and has a great view overlooking the pool. The resort was perfect for our family and everyone loved the pool, splash pad, and slides. And being so close to Disney made it super easy to get to and from the parks. This is definitely going on our list to stay again next time we visit Disney World!!
FANTASTIC EXPERIENCE! Everything about this rental was wonderful. As soon as you enter the property you'll know you made the right choice. Great Communication from Host, Extremely Clean, Disney themed with signage everywhere to guide you. The owners have anticipated everything you might need. Thank you so much for making our vacation special!
Andy C.
Stayed 3 nights in Oct 2025
Response from VrboOwner on 12 Nov 2025
Thanks so much, Andy! I’m really happy to hear you and your family had such a great stay. I put a lot of heart into making sure everything feels easy, comfortable, and a little extra magical for families visiting the parks. It was a pleasure having you, and I’d love to have you back anytime you plan another Disney getaway!
What a gem! We loved all of the Disney decorations and our kids had a blast at the pool area. Everything was so clean and well thought out. Plenty of space and everything we needed. The hosts were also very accommodating and easy to communicate with. We will definitely stay here again next time we visit the Orlando area!
It was very nice with the pool and water pad the Disney theme was awesome and the different coffee machines were enjoyed by the coffee drinkers we felt very safe there a lot of families with different age kids
Amazing stay at Windsor Hills. An absolutely wonderful condo in an ideal location within both the resort and Orlando. The owners have thought of everything and the condo has everything you need from utensils to pushchairs. When we come back we will be staying here again.
The location was perfect, the condo was decorated beautifully and the hosts were very accommodating. Perfect for a family holiday. We would definitely stay again.
We absolutely love the condo that we stayed at in Orlando. We were impressed with the amount of security on the premises and as far as our unit goes, it was gorgeous. The owner decorated every room in the Disney theme. So impressive. Our unit had everything we could need and it was just a few miles to the parks. We would definitely stay here again.
Tracy C.
Stayed 2 nights in Sep 2025
Response from VrboOwner on 19 Sept 2025
I’m thrilled you had such a great stay! Knowing you felt at ease and had everything you needed means a lot. I love that the Disney vibe came through and that the spot worked well for your park plans. I’d be happy to welcome you back anytime.
Beautiful Disney apartment! Great size for a family of 5. We all loved the Disney decorations. Very well presented and had everything we could possibly need. Complex very clean, safe and quiet and a great base to visit the theme parks.The owner was very quick to respond to our messages.Highly recommend!
Sayyed,
So glad that your family had such a great vacation and really enjoyed your stay at the condo.
You are always most welcome if you'd like to stay once again.
Property was extremely clean and great access to Orlando !
James H.
Stayed 5 nights in Jul 2020
Response from VrboOwner on 7 July 2023
James, it was truly my pleasure sharing my home with your family. I am so glad to know that your family were so happy. That is all I ever wish for. Hopefully some day you'll consider calling my home your very own once again. Your family are always welcome. Richie
About the host
Hosted by Jennifer Calegari
Hi there! We’re Jennifer and Damion, and we’re from central New Jersey. While we love our hometown, we’ve always had a special place in our hearts for Florida—the sunshine, the beaches, and of course, all the amazing attractions! We’re huge fans of Disney and Universal, and love spending time at the parks whenever we can. We also enjoy going to the movies and hitting the beach (even though we only get a few months of summer back home!).
This is our first home as hosts, and we’re so excited to welcome guests like you to enjoy it as much as we do. We’ve put a lot of love into making this condo feel like a true home away from home, and we would love for all our guests to fall in love with it just as we have. Whether you're here for a family vacation, a couples’ getaway, or a trip with friends, we hope you’ll create lasting memories during your stay.
Why they chose this property
Nestled in the heart of Orlando, Windsor Hills Resort is the ultimate family-friendly getaway. What we love most about this neighborhood is how it perfectly blends resort-style amenities with the comfort of home. As soon as you enter, you’re greeted by beautiful, well-kept grounds, palm tree-lined streets, and a peaceful atmosphere that’s perfect for families, couples, or anyone looking for a relaxing stay.
The resort itself offers a range of amazing amenities that will keep everyone entertained. You can spend your day lounging by the lagoon-style pool, complete with water slides and a splash pad for the kids. There’s also a game room, movie theater, fitness center, and even tennis and basketball courts if you’re feeling active. The little ones will love the themed playgrounds, while the whole family can enjoy mini golf right on the property.
One of the best things about Windsor Hills is how close it is to all the major Orlando attractions. Disney World is just a 5-minute drive away, making it easy to pop over to the parks and experience the magic. Universal Studios, SeaWorld, and all the best shopping and dining options are just a short drive from the resort as well. Whether you’re looking to explore Orlando’s famous theme parks or take a day trip to either coast, Windsor Hills is perfectly located for all your vacation adventures.
What makes this property unique
What truly makes our condo unique is the combination of comfort, style, and its perfect location within Windsor Hills Resort. From the moment you walk in, you’ll notice the attention to detail we’ve put into making this space a true home away from home. Here’s what sets us apart:
Stunning Poolside Views: Our condo offers a beautiful view of the main resort pool right from your private balcony, creating the perfect spot to relax and enjoy your morning coffee or unwind in the evenings.
Newly Updated and Fully Equipped: We’ve thoughtfully furnished and stocked our condo to ensure everything you need is at your fingertips. From a fully equipped kitchen to smart TVs in every room, we’ve made sure our home is both modern and comfortable.
Family-Friendly Touches: Traveling with little ones? We’ve got you covered with amenities like a pack-n-play, high chair, and pool toys. We want to make sure families feel right at home.
Close to Disney and More: Location is everything! Our property is just 5 minutes from the magic of Disney World, and only a short drive from Universal Studios, SeaWorld, and all the best that Orlando has to offer. You get the best of both worlds—proximity to the action while enjoying the peaceful retreat of Windsor Hills.
We’ve poured our heart into this home, and we hope that every guest loves it as much as we do. Whether it’s for the unbeatable location, the relaxing views, or the thoughtful touches, we believe our condo is the perfect spot for your next Orlando vacation.
Languages:
English, Portuguese
Premier Host
They consistently provide great experiences for their guests