Condo

Windsor Poolside Escape with Stunning Pool View-Perfect for Families!

Photo gallery for Windsor Poolside Escape with Stunning Pool View-Perfect for Families!

A resort with a large pool, a water park, and a well-maintained lawn area.
A ceiling with a circular light fixture and a vent. There is a door on the left and a wall with a Mickey Mouse mural and a 'HELLO SALUT Hola Hola' sign.
A balcony with a view of a pool and resort area, furnished with chairs and a table.
A modern kitchen with white cabinets, a granite countertop, stainless steel appliances, and a coffee maker.
A living room with a large flat-screen TV displaying a castle, a ceiling fan, and a couch with decorative pillows.

Reviews

10 out of 10, Loved by Guests
Top 1% of guest reviews in this area

Highlights

  • Top-rated comfy beds
    Guests liked the comfy beds here.
  • Outdoor pool
    The outdoor pool is a refreshing retreat under the open sky - a rare gem in this area.
  • Centrally-located
    You're never far from where you need to be with this convenient location.

Popular amenities

  • Balcony
  • Outdoor pool
  • On-site fitness center
  • Arcade/game room
  • Air conditioning
  • Refrigerator

Explore the area

View in a map
Kissimmee, FL
  • Place, Bonanza Golf & Gifts
    ‪3 min drive‬
  • Place, Mighty Jungle Golf
    ‪3 min drive‬
  • Place, Mystic Dunes Golf Club
    ‪4 min drive‬
  • Airport, Orlando, FL (MCO-Orlando Intl.)
    ‪32 min drive‬

Rooms & beds

3 bedrooms (sleeps 8)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

2 Twin Beds

Living Room 1

1 Queen Sofa Bed

2 bathrooms

Bathroom 1

Towels provided · Toilet · Shower only · Hair dryer

Bathroom 2

Towels provided · Bathtub or shower · Toilet · Hair dryer

Spaces

Kitchen
Balcony
Outdoor play area
Dining area

Add dates for prices

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About the neighborhood

Kissimmee

Located in Windsor Hills, a neighborhood 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. Traveling 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.
Map
Kissimmee, FL

What's nearby

  • Bonanza Golf & Gifts - 3 min drive - 2.7 km
  • Mighty Jungle Golf - 3 min drive - 3.1 km
  • Mystic Dunes Golf Club - 4 min drive - 2.4 km
  • Island H2O Live! - 5 min drive - 4.7 km
  • Orange Lake Golf - 7 min drive - 7.5 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
  • ‪El Cafetal Bakery & Restaurant - ‬2 min drive
  • ‪Del Taco - ‬3 min drive
  • ‪IHOP - ‬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 Nov 1, 2026, prices found for a 1-night stay for 2 adults at Windsor Poolside Escape with Stunning Pool View-Perfect for Families! on Nov 8, 2026 start from $262, 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?

Onsite 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!?

Check-out 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 labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 306 out of 323 reviews
Rating 8 - Good. 13 out of 323 reviews
Rating 6 - Okay. 4 out of 323 reviews
Rating 4 - Poor. 0 out of 323 reviews
Rating 2 - Terrible. 0 out of 323 reviews

10/10

Cleanliness

9.8/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Honestly we have been to Florida a few times as a family of 5 with 3 below the ages of 12. This is, by an absolute country mile, the best apartment and destination we have ever stayed in. Clean, easy, and great communication with the host, throughout our stay. I couldn’t recommended this apartment any higher. On top of the above, the location is spot on… approx 10 mins from Disney parks, making it prime spot. Thanks for great memories, we will be back in 2028!!
Stayed 14 nights in Oct 2026
Response from VrboOwner on Oct 28, 2026
Thank you so much for such a wonderful review! It really makes me happy to hear this. I always want my guests to feel right at home, especially when traveling with family. It was a pleasure having you all, and I truly appreciate you choosing our little home away from home. Looking forward to welcoming you back in 2028! ❤️
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent location for Disney and IDrive. Condo had everything we needed for 10 days. Kitchen is well equipped and coffee was god send. Kids loved the Disney theme and the board games when we needed to chill. Access to pool and facilities is super easy with loads of space in the pool and loungers. Jennifer was on had to help with questions. All in all a super smooth vacation condo rental.
Stayed 9 nights in Aug 2026
Response from VrboOwner on Aug 30, 2026
Thank you so much for the wonderful review! I’m so happy you and your family enjoyed your stay and were able to make yourselves at home. It was a pleasure having you as our guests, and I truly appreciate you choosing our condo for your vacation. We would love to welcome you back anytime! 🐭🏰☀️
Verified review

10/10 Excellent

Liked: Cleanliness, communication, location, listing accuracy
Property was excellent, facilities very good. Beautiful spot to stay for visiting Disney.
Stayed 4 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our condo at Windsor Hill Resort was great. It was close to the parks and our condo was clean and comfortable. Our grandkids loved the pool and water park. Our Host was wonderful to work with and was really good at getting us in.
Stayed 6 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our stay at this property was fantastic! It was clean, fully stocked with everything you would need and in a great location! The hosts Jennifer and Damion were extremely communicative and very helpful. We would stay here again in a heartbeat!
Stayed 5 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We would summarize our experience as “Magical”!Jennifer was a top notch host from the moment we booked our trip! There was never a lapse in communication and she was on her game. Jennifer made sure we had all check-in information down to the minor details before we even asked. She knew we had two little 2year olds with us and even added extra stuffies!! The video we have of them seeing the condo for the first time, is priceless! It was like walking into the Disney store!!!All the wall decor, dishes, towels, Mickey Mouse waffle maker and toaster were so much fun. Everywhere you turned, there was a character popping out to say hi! The items to use for toddlers such as the high chair, booster seat, crib and stroller made it a breeze. The condo was spotless and was a great location for going to the pool laden with swimmies etc. It truly felt like home. We are already talking about our next Disney vacation, and we won’t have to search for a condo! This will be it!Thank you Jennifer for all your help and being such a gracious host!Kathy
Stayed 7 nights in Sep 2026
Response from VrboOwner on Oct 5, 2026
Thank you so much! ❤️ This seriously made my day. I’m so happy you and your family had such a great time and enjoyed the condo. One of my biggest goals has always been to make it as kid-friendly as possible, because traveling with little ones is already a lot 😂 and I want parents to be able to come on vacation and actually enjoy their vacation too! It means so much to me that you took the time to write such a sweet review. I would absolutely love to have you all back for your next Disney trip! 🏰✨❤️
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
There was everything to love about this vacation rental. Location Clean, well stocked unit Lovely pool/resort vibe Great communication/responsiveness from Jennifer. Would definitely stay again!
Stayed 21 nights in Feb 2026
Response from VrboOwner on Feb 23, 2026
Thank you so much for staying with us and for taking the time to leave such a kind review. I’m really glad you enjoyed your stay and felt comfortable throughout your visit. It truly means a lot to me, and I’d love to host you again whenever you’re back in the area!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location close to parks, great pool and water park.
Stayed 6 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful condo with a great location. Kitchen is very well stocked. Jennifer is very responsive to any questions/concerns we had.
Stayed 28 nights in Feb 2026
Response from VrboOwner on Mar 23, 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 review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 2 nights in Nov 2025
Response from VrboOwner on Dec 2, 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! 🏰💫
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beds were comfy, view was great! Would definitely stay again!
Stayed 7 nights in May 2025
Response from VrboOwner on Jun 24, 2025
It was our pleasure hosting you!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The unit is very nice. It is situated in a great spot overlooking the pool.
Stayed 1 night in Jan 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Just as in the pictures. Great location. Comfortable rooms and beds. Communication with host was excellent. Had a wonderful vacation.
Stayed 7 nights in Jan 2026
Response from VrboOwner on Jan 16, 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! 😊
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 2 nights in Jan 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 7 nights in Jan 2026
Verified review

10/10 Excellent

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!
Stayed 7 nights in Apr 2026
Response from VrboOwner on Apr 24, 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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Good for family vacation

The resort is good for family vacation.
Stayed 3 nights in Mar 2023
Response from VrboOwner on Jul 7, 2023
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.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great accommodations!

Property was extremely clean and great access to Orlando !
Stayed 5 nights in Jul 2020
Response from VrboOwner on Jul 7, 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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place

Great place, so close to Disney, great pool
Stayed 6 nights in Apr 2022
Response from VrboOwner on Jul 7, 2023
Scott, So glad that you really enjoyed your stay at the condo. I've really been trying to upgrade the condo lately as best as I can and your review really has allowed me to know that it was all worth while. Your family are always so welcome as my guests. Can't wait to share it with you once again. Thanks so much for your kind words. I really do appreciate it. Richie
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We absolutely loved this condo. Everything was great and exactly as shown. We had no problems and would love to stay there again when we return.
Stayed 6 nights in Nov 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay

This is a perfect place if you have 2 families because of the 2 king rooms! Super clean and had everything you need!!
Stayed 3 nights in May 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 10 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Stay

We love this condo and would happily stay here any time!
Stayed 4 nights in Sep 2020
Response from VrboOwner on Jul 7, 2023
Andrew, when you emailed me to let me know how pleased your family was the moment they checked in that literally made my entire day. I still remember reading your email. So thank you. Nothing makes me happier to than know that my guests were as happy as your family. I mean to think that your kids actually were looking forward to leaving Disney early to come back to the resort. That very well might be the most perfect email I ever received. Can't wait to share my home with your family once again. Richie
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!!
Stayed 7 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great property for families!

Great location and amenities, close to Disney, airport and Universal.
Stayed 6 nights in Mar 2021
Response from VrboOwner on Jul 7, 2023
Chris, It really was my pleasure sharing my home with you and your family. I'm so glad to know that you really enjoyed your perfect vacation at Disney and Universal. So happy for your family Just know that if ever your family decides to vacation once again in Orlando you'll always be more than welcome as my guests. I wish you and your family well. Richie
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