Condo

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

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

Relax and unwind with a stunning pool view from our third-floor condo at Windsor
Pool
Pool
Pool
Pool

Reviews

10 out of 10

Exceptional

3 bedrooms2 bathroomsSleeps 8

Popular amenities

  • Parking available
    Parking available
  • Kitchen
    Kitchen
  • Air conditioning
    Air conditioning
  • Dryer
    Dryer
  • Washer
    Washer
  • Gym
    Gym

Explore the area

Map
Kissimmee, FL
  • Mystic Dunes Golf Club
    5 min drive
  • Island H2O Live!
    5 min drive
  • Walt Disney World® Resort
    7 min drive
  • Kissimmee, FL (ISM-Kissimmee Gateway)
    30 min drive

Rooms & beds

3 bedrooms (sleeps 8)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

2 Single 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
Outdoor play area

About this property

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.

Property manager

Jennifer Calegari
Premier Host

Languages

English, Portuguese

Add dates for prices

Amenities

Kitchen
Washer
Dryer
Air conditioning
Gym
Parking available

Similar properties

House Rules

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

No pets allowed

Smoking

Smoking is not permitted

Important information

You need to know

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

About the area

Kissimmee

Located in Windsor Hills, a neighbourhood in Kissimmee, this condo is near theme parks. 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.
Map
Kissimmee, FL

What's nearby

  • Mystic Dunes Golf Club - 5 min drive
  • ESPN Wide World of Sports - 10 min drive
  • Disney's Blizzard Beach Water Park - 11 min drive
  • Disney's Hollywood Studios® - 12 min drive
  • Disney's Animal Kingdom® Theme Park - 15 min drive

Getting around

  • Brightline Orlando Station - 29 min drive
  • Kissimmee, FL (ISM-Kissimmee Gateway) - 30 min drive

Restaurants

  • ‪McDonald's - ‬3 min drive
  • ‪Starbucks - ‬18 min walk
  • ‪Taco Bell - ‬4 min drive
  • ‪IHOP - ‬3 min drive
  • ‪Giordano's - ‬4 min drive

Frequently asked questions

Is Windsor Poolside Escape with Stunning Pool View-Perfect for Families! pet-friendly?

No, pets are not allowed at this property.

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.
Learn moreOpens in a new window
Rating 10 - Excellent. 259 out of 276 reviews" "
Rating 8 - Good. 13 out of 276 reviews" "
Rating 6 - Okay. 4 out of 276 reviews" "
Rating 4 - Poor. 0 out of 276 reviews" "
Rating 2 - Terrible. 0 out of 276 reviews" "

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Ashley G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Universal and Disney family trip
Our stay was perfect! This resort has everything a family could ask for! Richie was wonderful to work with!
Stayed 7 nights in Aug 2024

10/10 Excellent

Bo L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent Location and Resort Amenities
Great location that is very close to Disney World Parks. Kids loved the onsite pool and waterslide. Only comment is that the water pressure in the unit is very low.
Stayed 5 nights in Aug 2024

10/10 Excellent

Noreen Q.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic Home Away From Home
Parents who travel for out-of-state tournaments know how important it is to keep your athlete’s daily sleeping/eating/training routine the same. This property allowed us to do that easily. All appliances were up to date - microwave, stove, dishwasher, washer/dryer, etc. The property was clean l, well stocked with towels and conveniently located within the resort. I noticed some families had to drive and park at the pool but we could easily walk there. We took advantage of all of the resort offerings and used the Marketplace as well. Richie is an extraordinary owner as well. He is extremely responsive and thoroughly communicates. I highly recommend Richie and his property for your next stay.
Stayed 8 nights in Jul 2024

10/10 Excellent

Fabio B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Just perfect
Everything was really well done. Very organized, cleaned e perfect communication. Place is very well located, close to main attractions at Orlando, but also within the condominium. Close to the club house area, main entrance and elevator. I will definitely stay there again!
Stayed 8 nights in Jul 2024

10/10 Excellent

Heather M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great condo
We loved staying here! Super clean, comfy beds, well stocked linens and kitchen items, and close to disney! We loved the mickey decor! My kids thought we were in the "disney bubble" and loved their bedroom. I loved being so close to the parks without paying the disney prices. We will definitely stay here again!
Stayed 7 nights in Jun 2024

6/10 Okay

Cal V.

Liked: Cleanliness, check-in
Disney in June
Overall very pleased with the location, pretty easy to Disney. Disney themed condo was nice and kid friendly. Well equipped with everything you need. Comfortable beds and the tv's were great. Owner's guide was very helpful. Maybe a little more transparent about temperature restrictions. I expect to be cool on my vacation and having to rely on 74 is not what I consider reasonable given the June weather. The pool was great but no monitoring of weekly wrist bracelets. Felt like the locals being at the pool the entire week with no enforcement of wristbands or beverages near or in the pool. Probably 1/4 of the people in the pool had bracelets. Pool grill is great and quick service.
Stayed 6 nights in Jun 2024

6/10 Okay

Vance W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Good location, problem elevator
This condo was in a good location for our Disney World visit. All the parks were a 10-15 minute drive away. The only issue we had was our building's elevator was broken. Now this might not sound like a big deal, but it was broken upon our check-in, so we had to carry 4 large suitcases up 2 flights of stairs to the third floor. They did get it fixed, but it took 4 days. Luckily the elevator was working when we checked out.
Stayed 6 nights in May 2024

10/10 Excellent

Jennifer G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Place to Stay
Very nice place to stay, convenient location, nice pool, easy access and AWESOME communication with the owner. Responds quickly and very friendly. I would definitely recommend staying here and we will be back
Stayed 4 nights in May 2024

10/10 Excellent

Kim F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
A Gem
We enjoyed our stay immensely! The property was as listed and I can not say enough good things about how well stocked the kitchen was! I cook all the time and seldom do I find a kitchen that I can actually cook in and not have to improvise because there is little to no appliances/pots/pans etc. Truly a well stocked kitchen! Beds were comfortable, everything was clean. Communications with the owner were amazing and very rhoirough absolutely would stay again!
Stayed 6 nights in May 2024

10/10 Excellent

Melissa R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location near Disney!
Loved the condo, neighborhood, and location. The owner was an excellent communicator and was very helpful!
Stayed 5 nights in May 2024

10/10 Excellent

Daniel S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing stay!
The condo was perfect for my stay with my wife, parents and two younger children. The condo provided everything we needed with amazing amenities and a great location. My kids fell in love with the fantastic swimming pool and slides, whilst my wife and I were very impressed with the great value found in this great location. The condo was clean and spacious with a Disney theme which really helped add to the magic for my children. The host has been more than helpful with swift responses to any questions we had, alleviating any stresses and concerns we may have had prior to our stay. Richie really went above and beyond to always be on hand if we needed anything. We strongly recommend staying at this condo and will be seeking to return in the coming years.
Stayed 3 nights in Apr 2024

8/10 Good

Claire W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice stay at Disney themed property
My husband, kids and I had a nice stay at this property. Richie is very thorough with his communication and responsive to questions. Our kids enjoyed all the stuffed animals and the pool/water slides. The condo was very clean and located close to Disney. The only minor downside was the bed in the master bedroom was soft and squeaked when you moved around. It would have been nice if a sponge and dish soap were included but it was noted that only small bar soap would be available. Not the condo owner's fault, but there was a very loud, large group by the pool who kept their party going until it closed at 10pm for two nights during our stay. All in all it was a positive experience. Thank you for sharing your condo!
Stayed 5 nights in Apr 2024

10/10 Excellent

Riki H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Property
Excellent stay. Property was conveniently located to all of the Disney parks and decorated throughout with Disney decor. Would definitely stay again.
Stayed 3 nights in Apr 2024

10/10 Excellent

Elizabeth C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Disney/Universal Spring Break
We chose this resort on a recommendation of a friend. This condo was perfect for us! initially we had the wrong access code to the door, but the owner was super fast in responding and answering our call. Even at 11:30pm (Our flights were delayed for hours). My kids loved the theme of the condo and all the animals around the place. The closeness to the pool was a plus. The really enjoyed an afternoon playing and swimming there. We loved how close the unit was to the gate and that the parking was close and readily available. The unit had plenty of extra towels, and even came with towels for the pool! Only downside was the water pressure in the showers. Overall we loved staying here!
Stayed 6 nights in Mar 2024

10/10 Excellent

Ryan E.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Awesome resort!
Great place to stay and only just a few mins from all the disney parks. Kids loved the heated pool. The waterpark area isnt heated so it was chilly. Very nice place overall. Would definitely stay here again!
Stayed 6 nights in Feb 2024

10/10 Excellent

Dani L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Family Vacation at Disney
This incredible condo was extremely clean and perfectly located just miles from Disney. The host was wonderful to work with and provided responses to all questions very quickly. The pool and amenities were wonderful. We will stay here again!
Stayed 6 nights in Feb 2024

10/10 Excellent

Sharron P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect stay!
This condo was exactly as described and perfect in every way. It was very well equipped and beds were extremely comfortable. Will definitely be back again!
Stayed 4 nights in Feb 2024

10/10 Excellent

Nerit G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Overall good
Well equipped, great location, heated pool. The only thing that bothered us was the moldy scent.
Stayed 5 nights in Jan 2024

10/10 Excellent

Candace W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Most gracious host….
For a person that does a fair amount of traveling… we very pleased with the house, clean and had amazing amenities at the property. Ritchie was so accommodating and made sure I was well informed prior to my arrival! He is by far one of the best VRBO hosts I have ever experienced! We will definitely keep in and this property in mind in the future!
Stayed 3 nights in Jan 2024

10/10 Excellent

Cheryl C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Home Away From Home
This condo was everything advertised. The owner thought of everything a family with children might need while away. The beds were comfortable and the condo layout worked well for a family of six. Thank you, Richie.
Stayed 10 nights in Dec 2023

10/10 Excellent

Jon M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great for family vacation
This place was exactly what we were looking for. Location was perfect for a Disney vacation. The host was very helpful and organized. Condo was very clean and well kept. We would recommended this place to anyone!
Stayed 7 nights in Dec 2023

10/10 Excellent

Ashley W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect Thanksgiving Stay
This property was exactly what we needed. The proximity to Disney was amazing. The condo was just as listed. The kids loved playing with ALL of the stuffed animals. Everything you might need was included in the condo! Perfect for families with multiple kiddos. We had a fantastic trip. The pool was heated nicely, and we were able to swim comfortably even on cooler days in November. We would definitely stay here again.
Stayed 8 nights in Nov 2023

6/10 Okay

Kelsey W.

Liked: Cleanliness, communication, location, listing accuracy
Fun place to stay near Disney
We enjoyed our stay here. The condo was clean and well maintained as per the pictures. The pool area was fun and it was in a good location. Giving it an overall of 3 stars for a few reasons. The check in process was very extensive with a lot of paperwork and we had to sign additional forms since it’s a condominium community. Communicating with the host was great, but we weren’t able to get an early check in nor late check out. Had to sign forms and get wrist bands for the pool which was okay but another thing to keep up with. The day we checked out the house cleaner was there literally at 9:50 even though we were still packing up to leave at 10. Good price and cute place near Disney, just know it’s definitely more complicated to stay at than other places we’ve stayed.
Stayed 5 nights in Nov 2023

10/10 Excellent

Valerie L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect for families!
Richie was the best host! He always was quick to respond and very helpful. The place was extremely clean, comfortable and fun for our littlest! We cannot wait to go back! We found our new home away from home! :)
Stayed 4 nights in Nov 2023

10/10 Excellent

Katherine B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great week!!!!
Wonderful time had by all! We will definitely be back! Clean, comfy, and so close to Mickey!!!
Stayed 6 nights in Oct 2023

About the host

Hosted by Jennifer Calegari

Host profile image
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
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