Condo
Windsor Poolside Escape with Stunning Pool View-Perfect for Families!
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Reviews
10 out of 10, Loved by Guests
Top 10% based on
3 bedrooms2 bathroomsSleeps 8
Popular amenities
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
Balcony
Outdoor play area
Dining 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.
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- Pool
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9.6 out of 10, Exceptional, (62 reviews)
House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets allowed
Smoking
Smoking is not permitted
Check-out instructions
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
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
- Mystic Dunes Golf Club - 3 min drive - 1.7 km
- Mighty Jungle Golf - 3 min drive - 2.8 km
- Walt Disney World® Resort - 6 min drive - 4.4 km
- Disney Springs™ - 11 min drive - 13.4 km
Getting around
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
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window10/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
1 February 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 1 night in Jan 2026
10/10 Excellent
Jan M.
1 February 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Jan M.
Stayed 7 nights in Jan 2026
10/10 Excellent
Mary F.
27 January 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Mary F.
Stayed 2 nights in Jan 2026
10/10 Excellent
Jared S.
15 January 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Jared S.
Stayed 7 nights in Jan 2026
10/10 Excellent
Josh F.
2 December 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Josh F.
Stayed 2 nights in Nov 2025
10/10 Excellent
William M.
20 January 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
William M.
Stayed 4 nights in Jan 2026
10/10 Excellent
Chanee T.
29 November 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Chanee T.
Stayed 6 nights in Nov 2025
10/10 Excellent
Thomas L.
2 August 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Thomas L.
Stayed 6 nights in Jul 2025
10/10 Excellent
Jennifer C.
7 June 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Jennifer C.
Stayed 7 nights in May 2025
10/10 Excellent
Anne B.
26 September 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Anne B.
Stayed 7 nights in Sep 2025
10/10 Excellent
Ali E.
1 October 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Ali E.
Stayed 3 nights in Sep 2025
10/10 Excellent
linda b.
13 July 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
linda b.
Stayed 7 nights in Jul 2025
10/10 Excellent
Kayla R.
29 August 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Kayla R.
Stayed 5 nights in Aug 2025
10/10 Excellent
Tracy C.
18 September 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Tracy C.
Stayed 2 nights in Sep 2025
10/10 Excellent
April S.
9 May 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay
April S.
Stayed 3 nights in May 2025
10/10 Excellent
Chris P.
26 July 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Chris P.
Stayed 5 nights in Jul 2025
10/10 Excellent
Debbie P.
30 August 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy

Debbie P.
Stayed 13 nights in Aug 2025
10/10 Excellent
Lee K.
2 May 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful Condo
Lee K.
Stayed 4 nights in Apr 2025
10/10 Excellent
Sayyed Farid A.
12 March 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Good for family vacation
Sayyed Farid A.
Stayed 3 nights in Mar 2023
10/10 Excellent
James H.
8 July 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great accommodations!
James H.
Stayed 5 nights in Jul 2020
10/10 Excellent
Scott F.
9 May 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place
Scott F.
Stayed 6 nights in Apr 2022
10/10 Excellent
Sandy M.
29 December 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Family Christmas trip to Disney.
Sandy M.
Stayed 4 nights in Dec 2024
10/10 Excellent
Erin S.
16 May 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Pool View
Erin S.
Stayed 7 nights in May 2025
10/10 Excellent
Andrew G.
29 September 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Stay
Andrew G.
Stayed 4 nights in Sep 2020
10/10 Excellent
Corryn D.
11 November 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Corryn D.
Stayed 7 nights in Nov 2025
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.
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.
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.
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
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