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Private Cocktail Pool: Kissimmee Resort Retreat!

Photo gallery for Private Cocktail Pool: Kissimmee Resort Retreat!

An indoor swimming pool with a glass ceiling, surrounded by lounge chairs and a table with an umbrella.
A large, clear swimming pool with a tiled deck, surrounded by palm trees and a building with a red roof in the background.
A modern living room with a sofa, coffee table, and a dining area with chairs and a table.
A modern living room with a dining area, large windows, and a pool view.
A modern kitchen with stainless steel appliances, white cabinetry, and a central island.

Reviews

8.6 out of 10
Excellent

Popular amenities

  • Balcony or patio
  • Hot tub on site
  • Private pool
  • On-site fitness centre
  • Arcade/game room
  • Air-conditioning

Explore the area

View in a map
Kissimmee, FL
  • Place, Mystic Dunes Golf Club
    ‪20 min walk‬
  • Place, Disney's Animal Kingdom® Theme Park
    ‪10 min drive‬
  • Place, Disney Springs™
    ‪13 min drive‬
  • Airport, Orlando, FL (MCO-Orlando Intl.)
    ‪33 min drive‬

Rooms & beds

3 bedrooms (sleeps 8)

Additional Sleeping (Living Room)

1 Double Sofa Bed

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Double Bed and 3 Single Beds

3 bathrooms

Full Bathroom

Full Bathroom

Full Bathroom

Spaces

Deck or patio
Kitchen
Separate dining area
Outdoor play area

Add dates for prices

Similar properties

Living room that opens up to the pool and patio.
Minutes Away from Theme Parks! 3-Bed Townhome, 6 minutes to Disney World!
Windsor Hills
  • Pool
  • Hot tub
  • Kitchen
  • Washing machine
10.0 out of 10, Exceptional, (219 reviews)
Minutes Away from Theme Parks! 3-Bed Townhome, 6 minutes to Disney World!

About the area

Kissimmee

Windsor Hills, a neighbourhood in Kissimmee, is home to this holiday home. 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 Hollywood Studios® and Disney's Animal Kingdom® Theme Park.
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Map
Kissimmee, FL

What's nearby

  • Mystic Dunes Golf Club - 20 min walk - 1.7 km
  • Disney's Animal Kingdom® Theme Park - 10 min drive - 6.5 km
  • Disney Springs™ - 13 min drive - 16.0 km
  • Magic Kingdom® Park - 15 min drive - 16.6 km
  • Universal Studios Florida - 25 min drive - 32.4 km

Getting around

  • Kissimmee Station - 26 min drive
  • Kissimmee, FL (ISM-Kissimmee Gateway) - 23 min drive

Restaurants

  • ‪McDonald's - ‬4 min drive
  • ‪Starbucks - ‬3 min drive
  • ‪El Cafetal Bakery & Restaurant - ‬3 min drive
  • ‪Del Taco - ‬3 min drive
  • ‪IHOP - ‬3 min drive

Frequently asked questions

Does Private Cocktail Pool: Kissimmee Resort Retreat! have a pool?

Yes, this property has a pool.

Is Private Cocktail Pool: Kissimmee Resort Retreat! pet-friendly?

Yes, pets are allowed at this property.

How much is parking at Private Cocktail Pool: Kissimmee Resort Retreat!?

On-site parking is available at the property.

What time is check-in at Private Cocktail Pool: Kissimmee Resort Retreat!?

Check-in begins at 4:00 PM.

What time is check-out at Private Cocktail Pool: Kissimmee Resort Retreat!?

Checkout is at 10:00 AM.

Where is Private Cocktail Pool: Kissimmee Resort Retreat! located?

This family-friendly Kissimmee holiday home is located in Windsor Hills, within 3 mi (5 km) of Mystic Dunes Golf Club, Island H2O Live! and Jack Nicklaus Course. Walt Disney World® Resort and Old Town are also within 6 miles (10 km).

Reviews

8.6

Excellent

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 14 out of 28 reviews
Rating 8 - Good. 9 out of 28 reviews
Rating 6 - Okay. 3 out of 28 reviews
Rating 4 - Poor. 2 out of 28 reviews
Rating 2 - Terrible. 0 out of 28 reviews

8.2/10

Cleanliness

9.4/10

Check-in

9.0/10

Communication

9.4/10

Location

9.0/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

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

Clean nice accommodation

The owner was very responsive to any issues we had.
Stayed 5 nights in Jun 2024
From a partner site

8/10 Good

WINDSOR HILLS TOWNHOUSE

Good..It was clean and in good condition.
Verified review

10/10 Excellent

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

Windsor Hills

The perfect location near the theme parks. The home had all the amenities we needed, and then some. Love having the private pool! The association property has so much to enjoy. Weekend entertainment pool side was fun for the kids. All the guests were so friendly, everyone seemed to love where they were as much as we did.
Stayed 7 nights in Jan 2023
Verified review

6/10 Okay

Liked: Check-in, location, listing accuracy
Disliked: Communication

Nice condo

We enjoyed the condo. We had 1 issue with bed bug bites in the twin bed of the children bedroom.
Stayed 4 nights in Jul 2022
Response from VrboOwner on 31 Oct 2022
Hi Anjeanetta, we are so glad you enjoyed our condo! - We are very sorry your children got bug bites in the twin bed. - We wish you had reached out to us during your stay so that we could have immediately addressed your concerns - After your review, our cleaner treated the sheets and mattress. This treatment solved the issue, as we have not heard from other guests about this issue, since your stay Thanks for your valuable feedback as we continue to improve for future guests!
Verified review

8/10 Good

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

Good overall

Nice place overall where we had a good time. My kids were disappointed their bedroom didn't have the same decorations as were in the listing. Having so many beds was key for us staying there vs other listings. Check-in process was easy and property manager was quite responsive. Some TLC would be good - most chairs in pool area were broken and/or rusty.
Stayed 7 nights in Mar 2024
From a partner site

10/10 Excellent

Worlds break

This town house was booked much later than usual but didn’t disappoint. I’m quite fussy on room sizes so really pleased with 3 really good size en-suite bedrooms. Plenty of space in the lounge and kitchen for a family. The splash pool is a great facility, for an evening dip and was in the sun for most of the day. A good amount of seating and a proper size table pool side which was lovely for outside dinning and we could all have a seat. Travelled with a baby, the host was very accommodating providing a high chair and cot. Would definitely book again.
Verified review

8/10 Good

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

Always love Windsor Hill properties

We've stayed in a condo like this several times before we enjoy this location we enjoy the amenities the only thing I would say about this one is that ceiling fans would be a huge addition to the property I would probably invest in pillows for each of the rooms they seem to have been used and are in need of replacement all of the amenities in the home were very good condition of it was good as well the communication with the manager was convenient follow-up was very good any questions I had were answered quickly we enjoyed our stay and would highly recommend this property
Stayed 5 nights in Mar 2024
Verified review

8/10 Good

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

Recent stay

The host/manager was very responsive when we had trouble with an alert going off on the alarm and got it fixed promptly. Overall our stay was good. Kitchen has the basics but if you are there longer than a couple of days, you will need your own stock of trash bags, toilet paper, laundry soap, and dishwashing soap. Not a huge deal but just so you are prepared. Resort pool was nice. They had other activities as well but our schedule didn’t allow to check those out.
Stayed 6 nights in Jun 2025
Verified review

4/10 Poor

Disliked: Cleanliness, listing accuracy

Okay Stay

This place is okay for a couple of nights. It’s not the cleanest and certainly looks better in the photos. The downstairs bed was extremely uncomfortable and the host could have been more responsive ahead of time regarding how to enter the gate and the keypad. They also didn’t list what the home was and was not stocked with. We ended up buying a lot of stuff for our stay. At the end cleaning staff was incredibly rude.
Stayed 2 nights in Jun 2024
Verified review

4/10 Poor

Liked: Check-in
Disliked: Cleanliness, communication, listing accuracy
We've stayed at Windsor Hills before have had a great experience. Unfortunately, this unit is definitely not worth staying at. It is clear cleaning is not a priority. I am convinced nothing is cleaned in between rental stays besides the laundry. Everything we touched with a clorox wipe turned gray with dirt and grime. The pool area, patio floor, was dirty and had lots of weeds growing. The pool bottom had lots of debris and it was clear it isn’t cleaned thoroghly on a regular basis. The person we were told to communicate with didn't respond until we asked for confirmation that he received our email. Just scroll past this unit and reserve with another owner. There ate definitely better units available.
Stayed 5 nights in Mar 2026
Verified review

8/10 Good

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

Minor Problems

Had a couple problems with television. Dead remotes needing batteries and trying to connect with basic cable on a Roku system.
Stayed 8 nights in Apr 2023
Verified review

8/10 Good

Liked: Check-in, communication, location, listing accuracy

Nice family vacation

It was a convenient location and a great size and layout for our family. Having the small private pool was awesome. We did have a chance to visit the community amenities once and that was nice too. The place was mostly clean other than not all surfaces being wiped down thoroughly. I had to clean the fridge and microwave handles as well as the dining table. I also thought the staircase handrail was in need of paint, but turns out it was just that dirty. Overall I think the cleaning crew could have done better, but it wasn't anything I couldn't quickly take care of when we got there. The process to initially check in took a few minutes, but wasn't terrible and then no issues with exiting and entering. The community is quite and after a long day at Disney it was nice to just relax instead of being in a loud hotel. We enjoyed our stay!
Stayed 6 nights in Jun 2022
Response from VrboOwner on 24 Jul 2022
From the owner: "Thanks for the feedback on the cleaner. We had already had concerns prior to receiving your feedback, and switched cleaning services 2 weeks ago to ensure our guests are getting the best possible service. We do appreciate the comments we receive. They help us to continually improve the guest experience for all future guests."
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was just as the pictures showed. When I needed to get in touch with the host it was no problem. Very friendly and helpful. Grandkids loved the private pool. Would most definitely stay again. 10/10 for me.
Stayed 5 nights in Jun 2026
Verified review

10/10 Excellent

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

Great time!

We spoke to Greg because we had questions about check in and he was great! Helpful! Nice! All in all we had a great time!
Stayed 2 nights in Nov 2022
Verified review

10/10 Excellent

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

Disney Vacation

We really enjoyed our stay here. We did a 9 day Disney vacation. Rental is close to the parks as well as food and Walmart. Had plenty of stuff stocked such as cups,plates and wipes and such to tidy up after yourself. We did have to go purchase trash bags we only had 2 left for us and toilet paper but wasnt a huge deal. Was a beautiful home my kids loved the private pool. The good options up by the clubhouse was good and decent priced. Plenty of space for 7 people didnt feel crowded or ontop of one another. Definitely will recommend in future
Stayed 8 nights in Nov 2022
Verified review

8/10 Good

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

Beautiful place

It was fantastic place..We Will deff go back when going to Orlando..Pool was cold but we are Floridians so if it’s 70 degrees out it’s to cold to go in a pool..Enough space for everyone..Only complaint was the two toilets upstairs kept clogging up but we found plunger to unclog them…Thank you for letting us stay and everything was perfect..
Stayed 2 nights in Oct 2022
Verified review

10/10 Excellent

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

Great place

Stayed here for our Disney vacation. The home was clean and the small pool was nice for a quick cool off and kids to play. Loved that the kids had their own bathroom. Plenty of space for the five of us. The main pool was nice as well. Location was only about a 15 minute drive to the parks. Walmart is down the street and the Kissimmee promenade is about 5 minutes away. We’d stay here again.
Stayed 7 nights in May 2022
From a partner site

8/10 Good

Met our needs

The townhome met our needs. I would recommend sturdier kids bedroom furniture. If more then 1 child we’re staying in the room I would worry about injuries from kids playing too rough. Cabinetry could use an update and/or permanent fix. Some of the panels were loose otherwise all was fine. A clock by the living room tv would be a great addition. Appreciated the Tide pods near the laundry. A stool would be great to reach the dryer controls (I’m short). Windsor Hills is a lovely place to stay. My daughter loved the big pool. The townhome is walkable to the pool area. Little kids might find it too much though. Overall a wonderful stay and the owner was super quick with responses to my texts. That was great! Would recommend this townhome to a small family.
Verified review

10/10 Excellent

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

My stay was very pleasant I will stay at property again.

My only problem was there were no wash cloths just hand towels and towels.
Stayed 2 nights in Apr 2022
Response from VrboOwner on 31 May 2022
Hi LaRhonda, the homeowner would like to share the following: "We are the new owners of this property. New towels, hand towels and washcloths have been purchased and put in place for guest use. Thank you for bringing it to our attention as this helps us in providing our guests with everything they need. We are glad you enjoyed your stay and look forward to having you again in the future!"
Verified review

8/10 Good

Liked: Cleanliness, communication, location, listing accuracy
Disliked: Check-in

Allright

The property was nice it had everything we needed. The only thing the clear linen on the shower was dirty it needs a new one. The pool is small not big. To check in ohhh god waited about an hour. Check in was at 4 but so many cars in line that it moved very slow and the people at check in are not that nice they stay in a bad mood maybe because so many people checking in. The owner does answer when you have a question or need something. Everything else is fine. It is close to everything.
Stayed 7 nights in Mar 2022
Verified review

10/10 Excellent

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

Great stay

We enjoyed our stay. Location of the house was fantastic. House had everything we needed. Thanks for a great time.
Stayed 8 nights in Feb 2022
Verified review

6/10 Okay

Liked: Check-in, communication, listing accuracy
Disliked: Cleanliness

Stay 2/12 to 2/20/21

The location of the property is good for those visiting Disney. The actual property receives no sunlight on the pool area and backs up to other townhouse. There is little privacy. The furniture and carpets are worn. The price was high for area. The kitchen cabinets need work. The community areas are very nice. Overall property is average.
Stayed 8 nights in Feb 2022
Response from VrboOwner on 12 May 2022
Hi John, Thanks for sharing your feedback with us - we're glad you enjoyed the property's great location. A new owner recently purchased the townhome and will be making updates. We hope that you can come enjoy the improvements during your next trip to Kissimmee!
Verified review

10/10 Excellent

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

Enjoyed our stay

Perfect location for drive to Disney! Thanks for the stay
Stayed 3 nights in Feb 2022
Verified review

10/10 Excellent

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

Awesome Location

The condo is located in an excellent neighborhood that that is very quiet and close to the amusement parks.
Stayed 4 nights in Oct 2021
Verified review

6/10 Okay

Liked: Check-in, location
Disliked: Cleanliness, communication, listing accuracy

Disney Vacation

This was our third stay at Windsor Hills and the location is perfect for a Disney stay. However this home was not recently renovated as advertised, and is in need of a good cleaning. There wasn’t a starter kit of supplies in the home, so a late arrival meant getting up early to shop before going to the park. The style of the home suited our needs for a family of teens and adults. Will definitely stay at Windsor Hills again but choose a different home.
Stayed 4 nights in Jul 2021
Response from VrboOwner on 4 Sept 2021
Hi Judy, we’re sorry to hear that you didn’t have a five-star experience at this property. The owner has some feedback for you about your stay: I’m disappointed that you didn’t enjoy your stay. - We take pride in our home and that’s why in January we put in all new appliances, refurbished the kitchen cabinets, new furniture, painted, and four new Roku TVs. We’re sorry that the rest of the house didn’t meet your expectations, but the photos you saw before booking are all still accurate representations of our home. - We’re also sad that the home didn’t meet your cleanliness standards. We didn’t have time to spot clean the carpet after the last guest left, but it was vacuumed. We can assure you that the rest of the home was very clean. - There is dishwasher detergent and dish soap with a sponge under the sink and laundry detergent in the laundry room closet. Also, we provide personal soap bars in the bathroom, but we’re sorry that you were expecting other personal products like a hotel. We do sanitize the toilet and put a paper strip just like hotels. Even though this was not the right home for you, we are glad that you stayed with us and you’re welcome back anytime.
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