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Private Cocktail Pool: Kissimmee Resort Retreat!

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Kissimmee Vacation Rental Townhome | 3BR | 3BA | 1,440 Sq Ft | 2 Stories
Windsor Hills Resort Amenities | Pool & Hot Tub | Playground
Interior | Open Floor Plan | Free WiFi | Dining Table | 2-Story Townhome
Living Room | 1st Floor | Smart TV | Queen Sleeper Sofa
Kitchen | 1st Floor | Cooking Basics | Drip & Keurig Coffee Makers | Dishes

Reviews

8.6 out of 10
Excellent
3 bedrooms3 bathroomsSleeps 8133.8 sq m

Popular amenities

  • Pool
  • Spa pool
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly

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

About this property

Private Cocktail Pool: Kissimmee Resort Retreat!

Windsor Hills Resort Amenities | Pet Friendly w/ Fee | Close to Disney Parks!

Leave daily life behind for the sunshine of Florida and stay at this Kissimmee vacation rental! The 3-bedroom, 3-bath townhome boasts a cocktail pool and screened lanai, not to mention resort amenities like an Olympic-sized pool, splash park, and an arcade that kids will love. Disney is less than 5 miles away for easy day trips with the kids, while Universal Studios and SeaWorld Orlando are not much further!

-- THE PROPERTY --

SLEEPING ARRANGEMENTS
- Bedroom 1: 1 king bed
- Bedroom 2: 1 queen bed
- Bedroom 3: 1 bunk bed (twin/full), 1 twin bed w/ twin trundle
- Living Room: 1 queen sleeper sofa
- Additional Sleeping: 1 portable crib

WINDSOR HILLS COMMUNITY AMENITIES (up to 8 people)
- Outdoor pool, hot tub, water park
- Clubhouse, fitness center, ping pong
- Tennis, basketball & volleyball court
- Playground, putting green
- Game room, arcade, movie theater
- Marketplace & grille, dog park

PROPERTY PERKS
- Smart TVs (1 70-inch screen, TVs in all bedrooms)
- 6-person dining table. dishes & flatware
- Screened lanai, outdoor dining
- Private pool, loungers

KITCHEN
- Stainless steel appliances
- Electric stove, oven, dishwasher, microwave
- 4-person breakfast bar, high chair
- Drip & Keurig coffee makers
- Cooking basics

GENERAL
- Free WiFi
- Linens/towels
- In-unit laundry
- Central heat & A/C
- Cleaning essentials

FAQ
- Pet fee (paid pre-trip)

ACCESSIBILITY
- Step-free access, 2-story townhome
- Bedroom & bathroom on 1st floor

PARKING
- Driveway (1 vehicle)
- Parking pad (2 vehicles)

-- THE LOCATION --

- Located in Windsor Hills Resort with on-site amenities
- 4 miles to Disney World: Walt Disney World Resort, Hollywood Studios, Animal Kingdom, Epcot, Typhoon Lagoon Water Park, Disney Springs, Magic Kingdom
- 16 miles to Universal Studios: Island of Adventure, Universal Orlando Resort, Volcano Bay, Wizarding World of Harry Potter
- 6 miles to Fun Spot America Theme Parks, Old Town & ESPN Wide World of Sports Complex
- 13 miles to SeaWorld Orlando
- 24 miles to Orlando International Airport

-- REST EASY WITH US --

Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.

-- POLICIES --

- No smoking
- Pet friendly with a $100 fee (+ fees & taxes, 1 pet only)
- No events, parties, or large gatherings
- Must be at least 25 years old to book
- Additional fees and taxes may apply
- Photo ID may be required upon check-in

ADDITIONAL INFORMATION
- A maximum of 8 wristbands are given out to use the community amenities during your stay

Add dates for prices

Amenities

Pool
Hot tub
Kitchen
Washing machine
Dryer
Pet-friendly

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed
A maximum of 1 pet is allowed.
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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
Safety features at this property include a fire extinguisher and a first aid kit

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 Blizzard Beach Water Park.
View more Holiday homes in OrlandoOpens in a new window
Map
Kissimmee, FL

What's nearby

  • Mystic Dunes Golf Club - 18 min walk - 1.5 km
  • Bonanza Golf & Gifts - 3 min drive - 2.8 km
  • Walt Disney World® Resort - 6 min drive - 4.8 km
  • Disney's Animal Kingdom® Theme Park - 8 min drive - 4.5 km
  • Disney Springs™ - 12 min drive - 13.8 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
  • ‪Del Taco - ‬3 min drive
  • ‪Osaka Bay Buffet - ‬3 min drive
  • ‪Sickies Garage Burgers & Brews - ‬4 min drive

Frequently asked questions

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

Yes, this property has a pool.

How much does it cost to stay at Private Cocktail Pool: Kissimmee Resort Retreat!?

As of 29 Mar 2026, prices found for a 1-night stay for 2 adults at Private Cocktail Pool: Kissimmee Resort Retreat! on 11 July 2026 start from AU$202, 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 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. 13 out of 27 reviews
Rating 8 - Good. 9 out of 27 reviews
Rating 6 - Okay. 3 out of 27 reviews
Rating 4 - Poor. 2 out of 27 reviews
Rating 2 - Terrible. 0 out of 27 reviews

8.0/10

Cleanliness

9.2/10

Check-in

9.0/10

Communication

9.4/10

Location

9.0/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Heather B.

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

Patricia

WINDSOR HILLS TOWNHOUSE

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

10/10 Excellent

Diane B.

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

6/10 Okay

Anjeanetta B.

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
From a partner site

10/10 Excellent

Mrs F

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

8/10 Good

Francis W.

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
Verified

8/10 Good

Jessica D.

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

8/10 Good

linda c.

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

4/10 Poor

Jennifer P.

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

8/10 Good

Pat L.

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

8/10 Good

Kacie B.

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
Verified

4/10 Poor

Andrea V.

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

10/10 Excellent

Verified traveller

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

10/10 Excellent

Brianna T.

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

8/10 Good

Christi J.

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

10/10 Excellent

Jennifer M.

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

Michelle M

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

10/10 Excellent

LaRhoda W.

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
Verified

8/10 Good

Brenda A.

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

10/10 Excellent

Verified traveller

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

6/10 Okay

john h.

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
Verified

10/10 Excellent

Danesa B.

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

10/10 Excellent

Joe B.

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

6/10 Okay

Judy B.

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
Verified

10/10 Excellent

Jean G.

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

Good weekend gate away

Clean home good price the only thing the Wi-Fi needs and upgrade
Stayed 2 nights in Jun 2021

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