See all properties
Entire condo

Poolside ! Luxury Chic !

Condo near ESPN Wide World of Sports Complex in Kissimmee

Choose dates to view prices

Photo gallery for Poolside ! Luxury Chic !

Outdoor pool, a heated pool
Fridge, microwave, oven, stovetop
Dining
Fitness facility
TV, table tennis

Reviews

9.6 out of 10
Exceptional

Entire condo

3 bedrooms2 bathroomsSleeps 6

Popular amenities

  • Hot tub
  • Kitchen
  • Washer
  • Dryer
  • Air conditioning

Explore the area

View in a map
Orlando, FL
  • Place, Bonanza Golf & Gifts
    ‪3 min drive‬
  • Place, Walt Disney World® Resort
    ‪7 min drive‬
  • Place, Disney Springs™
    ‪13 min drive‬
  • Airport, Orlando, FL (MCO-Orlando Intl.)
    ‪32 min drive‬

Room options

You may also like

Ad

SPOT X Hotel Orlando/Intl Dr by The Red Collection

Orlando
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
4.3 out of 5, Excellent, 3,375 reviews
The price is CA $89
CA $125 total
includes taxes & fees
Jun 21 - Jun 22
SPOT X Hotel Orlando/Intl Dr by The Red Collection

About the area

Kissimmee

Windsor Hills stay.Your stay at this Windsor Hills condo places you within 3 miles (5 km) of Island H2O Live! and Mystic Dunes Golf Club. Walt Disney World® Resort and ESPN Wide World of Sports Complex are also within 6 miles (10 km).
View more Condo rentals in OrlandoOpens in a new window

What's nearby

  • Bonanza Golf & Gifts - 3 min drive - 2.7 km
  • Walt Disney World® Resort - 7 min drive - 5.1 km
  • Disney's Animal Kingdom® Theme Park - 9 min drive - 5.8 km
  • Disney Springs™ - 13 min drive - 15.3 km
  • Magic Kingdom® Park - 14 min drive - 16.0 km

Getting around

  • Kissimmee Station - 26 min drive
  • Kissimmee, FL (ISM-Kissimmee Gateway) - 22 min drive

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

About this property

Entire place

You'll have the entire condo to yourself and will only share it with other guests in your party.

Poolside ! Luxury Chic !

The best and most luxurious pool view condo in Windsor Hills! Stunning fully remodeled 3/2 condo in the beautiful and closest Disney vacation rental community in Windsor Hills, located in the closest building to the clubhouse, with a beautiful pool and pond view from the balcony, this second floor condo is sure to delight you. The stainless steel appliances, granite countertops, updated fixtures, open floor plan and bathroom layout will make your family vacation the lovable and magical one!

The children's water park (slides) will be closed for maintenance from Monday, January 17, 2022 to Friday, January 28, 2022. The swimming pool will be open.

Similar properties

6 outdoor pools, free cabanas, pool umbrellas
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Orlando
  • Pool
  • Hot tub
  • Kitchen
  • Washer
4.6 out of 5, Wonderful, 5,551 reviews
The price is CA $175
CA $197 total
includes taxes & fees
Jun 3 - Jun 4
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Property amenities

Pool/Spa

  • Communal pool
  • Heated pool
  • Hot tub
  • Outdoor pool

Internet

  • Available in the condo: WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Ice maker
  • Kitchenette
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shower
  • Towels provided

Entertainment

  • TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Barbecue grill

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near an outlet shopping mall

Things to do

  • Gym
  • Heated pool
  • Table tennis
  • Theme park nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

Policies

Check-in

Check-in time starts at 4:00 PM

Contactless check-in available

Minimum check-in age: 21

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Information provided by the property may be translated using automated translation tools

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.

Events

No events 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
Onsite parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a fire extinguisher, a smoke detector, and a deadbolt lock in each accommodation.

Property is also known as

Poolside ! Luxury Chic ! Condo

Poolside ! Luxury Chic ! Kissimmee

Poolside ! Luxury Chic ! Condo Kissimmee

Frequently asked questions

How close is Poolside ! Luxury Chic ! to the airport?

This condo is 12.4 mi (22-min drive) away from the Kissimmee, FL (ISM-Kissimmee Gateway) airport, the closest popular airport to the property.

Does Poolside ! Luxury Chic ! have an airport shuttle?

Airport shuttle services are not available at this condo.

How close is Poolside ! Luxury Chic ! to the beach?

This condo is 8.3 mi (19-min drive) from Beachcomber Beach and 9.1 mi (17-min drive) from Hideaway Bay. Don't forget your sunscreen!

Does Poolside ! Luxury Chic ! offer free breakfast?

This condo does not offer free breakfast.

Is there a casino at Poolside ! Luxury Chic !?

No, there is no casino at this condo.

What time is check-in at Poolside ! Luxury Chic !?

Check-in begins at 4:00 PM.

Is there free parking at Poolside ! Luxury Chic !?

Free parking is not available at this condo.

Does Poolside ! Luxury Chic ! have a pool?

This condo features an outdoor pool.

Does Poolside ! Luxury Chic ! have a spa?

There are no spa services available at this condo.

How close is Poolside ! Luxury Chic ! to downtown Kissimmee?

This condo is 2.4 mi away from Four Corners.

Poolside ! Luxury Chic ! Reviews

Reviews

9.6

Exceptional

Rating 10 - Excellent. 39 out of 45 reviews
Rating 8 - Good. 4 out of 45 reviews
Rating 6 - Okay. 1 out of 45 reviews
Rating 4 - Poor. 1 out of 45 reviews
Rating 2 - Terrible. 0 out of 45 reviews

9.6/10

Cleanliness

Reviews

10/10 Excellent

Val B.

Liked: Cleanliness
Well stocked, lovely pool area and welcome items really appreciated
Stayed 14 nights in Apr 2026

10/10 Excellent

Dan T.

Liked: Cleanliness
This was a great place to stay. Close to everything, good food, clean pool, waterslide, volleyball. A lot of fun! Hosts are quick to reply!
Stayed 7 nights in Apr 2026

4/10 Poor

Abe W.

Disliked: Cleanliness
Stayed 7 nights in Mar 2026

10/10 Excellent

Liz B.

Liked: Cleanliness
Great location and beautiful home. Has some minor issues but the owner dealt with it professionally and quickly. Would visit again!
Stayed 3 nights in Dec 2025

10/10 Excellent

Kaisa v.

Liked: Cleanliness
Lovely condo, well appointed and close to attractions. Comfortably accommodated the whole family.
Stayed 2 nights in Nov 2025

10/10 Excellent

lstackpole

Liked: Cleanliness

Excellent

Listing was accurate, everything was nice and clean. Walmart close by for groceries
Stayed 5 nights in Jun 2025

10/10 Excellent

natalie w.

Liked: Cleanliness
Very nice property- comfortable beds and well stocked! Great location!
Stayed 2 nights in May 2025

10/10 Excellent

Michael E.

Liked: Cleanliness

20 day stay - Easter 2025

Property was as advertised. Located in a very convenient location on the complex. Pool cleaning started at 7am, pool opened at 8am, pool closed at 10pm. Not a major issue for us or kids but worthy of consideration if you want total tranquility then you may want to choose some other accomodation. Accommodation was clean, tidy, modern and everything we needed was available at the property. Parking spaces were plentiful. The wider complex was beautifully maintained, including tennis, basketball, volleyball courts, various kids play anreas located around the complex along with table tennis, pool table, pool and water slides. On site shop was reasonably priced. Access to Disney parks were easy enough to commute to although some roadworks nearby elongated the return journey from the parks. Universal was a bit further away but not a chore. Well located for further ventures such as clear water on west coast, Orlando city, lake access for airboat rides, fishing etc, cape canaveral, I-drive, etc…..All in all for our 20 day stay was comfortable, clean, well located, relaxing and had no major issues. Some very minor issues where the en suite tap drips constantly and some of the kitchen sockets don’t work with certain appliance types which took us a while to work out - but really these are very minor and would still rate the property highly. Price wise I feel we paid a premium compared to some other properties available, but that’s down to individual wants and needs.
Stayed 19 nights in Apr 2025

10/10 Excellent

Deanna S., USA

Liked: Cleanliness

Wonderful stay at Windsor Hills

Thank you so much for sharing your place with us! Best location in Windsor Hills! You have everything you need to fully enjoy all the amenities that Windsor Hills offers! Looking forward to our next vacation!!!
Stayed 7 nights in Apr 2025

10/10 Excellent

Verified traveller

Liked: Cleanliness

The best spot in the resort!

The best communication I’ve ever had from the owners. Ideal spot for everything, pool, games, and close to main entrance of community. Will definitely book again!
Stayed 3 nights in May 2024

10/10 Excellent

Cindy B., Nebraska

Liked: Cleanliness

Great Property, Great Location

Very nice place to stay. Fully stocked, spacious and clean with great views of the pool. Even better than the photos. Close to all the area theme parks. Nice place to relax at the end of the day. Would highly recommend it!
Stayed 3 nights in Jul 2023

8/10 Good

Lauren L.

Liked: Cleanliness

Great place and owners

Overall, the condo is in great condition and has all of the amenities in it that you will need.... everything from pool towels, to an air fryer, coffee maker, blender, etc... There wasn't a single thing I thought it was lacking during our stay. And the owners were very responsive to our questions prior to our trip and provided great information to get us in quickly and everything we needed for the stay. The pool area is great and was never overly crowded - which was surprising for mid-July. Yes, it was busy, but we always found chairs and never felt like we needed to go down and "save" chairs at 9:00 am or anything similar. Our only complaint, which has nothing to do with the owners of this condo or the condo itself, is that every morning the pool maintenance/staff run a very loud blower starting at 7:00-7:15 every morning and it goes for about 20-25 minutes. So, unless you are a crazy heavy sleeper, plan to be woken up early every day. I use a white noise machine and still couldn't sleep through it. It's sincerely the only reason I wouldn't stay in this unit again. The owners were great to work with, the condo is great, you just won't be able to sleep in past 7:00 am.
Stayed 7 nights in Jul 2023

10/10 Excellent

Margaret L.

Liked: Cleanliness

Grandchildren Trip

Grandchildren loved the pool and amenities! Very close to Animal Kingdom!
Stayed 5 nights in Jun 2023

10/10 Excellent

Pollyanna D.

Liked: Cleanliness

Beautiful

We loved this apartment. Really lovely inside and it really was home away from home. Could not fault it. The beds were super comfy too. Windsor Hills itself is a beautiful community. Very well kept. Really close to all the parks too:-) The apartment overlooks the swimming pool and is literally a 3 min walk away. We loved the convenience of this. The only negative for me was the leaf blower around the pool every morning at 7am:-( If you had young kids they’d prob be up at that time anyway, so you might not notice it. But our teenagers weren't happy with him! I still would rent this place again though. The quality of the furnishings and fittings were absolutely brilliant:-) Thank you!
Stayed 4 nights in May 2023

10/10 Excellent

Verified traveller

Liked: Cleanliness

Immaculate!

One of the best experiences I’ve ever had. I really appreciate the owners and will definitely be back!
Stayed 4 nights in Jun 2023

10/10 Excellent

justin h.

Liked: Cleanliness

One of the best!

We've been coming to Windsor Hills for many years and this was surely one of our best stays! The proximity to the pol and the updates to the condo are fantastic. Daniel (Property host) was a pleasure to work with and accommodating and prompt on any correspondence. If you have a chance to vacation here don't miss out, thanks again Daniel!
Stayed 9 nights in Mar 2023

10/10 Excellent

Michael S., Green Bay Wisconsin

Liked: Cleanliness

Awesome

Stayed at Windsor Hills 4 out of last 5 years. Without a doubt this was the best place compared to the rest. Everything you need is in the condo, and it was very clean. Owner was great. I sent a few emails throughout my stay. Every email was answered within a few minutes. Awesome condo.
Stayed 7 nights in Feb 2023

8/10 Good

Pamela V.

Liked: Cleanliness

Great location

This condo is as close as you can get to the pool, fitness center, and convenience store. This was awesome for our family as you could come and go to the pool as you wanted, not having to wait for everyone to be ready at the same time to drive there.
Stayed 7 nights in Jan 2023

10/10 Excellent

Jon R.

Liked: Cleanliness

comfortable

Our family enjoyed this condo. It was comfortable. Themes in previous reviews are accurate. The single beds will feel a bit short if you're over six feet tall.
Stayed 2 nights in Jan 2023

10/10 Excellent

Folukemi O.

Liked: Cleanliness

Best vacation rental

It was a short stay but we enjoyed ourselves. The home was clean and the appliances were all new and functional. The unit was was looking at the pool so I could actually see my teenagers from the porch. My husband who is not easily thrilled with taken by anything besides our home actually gave me an high five for booking this property. Just minutes away from restaurants and shopping. I'll definitely look out for this property when visiting Florida again. I already recommend this property to a family friend. Thank you to our host.
Stayed 2 nights in Jan 2023

8/10 Good

Alex G.

Liked: Cleanliness

Very nice place except...

We were very pleased with the condo with everything except the Air Conditioning. The owner stated that the A/C could not be set below 74 degrees or else the system would freeze up and malfunction. So basically during our stay it stayed about 75 degrees in the room and since it was approximately 80 degrees everyday outside, the system rarely ran and barely took the humidity out of the air. The thermostat was a Internet controlled smart thermostat that could only be changed by the owner. Although the place was beautifully furnished and very clean, I will not be staying here again due to the A/C situation. We would go to bed at night on the verge of sweating and that was just not okay especially since the condo that we stayed at just the week before in the same building had A/C that was so cold that it fogged up the windows in the living room. Being from the north, the lack of cooling on the place was a deal breaker for me. I will not be staying in this condo again.
Stayed 4 nights in Jan 2023

10/10 Excellent

christi m.

Liked: Cleanliness

Great condo

We enjoyed Windsor hills . The condo was redone and very comfortable. The location was nice bc it was close to pool
Stayed 5 nights in Dec 2022

10/10 Excellent

Lindsay S.

Liked: Cleanliness

Disney Getaway

We had a great stay here for the week! It’s about 10-15 minutes from the Disney parks and the pool area was amazing for our rest days. Our boys loved the waterslides and splash pad! Victoria and Daniel were great to work with and super responsive! It was super easy getting into the condo as well. Just a note if you are going with small kids the beds are twin size and super high off the ground, you may want to think about getting some sort of railing so they don’t fall out or like a pool noodle you can put under the sheet to stop them from falling out of bed. Other than that everything was perfect! Thank you again! If we ever go back to Disney I will definitely be looking to stay here again!
Stayed 7 nights in Nov 2022

10/10 Excellent

Nisha M.

Liked: Cleanliness

Excellent location & property

Prime location next to the pool. Few minutes away from Disney world, espn world of sports, and most other attractions. Condo was very clean with all the amenities to make our visit enjoyable and comfortable. Thanks!
Stayed 3 nights in Nov 2022

8/10 Good

Jay W.

Liked: Cleanliness

Good stay.

Place is nicely setup.
Stayed 4 nights in Apr 2022