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Windsor at Westside | Private Pool | Lazy River | 5 bed 4.5 bath | Sleeps 11

Photo gallery for Windsor at Westside | Private Pool | Lazy River | 5 bed 4.5 bath | Sleeps 11

Windsor @ Westside Main Clubhouse and Amenity Area
Open Kitchen/Dining/Living Room with New Furniture, Large Flat Screen TV, Pool Access
Your own private pool with lounge space, outdoor restroom and pool toys in the closet!
Fun 'Mickey' Themed Bunk Room - Twin over Full Bunk Bed and Flat Screen TV (Rooms Sleeps Up To 3)
Upstairs Queen Bedroom w/En-Suite Bathroom and Flat Screen TV

Reviews

9.0 out of 10
Wonderful
5 bedrooms4+ bathroomsSleeps 11210.2 sq m

Popular amenities

  • Dryer
  • Washer
  • Hot tub
  • Outdoor space
  • Air conditioning

Explore the area

Map
Kissimmee, FL
  • ChampionsGate Golf Club
    ‪10 min drive‬
  • Mystic Dunes Golf Club
    ‪10 min drive‬
  • Disney's Animal Kingdom® Theme Park
    ‪20 min drive‬
  • Kissimmee, FL (ISM-Kissimmee Gateway)
    ‪38 min drive‬

Rooms & beds

5 bedrooms (sleeps 11)

Downstairs Queen Bedroom

1 Queen Bed

Upstairs Bunk Bed Room

2 Single Bunk Beds

Upstairs Full Bedroom

1 Double Bed

Upstairs King Suite

1 King Bed

Upstairs Queen Suite

1 Queen Bed

4 bathrooms, 1 half bathroom

Hall Shared Bathroom

Toilet · Shower only

King Master En-Suite

Toilet · Shower only

Mickey Shared Bathroom

Bathtub or shower · Toilet

Pool Half Bathroom

Toilet

Queen Master En-Suite Bathroom

Toilet · Shower only

Spaces

Deck or patio
Kitchen

About this property

Windsor at Westside | Private Pool | Lazy River | 5 bed 4.5 bath | Sleeps 11

Looking for a great deal? Discounts are automatically applied based on your length of stay—whether it’s 5 nights, 7 nights, 28 nights, or more! No need for promo codes or requests. The total price you see includes your savings, so you can book with confidence. Discounts may display differently across booking platforms, but rest assured, they’re built into your final price!
So close to Disney World! This immaculate 5 Bedroom, 4.5 Bath Townhome with a private splash pool is only 15 minutes from Walt Disney World and provides all of the comforts of home!

This home is filled with designer touches that will make your stay truly special, including upgraded furniture, beautiful art décor, a gourmet kitchen, and deluxe sleeping accommodations.With two living areas, you'll have plenty of space to relax and unwind. The main living area features modern and cozy furniture, along with a large wall-mounted flat-screen TV. The attention to detail in the décor of this home is evident, making it the perfect place to kick back and relax.

The dining area comfortably seats six (6) guests, and there is additional breakfast bar seating for four (4).

The kitchen is fully equipped with everything you need to prepare full meals or simply enjoy a cup of coffee or snacks. With granite countertops, stainless steel appliances, and a wide range of kitchen gadgets, mealtime becomes a pleasure and an adventure.

One of the highlights of this home is the oversized Lanai and Private Splash Pool Area. With patio seating and sun loungers, you can have fun and relax by the pool. For added safety, there is a Pool Safety Fence and an outdoor Half Bathroom. Pool floats are included in the outside closet. Pool heating is available for an additional $f40/night from varying dates in October to April (3 night minimum).

On the second floor, you'll find another Living Area with comfortable side chairs, a wall-mounted flat-screen TV, and a tabletop arcade game for added entertainment. Whether you want to watch your favorite shows, read a book, or challenge your friends to a friendly game, this living area is the perfect retreat for your vacation.

The Bedding and Bath Layout are as follows:

GROUND FLOOR:
(Bedroom 1) Queen Bedroom w/Upgraded Bedding and Furniture, Flat Screen TV
(Bathroom 1) Hall Shared Bathroom w/Walk In Shower
(Bathroom .5) Outdoor Pool Half Bathroom

SECOND FLOOR:
(Bedroom 2) Twin Over Full Bunk Bed Room w/Flat Screen TV (Sleeps 3 Guests)
(Bathroom 2) ‘Mickey’ Shared Hall Full Bathroom w/Double Sinks and Shower/Tub Combination
(Bedroom 3) Full Bedroom w/Upgraded Bedding and Furniture w/Flat Screen TV
(Bedroom 4) King w/En-Suite Bathroom, Upgraded Bedding & Furniture, Flat Screen TV
(Bathroom 3) En-suite bathroom to King Master w/Walk In Shower
(Bedroom 5) Queen w/En-Suite Bathroom, Upgraded Bedding & Furniture, Flat Screen TV
(Bathroom 4) En-Suite Bathroom to Queen Master w/Walk In Shower

ADDITIONAL AMENITIES:
Contact Free Check In and Check Out
Free Wi-Fi
Cable and Streaming Television
Tile Flooring Throughout Main Areas
Carpeted Bedrooms
Main Living Area w/Oversize Flat Screen TV
Upgraded Living Room Furniture
Granite Countertops in Kitchen and Baths
Full-Size Washer & Dryer (Upstairs)
Iron & Ironing Board
Hair DryersLinens & Towels
Plentiful Parking

WINDSOR AT WESTSIDE COMMUNITY AMENITIES:
Indulge in the lavish resort amenities of the prestigious Windsor at Westside, one of the newest Gated Communities in Kissimmee.
Amazing Pools with lounge chairs and cabanas
Lazy River
Water playground
Tiki Bar and Spa
Pier on the lake
Clubhouse and Bar
Serene Landscaping
Sports Arena
Fitness Center

No matter how long you stay in this beautiful townhome, each time you come back from your day's adventures, you will feel 'right at home'!

HEAR FROM OUR RECENT GUESTS:
5 Stars - My wife and I are very impressed with iTrip as well as the home we are staying in. I trip made the rental process very easy. Everything they described in their property description was 100% accurate. I would give this home and iTrip both a 5 star rating. Robert S.

5 Stars - Highly recommend staying here. The house looks just like the photos and was very spacious. The kids loved the pool and the retro arcade game! Ignore the bad reviews, bunch of Karen’s complaining about nothing. Lauren H.

5 Stars - Rental home was great with plenty of space, bedrooms, and restroom for our large family. The private pool was great for the kids. Joshua S.

5 Stars - I'm so glad I didn't listen to the reviews about Windsor at Westside...we had 2 homes and I stayed at 2409. All my needs were met, the place was amazing. I would highly recommend this place. No loud music and all that other stuff that I seen on the reviews. Latanya Pierce

5 Stars - House was very clean. More space than we needed, but it ended up being perfect. The two teens took the upstairs and I slept in the main floor bedroom. Lots of towels and extra linens. Kitchen was well appointed. Pool was clean. There were some pool floats in the outdoor closet. The refrigerator and microwave were so clean they looked brand new. Gated, quiet neighborhood. 3 miles from tons of restaurants and shopping. Including a Target, Starbucks and Chipotle lol about 10 or so miles from Disney. Depending on traffic that commute varied. I would 100% recommend this property. Amber B.

Property manager

Property Manager

Languages

English

Add dates for prices

Amenities

Pool
Hot tub
Kitchen
Washer
Dryer
Air conditioning

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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

No pets 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 deadlock

About the area

Kissimmee

Kissimmee is home to this holiday home. ChampionsGate Golf Club and Mystic Dunes Golf Club are worth checking out if an activity is on the agenda, while those in the mood for shopping can visit Flamingo Crossings Town Center and Old Town. Walt Disney World® Resort and Disney's Animal Kingdom® Theme Park are not to be missed.
Map
Kissimmee, FL

What's nearby

  • Highland Reserve Golf Club - 6 min drive - 5.3 km
  • ChampionsGate Golf Club - 10 min drive - 7.6 km
  • Mystic Dunes Golf Club - 10 min drive - 8.5 km
  • Reunion Resort Golf Course - 20 min drive - 15.2 km
  • Disney's Animal Kingdom® Theme Park - 20 min drive - 15.6 km

Getting around

  • Kissimmee Station - 30 min drive
  • Kissimmee, FL (ISM-Kissimmee Gateway) - 38 min drive

Restaurants

  • ‪Starbucks - ‬8 min drive
  • ‪McDonald's - ‬6 min drive
  • ‪Culver's - ‬5 min drive
  • ‪Taco Bell - ‬5 min drive
  • ‪Best of British Cafe - ‬6 min drive

Frequently asked questions

Does Windsor at Westside | Private Pool | Lazy River | 5 bed 4.5 bath | Sleeps 11 have a pool?

Yes, this property has a pool.

Is Windsor at Westside | Private Pool | Lazy River | 5 bed 4.5 bath | Sleeps 11 pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Windsor at Westside | Private Pool | Lazy River | 5 bed 4.5 bath | Sleeps 11?

Check-in begins at 4:00 PM.

What time is check-out at Windsor at Westside | Private Pool | Lazy River | 5 bed 4.5 bath | Sleeps 11?

Checkout is at 10:00 AM.

Where is Windsor at Westside | Private Pool | Lazy River | 5 bed 4.5 bath | Sleeps 11 located?

Situated in Kissimmee, this holiday home is 1.8 mi (2.9 km) from Lake Davenport and 2.9 mi (4.6 km) from Northeast Regional Park. Highland Reserve Golf Club and Surfari Water Park are also within 6 miles (10 km).

Reviews

9.0

Wonderful

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. 25 out of 38 reviews
Rating 8 - Good. 8 out of 38 reviews
Rating 6 - Okay. 4 out of 38 reviews
Rating 4 - Poor. 0 out of 38 reviews
Rating 2 - Terrible. 1 out of 38 reviews

8.8/10

Cleanliness

9.8/10

Check-in

9.2/10

Communication

9.8/10

Location

9.4/10

Listing accuracy

Reviews

10/10 Excellent

Verified traveller

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

Spring Break

Everything was great, warm weather sun and a pool, can’t go wrong!!
Stayed 6 nights in Mar 2025

10/10 Excellent

Roy S.

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

Great Place

We stayed here for a week on our Disney trip. On the first night we somehow managed to trip a fuse, but the management was very helpful with getting it fixed and sent someone out the next day to take care of the circuit box to ensure it would not happen again. We would happily stay here again if we make another trip to Orlando.
Stayed 7 nights in Mar 2025

10/10 Excellent

Kiance H.

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

Disney World Getaway

Me and my kids enjoyed the stay! The house was kids friendly.
Stayed 2 nights in Jan 2025

10/10 Excellent

Melinda L.

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

Great place

Great space for our family
Stayed 7 nights in Nov 2024

8/10 Good

Ofelia D.

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

Good Location

This home was clean and very well located
Stayed 2 nights in Nov 2024

8/10 Good

Chris M.

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

Great place to stay with a large group!

Overall, we were extremely pleased with our stay. With full days planned at the parks, we didn’t spend a ton of time at the property other than the 2 days we spent at the resort pool. We felt that the house was a bit too warm for this time of year to only be allowed to have the AC set to 72. I would recommend seasonal guidelines to keep guests more comfortable, Without the fear of maintenance fees; especially since there weren’t any ceiling fans in the house. The floors weren’t very clean, especially on the rug downstairs in the living room. Lastly, many of the doors in the house could use some maintenance. Especially the laundry room doors and the shower doors in the master bedroom.
Stayed 5 nights in Mar 2025

10/10 Excellent

Delronisha B.

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

Love this house

Love everything about this house
Stayed 3 nights in Aug 2024

10/10 Excellent

ralph m.

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

Clean Condo

Condo was very clean. Very spacious, great for a big family.
Stayed 7 nights in Sep 2024

10/10 Excellent

Michelle M.

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

Fantastic property with everything you need.

Fantastic property with everything you need.
Stayed 7 nights in Apr 2023

10/10 Excellent

David D., Saint Simons Island GA

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

Everything we needed!

Great location, very clean and plenty of room for two families. Would definitely stay again!
Stayed 4 nights in Feb 2023

10/10 Excellent

Ashley W.

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

Great place

We celebrated my sister 30th at Islands of adventure and this property was exactly as advertised in the pictures. Clean and spacious. Would stay there again.
Stayed 3 nights in Mar 2023

10/10 Excellent

Xenia G.

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

Excellent

Our stay was wonderful, family friendly. Easy to locate and convenient code entry.
Stayed 6 nights in Jul 2023

10/10 Excellent

Joshua S., San Antonio

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

Disney/Orlando Vacation Stay

The rental was great. Check in couldnt have been more easier, the private pool was great for the kids, and the space of the rooms and multiple restrooms made a great stay for the entire family!
Stayed 4 nights in Mar 2023

10/10 Excellent

Verified traveller

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

Awesome Rental

Home was perfect, everything was as described and clean. Home looked just as good as it did in the pictures. Would love to stay here again
Stayed 5 nights in Jun 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Highly recommend staying here.

Highly recommend staying here. The house looks just like the photos and was very spacious. The kids loved the pool and the retro arcade game! Ignore the bad reviews, bunch of Karen’s complaining about nothing.
Stayed 7 nights in Jun 2022

10/10 Excellent

Christy D.

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

Perfect for a girls getaway!

I stayed at this lovely home with 3 of my girlfriends and we had the most wonderful weekend! The house is adorable and charming with an amazing back yard / pool. The location was so convenient to the airport, but also to so many great shops, particularly one of the best bakeries we have ever visited! Hope to come back soon!
Stayed 3 nights in Feb 2023

10/10 Excellent

Patricia D.

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

Great location

Loved how close to the Disney properties. Also it was great to have a bedroom and bathroom for each. Compared to a hotel at the Disney property. MORE Room! The cost was cheaper than getting 2 hotel rooms. Clearly sharing bathrooms and etc at the Disney property
Stayed 6 nights in Dec 2022
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Amber B.

Great stay!

House was very clean. More space than we needed, but it ended up being perfect. The two teens took the upstairs and I slept in the main floor bedroom. Lots of towels and extra linens. Kitchen was well appointed. Pool was clean. There were some pool floats in the outdoor closet. The refrigerator and microwave were so clean they looked brand new. Gated, quiet neighborhood. 3 miles from tons of restaurants and shopping. Including a Target, Starbucks and Chipotle lol about 10 or so miles from Disney. Depending on traffic that commute varied. I would 100% recommend this property.
Stayed 4 nights in Oct 2023

6/10 Okay

Aneka F.

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

05/20-05/23

The house was beautiful and clean. Very spacious and it served the purpose for the weekend. The only complaint I have is the rooms had black ants crawling on the dresser and bed. The house was hot, the thermostat read 78 everyday all day even when it was set to 72. The beds were very uncomfortable, my guest and I woke up very stiff and sore each day.
Stayed 3 nights in May 2022

10/10 Excellent

Denise B., Canton, Georgia

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

Fun Disney house

We love how nice the house was decorated! 30-45 mins to Aquatica , Rock Spings most amusement parks. Many places to eat 15 min away .Sickies burgers ,Juicy and Crab, Island wings reasonably priced .We loved the ammenties large pools one on sight and a larger one in the next community with club house . Club house had a nice gym , café ,a neat robotic yogurt machine .A craft room with a schedule of daily activities(some free some with with a small charge). House is not stocked so bring everything from toilet paper, trash bags, garbage bags, dish soap, dish cloths, coffee filters, salt pepper etc . The only complaint we had was the house could have been a little cleaner.
Stayed 7 nights in Jul 2022

8/10 Good

Olivia T.

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

Enjoyed it

Great property, clean, with plenty of space. We loved the clubhouse pool, it was excellent. Kitchen space is big and easy to cook in. We had little kids and there were a lot of decorations around that they had access to, so not the most kid friendly in that aspect. Management was good at communicating and fixing issues we had. There were supposed to be lights in the pool, and they did not work. They also told us that they did not have pack n plays at the property, so we bought one when we arrived, only to find 2 pack n plays in a closet, so that was frustrating and wish they had checked that better. The pool was fun and loved all the bathrooms for almost every bedroom. We stayed here for 2 weeks and overall, had a great experience.
Stayed 14 nights in Jan 2023
This review comes from a trusted partner site and has not been verified.

6/10 Okay

Robert R.

2409 Windsor at Westside

Overall just a decent property for our Disney trip. Upon arrival there were brown stains on stairs. Realized it was grease stains from the grill outside that was tracked into house. Grill has obviously never been cleaned. Notified company and offered to clean carpets during our stay. We said they could wait until after we left and wanted to ensure we would not be charged. Cheap quality bedding, pillows, and beds. $1,700 for a week of restless sleep. Cheap cooking supplies provided. Cookware, dishes, tableware are all cheap quality. Where is the pizza cutter? Where are the fans? Additional basic necessities would be appreciated for the price we paid. We would not stay at this property again. There are better properties for this price. Would not recommend to family and friends. Decent clubhouse, home pool, and overall clean are the positive things.
Stayed 7 nights in Oct 2022

10/10 Excellent

Kathleen M.

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

Great place.

We enjoyed staying at this property. It’s in a great location; convenient to restaurants, grocery stores, and Disney. The overall property is very nice. Walking trails are perfect for a long or short walk. The clubhouse amenities were nice; we really enjoyed the lazy river. We did have to buy our own tubes. $6 at Walmart as opposed to $15 at the clubhouse. They do charge $1 to blow up each tube which seems excessive. The house had some areas that appear to have not been dusted for a while. Also, assuming it was Ian related, all of the pool and patio furniture was in the living room when we arrived so we had to move all of it ourselves. We were told that we would have to check in with security when we arrived and provide all vehicle information but when we arrived the security person only asked what unit we were staying in. He never asked for any identification or our confirmation letter. I thought that was strange. We were allowed to access the property two hours early on our arrival day which was greatly appreciated. The property managers were responsive to email inquiries. Overall, we all agree that we would return to Westside.
Stayed 7 nights in Oct 2022

8/10 Good

Sarah C.

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

Perfect Property, less than perfect supplies

We love love LOVED the house. It suited our family perfectly for multiple days at Disney. However, when we booked I don’t recall seeing the limited list of supplies. We were provided with one roll of toilet paper per bathroom (atleast all but one), one laundry pod, two kitchen bags, and two dishwasher pods. We had the max amount of guests there for 5 days. The toilet paper thing wasn’t a big deal since packs of 4 are common. However laundry soap isn’t as easily found in small quantity. Additionally the kitchen bags were of such low quality that both ripped before they were full, rendering them useless. Two pods of dishwashing detergent was not enough for 5 days and 11 people, they should at least provide one pod per day of stay. The provided hand washing soap for dishes was sufficient. Also there were no provided cleaning supplies in terms of Lysol spray or the like for wiping down the kitchen while were were there. I didn’t locate the broom until the last day (it was in a closet who’s door appeared to be locked however was just a deadbolt instead of a door handle). I would gladly pay more for this property if it came with more cleaning supplies. I didn’t anticipate having to buy all that until our welcome email was sent. All that aside, as I said, the house itself and location were absolutely perfect for a Disney family vacation!
Stayed 4 nights in Feb 2023

8/10 Good

Tonia G.

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

Beautiful Condo, but needs a good cleaning and/or a different cleaning company.

Overall, we were happy with the rental. The decor was very nice and there was plenty of space for our group of 8 to spread out when needed and come together in the public areas as well. My son absolutely loved the arcade game upstairs and having the Rokus in each room was great for our down times. The location is in great proximity to the parks, about 10-15 minutes from Disney and 30 from Universal. There is a Publix not too far for grocery needs. Keep in mind, as with most rentals, it only comes with starter supplies. Plan ahead and get things like toilet paper, paper towels, cleaning wipes, etc. Also, there were no wash cloths so we had to get some of our own. The pool was a nice size, we were expecting a little smaller from the pictures and the heat was nice. We saw there was a pool light in it, but could not find the switch for it, even after messaging the owner. No big deal, but my 10 year old did not want to swim in the dark pool. The only thing we really had issue with was the cleanliness of the property. The cleaning company obviously just comes in and hits the high points. However, they missed several things. When getting ready for bed the first night, we found sheets missing on two of the beds. Not even all sheets, one bed was just missing a top sheet and the other a bottom. The worst bed situation was finding dirt and a lot of pubic hair in the bed my son was to sleep in! Super gross! There are extra sheets in the closets so we put fresh sheets on, but after a long 12 hour driving day, the last thing you want to do is deal with that. Some of the comforters has stains on them that were put face down so as not to be seen until removed or folded down. There were also things like a dust bunny falling in my daughter's cereal from the pendants over the island. After looking at them closer, you could see they were covered in dust. The dining room table was also dusty and had old food on it. The microwave had dried food on the glass tray as well. The grill on the patio looked like it had never been cleaned. We had to buy a grill brush to clean it before we used it since one is not provided. All communication with the owners was very cordial and they were quick to respond and do everything they could to make things right for us. Overall, aside from the cleanliness, we were happy with our stay.
Stayed 6 nights in Nov 2022

About the host

Hosted by Property Manager

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Languages:

English