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Luxury Villa Pool/HotTub/Karaoke 7B Windsor Westside Resort,Disney,Kissimmee

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Downstairs living room
Private hot tub and pool
Game room: Pool, air hockey, karaoke, bar touchscreen game, TV, DJ lights+mikes
Clubhouse pool
parlor

Reviews

9.6 out of 10
Exceptional
7 bedrooms5+ bathroomsSleeps 173400 sq ft

Popular amenities

  • Parking available
  • Dryer
  • Washer
  • Barbecue grill
  • Outdoor space

Explore the area

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

Rooms & beds

7 bedrooms (sleeps 17)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

1 King Bed

Bedroom 4

1 King Bed

Bedroom 5

2 Single Beds

Bedroom 6

1 Single Bed and 1 Double Bed

Bedroom 7

1 Single Bed and 2 Double Beds

5 bathrooms, 1 half bathroom

Bathroom 1

Bathtub · Toilet · Shower only

Bathroom 2

Toilet

Bathroom 3

Toilet · Shower only

Bathroom 4

Toilet · Shower only

Bathroom 5

Toilet · Shower only

Bathroom 6

Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Outdoor play area
Dining area

About this property

Luxury Villa Pool/HotTub/Karaoke 7B Windsor Westside Resort,Disney,Kissimmee

See NEW last minute discounts + FREE POOL HEAT for limited time, only. Orlando-Kissimmee's Windsor at Westside's "Second Star to the Right". Luxury 7 bedroom pool-spa vacation home. WOW Karaoke TV DJ lights game room. Patio TV, Just steps to amazing clubhouse! In Kissimmee! We offer generous cancellation terms.

Windsor at Westside (newer sister to Windsor Hills) is an upscale gated resort completed 5 years ago. A very short walk from our home is all it takes to the amazing world class 10,000 sq foot clubhouse featuring a bar, food, drinks, fireplace, sundries shop, Lazy River, huge zero entrance resort heated pool, Aquapark, lake, cabanas, large hot spa, multiple sports courts including pickleball, extended hours gym, covered playground, arcade room, frozen yogurt area, and activities for more fun in the sun.

Then there's the world renown theme parks. 8-10 miles is all it takes to Disney’s World Drive and nearby there's Universal Studio/ Sea World. Excellent dining, golf, water parks, shopping, and outlets are all close by.

Vacation Home: Your new villa-home is designated as a Grand Collection villa. The professionally decorated exceptionally beautiful villa features 7 BR with 4 Kings (1 downstairs) sleeps 14-17*, a 1st floor parlor plus a huge 2nd floor parlor with a poker table and playstation4, 11 wall mounted smart TV. There's an outside TV and free 100 Mbps- Wi-Fi /DVDs/ phone calls to USA Canada and Puerto Rico. At night poker and card games with the kids were great. Both Keurig type and regular drip coffee makers and fully furnished open design kitchen with everything you’d need. Downstairs master with its own bath (shower and separate tub) and separate access to pool is so convenient and there's another 1/2 bath downstairs, 5 1/2 baths in all. Pool and patio access to the bathroom is also very convenient. The full size GREAT gameroom man-cave, features a stage/karaoke machine, real DJ lights, cordless mikes and various karaoke CDs, for singing or a PLAY. The smart TV is also connected to the karaoke so that everybody can sing along, if you dare! Watch TV/YouTube music videos with lyrics. Connect ability for your music devices. There's a bluetooth PA system, a Megatouch touchscreen bar table game with over 100 games, bar table, pool table, and air hockey. The touchscreen game offers 1-4 players and has card games, trivia/puzzles, action games, strategy, and kids games for hours of fun and competition. Our favorite game is Take 2....try it.

Private Pool-spa, you’ll love the hot tub while watching the outside TV.
Outside, there's a lanai-patio, large table for dinning, DRYER, and private heated lit pool and spa, we're always there. Outdoor dryer for wet bathing suits and warm towels is a surprising luxury….Step outside, morning coffee, relaxing, planning the day, the kids in the pool and watching TV in the Florida sun...Ah heaven. We have pool children gate.

The washer and 2 dryers are on the first floor and there's multiple children's accessories (high chair, 2 pack & play cribs, pool safety fence, and a stroller), linens, and there's even blow driers. You're just a few miles from Disney's magic and Universal/Seaworld and the famous route 192 all its attractions/restaurants and a bit further is International Drive with its entertainment, dining, Eye and Convention Center. Tampa's Hardrock Casino is an hour away, if you're feeling lucky.

Our family/friends have vacationed in Kissimmee as renters for years and renting a dream home has come to be a better way to spend quality time together. We hope that you consider renting from us during your next trip and we sincerely wish you and your family the very best experience possible.

No smoking inside game room or villa. Smoking permitted in the pool area. No pets. No diving, glass, or unsupervised children in the pool area. Use the children safety pool fence. FREE POOL SPA-HEAT Spa/Jacuzzi heat requires the pool to be heated.) No resort fees. Compare. There is only an additional tax, $285 cleaning fee, plus tax, and VRBO charge (see price details). (*17 guests usually requires sleeping 4 children in the bunk bed-trundle room ( 1 on top, 2 bottom, 1 in pullout trundle) and 2 guests in the double bed.)

Please review POLICY and PAYMENT at the bottom of the" Rate" page. There’s a 10% discount for returning guests, military members, and stays for 7 nights or more (only one discount per reservation).

Construction in the resort totally complete for some years. Only starter amounts of toilet paper cleaning goods and garbage bags are provided and no starter food is provided (per law). If you have any questions or concerns please don't hesitate to ask. People do business with people give us a call and begin your vacation dreams.
Free Pool/spa heat currently running a special. All prior reservations will remain unchanged.

WHY US?:
REALLY VERY CLOSE to the clubhouse (800 feet) such a plus!
Gated WINDSOR AT WESTSIDE RESORT with a world class clubhouse and all but purchases are complimentary!
WOW Game room Karaoke + stage with speakers-mikes-real DJ lighting- Megatouch gaming-TV-pool table- air hockey- bar table! Large Connect 4 game
Beautifully decorated 7 bedroom villa with everything and over 95 five out of 5 star reviews.
Outdoor TV! and free spa/pool heat, outdoor closet with one of the two dryers, overhead fan, and kid pool fence.
Convenient to theme parks, golf, restaurants, and attractions.
Our great, friendly , professional management company over 30 years strong, 24/7hours on call, straight to the villa entry. Smoke and pets free (outdoor smoking permitted).
Our updated vacation emails with all sorts of hints and shortcuts. Discounts and specials.
Enhanced cleaning/sanitation as well as relaxed refund policy related to the pandemic.

We have been asked to name our villa and loved 'the second star to the right' after Peter Pan's Neverland, a place where you never grow up.
Thank you

Property manager

James and Karen Smith
Premier Host

Languages

English

Add dates for prices

Amenities

Pool
Hot tub
Kitchen
Washer
Dryer
Free WiFi

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House Rules

Check in after 4:00 PM
Minimum age to rent: 28
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
No Smoking in the house or game room but allowed in the lanai-patio
E-check payments are accepted only if booking/payment made 30 days prior to the arrival date. Minimal time from booking request to arrival is 7 days.
Check-in can be done in person or via express check in by calling Global, our management company. This in a must for late arrivals and us preferred.

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 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 that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock

We should mention

A car is required for transport to and from this property

About the area

Kissimmee

Located in Kissimmee, this villa is near theme parks and on a lake. ChampionsGate Golf Club and Mystic Dunes Golf Club 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 Disney's Animal Kingdom® Theme Park. Travelling with kids? Make time for Old Town, or head to an event or a match at ESPN Wide World of Sports Complex. Discover the area's water adventures with nearby swimming, or enjoy the great outdoors with horse riding.
Map
Kissimmee, FL

What's nearby

  • Highland Reserve Golf Club - 7 min drive - 6.2 km
  • ChampionsGate Golf Club - 10 min drive - 7.9 km
  • Mystic Dunes Golf Club - 14 min drive - 10.1 km
  • Reunion Resort Golf Course - 20 min drive - 15.1 km
  • Disney's Animal Kingdom® Theme Park - 21 min drive - 16.5 km

Getting around

  • Kissimmee Station - 34 min drive
  • Kissimmee, FL (ISM-Kissimmee Gateway) - 31 min drive

Restaurants

  • ‪McDonald's - ‬8 min drive
  • ‪Culver's - ‬6 min drive
  • ‪Taco Bell - ‬6 min drive
  • ‪Best of British Cafe - ‬7 min drive
  • ‪Denny's - ‬7 min drive

Frequently asked questions

Does Luxury Villa Pool/HotTub/Karaoke 7B Windsor Westside Resort,Disney,Kissimmee have a pool?

Yes, this property has an outdoor pool. Pool types include heated pools.

Is Luxury Villa Pool/HotTub/Karaoke 7B Windsor Westside Resort,Disney,Kissimmee pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Luxury Villa Pool/HotTub/Karaoke 7B Windsor Westside Resort,Disney,Kissimmee ?

Check-in begins at 4:00 PM.

What time is check-out at Luxury Villa Pool/HotTub/Karaoke 7B Windsor Westside Resort,Disney,Kissimmee ?

Checkout is at 10:00 AM.

Where is Luxury Villa Pool/HotTub/Karaoke 7B Windsor Westside Resort,Disney,Kissimmee located?

This family-friendly Kissimmee villa is located on a lake, 2.2 mi (3.5 km) from Lake Davenport, and within 6 mi (10 km) of Surfari Water Park and Island H2O Live!. Mighty Jungle Golf and ChampionsGate Golf Club are also within 6 miles (10 km).

Reviews

9.6

Exceptional

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. 98 out of 115 reviews
Rating 8 - Good. 12 out of 115 reviews
Rating 6 - Okay. 3 out of 115 reviews
Rating 4 - Poor. 2 out of 115 reviews
Rating 2 - Terrible. 0 out of 115 reviews

9.4/10

Cleanliness

9.8/10

Check-in

9.8/10

Communication

9.6/10

Location

9.6/10

Listing accuracy

Reviews

10/10 Excellent

Amy P.

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

They’ve thought of everything!

This place has it all… every detail is well thought out. Pack n play, strollers, kitchen gadgets, game room, even an outdoor TV for so when guys grilled, they didn’t have to miss any of the March Madness games! This family has been wonderful to work with and we would definitely stay here again!
Stayed 7 nights in Mar 2025

8/10 Good

Brayan l.

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

Pretty good stay over all.

Enjoyed our stay for the most part. Had a lot of problems with keeping the hot tub working. House has plenty of room for large groups. We really enjoyed the game room.
Stayed 6 nights in Feb 2025

10/10 Excellent

ARTHUR P.

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

Accurate and clean

Overall this is both a excellent property, and a good owner to the property. The owner spelled out the how, where, and when to get into the property. The location is really good. Close enough to the action, but far enough away that you don't feel crowded. The neighborhood was quiet despite it being a holiday week, and the property was as described. Beds are comfortable, and there is plenty of room for everyone. Thank you for a pleasant stsy!
Stayed 6 nights in Nov 2024

10/10 Excellent

Cathy R.

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

Fabulous Family place

Great accommodations that were close to all the parks! Easy access to shopping, groceries etc. The amenities included allowed our family to have a place to enjoy following our busy days at the theme parks, Space Station and beach! Would recommend to anyone travelling with children 8 and older. Hope to return in the near future!
Stayed 7 nights in Aug 2024

10/10 Excellent

John S.

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

Great house, kids loved the pool . Everything was as pictured , very clean, well stocked and worked

4 days at Universal and great to go back to the pool and we didn't mind staying in so the others could go shopping. Really great house and we enjoyed our stay there.
Stayed 7 nights in Mar 2024

10/10 Excellent

Beau S.

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

Great host!

Property was as described. Our family had a great time at the house and having the resort close by was convenient. Any issues that arose were handled quickly. Would stay here again!!
Stayed 7 nights in May 2024

8/10 Good

Ashley S.

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

Family trip

Great experience we loved our stay !
Stayed 4 nights in Jul 2021

10/10 Excellent

prowler282

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

As advertised

Pool was smaller than appeared in photos but still a great house.
Stayed 7 nights in Jun 2024

10/10 Excellent

Lyle B.

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

Very nice

Property was everything as advertised. Very clean and roomy. Had a great stay.
Stayed 7 nights in Aug 2023

10/10 Excellent

Tyra G.

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

Perfect for family

This home is perfect for families with children. Plenty of space.
Stayed 4 nights in Jul 2023

10/10 Excellent

James H.

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

Great house and location

We chose to bring our children and grandchildren to Florida for spring break and choosing to stay in this house did not disappoint. The location was perfect to visit the parks and shop. The resort amenities were a plus. The house itself was clean and well stocked for everything we would need. The owners answered questions before our visit and during as well and in a timely manner. Would definitely recommend!!!
Stayed 7 nights in Mar 2024

10/10 Excellent

Paul J.

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

Superb

We absolutely loved it from start to finish, highly recommended
Stayed 14 nights in Jul 2023

10/10 Excellent

YANIRIS F., Miami, FL

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

Beautiful house for vacation

My family and I had a wonderful winter vacation. The house is perfect and confortable for a big family. We recommend 100%. Thank you and many blessings!
Stayed 4 nights in Dec 2023

10/10 Excellent

jose b.

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

Great experience

The property was clean and communication with host was great, host is very responsive. No issues, would stay here again!
Stayed 7 nights in May 2022

10/10 Excellent

Jeannine H., Chambersburg, PA

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

Great Orlando vacation

Lots of room and very clean. We had a multigenerational family group and everyone had fun. Pool and hot tub were great, and community had nice amenities. We plan on renting this house again!
Stayed 7 nights in Jan 2023

10/10 Excellent

SHALEN S.

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

Great vacation and relaxation!

Enjoyed our stay very much although unfortunately it was cut short due to family emergency and having to return home earlier than planned. Really enjoyed our stay and hope to return again in the near future…thank you so much for sharing your home with us!!! There was plenty of room and had everything we needed with very close shopping and short travel time to parks.
Stayed 6 nights in Jun 2023

10/10 Excellent

Diane M.

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

Fantastic Vacation

We had a great time in Orlando, and the house was fantastic!! We enjoyed it thoroughly and hated to leave! If I had to make a suggestion it would be to upgrade the coffee maker to a Keurig.
Stayed 5 nights in Oct 2022

10/10 Excellent

Michael B., Indianapolis, Indiana

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

House was amazing everything was clean and worked great!!!

Host is the BEST !!! Communication was excellent!!!! Would definitely book again !!!
Stayed 4 nights in Mar 2022

10/10 Excellent

Jennifer R.

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

It was a pleasure to stay here.

Stayed Saturday until Thursday and it wasn't long enough. The house was beautiful and there was everything there we needed. Pool days were great even with the rain storms we could still sit out and enjoy ourselves at the outdoor table.
Stayed 5 nights in Jul 2023

10/10 Excellent

Verified traveller

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

Great house for a large group.

We enjoyed the 7 bedrooms so everyone had a bed. And the two pack n plays were used as well. The pool was an added treat and the clubhouse pool and playground were big hits with our grandkids.
Stayed 10 nights in Dec 2019

10/10 Excellent

Terrence A., Nova Scotia, Dartmouth

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

A Most Excellent Family Vacation

From the house layout to the games room and of course the pool, the entire family enjoyed the beautiful house and of course had a terrific time. The house was very well appointed and the bedrooms worked perfectly for a smattering of ages. Primary Suite on the main floor next to the pool -perfect for the seniors. Extra separate family rooms ensured multiple functions could be accommodated concurrently. Pool table and air hockey games were the hits inside. Great neighborhood close to all amenities.
Stayed 6 nights in Mar 2024

10/10 Excellent

Malcolm H.

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

Crazy about it

Loved the house. Dream come true!
Stayed 7 nights in Jul 2022

8/10 Good

Taylor B.

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

Great time

This was a great property our family had a ton of fun! We had a few minor issues with the pool not looking super clean, some garbage missed from guest before us and the microphones didn’t work for the karaoke.
Stayed 4 nights in Dec 2021

8/10 Good

Christy C.

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

Florida trip

Nice home! We had some minor concerns that we’re addressed quickly. Communication with owner was great
Stayed 4 nights in Oct 2019

10/10 Excellent

Carolyn S.

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

Amazing home!

This home is exactly as advertised. Beautiful, spacious, and clean. Everything you need and more. The pool and hot tib had some difficulty keeping up with the cooler weather, but Global came quickly and did what rhey could. The property owner was quick to respond all through the process. 5 stars all around!
Stayed 7 nights in Dec 2023

About the host

Hosted by James and Karen Smith

Host profile image
I'm a grandfather of 15 and bought our place for family times. Our family/friends have vacationed in Kissimmee as renters for years and renting a dream home has come to be a better way to spend quality time all together. We love seeing Disney again through our kids and grandchildren's eyes and hope that everybody has that opportunity. We believe that people do business with people so call us so we can help it happen. We've done it all.

Why they chose this property

Our favorite times are sitting around in the morning
Floridian sunshine, having our cup of coffee the kids in the pool and watching the outside TV, we're always there. At night the kids and adults after a dip in the pool or a long day at the parks meet in the game room, singing, dancing, and playing the games (I always lose). There's been many a night upstairs when the adults and kids play poker. The clubhouse is the best we've seen and so close...Head over there DAY 1 and get excited. To us our place down in Kissimmee is our favorite place to be.

What makes this property unique

Really very close to the clubhouse (800 to 1000 feet)
New gated WINDSOR AT WESTSIDE RESORT with a world class clubhouse and all but purchases are complimentary!
WOW Game room Karaoke with speakers-mics-real DJ lighting- Megatouch gaming-TV-pool table- air hockey- bar table!
Beautifully decorated 7 bedroom villa with everything and with over 75 five star reviews
Outdoor TV- FREE pool and spa heat.
We are in Kissimmee so Convenient to theme parks and attractions.
Our management company 27 years strong and 24/7 availability.
Check for our discounts
Our Welcome guide, directions, and accessibility
Enhanced cleaning/sanitation as well as refund policy related to the pandemic.

Languages:

English

Premier Host

They consistently provide great experiences for their guests