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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 17315.9 sq m

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

Carolyn B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 9 nights in Mar 2025

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

8/10 Good

Brian B.

Liked: Cleanliness, check-in
Disliked: Communication
Decent - Not Perfect
House was well enough to stay at for Disney/Universal trip. The pictures definitely are professionally staged to give it that appeal. Reality says the house has been "lived" in though. Carpet is matted & thin around tack strips, doors don't close completely, tile flooring shows signs of age with tinged color, appliances are older/not smart enabled. One TV in the room our son was in didn't work (& I'm a technilogically saavy person). The place really could do with some updating at this point. Biggest issue we experienced was the internet connection not working. It'd be nice to have directions on troubleshooting steps, like location of router. There was a weird communication flow where when reaching out to the VRBO listing, it goes to the owner. Who then tells me to contact a property management company. When I'm on vacation & coordinating a large family/friends event, I don't want to or feel I should have to play Project Manager, I'm likely dealing with park chaos during the day. Whoever I reach out to on VRBO should be the one managing the issue resolution. Neighborhood is clearly being used for mass VRBOs. Be ready to potentially deal with partiers breaking noise ordinances. Additionally, the supplies provided for initial day or two worth stay are super cheap. The house successfully met our needs & was convenient for a larger group of people. The host was attentive & friendly. Check in was super easy. Location is super close to AK & stores for supplies.
Stayed 8 nights in Dec 2024

6/10 Okay

Maria G.

Liked: Location
Disliked: Check-in
Universal trip
We appreciated the size of the property, there was plenty of space for 11 of us. We choose this place because we were told flexibility with check in and check out based on our flights from New York would be possible- but it turned out not to be and created a lot of issues for us that we don’t usually have when we visit the area. Of course the arrival/departure flexibility changed once we could no longer cancel without loosing money- We understand it takes a lot of coordination to clean and ready places, but we were told scheduling early would be workable. We would have appreciated transparency when booking so we could have chosen differently instead of being told it shouldn’t be a problem to check in or out early or late. It felt very misleading. We also had problems with our spa and pool heat, we got quick phone responses to our issues but it left us with only 2 of our 5 day trip with heated spa. We had a few issues with urine on 2 of the bathroom toilets upon arrival, and other peoples garbage left behind and even though we tried to follow all the garbage rules it was often not picked up in the morning- but calling Gobal became a chore we didn’t want to engage in.We travel often and the places we have stayed usually go above and beyond to make a trip smooth. I have never had to leave a disappointing rating until now, it doesn’t feel good- but neither did our overall stay. It was bumpy and exhausting. So the excellent amount of space did not make up for issues experienced.
Stayed 5 nights in Dec 2024

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

Yolanda J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 6 nights in May 2024

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

Sneh P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Exactly as expected
13 family members including 6 children (aged 1 to 9) stayed at this gorgeous and spacious house and every one of us enjoyed our stay. The house was exactly like the pictures and clean. They had plenty of items for children - high chairs, strollers, playpens - which was convenient. The older children and adults enjoyed the games room and all items listed were present. There were plenty of kitchen items and towels for our 1 week stay. The washer and dryer were high capacity. The pool and spa were clean. We only went to the local amenities area once and had a great time. The owner is very easy to get a hold of and responds very quickly. The check in and out process was very easy. You get a code to enter the home on arrival, you enter another code at the end of your stay to let them know you've left. I would definitely recommend staying here!
Stayed 7 nights in Jun 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

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

Brenda P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Absolutely beautiful
The house is exactly as the pictures show which means no surprises. As many have stated, the beds are super comfortable and everyone had a great sleep each night. The location is a quick trip to Disney and there are plenty of conveniences close by. The owners always replied quickly and were extremely accommodating. There was a little issue with the one drier however within 12 hours it was all fixed. Wish I had that kind of service at home. You will not be disappointed with this home. Our other family members rented a house around the corner and it didn’t compare to the comfort and beauty of this one. If this is available I highly recommend you grab it. You won’t be disappointed.
Stayed 8 nights in Apr 2024

10/10 Excellent

Joan and Curt K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fun Family Time!!
We loved every minute of our family vacation! We met our 3 grown kids/husbands and grandkids for a week of fun together! The house has a great lay-out with 6 bedrooms upstairs and 1 on the main floor. With 7 adults and 5 kids (all 6 and under) nobody ever felt crowded. The game room / karaoke was a hit - even with the little ones. There was one high chair and one more that hooked onto a chair - perfect for our two babies. Also, I had requested an additional pack and play and they accommodated and had one onsite for us! The stroller was used daily :) The hot tub heated up great and only took about 30 minutes. There were enough beach/bath towels so we weren't washing often. We could have used a few more dish towels though. It was great to have a dryer by the pool! Some of us went to Clearwater Beach for the day. It was almost a 2 hour drive but once we got there it was gorgeous. They have chairs/umbrellas to rent right on the beach. Unfortunately we left at 4 pm and it took us 3 hours to get back! If you go- leave the beach earlier:) This house is only about 3 blocks from the Windsor Westside Resort so it was easy to walk back and forth. The resort felt like we were on a mini cruise! Festive and fun all day long. We loved it here and definitely recommend it. Curt and Joan :)
Stayed 7 nights in Apr 2024

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

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

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

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

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

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

8/10 Good

michael z.

Liked: Cleanliness, communication, location, listing accuracy
Disliked: Check-in
Very good price.
The Management company sent a lot of emails with information that was not updated. It made check in a wild goose chase. Turns out you didn't have to do anything but go to the house. The owner sent all the codes and info that you needed.
Stayed 6 nights in Jul 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

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

8/10 Good

Courtney V., North Chesterfield

Liked: Cleanliness, check-in, communication, location, listing accuracy
Good over all
Although there were a few tvs not working and a broken stool, the majority of the stay was very nice. Be aware that the floor is super slippery.
Stayed 4 nights in Jul 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

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