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

Kissimmee, Florida
$377 avg/night Minimum Stay 4 Nights
Bed 7

Bed

Bath 5

Bath

Home Villa

Property Type

Sleep 17

Max Sleeps

Night 4 nights

Min Stay

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 really very short walk from our home is all it takes to the amazing worldclass 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. Universal’s new parks opens this year! 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 TVs. 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. Large connections 4 game.

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 fence.

The washer and 2 dryers are on the first floor and there's multiple children's accessories (high chair, 2 pack & play cribs, stair 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, night life, 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, $300 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). There now is a maximum of 4 cars. 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 100 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).
Smoke and CO detectors, fire extinguishers, emergency lighting, urgent care just 2.5 miles away.
Our updated vacation emails with all sorts of hints and shortcuts. Discounts and specials.
Enhanced cleaning/sanitation as well as relaxed refund policy.

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. Enjoy.
Thank you

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • BEACH

    Beach Sun Loungers
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    7 Bedrooms Bed Sheets Provided
  • GENERAL

    Gated Community Smartphone Unit Size: 3400 Sq Ft (316 Sq M) Uses Some LED Lighting
  • KITCHEN

    Blender Coffee/tea Maker Dishwasher Kitchen Island Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Car Required Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Barbecue Grill Outdoor Furniture Patio
  • POOL/SPA

    Heated Pool Hot Tub Outdoor Pool Private Pool Shared/communal Pool
  • BATHROOMS

    5.5 Bathrooms Hair Dryer Shampoo Shower Soap Toilet Paper Towels Provided
  • WORKSPACES

    Desk Desk Chair
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Basketball Nearby Fitness Center Fitness Facilities Nearby Golf Nearby Golfing On Site Horse Riding Nearby Swimming Nearby Tennis On Site Theme Parks Nearby Water Park Nearby
  • ENTERTAINMENT

    Arcade/game Room DVD Player Games Karaoke Pool Or Billiards Table Stereo Video Games Video Library Smart TV With Cable/satellite Service
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Games Children's Toys Highchair Playground Pool Gate Stair Gate Travel Crib
  • LOCATION HIGHLIGHTS

    Near Outlet Shopping On The Lake
  • SERVICES AND CONVENIENCES

    Housekeeping (on Request) Iron/ironing Board Phone
  • SUITABILITY/ACCESSIBILITY

    Area Rugs In Public Areas Designated Smoking Areas Handrails In Stairways If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. Stair-free Path To Entrance Tile Flooring In Public Areas Well-lit Path To Entrance Wheelchair Accessible

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 17

Map Map

School District Rates & Availability

Review Review

  • Stephanie M.

    Submitted Jan 21, 2026

    Stayed Dec 20, 2025

    The host was very responsive along with the management company, Global Rentals. I truly loved the detailed information they provided for surrounding places and how to use specific items within the house. I would definitely stay here again. Kids and grandkids stayed in the pool!

  • Misti A.

    Submitted Jun 17, 2025

    Stayed Jun 7, 2025

    This vacation rental was spectacular and exactly what we expected and more! We were beyond pleased with everything this home had to offer. It was a wonderful place to stay and we will definitely be back! Everything from the kitchen, bedrooms, bathrooms, to the game room and the pool area were amazing. We thoroughly enjoyed every bit of our vacation due to this awesome place!

  • Yvonne G.

    Submitted Jun 11, 2025

    Stayed May 31, 2025

    Our family recently stayed at this VRBO house in Kissimmee, Florida, and it was absolutely perfect for our group, which included everyone from kids to adults. The house had plenty of space, with enough bedrooms and bathrooms for everyone to be comfortable. We did have a small air conditioning issue the first night, but it was quickly resolved within a couple of hours — the communication with the host was excellent throughout our stay.The private pool was a huge hit, giving us a great place to cool off and letting the kids splash around safely. The clubhouse pool and lazy river, plus all of the food, drink and snack options was wonderful and just a short walk away. The neighborhood felt so safe. The game room and karaoke setup added even more fun for the entire family — we all had a blast! The location was ideal, just a short drive to both Disney and Universal, which made getting to the parks super easy.We would definitely recommend this property and plan to book it again for future trips!

  • Tom T.

    Submitted May 21, 2025

    Stayed May 1, 2025

    Great stay. Owner was very responsive and helpful. Took longer than we expected to get back/forth to Disney World.

  • Amy P.

    Submitted Mar 29, 2025

    Stayed Mar 22, 2025

    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!

  • Brayan l.

    Submitted Feb 26, 2025

    Stayed Feb 17, 2025

    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.

  • Brian B.

    Submitted Jan 10, 2025

    Stayed Dec 21, 2024

    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.

  • Maria G.

    Submitted Jan 4, 2025

    Stayed Dec 29, 2024

    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.

  • ARTHUR P.

    Submitted Dec 11, 2024

    Stayed Nov 23, 2024

    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!

  • Cathy R.

    Submitted Aug 25, 2024

    Stayed Aug 17, 2024

    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!

  • prowler282

    Submitted Jul 1, 2024

    Stayed Jun 22, 2024

    Pool was smaller than appeared in photos but still a great house.

  • Sneh P.

    Submitted Jun 26, 2024

    Stayed Jun 1, 2024

    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!

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Total

Includes taxes and fees
$377+
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