Upstay presents this newly renovated 9-bedroom home at the sought-after Windsor at Westside Resort—just 8 miles from Disney! Recently updated to include a brand-new movie theater and an upgraded games room with a PlayStation, this home offers even more space for fun and relaxation. Enjoy your own private swimming pool, jacuzzi hot tub, and a spacious, fully furnished sundeck. Inside, you’ll find modern, airy rooms and entertainment for all ages, including air hockey, billiards, and foosball.
The Space:
This newly renovated 9-bedroom, 6-bathroom home at Windsor at Westside has been enhanced with a brand-new private movie theater and upgraded games room with a PlayStation—making it the ultimate group getaway. Enjoy a private pool, outdoor hot tub, and a large sundeck with serene pond views. The home sleeps up to 20 guests comfortably, with smart TVs in every bedroom and high-speed WiFi throughout.
Enjoy pond-facing views and no rear neighbors while you soak up the Florida sunshine from your private screened-in patio. Cool off in the sparkling swimming pool, unwind in the jacuzzi hot tub, or enjoy BBQ lunches around the outdoor dining area—there’s plenty of space for everyone.
Inside, the fully equipped kitchen features double fridge/freezer combo units, two large-capacity dishwashers, quartz countertops, stainless steel appliances, and a deep double sink. Dine together at the 10-person indoor dining table, with additional seating for 4 at the kitchen island and even more outdoors.
Every bedroom has a Smart TV, and high-speed internet keeps everyone connected.
Bedroom breakdown:
First Floor:
First Floor:
Bedroom 1: King bed
Bedroom 2: Two (2) Queen beds with ensuite
Second Floor:
Bedroom 3: King bed with ensuite
Bedroom 4: Bunk-bed (twin/full)
Bedroom 5: King bedroom suite
Bedroom 6: King bedroom suite
Bedroom 7: Bunk bed (twin/full)
Bedrooms 8&9: Two rooms, each with 2 twin beds
Bonus: Upstairs loft lounge now enhanced with air hockey, billiards, and foosball
Need to throw in a load of laundry? No problem—this home includes in-home washers and dryers, central A/C, and free parking for up to 4 vehicles on-site.
As part of your stay, you’ll also enjoy full access to the incredible Windsor at Westside Resort, complete with a lazy river, water slides, a Tiki bar, and so much more. Whether you're heading to Disney (just 8 miles away), relaxing poolside, or enjoying a movie night at home—this property offers a vacation experience unlike any other.
Guest Access:
You'll have private access to the property, so please make yourself at home. You can park 2 cars in the driveway. Our guests also get access to the resort clubhouse and its amenities, they are open from 9am to 9pm daily.
The Neighborhood:
Windsor at Westside is a brand new Mediterranean-themed community of luxury Orlando vacation rentals just 8 miles from Disney World. Guests get full access to the clubhouse and all of its amenities.
Getting Around:
Windsor at Westside is perfectly located to give you easy access in to the back entrance of Disney World via Black Lake Road followed by Sherbeth Road, so you will experience very minimal traffic. Close to shops, supermarkets (publix) and restaurants it's a great location to explore all the Orlando theme park attractions.
Windsor at Westside is just 30 miles from Orlando International Airport via the 417 toll road which normally takes about 35 minutes and only costs a few Dollars for the convenience.
Other Things to Note:
• For a smooth and secure check-in experience, all guests may be required to complete ID and Enso Boarding Pass verification before arrival. Check-in instructions will be shared once verification is completed. Thank you for helping us ensure a seamless stay!
• Up to 2 vehicles may park in the driveway while extra parking is available at the clubhouse. The garage is not available, and a maximum of 5 vehicles is allowed per residence.
• Please note that washcloths are not provided—kindly bring your own for your stay.
Additional Services:
• Pool and hot tub heating are available upon request and are not included in the booking price. The fee is $45/night per service or $79/night for both, with a 2-night minimum. At least 24 hours’ notice is required if you would like to add this service.
• Planning a BBQ? A propane tank is available for a one-time $69 charge. Let us know in advance, and we’ll make sure you’re all set to grill and enjoy!
• Rent a Pack 'n play for $39 (one-time fee)
• Rent a highchair for $29 (one-time fee)
• Mid-stay cleaning for reservations over 3 days in duration. This service is available for an extra fee and will need to be booked in advance.
House Rules:
1. Parties, events, and smoking/vaping are prohibited in or around our property.
2. Please check-out on time. Late departures will result in a charge for each additional hour the property cannot be accessed for turnover.
3. Outside of service animals, pets are not permitted at this property. Any evidence of pets will result in a fine and/or forfeiture of your full deposit.
4. Firearms and weapons are strictly prohibited on the property.
5. We do not assume liability for any injuries sustained by using the pool. Please follow all safety precautions and use at your own discretion.
If any of these house rules are broken, you and your group may be subject to additional charges or be requested to vacate the property immediately without refund.
Interaction with Guests:
We work with a team of dedicated hospitality professionals who will assist us in providing you with 5-star quality service. Your recommendations and questions are important to us and we're here 24/7 to assist you. Please don't hesitate to reach out to us at any time.
Accommodatie-voorzieningen
Strand
Strandlakens
Strandstoelen
Zwembad/spa
Bubbelbad
Buitenzwembad
Gemeenschappelijk zwembad
Privézwembad
Internet
Beschikbaar in de woning: gratis wifi
Parkeren en vervoer
Parkeerplekken ter plaatse
Keuken
Afwasmachine
Blender
Broodrooster
Elektrische waterkoker
IJsmachine
Keukeneiland
Koelkast
Koffiezetapparaat/waterkoker
Kookgerei, borden en bestek
Kookplaat
Magnetron
Oven
Eetopties
Eettafel
Slaapkamers
9 slaapkamers
Beddengoed inbegrepen
Badkamer
6 badkamers
Douche
Haardroger
Handdoeken inbegrepen
Shampoo
Zeep
Woonruimtes
Eettafel
Woonkamer
Entertainment
Smart-tv
Spellen
Buiten
Balkon
Barbecue
Tuin
Tuinmeubels
Wasvoorzieningen
Wasmachine
Wasserette
Comfort
Airconditioning
Verwarming
Huisdieren
Geen huisdieren toegestaan
Toegankelijkheidsvoorzieningen
Hardhouten vloer in gemeenschappelijke ruimtes
Rookvrije accommodatie
Diensten en faciliteiten
Strijkijzer/strijkplank
Uitgelichte locatiekenmerken
Dicht bij een spa
In het stadscentrum
Dingen om te doen
Biljart/pooltafel
Spelletjesruimte
Sportschool
Tafeltennis
Tafelvoetbalspel
Pretpark in de buurt
Veiligheidsvoorzieningen
Koolmonoxidemelder (de eigenaar heeft aangegeven dat er een koolmonoxidemelder aanwezig is in de accommodatie)
Rookmelder (de eigenaar heeft aangegeven dat er een rookmelder aanwezig is in de accommodatie)
Je ontvangt een e-mail van de eigenaar met instructies voor het in- en uitchecken
De informatie die de accommodatie verstrekt, is mogelijk vertaald met automatische vertaaltools
Huisregels
1. Parties, events, and smoking/vaping are prohibited in or around our property.
2. Please check-out on time. Late departures will result in a cha...
Huisdieren
Geen huisdieren toegestaan
Kinderen en extra bedden
Kinderen zijn van harte welkom.
Evenementen
Geen evenementen toegestaan
Roken
Roken is niet toegestaan
Belangrijke informatie
Algemene info
Deze accommodatie wordt beheerd door een professionele eigenaar die handelt vanuit zijn/haar vakgebied, bedrijf of beroep.
Afhankelijk van het accommodatiebeleid kan voor extra personen een toeslag in rekening worden gebracht.
Bij het inchecken dien je mogelijk een erkend identiteitsbewijs met foto en een creditcard, pinpas of borgsom in contanten te verstrekken voor incidentele kosten.
Speciale verzoeken worden onder voorbehoud van beschikbaarheid bij het inchecken ingewilligd. Hiervoor kunnen extra kosten in rekening worden gebracht. Speciale verzoeken kunnen niet worden gegarandeerd.
Deze accommodatie accepteert contante betalingen.
Feesten of groepsevenementen ter plaatse zijn ten strengste verboden.
Huren op lange termijn is mogelijk.
De eigenaar heeft aangegeven dat er een koolmonoxidemelder aanwezig is in de accommodatie.
De eigenaar heeft aangegeven dat er een rookmelder aanwezig is in de accommodatie.
De accommodatie beschikt over de volgende veiligheidsvoorziening: een brandblusser
Deze accommodatie heeft buitenruimtes, zoals balkons, patio's en terrassen, die mogelijk niet geschikt zijn voor kinderen. We raden aan om in geval van twijfel vóór aankomst de accommodatie te contacteren en te vragen of ze een geschikte kamer voor je hebben.
Onze partner, Vrbo, beheert deze accommodatie. Je ontvangt een e-mail van Vrbo met een link naar een Vrbo-account, waarmee je je boeking kunt aanpassen of annuleren.
Als je je boeking annuleert, ben je onderhevig aan het annuleringsbeleid van de eigenaar. In overeenstemming met de EU-regelgeving over consumentenrechten, vallen boekingsservices voor accommodaties niet onder het herroepingsrecht.
Over deze buurt
Je kunt dit vakantiehuis in het stadscentrum vinden in de buurt van pretparken in Kissimmee. Als je graag iets actiefs gaat doen, breng dan een bezoek aan ChampionsGate Golf Club en Mystic Dunes Golf Club. Ben je liever in de winkelstraten te vinden? Dan kun je je hart bij Oude stad en Disney Springs™ ophalen. Eropuit met de kinderen? Sla Walt Disney World® Resort dan zeker niet over en bezoek een evenement of wedstrijd bij ESPN Wide World of Sports Complex. Bekijk onze reisgids voor Kissimmee
Kissimmee, Florida (ISM-Kissimmee Gateway) - 42 min. rijden
Restaurants
McDonald's
5 min. rijden
7-Eleven
19 min. lopen
Twistee Treat Berry Town
5 min. rijden
Dutch Bros Coffee
6 min. rijden
Culver's
7 min. rijden
Veelgestelde vragen
Is Upstay: Renovated 9BR Home w Theater & Games Room voorzien van een zwembad?
Ja, deze accommodatie heeft een buitenzwembad.
Zijn huisdieren welkom bij Upstay: Renovated 9BR Home w Theater & Games Room?
Nee, huisdieren zijn bij deze accommodatie niet toegestaan.
Wat kost het om bij Upstay: Renovated 9BR Home w Theater & Games Room te parkeren?
Je kunt ter plaatse parkeren bij de accommodatie.
Hoe laat kan ik inchecken bij Upstay: Renovated 9BR Home w Theater & Games Room?
Je kunt vanaf 16.00 uur inchecken.
Tot hoe laat kan ik bij Upstay: Renovated 9BR Home w Theater & Games Room uitchecken?
Je dient uiterlijk om 10.00 uur uit te checken.
Waar ligt Upstay: Renovated 9BR Home w Theater & Games Room?
Dit gezinsvriendelijke vakantiehuis ligt in het stadscentrum, binnen 5 km afstand van Highland Reserve Golf Club en Lake Davenport. Ook Surfari Water Park en Island H2O Live! liggen binnen 10 km afstand.
Beoordelingen over Upstay: Renovated 9BR Home w Theater & Games Room
Beoordelingen
Zeer goed
Alle weergegeven beoordelingen zijn gebaseerd op echte gastenervaringen. Alleen reizigers die een verblijf bij ons hebben geboekt, kunnen een beoordeling indienen. We verifiëren beoordelingen op basis van onze richtlijnen en plaatsen alle beoordelingen, of ze nu positief of negatief zijn.
Gastenscore: 10 - Uitstekend. 7 van 15 beoordelingen
10 - Uitstekend
7
Gastenscore: 8 - Goed. 4 van 15 beoordelingen
8 - Goed
4
Gastenscore: 6 - Redelijk. 4 van 15 beoordelingen
6 - Redelijk
4
Gastenscore: 4 - Matig. 0 van 15 beoordelingen
4 - Matig
0
Gastenscore: 2 - Ontzettend slecht. 0 van 15 beoordelingen
2 - Ontzettend slecht
0
9,2
Netheid
9,6
Locatie
Beoordelingen
Geverifieerd
10/10 – Voortreffelijk
Dre
30 sep 2025
Positief: Netheid, inchecken, communicatie, locatie en accuraatheid advertentie
Wonderful home, felt safe with family and had a lot of fun.
Dre
2 nachten verbleven in september 2025
Geverifieerd
8/10 – Goed
Tracey O.
10 okt 2025
Positief: Netheid, inchecken, communicatie en locatie
All great.
Tracey O.
5 nachten verbleven in oktober 2025
Geverifieerd
10/10 – Voortreffelijk
Albert N.
23 apr 2025
Positief: Netheid, inchecken, communicatie, locatie en accuraatheid advertentie
Orlando family trip
Great property. Very engaged host
Albert N.
3 nachten verbleven in april 2025
Geverifieerd
10/10 – Voortreffelijk
Lillian R.
29 jul 2025
Positief: Netheid, inchecken, communicatie, locatie en accuraatheid advertentie
Excellent vacation family home
" We had a wonderful stay at your vacation rental home! The spacious home provided plenty of room for a family of 20, and there was something for every age group to enjoy. The open kitchen was fantastic—it had enough space for everyone to eat together, making our family gatherings even more special. The whole family enjoyed the pool and the amenities at the clubhouse, which added to our fun! Highly recommend for a memorable and comfortable getaway!"
Lillian R.
4 nachten verbleven in juli 2025
Geverifieerd
10/10 – Voortreffelijk
Jacques J.
14 jun 2025
Positief: Netheid, inchecken, communicatie, locatie en accuraatheid advertentie
Amazing Accomodations!
Beautiful home. Close to the Clubhouse. Great communication with property manager. Amenities Galore! Highly Recommend!
Jacques J.
5 nachten verbleven in juni 2025
Geverifieerd
6/10 – Matig
Stephanie G.
14 jan 2026
Positief: Netheid, locatie
Negatief: Inchecken, accuraatheid advertentie
There was an address error in the VRBO listing, and it was challenging to find the correct place to be. We had been approved for an early check-in, but the code didn’t work when we arrived. We had paid for two nights of heat in the hot tub that didn’t work when we tried to access it. I asked Repeatedly for a refund on the heating services and did not receive a response to that specific question. We were there over a holiday, which is understandably more challenging. The house itself was great, but the challenges along the way really dampened this day.
Stephanie G.
3 nachten verbleven in december 2025
Geverifieerd
10/10 – Voortreffelijk
Arthur V.
9 mrt 2025
Positief: Netheid, inchecken, communicatie, locatie en accuraatheid advertentie
Spacious Vacation Home for large groups!
Did a family trip to Disney with a total of 18 kids/adults. Primarily used for the basics (sleep/shower/breakfast) so it was perfect for that as everyone had their own space. Property manager was on top of their game and very responsive. Thanks for a great trip!
Arthur V.
6 nachten verbleven in februari 2025
Geverifieerd
10/10 – Voortreffelijk
Sandra S.
26 okt 2025
Positief: Netheid, inchecken, communicatie, locatie en accuraatheid advertentie
Everything Was On Point except tha AC Was not working up stairs
Sandra S.
2 nachten verbleven in oktober 2025
Geverifieerd
6/10 – Matig
Cynthia G.
1 dec 2025
Positief: Locatie
Negatief: Inchecken, accuraatheid advertentie
Although recently renovated, the dining room chairs were were in very poor condition, you had to add pillow not to sink in, bedroom drawers were not clean, closet door in bedroom 2 kept falling off, dryer timer does not work - once you turn it on it will not turn off until you turn it off which is a fire hazard. Ice machine in refrigerator leaks water had to add a towel underneath. Master bedroom bed makes a lot of noise with slightest movement. Seems an attempt was made to reinforce with braces that may be loose? Gave 2 stars instead of 1 because the game room was fun and a few bedrooms had cool renovated themes.
Cynthia G.
4 nachten verbleven in november 2025
Geverifieerd
8/10 – Goed
Froilan S.
22 jun 2025
Positief: Netheid, communicatie en locatie
Great Vacation house
Overall, this was a great vacation home spacious and comfortable, with more than enough bedrooms and bathrooms for our group of 14. The kids especially loved the arcade room, swimming pool, and the home movie theater. A few things to note: the listing mentioned parking for four cars, but since the garage has been converted into an arcade, only two cars can actually fit in the driveway. We had three cars and were told that street parking isn’t allowed and could result in towing. Management recommended the “Parkopedia” app, but the nearest available parking was about two miles away, and we weren’t sure if overnight parking was allowed there. We ended up parking on the street and took our chances.We also had a bit of an issue at check-in. We were told we could check in at noon, but when we arrived, we were informed of a maintenance delay. The house wasn’t ready until around 2 PM, and we ended up waiting outside unnecessarily. Clearer communication would’ve been helpful so we can plan accordingly. We would have preferred an answer of no early check in, vice waiting there until we are allowed to go in. Lastly, basic supplies like toilet paper and trash bags were not stocked adequately. For 14 people staying 8 days, we had to go out and buy extras pretty quickly.Despite these issues, we still really enjoyed the house and the location, just 20–30 minutes from Disney. We would consider staying here again in the future with a few adjustments.
Froilan S.
7 nachten verbleven in juni 2025
Geverifieerd
6/10 – Matig
Charity J.
8 feb 2026
Host was very responsive, and the house was very nice and clean. There was an array of kitchen gadgets, appliances, and cookware. Each room had a great tv. Bathrooms were nice. The kids very much enjoyed the game room, popcorn machine and pool. The sound for the theater was confusing for them, as well as the game room tvs, so they weren’t used as much as they’d hoped to. Our biggest issue were the uncomfortable beds. I personally had the Batman room and the mattress and pillows were worse than any hotel I’ve ever stayed in. In fact, everyone complained about their bed being uncomfortable and without real blankets. My brother and sister in law left with back problems, due to the divot in the master bedroom bed. It’s so unfortunate, especially for such a lovely looking house, for the beds to be not up to par. Another complaint was that the hot tub was warm, but never hot so we didn’t really use it. The kitchen sink had a leak, which soaked the floor and rug but that was just a general maintenance issue. We had issues with our booking, and our payments which was frustrating. All together though the house was nice and fit our large extended family. It just wasn’t as comfortable as we’d expected it to be.
Charity J.
7 nachten verbleven in januari 2026
Geverifieerd
10/10 – Voortreffelijk
Aaliyah M.
31 jan 2026
Positief: Netheid, inchecken, communicatie, locatie en accuraatheid advertentie
I wish I could give more stars to be honest! The pictures on this listing do not give this house justice! The house is breathtaking! So much space! My family and I stayed for my PhD graduation at Disney and we had so much fun! The host is wonderful and super responsive. If you are on the fence with booking this listing, let this review help you make the decision to book! I would definitely stay here again.