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"Exclusive Orlando Villa Resort in Prime Location to Disney theme Parks and Universal Studios"


Welcome to 5 Star Villa Holidays, the No.1 website for renting 5-Star villas on the exclusive Windsor at Westside. 109 luxury villas to choose from.

Windsor at Westside is located in Kissimmee with easy access to Orlando international airport, walt disney world theme parks and universal studios.

Windsor at Westside has free access to the water park, which has a lagoon style pool, lazy river, amazing lake views, private cabana’s, soccer pitch, basketball and volleyball courts.

The prestigious 10,000 square foot clubhouse has arcades, a full service restaurant, TU Casa, fitness centre, sundry shop and front reception.

 Location, location, location, your family will love the location to disney and universal theme parks. One of the best located villa resorts.

Our 5 star villas range in size from 4 - 9 bedroom, sleeping up to a maximum of 22 guests.

I look forward to helping you choose your dream villa on the exclusive windsor at westside resort.

All the best,

John Paul Donnelly

P.S You will love the location of Windsor at Westside, one of the closest resorts to Disney and universal theme parks.

P.P.S If you like this page Please Share on social Because it will help inspire us to keep writing great travel guides for you.

Why rent a villa on Windsor at Westside

  • 1. Located in Kissimmee, just off western way blvd, with easy access to Orlando International airport, disney world and universal.

  • 2. Free access to water park with water slides, lagoon style pool, private cabanas, fitness centre, lazy river and majestic lake views.

  • 3. Exclusive villas with private pools and spa from 4-9 bedroom, sleeping up to 22 guests.

  • 4. Great for sports teams due to the amazing amenities, for special events, wedding, business retreats and parties.

Water Park at Windsor at Westside

     You will love the water park at Windsor at Westside. Free access for all guests staying at the resort. What sets this water park apart from the rest is the majestic views overlooking the lake.

     Check out the kids splash park, lazy river, large lagoon style pool and private cabanas.

     If you are feeling in the mood for an ice cold drink, the poolside tiki bar can serve you up your favourite drink.

Team Sports Facilities - Windsor at Westside

     Windsor at Westside has amazing sports facilities to cater for travelling sports teams. Our villas can sleep from 6 - 22 people.

     Sports are one of the main features at Windsor at Westside - soccer field, muti purpose sports courts e.g tennis and basketball and sand volleyball courts.

There is also a kids playground.

Clubhouse at Windsor at Westside

     Spanish in style, the 10,000 square foot club house is a great place for friends and family to meet in the luxurious lounge and enjoy delicious food and drinks.

The arcade room will keep your kids entertained for hours.

Fitness Centre at Windsor at Westside

     Feeling energetic, check out the state of the art fitness centre with treadmills, free weights, all in one machine and bikes.

There are large floor to ceiling windows overlooking the water park.

Restaurant at Windsor at Westside

Tu Casa Bar and Lounge Restaurant

     Tu Casa Restaurant is great for casual dining serving a selection of mouth watering burgers, sandwiches and salads. You can dine here for breakfast, lunch or dinner. Great place to get all the family together.

     Happy hour is from 4pm to 7pm daily. You can enjoy your favourite drink whilst listening to Jimmy Buffet song and sounds of the caribbean.

Windsor at Westside sundry shop - you can also get all essentials here to enjoy a great vacation without having to leave the resort.


Private Chef and Bartender Experience direct to your Windsor and Westside vacation Home

     You may want to organise a special event e.g special birthday, team building event, renewing your vows etc

     Our experienced and highly skilled chefs and bartenders can prepare beaufful food and exotic drinks for your guests.

     So you can kick back and enjoy your special day from the comfort of your private vacation home.


Catering Delivery - Windsor at Westside

     If you are hosting a larger event e.g wedding, corporate meetings, retreats, parties, sports groups, or religious groups. The catering for this event can be arranged.

This can be hosted at your vacation home or another area within the encore resort.


Grocery and drink Delivery Service

     If you would like grocery and drinks delivered to your villa before arrival, please ask and all can be arranged for you.

Windsor at Westside Reviews

Windsor at Westside Resort Map - Florida


Windsor at Westside villas with Home Theatre

View all our Windsor at Westside villas with home theatre. Imagine relaxing with your family watching a great movie together while enjoying some popcorn.

View all Windsor at Westside Villas with Home Theatre

Windsor at Westside Villas with Games Room

Check out our Windsor at Westside villas with a game room. This will keep the kids and big kids at heart entertained for hours.

View all Windsor at Westside Villas with Games Room

Windsor at Westside Villas with Spa / Jacuzzi

Picture this...relaxing in your hot spa with an ice cold drink while your kids play in your private pool, Amazing.

View all Windsor at Westside Villas with Spa / Jacuzzi

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Properties on the Map

Meet Your Expert Travel Consultants

Our Story

In 2005, John Paul Donnelly, began his luxury villa journey. He spent three years building resorts and holiday apartments in Alanya, Turkey, along with his brother, Joe. The concept was to create the most luxurious villas on the Turkish coastline and provide clients, along with their family and friends, the opportunity to enjoy exclusive holidays together.

By 2008, after the successful development of 3 resorts, JP had well and truly fallen into the world of villa rentals. With a portfolio of 6 villas and a desire to explore new places, he decided it was time to take the villa rental business outside of Turkey. He wanted to give his clients access to beautiful holiday rentals in destinations across the globe.

The expanding villa rental company was rebranded in 2011 to 5 Star Villa Holidays, and today 5 Star Villa Holidays offers over 10,000 luxury villas around the world.

JP and his partner, Helena are currently travelling the globe, devoted to hand selecting the best villas and property management companies, and giving them their stamp of approval! 5 Star Villa Holidays' ambition goes beyond being an ordinary holiday rental company. It is a marketplace for luxurious and exclusive villas around the world.

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Helena Doyle

Please accept this FREE copy of “No More Stressful Travel Days! Here is a Proven Way to Travel in Style and Comfort with our Top 5 Secrets.” as my gift to you