5 Star Villa Holidays is proud to present Orlando Villa 1769. Windsor at Westside - Kissimmee, Florida is an upscale community located just 10 minutes from Walt Disney World. This luxury home sits nestled just outside of Orlando, Florida and has quickly become one of the most desired locations in the Orlando area. During your stay you will enjoy this well appointed home that has been designed and decorated to provide you and your family an abundance of luxury amenities and leaves you well equipped to vacation with all the usual items you would expect to find at home. Windsor at Westside is only a 30 minute drive from the Orlando International Airport, and is situated central to all of Orlando’s famous attractions. This spacious 4 bedroom holiday villa can comfortably accommodate a larger family or group of up to 8 people.
Home Features-
4 Bedrooms 3 Full Baths, 1Half bath Fully Equipped Kitchen with Granite Countertops and Stainless Steel Appliances Wireless Internet Patio with Outdoor Furniture and Spacious Deck Private Screened-in Splash Pool Full Size Washer/Dryer Dishwasher Central Air DVD Player Towels and Bed Linens Telephone with FREE Local Calls 2102 Square Feet Pool Direction West
Come stay in this wonderfully designed resort where you’ll enjoy luxury living at its finest. Whether you want to escape for peace and quiet, or would rather explore for a bit of adventure, Windsor at Westside can fulfill all of your desires. This resort community was developed with the discerning vacationer in mind offering privacy and peace, all just minutes away from Orlando’s famed attractions. Windsor at Westside was developed to ensure that it was close enough to access all that Orlando has to offer as well as to make certain there was plenty to do right within its gates. The neighborhood caters to groups, both family and business oriented, and continues to be one of the best and most sought after accommodations in the Orlando, Florida area.
Clubhouse Amenities
Resort Style Pool w/ Lazy River Outdoor Spa Children's Water Playground Tiki Bar Sand Volleyball Fitness center Game Room Sundry shop
One of the most loved homes on 5 Star Villa Holidays based on ratings, reviews and reliability
Overall rating
5
4
3
2
1
Cleanliness
4.8
Accuracy
4.8
Check In
4.8
Communication
4.8
Location
4.8
Value
4.8
Tommy, Little Rock, United States, Nov, 2021
3 Year(s) ago Stayed a few nights
Decent Air BnB could have been a little cleaner especially during covid. Was a bit confusing about w
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Brittany, Pasadena, United States, Nov, 2021
3 Year(s) ago Stayed a few nights
Great value for a big family vacation, spent most of our time at the parks. Make note that you have
Read More
Juan, Glendale, United States, Nov, 2021
3 Year(s) ago Stayed a few nights
Great location , easy access everything Will come again. Thank you Andy
Ruben, Brownsville, United States, Nov, 2021
3 Year(s) ago Stayed a few nights
We had a good time, but some of the furniture is getting long in the tooth.
Keria, Corona, United States, Nov, 2021
3 Year(s) ago Stayed a few nights
Our stay here was wonderful nice and clean good area very secured and spacious
Johana, Modesto, United States, Nov, 2021
3 Year(s) ago Stayed a few nights
The house was everything advertised, our experience was very good.
4.8
Guest favourite
One of the most loved homes on 5 Star Villa Holidays based on ratings, reviews and reliability
Overall rating
5
4
3
2
1
Cleanliness
4.8
Accuracy
4.8
Check in
4.8
Communication
4.8
Location
4.8
Value
4.8
6 Reviews
Tommy, Little Rock, United States, Nov, 2021
3 Year(s) ago Stayed a few nights
Decent Air BnB could have been a little cleaner especially during covid. Was a bit confusing about where the actual resort was when we contacted the owner, once it was clarified the resort was pretty nice!
Brittany, Pasadena, United States, Nov, 2021
3 Year(s) ago Stayed a few nights
Great value for a big family vacation, spent most of our time at the parks. Make note that you have to be ready for possible parking woes if you return late in the evening, especially if you have more than one vehicle for the unit. Overall great place with all the amenities needed.
Juan, Glendale, United States, Nov, 2021
3 Year(s) ago Stayed a few nights
Great location , easy access everything Will come again. Thank you Andy
Ruben, Brownsville, United States, Nov, 2021
3 Year(s) ago Stayed a few nights
We had a good time, but some of the furniture is getting long in the tooth.
Keria, Corona, United States, Nov, 2021
3 Year(s) ago Stayed a few nights
Our stay here was wonderful nice and clean good area very secured and spacious
Johana, Modesto, United States, Nov, 2021
3 Year(s) ago Stayed a few nights
The house was everything advertised, our experience was very good.
Helena Doyle Host
6
Reviews
4.8
Rating
10
years hosting
Host details
Currently travelling the world and working remotely, it's no surprise that Helena is the author of 5 Star Villa Holidays' collection of travel guides. She loves exploring new countries and experiencing new cultures. If you need some holiday tips, look no further! In her spare time she loves going to the gym, compiling her 'Living the Dream' travel blog and enjoying fine wines!
No services fees added, the price advertised is the price you pay with no hidden fees. Great!
Free Cancellation
Cancel within 48 hours of booking to get a full refund. More details.
Earn Villa Miles With This Booking
Happy days! You get credit to spend on your next 5 Star Villa Holiday. Expires 12 months from booking date.
Free Accidental Damage Insurance, Worth $1500
Your covered! If you accidentally break something, you will be covered up to $1500 Please note excess fees may apply.
Every 5 Star Villa Holiday Includes
Towels
Bed Linen
Free WiFi
Professional Clean
24/7 Client Support
Free Accidental Damage Insurance
No Hidden Fees
Meet the Team
John Paul Donnelly
Founder & CEO
John Paul's deep love for travel inspired him to turn his passion into a business and 5 Star Villa Holidays was founded in 2011. He is one of eight children and loves spending quality time with his larger-than-life family. In his spare time he loves immersing himself in different sporting activities around the world; skiing, surfing and football. He is always seeking new adventures and his philosophy is simple; love the journey of life.
Helena Doyle
Marketing Manager
Currently travelling the world and working remotely, it's no surprise that Helena is the author of 5 Star Villa Holidays' collection of travel guides. She loves exploring new countries and experiencing new cultures. If you need some holiday tips, look no further! In her spare time she loves going to the gym, compiling her 'Living the Dream' travel blog and enjoying fine wines!
Joe Donnelly
Sales Director
Living in Ireland, Joe is a family man with 2 beautiful daughters and a mischievous dog called Bruno. He is a very skilled chef who loves hosting dinner parties for family and friends. He is passionate about sport and boating. Joe is a keen golfer and loves nothing more than playing 18 holes on the best golf courses Europe has to offer. Joe has worked in the travel industry since 2005 and prides himself and his team as trustworthy travel experts.
Suzanne Pilcher
Creative Director
Born and raised by the beach in sunny Australia, Suzanne carries a deep-seeded affinity with the ocean and loves nothing more than exploring beautiful seaside destinations around the globe. As our travelling Creative, she is currently doing her best to experience and capture all that this incredible world has to offer, while living on a steady diet of coffee and art gallery visits.
Jitender Saini
Chief Technology Officer
Jitender Saini is our talented Chief Technology Officer, known for his exceptional programming skills and problem-solving abilities, honed since he started coding at the age of seven. A natural leader, he fosters innovation and excellence within his team. Jitender balances his professional life with personal commitments, being a devoted husband and father of two. Outside of work, he enjoys running, hiking, and playing cricket. His love for socialising shines through when he cooks delicious meals for friends and family, often paired with his appreciation for craft beers. Jitender’s passion and expertise are integral to our company’s success.
Amarpreet
Developer
As a Senior Web Developer at 5 Star Villa Holidays based in India, Amarpreet brings a blend of technical expertise, innovation, and teamwork to the role. Amarpreet primary focus is on developing solutions that engage the audience and drive business growth. Passionate about digital transformation, Amarpreet is committed to pushing the boundaries of web development and shaping the future of web experiences for 5 Star Villa Holidays. With a keen eye for detail and a dedication to excellence, Amarpreet continuously strives to enhance the company’s digital presence and overall user experience.
Ristley Rasonable
Executive Assistant
Hailing from the beautiful Philippines, Ristley lives with purpose, embracing every opportunity with gratitude. She often says, "Kindness and determination can move mountains." As a proud mom of four, including twin sons, she’s the calm in the storm, bringing order, efficiency, and care to every detail at 5 Star Villa Holidays. Ristley loves exploring nature, diving into a great book, and discovering new cuisines. She’s passionate about travel, creating lasting memories, and embracing new adventures.
Stephanie Peloriana
Expert Travel Consultant
Stephanie carries a profound philosophy in her heart: "All is well." It’s more than a belief; it’s a way of life that infuses her with calm resilience and optimism. Her favorite phrase, "memento vivere", meaning "remember to live," serves as both a reminder and a call to action, reflecting her deep appreciation for the fleeting yet beautiful nature of existence. At 5 Star Villa Holidays, Stephanie brings this same passion and mindfulness to her role, sharing her expertise in sales and creating unforgettable experiences for guests.
Emrah Guñes
Property Manager
Born in Erzincan, Turkey, Emrah is the youngest of eight siblings and a proud parent of four boys and two girls. His career journey began in accounting, followed by eight years as a stock tracking and warehouse shipment supervisor in the food industry. After 15 years as a call center team leader and manager, Emrah transitioned to property management with 5 Star Villa Holidays. He now combines his leadership skills and passion for hospitality to deliver exceptional experiences for guests.
Lisandra Varacha
Franchisee, 5 Star Villa Holidays
Lisandra is an open-minded traveler, active athlete, and nature lover with a deep appreciation for animals and culture. Her vibrant personality and career path span diverse fields, reflecting her adaptability and curiosity. A former professional equestrian, Lisandra combines discipline and grace with a passion for global exploration. At 5 Star Villa Holidays, she shares her dynamic perspective, creating opportunities for authentic and unforgettable travel experiences.
Meet the Team
John Paul Donnelly
Founder & CEO
John Paul's deep love for travel inspired him to turn his passion into a business and 5 Star Villa Holidays was founded in 2011. He is one of eight children and loves spending quality time with his larger-than-life family. In his spare time he loves immersing himself in different sporting activities around the world; skiing, surfing and football. He is always seeking new adventures and his philosophy is simple; love the journey of life.
Helena Doyle
Marketing Manager
Currently travelling the world and working remotely, it's no surprise that Helena is the author of 5 Star Villa Holidays' collection of travel guides. She loves exploring new countries and experiencing new cultures. If you need some holiday tips, look no further! In her spare time she loves going to the gym, compiling her 'Living the Dream' travel blog and enjoying fine wines!
Joe Donnelly
Sales Director
Living in Ireland, Joe is a family man with 2 beautiful daughters and a mischievous dog called Bruno. He is a very skilled chef who loves hosting dinner parties for family and friends. He is passionate about sport and boating. Joe is a keen golfer and loves nothing more than playing 18 holes on the best golf courses Europe has to offer. Joe has worked in the travel industry since 2005 and prides himself and his team as trustworthy travel experts.
Suzanne Pilcher
Creative Director
Born and raised by the beach in sunny Australia, Suzanne carries a deep-seeded affinity with the ocean and loves nothing more than exploring beautiful seaside destinations around the globe. As our travelling Creative, she is currently doing her best to experience and capture all that this incredible world has to offer, while living on a steady diet of coffee and art gallery visits.
Jitender Saini
Chief Technology Officer
Jitender Saini is our talented Chief Technology Officer, known for his exceptional programming skills and problem-solving abilities, honed since he started coding at the age of seven. A natural leader, he fosters innovation and excellence within his team. Jitender balances his professional life with personal commitments, being a devoted husband and father of two. Outside of work, he enjoys running, hiking, and playing cricket. His love for socialising shines through when he cooks delicious meals for friends and family, often paired with his appreciation for craft beers. Jitender’s passion and expertise are integral to our company’s success.
Amarpreet
Developer
As a Senior Web Developer at 5 Star Villa Holidays based in India, Amarpreet brings a blend of technical expertise, innovation, and teamwork to the role. Amarpreet primary focus is on developing solutions that engage the audience and drive business growth. Passionate about digital transformation, Amarpreet is committed to pushing the boundaries of web development and shaping the future of web experiences for 5 Star Villa Holidays. With a keen eye for detail and a dedication to excellence, Amarpreet continuously strives to enhance the company’s digital presence and overall user experience.
Ristley Rasonable
Executive Assistant
Hailing from the beautiful Philippines, Ristley lives with purpose, embracing every opportunity with gratitude. She often says, "Kindness and determination can move mountains." As a proud mom of four, including twin sons, she’s the calm in the storm, bringing order, efficiency, and care to every detail at 5 Star Villa Holidays. Ristley loves exploring nature, diving into a great book, and discovering new cuisines. She’s passionate about travel, creating lasting memories, and embracing new adventures.
Stephanie Peloriana
Expert Travel Consultant
Stephanie carries a profound philosophy in her heart: "All is well." It’s more than a belief; it’s a way of life that infuses her with calm resilience and optimism. Her favorite phrase, "memento vivere", meaning "remember to live," serves as both a reminder and a call to action, reflecting her deep appreciation for the fleeting yet beautiful nature of existence. At 5 Star Villa Holidays, Stephanie brings this same passion and mindfulness to her role, sharing her expertise in sales and creating unforgettable experiences for guests.
Emrah Guñes
Property Manager
Born in Erzincan, Turkey, Emrah is the youngest of eight siblings and a proud parent of four boys and two girls. His career journey began in accounting, followed by eight years as a stock tracking and warehouse shipment supervisor in the food industry. After 15 years as a call center team leader and manager, Emrah transitioned to property management with 5 Star Villa Holidays. He now combines his leadership skills and passion for hospitality to deliver exceptional experiences for guests.
Lisandra Varacha
Franchisee, 5 Star Villa Holidays
Lisandra is an open-minded traveler, active athlete, and nature lover with a deep appreciation for animals and culture. Her vibrant personality and career path span diverse fields, reflecting her adaptability and curiosity. A former professional equestrian, Lisandra combines discipline and grace with a passion for global exploration. At 5 Star Villa Holidays, she shares her dynamic perspective, creating opportunities for authentic and unforgettable travel experiences.
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What Our Clients Are Saying
Verified by
Great communication, very helpful and the villa was totally amazing even better than the photographs. I would highly recommend...
- Jessica Parkes, UK
EXCELLENT SERVICE!!!! I stayed in a Villa in Protaras that I rented from them. Joe was extremely nice and helpful. I strongly recommend this company. My next trip will surely include renting...
- Amanda Maalouf, Lebanon
We've used 5 star several times and they have been great. The test of any agency is when something goes wrong. This happen to us, nothing to do with 5 star, but we explained...
- Sid Gleeson, UK
We loved staying at the house. Will stay again and highly recommend to anyone! More than enough room and so close to everything...
- Laura Meeks, USA
5 star is now my number one pick for my vacations. They are very professional and always priced reasonably.
- Oneika, USA
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