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5 Star Villa Olympus – Elevated to Legendary Heights

Helena - Luxury Travel Expert at 5 Star Villa Holidays
Curated by Helena
Superhost 12 years hosting

5 Star Villa Holidays proudly presents 5 Star Villa Olympus – Elevated to Legendary Heights.

Ascend to a new level of luxury at this magnificent 8-bedroom, 6-bathroom Grand Category retreat, nestled within the prestigious Windsor at Westside Resort. Designed for unforgettable gatherings and legendary family escapes, Villa Olympus blends expansive elegance, immersive entertainment, and sun-drenched outdoor living — just 6 miles from the magic of Walt Disney World®.

Sleeping up to 16 guests, this extraordinary residence offers the perfect balance of refined comfort and playful imagination, making it an exceptional home base for experiencing the very best of Central Florida.

☀️ A Sun-Kissed Private Oasis

Step outside to your southwest-facing private pool and spa, perfectly positioned for maximum sunshine throughout the day. Whether you’re enjoying a morning swim, relaxing on one of four sun loungers, or dining al fresco with seating for four, every moment feels indulgent.

  • Private Pool + Spa

  • Optional pool heat ($30 per day + tax; spa heat requires pool heat activation)

  • Weekly professional pool service

  • Outdoor dining & lounge space


This is Florida living at its finest.

🎬 Entertainment Fit for the Gods

Inside, the villa is thoughtfully designed for both celebration and relaxation:

  • Expansive dining table with seating for 16 — ideal for shared meals and special occasions

  • Fully equipped gourmet kitchen with additional breakfast bar seating

  • Game room featuring pool table, foosball, and more

  • Smart TVs throughout the home

  • Pack n’ Play for little travelers


From lively game nights to peaceful movie evenings, Villa Olympus delivers entertainment on every level.

🛏️ Eight Bedrooms of Elevated Comfort

Each bedroom is beautifully appointed to provide privacy and restful luxury.

First Floor

  • King Suite with attached bathroom (43” TV)

  • Queen Bedroom (32” TV)


Second Floor

  • King Suite with attached bathroom (43” TV)

  • King Suite with attached bathroom (43” TV)

  • Queen Bedroom with Jack & Jill bathroom

  • Twin Bedroom (Harry Potter-themed)

  • Twin Bedroom (Mickey-themed)

  • Twin Bedroom (Frozen-themed)


The themed bedrooms bring imagination to life, while the spacious king suites offer serene retreats for adults.

🌴 Windsor at Westside Resort Privileges

Guests enjoy full access to the world-class amenities at Windsor at Westside Resort, including:

  • Resort-style zero-entry pool

  • Lazy river

  • Interactive splash park with water slide

  • Poolside tiki bar and restaurant

  • Fitness center

  • Arcade

  • Fire pit

  • Sand volleyball

  • Playground

  • Basketball and tennis courts


Everything you need for a resort-style vacation is just moments away.

📍 Prime Central Florida Location

  • Walt Disney World® – 6 miles

  • Universal Studios – 20 miles

  • SeaWorld – 16 miles

  • Orlando International Airport – 29 miles

  • Publix – 3 miles

  • Dining – 1.5 miles

  • Atlantic & Gulf Coast Beaches – under 90 miles


Adventure, dining, and entertainment are always within easy reach.

🌟 The 5 Star Villa Holidays Standard

  • Professionally managed with 26+ years of hosting experience

  • Over 200,000 families welcomed

  • Online email check-in for seamless arrival

  • 24/7 on-call maintenance

  • Smoke-free and pet-free environment

  • Complimentary WiFi

  • Towels and linens provided

  • Additional rental items available (BBQs, cribs, strollers, high chairs & more)


Parking is limited to 5 vehicles. Street parking and sidewalk blocking are not permitted. For security purposes, an exterior camera is located above the garage door.

Long-Stay Information (30+ Nights)

For extended stays of 30 nights or longer, a $1,500 deposit applies with specific cancellation terms and payment timelines.

5 Star Villa Olympus is more than a vacation home — it is a grand experience elevated to legendary heights. Whether you are gathering generations under one roof or celebrating life’s special milestones, this majestic retreat invites you to live, relax, and create memories worthy of the gods.

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Features

    Meals
  • Chef optional
  • Self Catering
    Housekeeping
  • Housekeeping optional
    Themes
  • Adventure
  • Away From It All
  • Family
  • Luxury
  • Spa
  • Sports and Activities
  • Tourist Attractions
    Location
  • Resort
    General
  • Air Conditioning
  • Clothes Dryer
  • Essentials
  • Free Wifi
  • Hair Dryer
  • Heating
  • Iron and Board
  • Laptop Friendly Workspace
  • Linens Provided
  • Living Room
  • Self Check in
  • Towels Provided
  • Washing Machine
    Kitchen
  • Coffee Maker
  • Dishes and Utensils
  • Dishwasher
  • Fully Equipped Kitchen
  • Kettle
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
    Dining
  • Dining Area
    Entertainment
  • Foosball Table
  • Pool Table
  • Satellite or Cable TV
  • TV in every bedroom
    Outside
  • Balcony
  • BBQ
  • Covered Lanai
  • Deck/Patio
  • Outdoor Dining Area
  • Sun Loungers
    Pool Spa
  • Heated Pool optional
  • Hot tub
  • Jacuzzi/Spa
  • Private Pool
    Outside Services
  • Airport Transfer - On Request, Additional Cost
  • Car Hire - On Request, Additional Cost
  • Experiences & Tours - On Request, Additional Cost
  • Free Parking
  • Private Chef - On Request, Additional Cost
  • Security 24/7
    Resort
  • Children's Playground
  • Children's Pool
  • Cinema
  • Club House
  • Communal Pool
  • Convenient Store
  • Fitness Centre
  • Games Room
  • Golf Course
  • Lazy River
  • Private Cabanas
  • Pro Shop
  • Spa centre
  • Spa/Jacuzzi
  • Soccer Fields
  • Tennis Courts
  • Tiki Bar
  • Volley Ball Courts
    HomeTruths
  • Family/Children Friendly
  • Long term renters welcome
  • Parking
  • Wheelchair Accessible
  • No smoking
  • Check In: 16:00
  • Check Out: 10:00
  • Size: 4034 SF
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    Sleeping Arrangements

  • Bedrooms 1:
    1 King bed
  • Bedrooms 2:
    1 Queen bed
  • Bedrooms 3:
    1 King bed
  • Bedrooms 4:
    1 Queen bed
  • Bedrooms 5:
    2 Twin beds
  • Bedrooms 6:
    2 Twin beds
  • Bedrooms 7:
    2 Twin beds
  • Bedrooms 8:
    1 King bed

Every 5 Star Villa Holiday Includes

  • Towels Towels
  • Bed Lines Bed Linen
  • Wifi Free WiFi
  • Clean Professional Clean
  • 24 support 24/7 Client Support
  • Free Accidental Free Accidental Damage Insurance
  • Hidden Fess No Hidden Fees

Windsor at Westside

Windsor at Westside : The Definitive Travel Guide
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Availability

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Cancellation Information Full Cancellation Conditions

  • Free cancellation within 48 hours of booking
  • Cancel up to 60 days before check in - balance refunded minus deposit
  • Cancel less than 60 days before check in - deposit & balance non-refundable
Helena - Luxury Travel Expert at 5 Star Villa Holidays
Helena Doyle Host

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!

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Meet the Team

John Paul Donnelly

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 - Luxury Travel Expert at 5 Star Villa Holidays

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

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

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

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

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

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

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

Emrah Guñes

Property Manager

Born in Erzincan, Türkiye, 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 - Luxury Travel Expert at 5 Star Villa Holidays

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

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 - Luxury Travel Expert at 5 Star Villa Holidays

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

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

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

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

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

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

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

Emrah Guñes

Property Manager

Born in Erzincan, Türkiye, 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 - Luxury Travel Expert at 5 Star Villa Holidays

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.