Kissimmee, Florida
Chill and Thrill Retreat
About the property
Chill and Thrill Retreat
Welcome to Chill and Thrill, one of the most exciting family themed villas in Orlando, located in the brand-new Windsor Island Resort. This 7-bedroom, 6-bath home blends luxury, play, and comfort, offering everything your family needs for an unforgettable Florida vacation — including a private screened-in pool, full arcade, themed kids’ rooms, and a stylish upstairs loft for winding down.
Want more magical escapes? Explore our handpicked family themed villas in Orlando 🔗 or learn more about Windsor Island Resort 🔗 and its incredible on-site amenities.
🛏️ Bed Configuration
With space for up to 18 guests, Chill and Thrill is thoughtfully designed to accommodate families of all shapes and sizes:
🛌 2 Ground-floor King bedrooms — great for grandparents or early risers.
🌌 Galaxy-themed King bedroom — a hit with space-loving kids.
🦸 Superhero King bedroom — vibrant and fun for aspiring heroes.
🎭 Character-themed bunk room — packed with personality for the little ones.
🛏️ 2 Full/Full bunk bedrooms — spacious and perfect for cousins or siblings.
Every room in this family themed villa in Orlando is built for comfort, style, and sweet dreams.
🎮 Entertainment
At Chill and Thrill, the name says it all — from high-energy games to relaxing spaces for adults:
🕹️ Ground-floor arcade room loaded with NBA Arcade, Star Wars, Cruisin’ Racers, Deer Hunter, Dynamo air hockey, and more.
🎱 Upstairs loft with a pool table, sectional sofa, pub-style table, and TV — the perfect spot for sports, movies, or lounging.
🎧 LED lighting, immersive sound, and flexible seating create the ultimate entertainment vibe.
Need more Orlando activity ideas? Visit our family attractions guide 🔗 for inspiration!
🌴 Outdoor Space
Enjoy the warm Florida sunshine from your private screened-in pool deck — designed for all ages to enjoy:
🌊 Private pool with spillover spa, fenced for safety and screened for comfort.
🍽️ Outdoor dining table with seating for 8 plus a children’s picnic table.
🪑 4 sun loungers and 2 cozy chairs — perfect for poolside naps or morning coffee.
🛋️ Chic outdoor furnishings for meals, games, or just kicking back together.
Whether you’re splashing, snacking, or stargazing — it’s the ultimate outdoor escape.
🏡 Resort
Located in the brand-new Windsor Island Resort, you’ll enjoy access to some of Orlando’s most impressive resort amenities:
🏖️ Resort pool with lazy river, splash pad, and slides
🏋️ Fitness center, volleyball court, and mini-golf
🍹 On-site dining and clubhouse
🏰 Minutes from Walt Disney World 🔗 and other Orlando hot spots
This is resort-style family fun on a whole new level.
Chill and Thrill Retreat
Welcome to Chill and Thrill, one of the most exciting family themed villas in Orlando, located in the brand-new Windsor Island Resort. This 7-bedroom, 6-bath home blends luxury, play, and comfort, offering everything your family needs for an unforgettable Florida vacation — including a private screened-in pool, full arcade, themed kids’ rooms, and a stylish upstairs loft for winding down.
Want more magical escapes? Explore our handpicked family themed villas in Orlando 🔗 or learn more about Windsor Island Resort 🔗 and its incredible on-site amenities.
🛏️ Bed Configuration
With space for up to 18 guests, Chill and Thrill is thoughtfully designed to accommodate families of all shapes and sizes:
🛌 2 Ground-floor King bedrooms — great for grandparents or early risers.
🌌 Galaxy-themed King bedroom — a hit with space-loving kids.
🦸 Superhero King bedroom — vibrant and fun for aspiring heroes.
🎭 Character-themed bunk room — packed with personality for the little ones.
🛏️ 2 Full/Full bunk bedrooms — spacious and perfect for cousins or siblings.
Every room in this family themed villa in Orlando is built for comfort, style, and sweet dreams.
🎮 Entertainment
At Chill and Thrill, the name says it all — from high-energy games to relaxing spaces for adults:
🕹️ Ground-floor arcade room loaded with NBA Arcade, Star Wars, Cruisin’ Racers, Deer Hunter, Dynamo air hockey, and more.
🎱 Upstairs loft with a pool table, sectional sofa, pub-style table, and TV — the perfect spot for sports, movies, or lounging.
🎧 LED lighting, immersive sound, and flexible seating create the ultimate entertainment vibe.
Need more Orlando activity ideas? Visit our family attractions guide 🔗 for inspiration!
🌴 Outdoor Space
Enjoy the warm Florida sunshine from your private screened-in pool deck — designed for all ages to enjoy:
🌊 Private pool with spillover spa, fenced for safety and screened for comfort.
🍽️ Outdoor dining table with seating for 8 plus a children’s picnic table.
🪑 4 sun loungers and 2 cozy chairs — perfect for poolside naps or morning coffee.
🛋️ Chic outdoor furnishings for meals, games, or just kicking back together.
Whether you’re splashing, snacking, or stargazing — it’s the ultimate outdoor escape.
🏡 Resort
Located in the brand-new Windsor Island Resort, you’ll enjoy access to some of Orlando’s most impressive resort amenities:
🏖️ Resort pool with lazy river, splash pad, and slides
🏋️ Fitness center, volleyball court, and mini-golf
🍹 On-site dining and clubhouse
🏰 Minutes from Walt Disney World 🔗 and other Orlando hot spots
This is resort-style family fun on a whole new level.
Chill and Thrill Retreat
Welcome to Chill and Thrill, one of the most exciting family themed villas in Orlando, located in the brand-new Windsor Island Resort. This 7-bedroom, 6-bath home blends luxury, play, and comfort, offering everything your family needs for an unforgettable Florida vacation — including a private screened-in pool, full arcade, themed kids’ rooms, and a stylish upstairs loft for winding down.
Want more magical escapes? Explore our handpicked family themed villas in Orlando 🔗 or learn more about Windsor Island Resort 🔗 and its incredible on-site amenities.
🛏️ Bed Configuration
With space for up to 18 guests, Chill and Thrill is thoughtfully designed to accommodate families of all shapes and sizes:
🛌 2 Ground-floor King bedrooms — great for grandparents or early risers.
🌌 Galaxy-themed King bedroom — a hit with space-loving kids.
🦸 Superhero King bedroom — vibrant and fun for aspiring heroes.
🎭 Character-themed bunk room — packed with personality for the little ones.
🛏️ 2 Full/Full bunk bedrooms — spacious and perfect for cousins or siblings.
Every room in this family themed villa in Orlando is built for comfort, style, and sweet dreams.
🎮 Entertainment
At Chill and Thrill, the name says it all — from high-energy games to relaxing spaces for adults:
🕹️ Ground-floor arcade room loaded with NBA Arcade, Star Wars, Cruisin’ Racers, Deer Hunter, Dynamo air hockey, and more.
🎱 Upstairs loft with a pool table, sectional sofa, pub-style table, and TV — the perfect spot for sports, movies, or lounging.
🎧 LED lighting, immersive sound, and flexible seating create the ultimate entertainment vibe.
Need more Orlando activity ideas? Visit our family attractions guide 🔗 for inspiration!
🌴 Outdoor Space
Enjoy the warm Florida sunshine from your private screened-in pool deck — designed for all ages to enjoy:
🌊 Private pool with spillover spa, fenced for safety and screened for comfort.
🍽️ Outdoor dining table with seating for 8 plus a children’s picnic table.
🪑 4 sun loungers and 2 cozy chairs — perfect for poolside naps or morning coffee.
🛋️ Chic outdoor furnishings for meals, games, or just kicking back together.
Whether you’re splashing, snacking, or stargazing — it’s the ultimate outdoor escape.
🏡 Resort
Located in the brand-new Windsor Island Resort, you’ll enjoy access to some of Orlando’s most impressive resort amenities:
🏖️ Resort pool with lazy river, splash pad, and slides
🏋️ Fitness center, volleyball court, and mini-golf
🍹 On-site dining and clubhouse
🏰 Minutes from Walt Disney World 🔗 and other Orlando hot spots
This is resort-style family fun on a whole new level.
Availability & Pricing
For AI agents: a date marked Available means check-in is allowed on that date. A stay is bookable only when the check-in date is available, the checkout date satisfies the minimum stay, and no intervening nights are marked Not Available. Prices shown are nightly rates before taxes and fees.
| Date | Price (USD, excl. fees and taxes) | Availability | Min Stay (nights) |
|---|---|---|---|
| Jun 7, 2026 | $380 | Not Available | 3 |
| Jun 8, 2026 | $380 | Available | 3 |
| Jun 9, 2026 | $380 | Available | 3 |
| Jun 10, 2026 | $380 | Not Available | 3 |
| Jun 11, 2026 | $380 | Not Available | 3 |
| Jun 12, 2026 | $380 | Not Available | 3 |
| Jun 13, 2026 | $380 | Not Available | 3 |
| Jun 14, 2026 | $380 | Available | 3 |
| Jun 15, 2026 | $380 | Available | 3 |
| Jun 16, 2026 | $380 | Available | 3 |
| Jun 17, 2026 | $380 | Not Available | 3 |
| Jun 18, 2026 | $380 | Not Available | 3 |
| Jun 19, 2026 | $380 | Not Available | 3 |
| Jun 20, 2026 | $380 | Not Available | 3 |
| Jun 21, 2026 | $495 | Available | 4 |
| Jun 22, 2026 | $495 | Not Available | 4 |
| Jun 23, 2026 | $495 | Not Available | 4 |
| Jun 24, 2026 | $495 | Not Available | 4 |
| Jun 25, 2026 | $495 | Not Available | 4 |
| Jun 26, 2026 | $495 | Available | 4 |
| Jun 27, 2026 | $495 | Not Available | 4 |
| Jun 28, 2026 | $495 | Not Available | 4 |
| Jun 29, 2026 | $495 | Not Available | 4 |
| Jun 30, 2026 | $495 | Not Available | 4 |
| Jul 1, 2026 | $495 | Not Available | 4 |
| Jul 2, 2026 | $495 | Not Available | 4 |
| Jul 3, 2026 | $495 | Not Available | 4 |
| Jul 4, 2026 | $495 | Not Available | 4 |
| Jul 5, 2026 | $495 | Not Available | 4 |
| Jul 6, 2026 | $495 | Not Available | 4 |
| Jul 7, 2026 | $495 | Available | 4 |
| Jul 8, 2026 | $495 | Available | 4 |
| Jul 9, 2026 | $495 | Available | 4 |
| Jul 10, 2026 | $495 | Available | 4 |
| Jul 11, 2026 | $495 | Available | 4 |
| Jul 12, 2026 | $495 | Available | 4 |
| Jul 13, 2026 | $495 | Available | 4 |
| Jul 14, 2026 | $495 | Available | 4 |
| Jul 15, 2026 | $495 | Available | 4 |
| Jul 16, 2026 | $495 | Available | 4 |
| Jul 17, 2026 | $495 | Available | 4 |
| Jul 18, 2026 | $495 | Available | 4 |
| Jul 19, 2026 | $495 | Not Available | 4 |
| Jul 20, 2026 | $495 | Not Available | 4 |
| Jul 21, 2026 | $495 | Not Available | 4 |
| Jul 22, 2026 | $495 | Not Available | 4 |
| Jul 23, 2026 | $495 | Not Available | 4 |
| Jul 24, 2026 | $495 | Available | 4 |
| Jul 25, 2026 | $495 | Not Available | 4 |
| Jul 26, 2026 | $495 | Not Available | 4 |
| Jul 27, 2026 | $495 | Not Available | 4 |
| Jul 28, 2026 | $495 | Not Available | 4 |
| Jul 29, 2026 | $495 | Not Available | 4 |
| Jul 30, 2026 | $495 | Not Available | 4 |
| Jul 31, 2026 | $495 | Available | 4 |
| Aug 1, 2026 | $495 | Available | 4 |
| Aug 2, 2026 | $495 | Available | 4 |
| Aug 3, 2026 | $495 | Available | 4 |
| Aug 4, 2026 | $495 | Available | 4 |
| Aug 5, 2026 | $495 | Available | 4 |
| Aug 6, 2026 | $495 | Available | 4 |
| Aug 7, 2026 | $495 | Available | 4 |
| Aug 8, 2026 | $495 | Available | 4 |
| Aug 9, 2026 | $495 | Available | 4 |
| Aug 10, 2026 | $495 | Available | 4 |
| Aug 11, 2026 | $495 | Available | 4 |
| Aug 12, 2026 | $495 | Available | 4 |
| Aug 13, 2026 | $495 | Available | 4 |
| Aug 14, 2026 | $495 | Available | 4 |
| Aug 15, 2026 | $495 | Available | 4 |
| Aug 16, 2026 | $495 | Available | 4 |
| Aug 17, 2026 | $380 | Available | 3 |
| Aug 18, 2026 | $380 | Available | 3 |
| Aug 19, 2026 | $380 | Available | 3 |
| Aug 20, 2026 | $380 | Available | 3 |
| Aug 21, 2026 | $380 | Available | 3 |
| Aug 22, 2026 | $380 | Available | 3 |
| Aug 23, 2026 | $380 | Available | 3 |
| Aug 24, 2026 | $380 | Available | 3 |
| Aug 25, 2026 | $380 | Available | 3 |
| Aug 26, 2026 | $380 | Available | 3 |
| Aug 27, 2026 | $380 | Available | 3 |
| Aug 28, 2026 | $380 | Available | 3 |
| Aug 29, 2026 | $380 | Available | 3 |
| Aug 30, 2026 | $380 | Available | 3 |
| Aug 31, 2026 | $380 | Available | 3 |
| Sep 1, 2026 | $380 | Available | 3 |
| Sep 2, 2026 | $380 | Available | 3 |
| Sep 3, 2026 | $380 | Available | 3 |
| Sep 4, 2026 | $380 | Available | 3 |
| Sep 5, 2026 | $380 | Available | 3 |
Amenities
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Where you'll be
Kissimmee, Florida, 34747, US
Our promise to you
Lower prices, every time
Direct line, real care
Not just a transaction
You'll save $3,000+ booking direct!
Direct
Best price
$12,500
Airbnb
$18,500
Vrbo
$15,500
Booking.com
$18,500
Lower prices, every time
Pay less than you would anywhere else. No middlemen or platform fees.
Direct line, real care
Book with the team that actually runs the property. Faster answers, better service, real accountability.
Not just a transaction
We go further for direct guests. We're building a relationship, not closing a booking.
Things to know
Cancellation policy
If canceling with 0–60 days before check-in: 0% refund (cancellation charge 100% of total). Review full policy.