Welcome to Chillax Inn Teascone Arcade
Free Arcade in the garage!
Chill on the couch
Windsor Hills amenities
Brrr!

Chillax Inn Teascone Arcade

5 bedrooms·5 baths
Kissimmee • Florida

$1,036.69 USD $938.60 USD total for 3 nights

Oct 20 – 23, 2026

Star Wars, Frozen, and Moana Escape! August open!
Star Wars, Frozen, and Moana Escape! August open!
Star Wars, Frozen, and Moana Escape! August open!
Star Wars, Frozen, and Moana Escape! August open!
Star Wars, Frozen, and Moana Escape! August open!

Star Wars, Frozen, and Moana Escape! August open!

4 bedrooms·1 bath
Kissimmee • Florida
5(7 reviews)

$2,113.00 USD total for 7 nights

Oct 20 – 27, 2026

Embassy by Hilton, Orlando 2 Double Suite image 1
Embassy by Hilton, Orlando 2 Double Suite image 2
Embassy by Hilton, Orlando 2 Double Suite image 3
Embassy by Hilton, Orlando 2 Double Suite image 4
Embassy by Hilton, Orlando 2 Double Suite image 5

Embassy by Hilton, Orlando 2 Double Suite

1 bedroom·1 bath
Orlando • Florida

$1,053.00 USD total for 3 nights

Oct 20 – 23, 2026

Embassy by Hilton, Orlando King Suite image 1
Embassy by Hilton, Orlando King Suite image 2
Embassy by Hilton, Orlando King Suite image 3
Embassy by Hilton, Orlando King Suite image 4
Embassy by Hilton, Orlando King Suite image 5

Embassy by Hilton, Orlando King Suite

1 bedroom·1 bath
Orlando • Florida

$1,053.00 USD total for 3 nights

Oct 20 – 23, 2026

Remarkable Themed Home with Resort Amenities
Remarkable Themed Home with Resort Amenities
Remarkable Themed Home with Resort Amenities
Remarkable Themed Home with Resort Amenities
Remarkable Themed Home with Resort Amenities

Remarkable Themed Home with Resort Amenities

6 bedrooms·4 baths
Kissimmee • Florida

$1,188.08 USD total for 3 nights

Oct 24 – 27, 2026

Neon arcade game room
Arcade racing simulators
Private screened pool and spa at twilight
Front of home at twilight
Spacious living room

Magical Themed Home, Arcade, Private Pool/Spa, Resort Amenities

6 bedrooms·4 baths
Kissimmee • Florida
$241 – $846/ night(excl. fees & taxes)
Twin Mansions: Both homes from the street
Twin Mansions: Aerial view of the homes and pools
Twin Mansions: Aerial of both homes and pools
Twin Mansions: Both homes and pools from the rear
Magical Home: Private screened pool and spa at twilight

The Windsor Hills Twin Mansions

12 bedrooms·8 baths
Kissimmee • Florida
$749 – $3,457/ night(excl. fees & taxes)
Moana kids' room with bunk bed
Comfort and relaxation is the theme for our master bedrooms. It is complete with a king-sized memory foam bed, a Smart Roku TV for your entertainment needs, and its own spacious en-suite bathroom
Nemo kids' room with a custom bunk bed wall mounted TV, and color changing lights.
Pool with lake-view. (pool heat available)
Beautiful pool and lake-view from the living room.

Lakeview Luxury Villa w/ Pool Heat available

5 bedrooms·3 baths
Davenport • Florida
4.94(80 reviews)

$898.64 USD $798.34 USD total for 3 nights

Oct 25 – 28, 2026

Chillax Inn the pool area under the big lanai
Frozen Bedroom with double
Welcome to Chillax Inn Teascone
Windsor Hills Slides
Star Wars Bedroom with two doubles

Chillax Inn Teascone

4 bedrooms·4 baths
Kissimmee • Florida

$812.32 USD total for 3 nights

Nov 2 – 5, 2026

Family Room with comfy couch and 70" TV with Cable
Free Heat Salt Water Pool & Spa
Star Wars Game Room with Pool, Foosball and PS5 with Games
Stocked Kitchen with Quartz Counter and stainless steel appliances
Free Access to the Windsor Hills Resort's community pool, dueling slides and splash pad play area!

Central Breeze Villa

6 bedrooms·4 baths
Kissimmee • Florida

$1,283.98 USD total for 3 nights

Oct 24 – 27, 2026

Relax on our extended screened pool deck that allows for full sunshine all day year round!
Enjoy endless game night possibilities in the Star Wars themed game room.
Experience a true home away from home in retreat in our first floor primary bedroom boasting a view of the pool and a tranquil ensuite bathroom for the ultimate comfort.
The Force is strong in the Star Wars themed hall, bathroom and bedroom.
Windsor Hills is Minutes From the Magic of Disney World

Pooh's Palace in Windsor Hills, Near Walt Disney World

5 bedrooms·5 baths
Kissimmee • Florida

$1,083.93 USD total for 3 nights

Oct 24 – 27, 2026

Welcome to Chillax Inn Pawnall
Pool and spa
Toy Story upstairs bedroom
Windsor Hills water slides
Star Wars upstairs bedroom

Chillax Inn Pawnall

5 bedrooms·5 baths
Kissimmee • Florida

$950.84 USD total for 3 nights

Nov 1 – 4, 2026

Retro lake Eola 1 Bedroom Condo Thornton park
Retro lake Eola 1 Bedroom Condo Thornton park
Retro lake Eola 1 Bedroom Condo Thornton park
Retro lake Eola 1 Bedroom Condo Thornton park
Retro lake Eola 1 Bedroom Condo Thornton park

Retro lake Eola 1 Bedroom Condo Thornton park

1 bedroom·1 bath
Orlando • Florida
4.7(302 reviews)

$444.15 USD $425.17 USD total for 3 nights

Oct 29 – Nov 1, 2026

Lake Eola view 1 bedroom Thornton Park
Lake Eola view 1 bedroom Thornton Park
Lake Eola view 1 bedroom Thornton Park
Lake Eola view 1 bedroom Thornton Park
Lake Eola view 1 bedroom Thornton Park

Lake Eola view 1 bedroom Thornton Park

1 bedroom·1 bath
Orlando • Florida
4.64(256 reviews)

$346.63 USD $332.53 USD total for 3 nights

Oct 26 – 29, 2026

Vintage 2 Bedroom Condo Lake Eola View
Vintage 2 Bedroom Condo Lake Eola View
Vintage 2 Bedroom Condo Lake Eola View
Vintage 2 Bedroom Condo Lake Eola View
Vintage 2 Bedroom Condo Lake Eola View

Vintage 2 Bedroom Condo Lake Eola View

2 bedrooms·1½ baths
Orlando • Florida
5(1 review)

$473.53 USD $453.68 USD total for 3 nights

Oct 25 – 28, 2026

Location Lake Eola View 1 Bedroom condo
Location Lake Eola View 1 Bedroom condo
Location Lake Eola View 1 Bedroom condo
Location Lake Eola View 1 Bedroom condo
Location Lake Eola View 1 Bedroom condo

Location Lake Eola View 1 Bedroom condo

1 bedroom·1 bath
Orlando • Florida

$413.60 USD $396.15 USD total for 3 nights

Oct 20 – 23, 2026

Modern Lake Eola Condo in the Heart of Thornton Park
Modern Lake Eola Condo in the Heart of Thornton Park
Modern Lake Eola Condo in the Heart of Thornton Park
Modern Lake Eola Condo in the Heart of Thornton Park
Modern Lake Eola Condo in the Heart of Thornton Park

Modern Lake Eola Condo in the Heart of Thornton Park

1 bedroom·1 bath
Orlando • Florida
5(1 review)

$413.60 USD $396.15 USD total for 3 nights

Oct 20 – 23, 2026

Renovated Condo Lake Eola View Great Location
Renovated Condo Lake Eola View Great Location
Renovated Condo Lake Eola View Great Location
Renovated Condo Lake Eola View Great Location
Renovated Condo Lake Eola View Great Location

Renovated Condo Lake Eola View Great Location

1 bedroom·1 bath
Orlando • Florida
5(2 reviews)

$413.60 USD $396.15 USD total for 3 nights

Oct 20 – 23, 2026

The Hogwarts Express has a Windsor Hills station in the game room of Villa 9 3/4.
Access to the community pool and waterslide are included free of charge with your rental. The community pool is a 15 minute walk from the house and has free onsite parking.
Welcome to Hogwarts! Our Hufflepuff Commons is the perfect place to hangout. It features a 75" smart TV and a custom made Nimbus 2000.
The Gryffindor dormitory features a custom made canopy bunk bed with two full size beds.
The Beauxbaton Castle is the perfect place to learn some wizardry.

Villa 9 3/4

6 bedrooms·4 baths
Kissimmee • Florida
4.75(28 reviews)

$2,460.23 USD $2,352.80 USD total for 5 nights

Nov 21 – 26, 2026

Lake Eola Thornton Park Studio with Balcony
Lake Eola Thornton Park Studio with Balcony
Lake Eola Thornton Park Studio with Balcony
Lake Eola Thornton Park Studio with Balcony
Lake Eola Thornton Park Studio with Balcony

Lake Eola Thornton Park Studio with Balcony

0 bedrooms·1 bath
Orlando • Florida
4.93(46 reviews)

$381.88 USD $366.02 USD total for 3 nights

Oct 20 – 23, 2026

Historic Home Lake Eola 1 Bedroom oasis Thornton Park
Historic Home Lake Eola 1 Bedroom oasis Thornton Park
Historic Home Lake Eola 1 Bedroom oasis Thornton Park
Historic Home Lake Eola 1 Bedroom oasis Thornton Park
Historic Home Lake Eola 1 Bedroom oasis Thornton Park

Historic Home Lake Eola 1 Bedroom oasis Thornton Park

1 bedroom·1 bath
Orlando • Florida
5(26 reviews)

$411.25 USD $393.92 USD total for 3 nights

Oct 31 – Nov 3, 2026

Historic Lake Eola studio Thornton Park
Historic Lake Eola studio Thornton Park
Historic Lake Eola studio Thornton Park
Historic Lake Eola studio Thornton Park
Historic Lake Eola studio Thornton Park

Historic Lake Eola studio Thornton Park

0 bedrooms·1 bath
Orlando • Florida
5(11 reviews)

$364.25 USD $349.27 USD total for 3 nights

Oct 20 – 23, 2026

Thornton park paradise 1 bedroom Lake Eola
Thornton park paradise 1 bedroom Lake Eola
Thornton park paradise 1 bedroom Lake Eola
Thornton park paradise 1 bedroom Lake Eola
Thornton park paradise 1 bedroom Lake Eola

Thornton park paradise 1 bedroom Lake Eola

1 bedroom·1 bath
Orlando • Florida
4.91(22 reviews)

$364.25 USD $349.27 USD total for 3 nights

Oct 20 – 23, 2026

Disney Playhouse, everything you need
Disney Playhouse, everything you need
Disney Playhouse, everything you need
Disney Playhouse, everything you need
Disney Playhouse, everything you need

Disney Playhouse, everything you need

3 bedrooms·2 baths
Kissimmee • Florida
4.92(133 reviews)

$886.43 USD total for 3 nights

Oct 23 – 26, 2026