Surprise your family with a trip to Disney and world class theme parks! ...while enjoying all the enormous amount of amenities that this resort offers!
Spend your best memories under amenities galore!
One is faster, the other more adventurous!
Magic is calling!
Enjoy an expansive dining room that flows into a Mickey Themed living room.

Windsor Hills Mickey’s Dream Home, 2mi to Disney!

3 bedrooms·2 baths
Kissimmee • Florida
4.84(267 reviews)

$580.42 USD total for 3 nights

Nov 7 – 10, 2026

Main
Your Sun, Fun and Everything Disney Destination!
Your Sun, Fun and Everything Disney Destination!
Your Sun, Fun and Everything Disney Destination!
Your Sun, Fun and Everything Disney Destination!

Your Sun, Fun and Everything Disney Destination!

3 bedrooms·2 baths
Kissimmee • Florida
5(4 reviews)

$635.60 USD total for 3 nights

Oct 26 – 29, 2026

Your Home Away From the Magic
Your Home Away From the Magic
Your Home Away From the Magic
Your Home Away From the Magic
Your Home Away From the Magic

Your Home Away From the Magic

2 bedrooms·2 baths
Kissimmee • Florida

$300.00 USD total for 3 nights

Oct 26 – 29, 2026

Kitchen
Kitchen
Kitchen Coffee Station
Kitchen
Living Room

Magic Holiday House

3 bedrooms·3 baths
Kissimmee • Florida

$662.84 USD total for 3 nights

Oct 27 – 30, 2026

Townhouse near Disney w/ pool & game room
Townhouse near Disney w/ pool & game room
Townhouse near Disney w/ pool & game room
Townhouse near Disney w/ pool & game room
Townhouse near Disney w/ pool & game room

Townhouse near Disney w/ pool & game room

3 bedrooms·3 baths
Kissimmee • Florida

$841.04 USD total for 3 nights

Oct 26 – 29, 2026

3BR Pool Home | 10 Min to Disney | Sleeps 10 image 1
3BR Pool Home | 10 Min to Disney | Sleeps 10 image 2
Spacious living room with comfortable seating for the whole group.
3BR Pool Home | 10 Min to Disney | Sleeps 10 image 4
3BR Pool Home | 10 Min to Disney | Sleeps 10 image 5

3BR Pool Home | 10 Min to Disney | Sleeps 10

3 bedrooms·2 baths
Kissimmee • Florida
5(3 reviews)

$757.00 USD total for 3 nights

Nov 30 – Dec 3, 2026

Slow mornings. Warm sun. A peaceful pool to enjoy: Your time to disconnect starts here.
A space that invites you to slow down: Where rest comes naturally and stress fades away.
Simple, elegant, and effortlessly relaxing: Your home away from home starts here.
Warm light, fresh coffee, and a peaceful start: The perfect way to begin your day.
Where comfort meets thoughtful design: The perfect place to end your day.

3 Full Baths | Resort Pool | 10 Min to Disney

3 bedrooms·3 baths
Kissimmee • Florida
Crush's favorite way to sleep.
relaxation after walking all day!
Crush Crash Pad WDW Vacation Villa
Crush Crash Pad WDW Vacation Villa
Relaxing Lakeview pool with hand- rails

Crush Crash Pad WDW Vacation Villa

6 bedrooms·4 baths
Kissimmee • Florida
5(1 review)

$1,660.23 USD total for 3 nights

Oct 26 – 29, 2026

The lanai has a table that seats 8, privacy bushes, 4 lounge chairs & BBQ
The outdoor table under the lanai seats 8 and the pool has a security fence
The Game room has a pool table, air hockey, foosball, & Air Conditioning
Private screened in, heated salt water pool and spa with oversized pool deck
The covered lanai, lounge chairs & basketball hoop, salt water pool & spa

Villa By The Castle

6 bedrooms·4 baths
Kissimmee • Florida
5(385 reviews)

$2,298.38 USD total for 3 nights

Nov 11 – 14, 2026

Mickey's pool & spa
Beautiful lake view from the pool
Handrails for easy entry
Windsor Hills Resort
Conservation pond out back

Chilllax Inn Daulby

6 bedrooms·4 baths
Kissimmee • Florida

$1,359.61 USD $1,239.12 USD total for 3 nights

Oct 26 – 29, 2026

Starlight Kingdom - Windsor Hills Resort image 1
Starlight Kingdom - Windsor Hills Resort image 2
Starlight Kingdom - Windsor Hills Resort image 3
Starlight Kingdom - Windsor Hills Resort image 4
Starlight Kingdom - Windsor Hills Resort image 5

Starlight Vacation Homes

3 bedrooms·3 baths
Four Corners • Florida
5(7 reviews)

$819.47 USD total for 3 nights

Dec 12 – 15, 2026

Pool
Front of house
Entry
Open area
Dreams Come True Villa LLC

Dreams Come True Villa LLC

5 bedrooms·5 baths
Kissimmee • Florida
4.93(27 reviews)

$1,897.54 USD total for 5 nights

Nov 11 – 16, 2026

Pool and Patio Area
Our Windsor Hills Water Park!
Welcome to Windsor Hills!
Layout of our 6BR 4 BA Disney Villa
Air-Conditioned Game room with air hockey, two video games, Basketball and fun for kids and teenagers!

Waterpark! 5 Star 6BR4BA Pool/Game Room/Disney

6 bedrooms·4 baths
Kissimmee • Florida
4.84(122 reviews)

$1,332.85 USD $1,137.40 USD total for 3 nights

Oct 26 – 29, 2026

Living room with new ceiling fan and view of saltwater pool.
Custom pool featuring Cinderella's Castle and fireworks display.
South facing saltwater pool with sun loungers.
Princesses Assemble
Princesses Assemble

Princesses Assemble

5 bedrooms·5 baths
Kissimmee • Florida
4.96(53 reviews)

$1,502.29 USD $1,201.81 USD total for 5 nights

Nov 15 – 20, 2026

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

$2,181.40 USD $1,985.19 USD total for 3 nights

Dec 20 – 23, 2026

The living room has direct access to the pool.
Come swim in the coolest pool in the galaxy!
A Villa Far, Far Away
The Jedi Master bedroom with custom made accent wall and king size bed.
The bed in the Sith bedroom also lights up!

A Villa Far, Far Away

5 bedrooms·5 baths
Kissimmee • Florida
4.92(26 reviews)

$1,662.33 USD $1,321.83 USD total for 5 nights

Nov 2 – 7, 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)

$2,123.00 USD total for 7 nights

Oct 26 – Nov 2, 2026

Swift BnB - Taylor themed rooms - Pool - sleeps 16
Swift BnB - Taylor themed rooms - Pool - sleeps 16
Swift BnB - Taylor themed rooms - Pool - sleeps 16
Swift BnB - Taylor themed rooms - Pool - sleeps 16
Swift BnB - Taylor themed rooms - Pool - sleeps 16

Swift BnB - Taylor themed rooms - Pool - sleeps 16

8 bedrooms·7 baths
Kissimmee • Florida
5(10 reviews)

$1,461.31 USD $1,303.50 USD total for 3 nights

Oct 26 – 29, 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

$1,356.70 USD total for 3 nights

Nov 17 – 20, 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

$1,341.48 USD total for 3 nights

Oct 26 – 29, 2026

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

$3,361.33 USD total for 3 nights

Nov 17 – 20, 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 $748.87 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

$1,212.47 USD total for 3 nights

Oct 26 – 29, 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 26 – 29, 2026