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!
One is faster, the other more adventurous!
Spend your best memories under amenities galore!
Magic is calling!
Relax, watch a movie in a Mickey Themed living room on brand new 58' LED Smart TVs.

New! Windsor Hills Magical Retreat, 2mi to Disney!

3 bedrooms·2 baths
Kissimmee • Florida
5(12 reviews)

$ 751,75 USD totaal voor 5 nachten

24–29 okt 2026

VS034 - The Villa of Somerset - Privacy - Apartment - 2rd Floor
VS034 - The Villa of Somerset - Privacy - Apartment - 2rd Floor
VS034 - The Villa of Somerset - Privacy - Apartment - 2rd Floor
VS034 - The Villa of Somerset - Privacy - Apartment - 2rd Floor
VS034 - The Villa of Somerset - Privacy - Apartment - 2rd Floor

VS034 - The Villa of Somerset - Privacy - Apartment - 2rd Floor

3 bedrooms·2 baths
Kissimmee • Florida

$ 752,00 USD totaal voor 4 nachten

29 sep – 3 okt 2026

Dress up area
Princess castle
View to the pool
Windsor Hills Resort amenities free with your stay!
Chillax by the pool

Chillax Inn Fitzclarence

3 bedrooms·3 baths
Kissimmee • Florida

$ 842,18 USD totaal voor 4 nachten

17–21 okt 2026

Just Right Disney
Just Right Disney
Just Right Disney
Just Right Disney
Just Right Disney

Just Right Disney

3 bedrooms·3 baths
Celebration • Florida
5(58 reviews)

$ 859,01 USD totaal voor 4 nachten

16–20 nov 2026

Nice view of the resort for your morning coffee.
Mickey and friends room
Welcome to Chillax Inn Comrow
Windsor Hills Resort amenities included FREE with your stay!
Dining for 6

Chillax Inn Comrow

2 bedrooms·2 baths
Kissimmee • Florida

$ 629,65 USD totaal voor 3 nachten

10–13 okt 2026

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)

$ 496,25 USD $ 465,04 USD totaal voor 3 nachten

29 sep – 2 okt 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 totaal voor 3 nachten

29 sep – 2 okt 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 totaal voor 3 nachten

29 sep – 2 okt 2026

Kitchen
Kitchen
Kitchen Coffee Station
Kitchen
Living Room

Magic Holiday House

3 bedrooms·3 baths
Kissimmee • Florida

$ 702,57 USD totaal voor 3 nachten

13–16 okt 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

$ 801,09 USD totaal voor 3 nachten

29 sep – 2 okt 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)

$ 777,00 USD $ 715,30 USD totaal voor 3 nachten

4–7 okt 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 totaal voor 3 nachten

29 sep – 2 okt 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 totaal voor 3 nachten

3–6 okt 2026

2BR Star Island Orlando Getaway – Kissimmee Resort
2BR Star Island Orlando Getaway – Kissimmee Resort
2BR Star Island Orlando Getaway – Kissimmee Resort
2BR Star Island Orlando Getaway – Kissimmee Resort
2BR Star Island Orlando Getaway – Kissimmee Resort

2BR Star Island Orlando Getaway – Kissimmee Resort

2 bedrooms·2 baths
Kissimmee • Florida
5(1 review)
$155/ nacht(excl. kosten & belastingen)
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

$ 1.471,59 USD $ 1.337,66 USD totaal voor 3 nachten

29 sep – 2 okt 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 totaal voor 3 nachten

17–20 okt 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)

$ 1.852,84 USD totaal voor 5 nachten

29 sep – 4 okt 2026

Westgate Vacation Villas, Orlando, FL
Westgate Vacation Villas, Orlando, FL
Westgate Vacation Villas, Orlando, FL
Westgate Vacation Villas, Orlando, FL
Westgate Vacation Villas, Orlando, FL

Westgate Vacation Villas, Orlando, FL

0 bedrooms·0 baths
Kissimmee • Florida

$ 595,00 USD totaal voor 7 nachten

29 sep – 6 okt 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 totaal voor 3 nachten

29 sep – 2 okt 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)

$ 1.812,15 USD $ 1.434,19 USD totaal voor 5 nachten

17–22 okt 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

$ 1.158,64 USD totaal voor 3 nachten

17–20 okt 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)

$ 1.447,81 USD $ 1.160,95 USD totaal voor 5 nachten

30 sep – 5 okt 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)

$ 2.047,00 USD totaal voor 7 nachten

29 sep – 6 okt 2026