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 total for 3 nights

Oct 10 – 13, 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!
Kids of all ages will love this waterpark all day! Enjoy access to pools, a water park, game room and more!
Spend your best memories under amenities galore!
Magic is calling!
Enjoy the decorated gallery walls and the largest, completely open floor plan available at Windsor Hills!

New! Windsor Hills Galaxy's Edge, 2mi to Disney!

3 bedrooms·2 baths
Kissimmee • Florida
4.84(205 reviews)

$538.34 USD total for 3 nights

Oct 5 – 8, 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 total for 3 nights

Sep 29 – Oct 2, 2026

Private Pool and Hot Tub / Spa backing on to Gardens
Home Theater - Cinema Room
Mickey Themed Bedroom
Star Wars Themed Kids Room
Master Suite with King Bed

Mickeys Palm Private Garden Views Huge Pool Hot Tub Cinema BBQ

6 bedrooms·4 baths
Kissimmee • Florida
5(36 reviews)

$2,314.05 USD total for 5 nights

Oct 29 – Nov 3, 2026

Surprise your family with a trip to Disney and world class theme parks! Stay at our fully themed out villa with special touches of magic throughout every room...while enjoying all the enormous amount of amenities that this resort offers!
5 fully themed bedrooms of Star Wars, Mickey, Avengers, Toy Story and Harry Potter. Enjoy a fully immersive experience staying here!
Enjoy countless hours and watch the sunset by the private pool relaxing with spacious patio area, an oversized pool and hot tub. Pool and Spa can be heated seasonally on request.
Enjoy the Mickey themed great room..."it was all started by a mouse". Touches of our favorite classic character by Walt move through the two floor grand foyer into a open living space.
Come hang out in our air conditioned fully equipped Avengers theme game room filled with entertainment, TVs, foosball, ping pong, and air hockey. Families of all ages will love countless hours spent here with your own privacy.

Windsor Hills Mickey Castle Villa, 2 mi to Disney!

5 bedrooms·5 baths
Kissimmee • Florida
4.87(99 reviews)

$855.22 USD total for 3 nights

Oct 10 – 13, 2026

The Hub Downtown
The Hub Downtown
The Hub Downtown
The Hub Downtown
The Hub Downtown

The Hub Downtown

4 bedrooms·3 baths
Sanford • Florida
5(81 reviews)

$715.00 USD total for 3 nights

Sep 29 – Oct 2, 2026

Retreat Near Downtown Sanford | Ping Pong + Patio
Retreat Near Downtown Sanford | Ping Pong + Patio
Retreat Near Downtown Sanford | Ping Pong + Patio
Retreat Near Downtown Sanford | Ping Pong + Patio
Retreat Near Downtown Sanford | Ping Pong + Patio

Retreat Near Downtown Sanford | Ping Pong + Patio

3 bedrooms·2 baths
Sanford • Florida

$2,406.00 USD total for 14 nights

Sep 29 – Oct 13, 2026

Newly built, Calming Vibes. Close to downtown!
Newly built, Calming Vibes. Close to downtown!
Newly built, Calming Vibes. Close to downtown!
Newly built, Calming Vibes. Close to downtown!
Newly built, Calming Vibes. Close to downtown!

Newly built, Calming Vibes. Close to downtown!

4 bedrooms·2 baths
Sanford • Florida

$789.00 USD total for 3 nights

Sep 30 – Oct 3, 2026

Disney Dreams Vacation Rentals
Disney Dreams Vacation Rentals
Disney Dreams Vacation Rentals
Disney Dreams Vacation Rentals
Disney Dreams Vacation Rentals

Disney Dreams Vacation Rentals

3 bedrooms·3 baths
Kissimmee • Florida
4.93(113 reviews)

$1,119.11 USD total for 5 nights

Oct 4 – 9, 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 total for 5 nights

Oct 17 – 22, 2026

Family vacation home just minutes from Walt Disney World Resort with private pool, themed rooms, and space for everyone.
Welcome to Disney Dreams Vacation Rentals
All NEW/ Just Renovated May 2022
Take a break from the parks and enjoy premium resort amenities
Large Dining Room Table (seats 6-8)

Disney Dreams Vacation Home

3 bedrooms·3 baths
Kissimmee • Florida

$1,041.61 USD total for 4 nights

Oct 4 – 8, 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 total for 7 nights

Sep 29 – Oct 6, 2026

Pool table room with TV
The Billiard close to downtown with fenced yard
The Billiard close to downtown with fenced yard
The Billiard close to downtown with fenced yard
The Billiard close to downtown with fenced yard

The Billiard close to downtown with fenced yard

3 bedrooms·2 baths
Sanford • Florida

$610.00 USD total for 3 nights

Sep 29 – Oct 2, 2026

Brand New Large Pool on Lake Front View
Large Disney Theme Twin Bedroom
Rack them up with the Pool Table
Cottage Style 4 bed/3 bath with South Facing Pool / Hot Tub / BBQ - Large House on 2/3's Arce
Master Bedroom in the Turret

Mickeys Homestead Lakefront Cottage Style South Facing Pool BBQ

4 bedrooms·3 baths
Kissimmee • Florida
5(106 reviews)

$1,478.63 USD total for 5 nights

Sep 29 – Oct 4, 2026

The perfect place to play - your very own arcade. Find your top free 3 point shooter!
The Arcade close to downtown with fenced yard
The Arcade close to downtown with fenced yard
The Arcade close to downtown with fenced yard
The Arcade close to downtown with fenced yard

The Arcade close to downtown with fenced yard

3 bedrooms·2 baths
Sanford • Florida

$601.00 USD total for 3 nights

Sep 29 – Oct 2, 2026

Large Deck for catching the Sun
Disney Theme Bedroom
Games Room
King Master Suites
Leather Sofas

Mickeys Corner Fantastic Huge Private Pool Hot Tub Game RM BBQ

5 bedrooms·4 baths
Kissimmee • Florida
5(92 reviews)
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 total for 5 nights

Sep 30 – Oct 5, 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 total for 4 nights

Nov 16 – 20, 2026

Huge Swimming pool, Deck and Lanai (Optional Pool Heating)
Games Room with Professional Pool Table and Ping Pong
Large Luxury Master Suites with California King Beds and Quality Hotel Linen
Theme Bedrooms with Luxury Twin Beds
Large Luxury Master Suites with California King Beds and Quality Hotel Linen

Mickeys Pearl Phenomenal Southeast Pool Hot Tub Game RM BBQ

7 bedrooms·5½ baths
Kissimmee • Florida
5(169 reviews)

$2,437.29 USD total for 5 nights

Sep 29 – Oct 4, 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 total for 4 nights

Oct 17 – 21, 2026

Stunning Outdoor Living with Pool and Hot Tub
Cinema / Home Movie Theater
Stunning Outdoor Kitchen and BBQ
Disney Theme Bedrooms
Grand Master King Suite with Lounge Area

Mickeys Getaway Pool Hot Tub Cinema GYM Outdoor Kitchen BBQ

8 bedrooms·7½ baths
Kissimmee • Florida
5(200 reviews)

$3,866.34 USD total for 5 nights

Nov 8 – 13, 2026

Mickey's Oyster 9 Bedroom 8 Bathroom Sleeps 18 People 2 Miles to Disney Gorgeous large tropical pool area with spa, surrounded by palm trees and shrubs.
Mulan Suite (king bed) with french doors to pool, with Ensuite Bathroom
Star Wars room - desk with chair in the corner
Movie/ game room - with air hockey, table tennis 🏓, darts 🎯, karaoke 🎤 machine
Air hockey and table tennis 🏓 table. Karaoke 🎤 machine for kids in the corner

Mickeys Oyster Amazing Southeast Pool Hot Tub Cinema Game RM BBQ

9 bedrooms·8 baths
Kissimmee • Florida
5(45 reviews)

$4,240.80 USD total for 5 nights

Oct 16 – 21, 2026

Cinema Movie Theater
Kids Theme Bedroom
Lakeview Pool and Hot Tub
Master Bedroom Suites
Kids Theme Bedroom

Mickeys Escape Lakeview (4 Masters) Pool Hot Tub Cinema BBQ

7 bedrooms·6 baths
Kissimmee • Florida
4.99(101 reviews)

$2,530.91 USD total for 5 nights

Oct 9 – 14, 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

Oct 17 – 20, 2026