Hours of family fun in the arcade!
Frozen bedroom upstairs. It even looks cold!
Night swimming!
A view from the top of water slides
Ratatouille themed kitchen

Chillax Inn Beechfield

5 bedrooms·5 baths
Kissimmee • Florida

$1,050.38 USD total for 3 nights

Nov 4 – 7, 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

$2,180.17 USD $1,984.07 USD total for 3 nights

Dec 20 – 23, 2026

Pool Outdoor
Pool Outdoor
Entspannende Familienvilla mit privatem Pool und Spa. Große Lanai mit reichlich
Entspannende Familienvilla mit privatem Pool und Spa. Große Lanai mit reichlich
Bedroom

Entspannende Familienvilla mit privatem Pool und Spa. Große Lanai mit reichlich

4 bedrooms·2 baths
Clermont • Florida
$200/ night(excl. fees & taxes)
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 $877.68 USD total for 3 nights

Nov 1 – 4, 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 27 – 30, 2026

Large Stunning Pool with a real Hut Tub overlooking the lake
Amazing Disney Move Room
Disney Mickey Mouse Themed Bedroom
Luxury Large King Master Suites
Luxury King Master Suite

Mickeys Waterside SouthE Pool Hot Tub Cinema Outdoor Kitchen BBQ

9 bedrooms·8 baths
Kissimmee • Florida
5(20 reviews)

$4,488.47 USD total for 5 nights

Oct 31 – Nov 5, 2026

Beautiful, spacious, well maintained home in a gated community
Beautiful, spacious, well maintained home in a gated community
Custom built pool / spa / kiddie pool
Luscious greenery from the conservation preserve is the backdrop
Enjoy the spa

Our Blue Oasis

6 bedrooms·7 baths
Kissimmee • Florida
5(1 review)

$1,546.88 USD total for 3 nights

Oct 27 – 30, 2026

Pool and Hot Tub
Cinema Movie Theater
Kids Theme Bedroom
Splash Pad
Under the Sea room - 2 x Pirate Beds

Mickeys Sunrise South Facing Pool Hot Tub Splashpad Theater BBQ

7 bedrooms·6 baths
Kissimmee • Florida
5(8 reviews)

$2,581.86 USD total for 5 nights

Nov 3 – 8, 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)

$4,249.10 USD total for 5 nights

Nov 17 – 22, 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)

$3,739.55 USD total for 5 nights

Nov 8 – 13, 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

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)

$2,471.66 USD total for 5 nights

Oct 30 – Nov 4, 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)

$2,477.58 USD total for 5 nights

Oct 27 – Nov 1, 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)

$1,689.56 USD total for 5 nights

Oct 27 – Nov 1, 2026

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 27 – 30, 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(107 reviews)

$2,023.73 USD total for 5 nights

Jan 2 – 7, 2027

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 total for 3 nights

Nov 9 – 12, 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

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

$819.81 USD total for 3 nights

Oct 27 – 30, 2026

A Date With Disney image 1
A Date With Disney image 2
A Date With Disney image 3
A Date With Disney image 4
A Date With Disney image 5

A Date With Disney

3 bedrooms·3 baths
Kissimmee • Florida
4.78(67 reviews)

$624.25 USD total for 4 nights

Oct 27 – 31, 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

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)

$1,622.60 USD $1,292.04 USD total for 5 nights

Nov 2 – 7, 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

$845.91 USD total for 3 nights

Nov 19 – 22, 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)

$2,129.00 USD total for 7 nights

Oct 27 – Nov 3, 2026