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 totaal voor 3 nachten

29 sep – 2 okt 2026

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

Chillax Inn Teascone

4 bedrooms·4 baths
Kissimmee • Florida

$ 850,88 USD totaal voor 3 nachten

19–22 okt 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

$ 1.332,83 USD totaal voor 3 nachten

11–14 okt 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

$ 1.091,87 USD totaal voor 3 nachten

4–7 okt 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

$ 1.125,04 USD totaal voor 3 nachten

10–13 okt 2026

Beautifully decorated Jocelyn who stayed in Dec 2022 said, "Awesome host! Clean house and near a ton of activities! Would consider this place again!"
Disney Family Retreat 3 BDR | Arcade Heated Pool
Relax and have fun in our bright living space featuring a private arcade, comfortable seating, and a large TV perfect for movie nights. Enjoy natural light through large windows while creating unforgettable memories after a day of Disney adventures.
Private entertainment space designed for unforgettable family memories. Challenge the kids (or the adults!) to a friendly arcade competition after a fun day at Disney. Classic arcade games for your kids and those young at heart!
Spacious dining area with seating for six, conveniently connected to the fully equipped kitchen. Perfect for enjoying family meals together after a fun day exploring Disney and Orlando.

Disney Family Retreat 3 BDR | Arcade Heated Pool

3 bedrooms·2 baths
Orlando • Florida
4.85(198 reviews)

$ 457,65 USD $ 443,18 USD totaal voor 3 nachten

5–8 okt 2026

Disney Magic Condo 1st Flr 3BR Disney-Themed Pool image 1
Disney Magic Condo 1st Flr 3BR Disney-Themed Pool image 2
Disney Magic Condo 1st Flr 3BR Disney-Themed Pool image 3
Disney Magic Condo 1st Flr 3BR Disney-Themed Pool image 4
Disney Magic Condo 1st Flr 3BR Disney-Themed Pool image 5

Stacy's Disney Retreat Kissimmee

3 bedrooms·2 baths
Kissimmee • Florida
4.83(77 reviews)

$ 492,14 USD $ 459,05 USD totaal voor 3 nachten

29 sep – 2 okt 2026

Centrally Located• Magic Village • NearDisney
Centrally Located• Magic Village • NearDisney
Centrally Located• Magic Village • NearDisney
Centrally Located• Magic Village • NearDisney
Centrally Located• Magic Village • NearDisney

Centrally Located• Magic Village • NearDisney

4 bedrooms·4½ baths
Kissimmee • Florida

$ 929,17 USD totaal voor 3 nachten

11–14 okt 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)

$ 2.094,76 USD $ 1.649,00 USD totaal voor 5 nachten

18–23 okt 2026

GemStone Retreat image 1
GemStone Retreat image 2
GemStone Retreat image 3
Club House( Restaurant & Bar , Cafe , Game , Gym )
Water Park

GemStone Retreat

11 bedrooms·10 baths
Kissimmee • Florida
5(3 reviews)
$522 – $1.267/ nacht(excl. kosten & belastingen)
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

$ 1.232,05 USD totaal voor 3 nachten

17–20 okt 2026

Cinderella's Castle 4/2 4m to Disney!
Cinderella's Castle 4/2 4m to Disney!
Cinderella's Castle 4/2 4m to Disney!
Cinderella's Castle 4/2 4m to Disney!
Cinderella's Castle 4/2 4m to Disney!

Cinderella's Castle 4/2 4m to Disney!

4 bedrooms·2 baths
Celebration • Florida
4.95(64 reviews)

$ 883,95 USD totaal voor 3 nachten

4–7 okt 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)

$ 867,14 USD totaal voor 3 nachten

3–6 okt 2026

Magic Disney Memory
Magic Disney Memory
Magic Disney Memory
Magic Disney Memory
Magic Disney Memory

Magic Disney Memory

5 bedrooms·5 baths
Kissimmee • Florida

$ 1.151,23 USD totaal voor 3 nachten

29 sep – 2 okt 2026

Welcome to our Villa Front view from street.
Layout of the home.
Welcome to Disney Adventure Villa!!
Drone shot of community pool and water park.
Disney Adventure Villa

Disney Adventure Villa

6 bedrooms·4 baths
Four Corners • Florida
4.89(227 reviews)

$ 2.063,95 USD $ 1.894,27 USD totaal voor 5 nachten

29 sep – 4 okt 2026

Sheraton Vistana Resort, Orlando, FL
Sheraton Vistana Resort, Orlando, FL
Sheraton Vistana Resort, Orlando, FL
Sheraton Vistana Resort, Orlando, FL
Sheraton Vistana Resort, Orlando, FL

Sheraton Vistana Resort, Orlando, FL

0 bedrooms·0 baths
Orlando • Florida

$ 595,00 USD totaal voor 7 nachten

29 sep – 6 okt 2026

Lilo's Paradise in Windsor Hills is the perfect vacation destination!
All of our guests have free access to the 5* amenities at Windsor Hills Resort in Kissimmee.
Jungle Cruise themed room has custom bunk beds, fun mural and reading "cave" under the bed.
The cozy living room is the perfect place to enjoy family time
Location! Location! Location! Lilo’s Paradise is just minutes from the Disney theme parks!

Lilo's Paradise in Windsor Hills Resort - Near Walt Disney World

5 bedrooms·5 baths
Kissimmee • Florida
4.89(35 reviews)

$ 1.117,98 USD totaal voor 3 nachten

29 sep – 2 okt 2026

Custom Mickey pool added January 2024
Original artwork created for our home.
Welcome to the Stormtrooper barracks on board a Star Destroyer.
Come hang out with Andy's toys.
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.

Galaxy Beyond

5 bedrooms·5 baths
Kissimmee • Florida
4.88(84 reviews)

$ 1.375,17 USD $ 1.106,47 USD totaal voor 5 nachten

3–8 okt 2026

Free arcade!
Welcome Home!
Little Mermaid twins
Windsor Hills Resort
Mandalorian twins

Chillax Inn Archfeld

5 bedrooms·5 baths
Kissimmee • Florida

$ 1.046,65 USD totaal voor 3 nachten

17–20 okt 2026

NEW LISTING-Disney Sunsets-Updated 6 Bedroom House
NEW LISTING-Disney Sunsets-Updated 6 Bedroom House
NEW LISTING-Disney Sunsets-Updated 6 Bedroom House
NEW LISTING-Disney Sunsets-Updated 6 Bedroom House
NEW LISTING-Disney Sunsets-Updated 6 Bedroom House

NEW LISTING-Disney Sunsets-Updated 6 Bedroom House

6 bedrooms·4 baths
Kissimmee • Florida

$ 1.105,00 USD totaal voor 3 nachten

29 sep – 2 okt 2026

afront (3).jpg
Impressive curb appeal
mcinema (4).jpg
awelcome.jpg
afront (4).jpg

Movie room,5 bed, Pool , Spa, Pickleball close by

5 bedrooms·3 baths
Kissimmee • Florida
4.6(53 reviews)

$ 1.000,00 USD totaal voor 3 nachten

29 sep – 2 okt 2026

Splish Splash at your own pool
Front of house
Open Entry area
Living room
Mickey Hideaway Villa

Mickey Hideaway Villa

6 bedrooms·4 baths
Kissimmee • Florida
5(70 reviews)

$ 1.766,45 USD totaal voor 5 nachten

10–15 okt 2026

Magical Mickey Villa LLC
Gorgeous Sunset
Beautiful overlook No rear neighbors
Relax and enjoy
Overlook

Magical Mickey Villa LLC

5 bedrooms·5 baths
Kissimmee • Florida
5(52 reviews)

$ 1.813,52 USD totaal voor 5 nachten

10–15 okt 2026

Fully fenced pool
Relaxing Pool
Mickeys Family Funhouse
hot tub
relaxing sun deck

Mickey's Funhouse, very cute and lots of fun

3 bedrooms·2 baths
Kissimmee • Florida
4.74(42 reviews)

$ 925,70 USD totaal voor 3 nachten

4–7 okt 2026