Handrails for easy entry
Beautiful lake view from the pool
Mickey's pool & spa
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

25–28 sep 2026

Pool
Front of house
Entry
Open area
Kitchen

Dreams Come True Villa LLC

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

$ 1.852,84 USD totaal voor 5 nachten

27 sep – 2 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

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 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

25–28 sep 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)

$ 974,75 USD totaal voor 3 nachten

25–28 sep 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

$ 1.036,69 USD $ 954,95 USD totaal voor 3 nachten

26–29 sep 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)

$ 1.419,44 USD $ 1.139,66 USD totaal voor 5 nachten

25–30 sep 2026

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Impressive curb appeal
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Movie room,5 bed, Pool , Spa, Pickleball close by

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

$ 1.064,00 USD totaal voor 3 nachten

27–30 sep 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

25 sep – 2 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)

$ 1.620,33 USD $ 1.290,34 USD totaal voor 5 nachten

30 sep – 5 okt 2026

Themed (Star Wars & Frozen) family-friendly villa with both a private and a community pool with a gorgeous view!
1 outdoor table, lounge chairs, and an outdoor shower in the pool area. The pool area has colored LED lights for night-time use.
The formal dining room has seating for 8 (there is another informal dining room)
Master bedroom with a king-size bed and a 50-inch Roku Smart TV.
Sit back and relax in the new massage chair after a long but rewarding day at the theme park!

Disney 5 mile Private Pool, Massage Chair, Tennis!

6 bedrooms·3 baths
Kissimmee • Florida
5(36 reviews)

$ 1.231,48 USD totaal voor 3 nachten

25–28 sep 2026

Pool with conservation view
Master bedroom
Family room
Jurassic Park bedroom
Fantasy Villa - Private Pool - Conservation view - close to Disney

Fantasy Villa - Private Pool - Conservation view - close to Disney

5 bedrooms·3 baths
Davenport • Florida

$ 759,04 USD totaal voor 3 nachten

6–9 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

$ 1.283,98 USD totaal voor 3 nachten

25–28 sep 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)

$ 2.011,00 USD totaal voor 7 nachten

25 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

$ 819,79 USD totaal voor 3 nachten

19–22 okt 2026

Fairview at Reunion - Games Room
Fairview at Reunion - Games Room
Fairview at Reunion - Games Room
Fairview at Reunion - Games Room
Fairview at Reunion - Games Room

Fairview at Reunion - Games Room

6 bedrooms·6 baths
Kissimmee • Florida

$ 909,37 USD totaal voor 3 nachten

26–29 sep 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)

$ 2.152,65 USD $ 2.060,59 USD totaal voor 5 nachten

18–23 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

27–30 sep 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

$ 1.186,00 USD totaal voor 3 nachten

10–13 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

$ 1.083,93 USD totaal voor 3 nachten

4–7 okt 2026

ICON Park 2 Queen Room | Water Park & Arcade image 1
ICON Park 2 Queen Room | Water Park & Arcade image 2
ICON Park 2 Queen Room | Water Park & Arcade image 3
ICON Park 2 Queen Room | Water Park & Arcade image 4
ICON Park 2 Queen Room | Water Park & Arcade image 5

ICON Park 2 Queen Room | Water Park & Arcade

1 bedroom·1 bath
Orlando • Florida

$ 561,39 USD totaal voor 3 nachten

1–4 nov 2026

ICON Park King Room | Water Park & Arcade image 1
ICON Park King Room | Water Park & Arcade image 2
ICON Park King Room | Water Park & Arcade image 3
ICON Park King Room | Water Park & Arcade image 4
ICON Park King Room | Water Park & Arcade image 5

ICON Park King Room | Water Park & Arcade

1 bedroom·1 bath
Orlando • Florida

$ 577,14 USD totaal voor 3 nachten

28 sep – 1 okt 2026