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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 total for 3 nights

Oct 20 – 23, 2026

Close to the Action, Peaceful When You Return
Close to the Action, Peaceful When You Return
Close to the Action, Peaceful When You Return
Close to the Action, Peaceful When You Return
Close to the Action, Peaceful When You Return

Close to the Action, Peaceful When You Return

2 bedrooms·1 bath
Orlando • Florida

$594.96 USD total for 3 nights

Oct 20 – 23, 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)

$505.61 USD total for 3 nights

Oct 25 – 28, 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

$569.70 USD $522.65 USD total for 3 nights

Oct 20 – 23, 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)
$125 – $357/ night(excl. fees & taxes)
House
Living Room
Haus in Davenport mit privatem Pool und Blick auf das Naturschutzgebiet
Living Room
House

Haus in Davenport mit privatem Pool und Blick auf das Naturschutzgebiet

4 bedrooms·3 baths
Orlando • Florida
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

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

$759.88 USD total for 3 nights

Oct 20 – 23, 2026

Your VERY Private Pool - Maintained & heated to 89° just for you! Photo June2017
Relax in the Comfort of Your Professionally Decorated Vacation Retreat!
The secluded & private Breezy Oak Villa, surrounded by tropical Florida forest.
Your King MasterBedroom awaits. Linens are replaced annually to ensure quality.
Master ensuite with large shower and direct pool access - brand new June 2017!

Breezy Oak Villa

4 bedrooms·2 baths
Loughman • Florida
4.87(63 reviews)

$901.60 USD total for 5 nights

Oct 25 – 30, 2026

GemStone Retreat image 1
GemStone Retreat
GemStone Retreat
GemStone Retreat
GemStone Retreat

GemStone Retreat

11 bedrooms·11 baths
Kissimmee • Florida
5(3 reviews)

$2,973.70 USD total for 3 nights

Oct 20 – 23, 2026

Your wonderful pool & hot tub. Catch some Florida sun in comfortable loungers!
There's plenty of room for the entire family to relax! Photo January 2023
The master bedroom features a Queen sleigh bed that will carry you off to sleep.
The peaceful and relaxing Happy Oak Villa. Where you want to be in Florida!
Meal prep is easy in our well stocked kitchen! Photo January 2023.

Happy Oak Villa

4 bedrooms·2 baths
Loughman • Florida
5(3 reviews)

$1,002.40 USD total for 5 nights

Oct 27 – Nov 1, 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 total for 7 nights

Oct 20 – 27, 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 20 – 23, 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

Oct 20 – 23, 2026

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 $1,239.12 USD total for 3 nights

Oct 20 – 23, 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

Nov 2 – 5, 2026

Downtown Lake Eola Historic House 1 or 2 Bed
Downtown Lake Eola Historic House 1 or 2 Bed
Downtown Lake Eola Historic House 1 or 2 Bed
Downtown Lake Eola Historic House 1 or 2 Bed
Downtown Lake Eola Historic House 1 or 2 Bed

Downtown Lake Eola Historic House 1 or 2 Bed

2 bedrooms·1 bath
Orlando • Florida
4.72(505 reviews)

$329.00 USD total for 3 nights

Oct 26 – 29, 2026

Downtown private Efficiency Lake Eola
Downtown private Efficiency Lake Eola
Downtown private Efficiency Lake Eola
Downtown private Efficiency Lake Eola
Downtown private Efficiency Lake Eola

Downtown private Efficiency Lake Eola

0 bedrooms·1 bath
Orlando • Florida
4.75(502 reviews)

$293.75 USD total for 3 nights

Oct 20 – 23, 2026

TINY unit in cottage in the middle of Downtown
TINY unit in cottage in the middle of Downtown
TINY unit in cottage in the middle of Downtown
TINY unit in cottage in the middle of Downtown
TINY unit in cottage in the middle of Downtown

TINY unit in cottage in the middle of Downtown

1 bedroom·1 bath
Orlando • Florida
4.86(29 reviews)

$258.50 USD total for 3 nights

Oct 20 – 23, 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)

$1,506.83 USD $1,205.21 USD total for 5 nights

Oct 20 – 25, 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)

$1,897.54 USD total for 5 nights

Nov 11 – 16, 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)

$1,662.33 USD $1,321.83 USD total for 5 nights

Oct 20 – 25, 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 total for 3 nights

Oct 20 – 23, 2026

3-Bedroom Luxury House
3-Bedroom Luxury House
3-Bedroom Luxury House
3-Bedroom Luxury House
3-Bedroom Luxury House

3-Bedroom Luxury House

4 bedrooms·2 baths
Orlando • Florida

$937.51 USD total for 3 nights

Oct 26 – 29, 2026