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)

$1,543.15 USD $1,232.45 USD total for 5 nights

Nov 15 – 20, 2026

Remarkable Themed Home with Resort Amenities
Remarkable Themed Home with Resort Amenities
Remarkable Themed Home with Resort Amenities
Remarkable Themed Home with Resort Amenities
Remarkable Themed Home with Resort Amenities

Remarkable Themed Home with Resort Amenities

6 bedrooms·4 baths
Kissimmee • Florida

$1,379.53 USD total for 3 nights

Nov 17 – 20, 2026

Neon arcade game room
Arcade racing simulators
Private screened pool and spa at twilight
Front of home at twilight
Spacious living room

Magical Themed Home, Arcade, Private Pool/Spa, Resort Amenities

6 bedrooms·4 baths
Kissimmee • Florida

$1,341.48 USD total for 3 nights

Nov 3 – 6, 2026

Twin Mansions: Both homes from the street
Twin Mansions: Aerial view of the homes and pools
Twin Mansions: Aerial of both homes and pools
Twin Mansions: Both homes and pools from the rear
Magical Home: Private screened pool and spa at twilight

The Windsor Hills Twin Mansions

12 bedrooms·8 baths
Kissimmee • Florida

$3,361.33 USD total for 3 nights

Nov 17 – 20, 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)
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)

$2,292.72 USD total for 5 nights

Oct 29 – Nov 3, 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
4.92(12 reviews)

$997.24 USD total for 4 nights

Oct 27 – 31, 2026

South facing sun deck with screen to keep bugs out and let sunshine in
Rattan Patio Set and dining table, sun chairs and lounger. It's so peaceful!
Living area with 65 inch HDTV, Bose cinema sound, upgraded cable and Netflix
Soft leather seating with 2 recliners & rocking, reclining chair. Lots of DVD
Open plan aspect and lots of natural lighting. Remote control ceiling fans

Sleepy at Vista

3 bedrooms·2 baths
Kissimmee • Florida
4.94(88 reviews)

$1,575.00 USD total for 7 nights

Oct 27 – Nov 3, 2026

The Enchanted Retreat
Pool
Theater Room
Minions Room
Seven Dwarfs Room

The Enchanted Retreat

7 bedrooms·6 baths
Kissimmee • Florida
4.98(43 reviews)

$2,349.45 USD total for 4 nights

Oct 27 – 31, 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 27 – Nov 1, 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)
$127 – $1,059/ night(excl. fees & taxes)
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)

$580.42 USD total for 3 nights

Nov 7 – 10, 2026

Mickey and Friends Room
Nice view of the resort for your morning coffee.
Windsor Hills Resort amenities included FREE with your stay!
Living room with smart TV
Kitchen stocked with what you need

Chillax Inn Comrow

2 bedrooms·2 baths
Kissimmee • Florida

$629.65 USD total for 3 nights

Nov 8 – 11, 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)

$1,088.44 USD total for 5 nights

Nov 25 – 30, 2026

Challenge your friends and family to a friendly game of billiards, test your aim at darts, or enjoy a strategic match of chess. Our game room is the perfect spot to unwind, have fun, and create unforgettable memories during your stay!
3BR Disney Area Home | Game Room, Pool & Workspace
3BR Disney Area Home | Game Room, Pool & Workspace
Challenge your friends and family to a friendly game of billiards, test your aim at darts, or enjoy a strategic match of chess. Our game room is the perfect spot to unwind, have fun, and create unforgettable memories during your stay!
3BR Disney Area Home | Game Room, Pool & Workspace

3BR Disney Area Home | Game Room, Pool & Workspace

3 bedrooms·2 baths
Clermont • Florida
4.86(14 reviews)

$460.00 USD total for 3 nights

Oct 28 – 31, 2026

Wasserpark Fantastischer Pool Nur wenige Minuten von Disney Parks entfernt
Wasserpark Fantastischer Pool Nur wenige Minuten von Disney Parks entfernt
Wasserpark Fantastischer Pool Nur wenige Minuten von Disney Parks entfernt
Wasserpark Fantastischer Pool Nur wenige Minuten von Disney Parks entfernt
Wasserpark Fantastischer Pool Nur wenige Minuten von Disney Parks entfernt

Wasserpark Fantastischer Pool Nur wenige Minuten von Disney Parks entfernt

3 bedrooms·2 baths
Orlando • Florida
Main
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 27 – 30, 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!
One is faster, the other more adventurous!
Spend your best memories under amenities galore!
Magic is calling!
Relax, watch a movie in a Mickey Themed living room on brand new 58' LED Smart TVs.

New! Windsor Hills Magical Retreat, 2mi to Disney!

3 bedrooms·2 baths
Kissimmee • Florida
5(12 reviews)

$519.64 USD total for 3 nights

Nov 3 – 6, 2026

Magical Adventure-Game Room-Skeeball-Free Waterpark
Immersive Toy Story Mania Experience
Access to the waterpark is included in your stay
Magical Adventure-Game Room-Skeeball-Free Waterpark
Double Olympic sized poolOn

Magical Adventure-Game Room-Skeeball-Free Waterpark

3 bedrooms·2 baths
Kissimmee • Florida
5(5 reviews)

$758.18 USD total for 3 nights

Oct 27 – 30, 2026

Your Home Away From the Magic
Your Home Away From the Magic
Your Home Away From the Magic
Your Home Away From the Magic
Your Home Away From the Magic

Your Home Away From the Magic

2 bedrooms·2 baths
Kissimmee • Florida

$300.00 USD total for 3 nights

Oct 27 – 30, 2026

Private Heat Pool & Hot Tub | Games Room image 1
Private Heat Pool & Hot Tub | Games Room image 2
Private Heat Pool & Hot Tub | Games Room image 3
Private Heat Pool & Hot Tub | Games Room image 5
Private Heat Pool & Hot Tub | Games Room image 6

Private Heat Pool & Hot Tub | Games Room

5 bedrooms·4 baths
Clermont • Florida

$1,395.27 USD total for 4 nights

Nov 13 – 17, 2026

Holiday Inn Club Orange Lake
Holiday Inn Club Orange Lake
Holiday Inn Club Orange Lake
Holiday Inn Club Orange Lake
Holiday Inn Club Orange Lake

Holiday Inn Club Orange Lake

2 bedrooms·1 bath
Kissimmee • Florida

$747.00 USD total for 3 nights

Oct 27 – 30, 2026

Margaritaville Cottage "Seas Life" 4 bedroom, 4.5 bathroom with hot tub
Seas Life Cottage is at Margaritaville Resort Orlando
Living room: Sectional couch with queen-size sleeper sofa
Bedroom #1: Main bedroom with king-size bed, balcony and ensuite bathroom with dual vanity
Private Margaritaville hot tub on backyard patio. Outdoor dining table and chairs with loungers.

Seas Life Cottage Margaritaville +HotTub by Disney

4 bedrooms·4½ baths
Kissimmee • Florida
4.85(40 reviews)

$1,205.62 USD total for 3 nights

Oct 27 – 30, 2026

Central Disney+pool, jacuzzi 2 En-Suite BD 2,5 BA
Central Disney+pool, jacuzzi 2 En-Suite BD 2,5 BA
Central Disney+pool, jacuzzi 2 En-Suite BD 2,5 BA
Central Disney+pool, jacuzzi 2 En-Suite BD 2,5 BA
Central Disney+pool, jacuzzi 2 En-Suite BD 2,5 BA

Central Disney+pool, jacuzzi 2 En-Suite BD 2,5 BA

2 bedrooms·2½ baths
Kissimmee • Florida
5(5 reviews)

$525.00 USD total for 3 nights

Oct 27 – 30, 2026