Kitchen
Kitchen
Kitchen Coffee Station
Kitchen
Living Room

Magic Holiday House

3 bedrooms·3 baths
Kissimmee • Florida

$702.57 USD total for 3 nights

Oct 13 – 16, 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

$1,471.59 USD $1,337.66 USD total for 3 nights

Sep 29 – Oct 2, 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

$801.09 USD total for 3 nights

Sep 29 – Oct 2, 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

Sep 29 – Oct 2, 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)
$349 – $650/ night(excl. fees & taxes)
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)

$2,437.29 USD total for 5 nights

Sep 29 – Oct 4, 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

Sep 29 – Oct 3, 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)

$4,412.63 USD total for 5 nights

Oct 10 – 15, 2026

101 Happy Memories Florida Villa
101 Happy Memories Florida Villa
101 Happy Memories Florida Villa
101 Happy Memories Florida Villa
101 Happy Memories Florida Villa

101 Happy Memories Florida Villa

7 bedrooms·6 baths
Kissimmee • Florida

$1,623.64 USD total for 3 nights

Sep 29 – Oct 2, 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 3 – 6, 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

Sep 29 – Oct 6, 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 total for 3 nights

Oct 4 – 7, 2026

Nautical getaway with big yard near Lake Monroe
Nautical getaway with big yard near Lake Monroe
Nautical getaway with big yard near Lake Monroe
Nautical getaway with big yard near Lake Monroe
Nautical getaway with big yard near Lake Monroe

Nautical getaway with big yard near Lake Monroe

3 bedrooms·2 baths
Sanford • Florida

$850.00 USD total for 3 nights

Nov 6 – 9, 2026

Beautiful South Facing Pool
Themed Game Room with Pool Table and Air Hockey
Mickey Mouse Theme Room
Beautiful South Facing Pool with Privacy
Super Sized Master Suites

Mickeys Floridian South Facing Pool Hot Tub Game RM GYM BBQ

5 bedrooms·4 baths
Kissimmee • Florida
4.98(128 reviews)

$1,957.37 USD total for 5 nights

Nov 3 – 8, 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 total for 3 nights

Oct 10 – 13, 2026

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 total for 3 nights

Oct 17 – 20, 2026

Happy Palette Home Close to downtown Fenced yard
Happy Palette Home Close to downtown Fenced yard
Happy Palette Home Close to downtown Fenced yard
Happy Palette Home Close to downtown Fenced yard
Happy Palette Home Close to downtown Fenced yard

Happy Palette Home Close to downtown Fenced yard

4 bedrooms·3 baths
Sanford • Florida

$720.00 USD total for 3 nights

Sep 29 – Oct 2, 2026

Sanford's Seahaven
Sanford's Seahaven
Sanford's Seahaven
Sanford's Seahaven
Sanford's Seahaven

Sanford's Seahaven

4 bedrooms·2 baths
Sanford • Florida

$9,870.00 USD total for 30 nights

Oct 16 – Nov 15, 2026

Stunning Cinema Movie Theater
Disney Theme Rooms
California King Master Suites
Large Kitchen and Dining Room Options
Stainless Steel Appliances

Mickeys Circle Gorgeous South Facing Pool Hot Tub Cinema BBQ

6 bedrooms·4 baths
Kissimmee • Florida
4.99(104 reviews)

$2,282.06 USD total for 5 nights

Oct 15 – 20, 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

$1,158.64 USD total for 3 nights

Oct 17 – 20, 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)

$1,852.84 USD total for 5 nights

Sep 29 – Oct 4, 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

Sep 29 – Oct 2, 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 total for 3 nights

Oct 19 – 22, 2026

Just a Massive House
Movie time in this large home theater
Professional Pool Table and Games Room
Stunning outside area with 5 star resort finishes
Massive Open Plan Kitchen and Family Room

Mickeys Atlantis Cinema Pool Hot Tub Game Outdoor Kitchen BBQ

8 bedrooms·8 baths
Kissimmee • Florida
5(138 reviews)

$3,990.77 USD total for 5 nights

Sep 29 – Oct 4, 2026