Location

Dates

Guests

Vacation rentals in Kissimmee, Florida, United States

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 total por 3 noites

25 – 28 de set. de 2026

Dreams Come True Villa LLC

5 bedrooms·5 baths

Kissimmee • Florida

4.93(27 reviews)

$ 1.852,84 USD total por 5 noites

27 de set. – 2 de out. de 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 total por 3 noites

3 – 6 de out. de 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 por 3 noites

17 – 20 de out. de 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 por 3 noites

25 – 28 de set. de 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 total por 3 noites

25 – 28 de set. de 2026

Welcome to Chillax Inn Teascone Arcade

Free Arcade in the garage!

Chill on the couch

Windsor Hills amenities

Chillax Inn Teascone Arcade

5 bedrooms·5 baths

Kissimmee • Florida

$ 1.036,69 USD $ 954,95 USD total por 3 noites

26 – 29 de set. de 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 total por 5 noites

25 – 30 de set. de 2026

Impressive curb appeal

mcinema (4).jpg

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

5 bedrooms·3 baths

Kissimmee • Florida

4.6(53 reviews)

$ 1.064,00 USD total por 3 noites

27 – 30 de set. de 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 por 7 noites

25 de set. – 2 de out. de 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 total por 5 noites

30 de set. – 5 de out. de 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 total por 3 noites

25 – 28 de set. de 2026

Pool with conservation view

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 total por 3 noites

6 – 9 de out. de 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 total por 3 noites

25 – 28 de set. de 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 total por 7 noites

25 de set. – 2 de out. de 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 total por 3 noites

19 – 22 de out. de 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 total por 3 noites

26 – 29 de set. de 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 total por 3 noites

11 – 14 de out. de 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 total por 5 noites

18 – 23 de out. de 2026

Fully fenced pool

Mickeys Family Funhouse

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 total por 3 noites

27 – 30 de set. de 2026

Welcome to Chillax Inn Pawnall

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 total por 3 noites

10 – 13 de out. de 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 total por 3 noites

4 – 7 de out. de 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 total por 3 noites

1 – 4 de nov. de 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 total por 3 noites

28 de set. – 1 de out. de 2026