Windsor Hills Resort holiday rentals

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Holiday rentals with weekly discounts - Windsor Hills Resort

Showing deals for:20 Feb - 27 Feb

Exceptional

(14 reviews)

Luxury 6 bedroom 4 bathroom pool villa in the world renowned Windsor Hills

Kissimmee, FL

7% off

for 7 nights, 1 villa

S$529 per night

includes taxes & fees

Exceptional

(44 reviews)

5% & 10% Discounts 2 King Ensuite on First Floor with Very Private Pool 5BD/5BA

Kissimmee, FL

7% off

for 7 nights, 1 villa

S$643 per night

includes taxes & fees

Exceptional

(245 reviews)

Our DisneyDreamVilla - minutes to DisneyWorld!!!

Kissimmee, FL

6% off

for 7 nights, 1 villa

S$373 per night

includes taxes & fees

Very good

(20 reviews)

Star Wars and Harry Potter Themed Lakeview Pool Home with Spa Near Disney World

Kissimmee, FL

7% off

for 7 nights, 1 villa

S$556 per night

includes taxes & fees

Exceptional

(64 reviews)

South facing pool with no rear neighbors! Free bbq grill and pool & spa heat.

Kissimmee, FL

7% off

for 7 nights, 1 home

S$499 per night

includes taxes & fees

Exceptional

(8 reviews)

Ultimate Adventure Villa Top Rated 5 Star Disney more

Kissimmee, FL

8% off

for 7 nights, 1 home

S$633 per night

includes taxes & fees

Exceptional

(11 reviews)

Spacious 4BR w/ Themed Rooms, Pool, Near Disney!

Kissimmee, FL

8% off

for 7 nights, 1 villa

S$471 per night

includes taxes & fees

Exceptional

(9 reviews)

Happy Thoughts Windsor Hills Resort 6BR Villa Private Heated Pool Spa Gameroom

Kissimmee, FL

7% off

for 7 nights, 1 home

S$683 per night

includes taxes & fees

Very good

(19 reviews)

Frozen & Star Wars Villa w/ Game Room and Private Pool – Minutes from Disney

Kissimmee, FL

7% off

for 7 nights, 1 villa

S$476 per night

includes taxes & fees

Enter the magical world of the Minions in our beautifully decorated bedroom

Wonderful

(9 reviews)

Family Paradise w/ Pvt Pool, BBQ Grill, Themed Bedrooms, Game Room & Club access

Kissimmee, FL

7% off

for 7 nights, 1 home

S$591 per night

includes taxes & fees

A gated resort community with water slides and many facilities

Exceptional

(70 reviews)

Fun for kids and parents 6BR/4BA with private pool & hot tub in resort community

Kissimmee, FL

7% off

for 7 nights, 1 home

S$445 per night

includes taxes & fees

Beautifully Updated Windsor Hills Town Home

Exceptional

(69 reviews)

Windsor Hills Townhome | Across from Clubhouse | Mickey-Themed Room | Sleeps 6

Kissimmee, FL

14% off

for 7 nights, 1 home

S$362 per night

includes taxes & fees

Exceptional

(5 reviews)

Themed VILLA in ORLANDO with Pool, Resort, Game room, Free BBQ next to DISNEY

Kissimmee, FL

7% off

for 7 nights, 1 home

S$851 per night

includes taxes & fees

Excellent

(18 reviews)

Frozen and Star Wars Themed Villa with Pool and Game Room Near Disney Parks

Kissimmee, FL

7% off

for 7 nights, 1 villa

S$513 per night

includes taxes & fees

Main Living Area Features Plush Furniture w/Flat Screen TV and Balcony Access

Exceptional

(22 reviews)

Disney Escape | Renovated Windsor Hills Condo w/ Balcony & Themed Bedrooms

Kissimmee, FL

15% off

for 7 nights, 1 apartment

S$423 per night

includes taxes & fees

Exceptional

(84 reviews)

Villa 2619 - 3 mi from Disney, Free Heated Pool/Spa, BBQ, Game/Theater Rm, & PS5

Kissimmee, FL

7% off

for 7 nights, 1 home

S$460 per night

includes taxes & fees

Exceptional

(11 reviews)

NEW,Luxury,ThemeParks,5B&BA,Pool,Theater,Arcades,Mario Theme

Kissimmee, FL

8% off

for 7 nights, 1 home

S$813 per night

includes taxes & fees

Your very own professional arcade game room (no coins needed)!

Exceptional

(64 reviews)

Villa 2655 - Arcade Rm Updated Sep 2025! 3 mi from Disney, Pool Heat, BBQ & PS5

Kissimmee, FL

8% off

for 7 nights, 1 home

S$700 per night

includes taxes & fees

Watch a Movie Poolside On Our 120" Theatre Screen

Exceptional

(44 reviews)

8 Mins To Disney W/Poolside Theater, South Facing Pool, Game Room And Waterpark

Kissimmee, FL

7% off

for 7 nights, 1 home

S$702 per night

includes taxes & fees

Wonderful

(14 reviews)

Magical Adv 5 Star Villa Movie Room Arcade Pool and More

Kissimmee, FL

7% off

for 7 nights, 1 home

S$541 per night

includes taxes & fees

Exceptional

(80 reviews)

Elegantly Upgraded 4 bedroom Windsor Hills home with COMPLIMENTARY POOL HEAT!

Kissimmee, FL

8% off

for 7 nights, 1 home

S$546 per night

includes taxes & fees

Excellent

(41 reviews)

Star Wars and Harry Potter Themed Villa w/ Pool and Game Room Near Disney World

Kissimmee, FL

7% off

for 7 nights, 1 home

S$509 per night

includes taxes & fees

Enjoy a refreshing dip in your very own private pool.

Excellent

(38 reviews)

Enchanting Retreat: A Charming 6-Bd Oasis with Themed Rooms and Pv Pool Bliss

Kissimmee, FL

7% off

for 7 nights, 1 home

S$535 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Windsor Hills Resort

Showing deals for: 14 Feb - 17 Feb

Premier Host

Fun for kids and parents 6BR/4BA with private pool & hot tub in resort community

Sleeps 12 · 6 bedrooms · 4 bathrooms

for 3 nights, 1 home

S$756 per night

includes taxes & fees

Take a look at the reviews! Great value! An awesome place!!! Sleeps up to 16.

Sleeps 16 · 6 bedrooms · 3+ bathrooms

for 3 nights, 1 home

S$485 per night

includes taxes & fees

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
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More space, more privacy, more amenities — more value

Holiday rentals with weekly discounts - Windsor Hills Resort

Luxury 6 bedroom 4 bathroom pool villa in the world renowned Windsor Hills

5% & 10% Discounts 2 King Ensuite on First Floor with Very Private Pool 5BD/5BA

Our DisneyDreamVilla - minutes to DisneyWorld!!!

Star Wars and Harry Potter Themed Lakeview Pool Home with Spa Near Disney World

South facing pool with no rear neighbors! Free bbq grill and pool & spa heat.

Ultimate Adventure Villa Top Rated 5 Star Disney more

Spacious 4BR w/ Themed Rooms, Pool, Near Disney!

Happy Thoughts Windsor Hills Resort 6BR Villa Private Heated Pool Spa Gameroom

Frozen & Star Wars Villa w/ Game Room and Private Pool – Minutes from Disney

Family Paradise w/ Pvt Pool, BBQ Grill, Themed Bedrooms, Game Room & Club access

Fun for kids and parents 6BR/4BA with private pool & hot tub in resort community

Windsor Hills Townhome | Across from Clubhouse | Mickey-Themed Room | Sleeps 6

Themed VILLA in ORLANDO with Pool, Resort, Game room, Free BBQ next to DISNEY

Frozen and Star Wars Themed Villa with Pool and Game Room Near Disney Parks

Disney Escape | Renovated Windsor Hills Condo w/ Balcony & Themed Bedrooms

Villa 2619 - 3 mi from Disney, Free Heated Pool/Spa, BBQ, Game/Theater Rm, & PS5

NEW,Luxury,ThemeParks,5B&BA,Pool,Theater,Arcades,Mario Theme

Villa 2655 - Arcade Rm Updated Sep 2025! 3 mi from Disney, Pool Heat, BBQ & PS5

8 Mins To Disney W/Poolside Theater, South Facing Pool, Game Room And Waterpark

Magical Adv 5 Star Villa Movie Room Arcade Pool and More

Elegantly Upgraded 4 bedroom Windsor Hills home with COMPLIMENTARY POOL HEAT!

Star Wars and Harry Potter Themed Villa w/ Pool and Game Room Near Disney World

Enchanting Retreat: A Charming 6-Bd Oasis with Themed Rooms and Pv Pool Bliss

Windsor Hills Retreat (Free Water Park & Resort)

Find spaces that suit your style

Find the best place to stay - Windsor Hills Resort

Fun for kids and parents 6BR/4BA with private pool & hot tub in resort community

Take a look at the reviews! Great value! An awesome place!!! Sleeps up to 16.

Peace of mind

More quality time

All the privacy of home

More for less

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Windsor Hills Resort holiday rentals

Holiday rentals with weekly discounts - Windsor Hills Resort

Image gallery for Luxury 6 bedroom 4 bathroom pool villa in the world renowned Windsor Hills

Luxury 6 bedroom 4 bathroom pool villa in the world renowned Windsor Hills

Find spaces that suit your style

Find the best place to stay - Windsor Hills Resort

Fun for kids and parents 6BR/4BA with private pool & hot tub in resort community

Peace of mind

More quality time

All the privacy of home

More for less

Holiday Rental options near Windsor Hills Resort

More Holiday Rentals ideas

People also search for