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$533 per night

includes taxes & fees

Living Area Features Easy Access To The Pool Area, A Large Wall Mounted Flat Screen TV

Exceptional

(69 reviews)

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

Kissimmee, FL

18% off

for 7 nights, 1 home

S$261 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$634 per night

includes taxes & fees

Exceptional

(245 reviews)

Our DisneyDreamVilla - minutes to DisneyWorld!!!

Kissimmee, FL

6% off

for 7 nights, 1 villa

S$376 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$685 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$412 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$502 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$652 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$587 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$449 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$452 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$692 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$771 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$711 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$548 per night

includes taxes & fees

Very good

(20 reviews)

Star Wars & Harry Potter-Themed Lakeview Pool Home Near Disney

Kissimmee, FL

7% off

for 7 nights, 1 villa

S$553 per night

includes taxes & fees

Very good

(19 reviews)

Frozen & Star Wars-Themed Villa with Private Pool Near Disney

Kissimmee, FL

7% off

for 7 nights, 1 home

S$482 per night

includes taxes & fees

Wonderful

(220 reviews)

Vacation Rental near Disney, Univeral Studios, Epic, w/free parking and Wi-Fi.

Kissimmee, FL

8% off

for 7 nights, 1 apartment

S$231 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$503 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$533 per night

includes taxes & fees

Amazing extended pool deck with no rear neighbors!

Exceptional

(62 reviews)

Private Pool/No Rear Neighbors/Windsor Hills Resort, 3 Miles from Disney®!

Kissimmee, FL

7% off

for 7 nights, 1 home

S$843 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: 20 Feb - 23 Feb

Premier Host

Our DisneyDreamVilla - minutes to DisneyWorld!!!

Sleeps 11 · 5 bedrooms · 5 bathrooms

for 3 nights, 1 villa

S$470 per night

includes taxes & fees

Relaxing 6BDR Villa just 15 mins from Disney w/ a Private Pool & Clubhouse!

Sleeps 12 · 6 bedrooms · 3+ bathrooms

for 3 nights, 1 villa

S$541 per night

includes taxes & fees

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$598 per night

includes taxes & fees

Vacation Rental near Disney, Univeral Studios, Epic, w/free parking and Wi-Fi.

Sleeps 6 · 3 bedrooms · 2 bathrooms

for 3 nights, 1 apartment

S$282 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$489 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

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

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

Our DisneyDreamVilla - minutes to DisneyWorld!!!

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

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

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!

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

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

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

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

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

Star Wars & Harry Potter-Themed Lakeview Pool Home Near Disney

Frozen & Star Wars-Themed Villa with Private Pool Near Disney

Vacation Rental near Disney, Univeral Studios, Epic, w/free parking and Wi-Fi.

Jedi Training Camp Top Rated 5 Star Villa

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)

Private Pool/No Rear Neighbors/Windsor Hills Resort, 3 Miles from Disney®!

Find spaces that suit your style

Find the best place to stay - Windsor Hills Resort

Our DisneyDreamVilla - minutes to DisneyWorld!!!

Relaxing 6BDR Villa just 15 mins from Disney w/ a Private Pool & Clubhouse!

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

Vacation Rental near Disney, Univeral Studios, Epic, w/free parking and Wi-Fi.

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

Tequilla Sunrise at Windsor Hills

Peace of mind

More quality time

All the privacy of home

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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

Our DisneyDreamVilla - minutes to DisneyWorld!!!

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