Windsor Hills Resort holiday rentals

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Holiday rentals with weekly discounts - Windsor Hills Resort

Showing deals for:9 Jan - 16 Jan

Exceptional

(103 reviews)

Villa 7757 - 3 mi from Disney, Free Heated Pool/Spa, BBQ, Game/Theater Rm, & PS5

Kissimmee, FL

7% off

for 7 nights, 1 home

S$490 per night

includes taxes & fees

SOUTH facing pool! Plenty of lounge chairs and tables. New pool/spa heater 2023

Exceptional

(128 reviews)

6 Bed - 4 Bath Villa SOUTH FACING POOL - 2 Miles From DISNEY - OVER 100 Reviews

Kissimmee, FL

7% off

for 7 nights, 1 villa

S$407 per night

includes taxes & fees

Enjoy the pool and spa hot tub available under a covered lanai

Exceptional

(85 reviews)

6 Bedroom Vacation Home with South Facing Pool in Windsor Hills close to Disney

Kissimmee, FL

8% off

for 7 nights, 1 home

S$603 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$433 per night

includes taxes & fees

Exceptional

(22 reviews)

Executive 6 bed, 4 bath home in 5 Star Windsor Hills Resort, minutes from Disney

Kissimmee, FL

7% off

for 7 nights, 1 villa

S$369 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$459 per night

includes taxes & fees

Exceptional

(17 reviews)

Luxury south facing pool home on Windsor Hills 3 miles from Disney! 5 star ⭐

Kissimmee, FL

8% off

for 7 nights, 1 villa

S$470 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$526 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$502 per night

includes taxes & fees

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

Exceptional

(62 reviews)

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

Kissimmee, FL

7% off

for 7 nights, 1 home

S$569 per night

includes taxes & fees

Exceptional

(43 reviews)

Amazing 6-bedroom Villa with Private Pool Minutes from Disney! 5 Star Theming!

Kissimmee, FL

8% off

for 7 nights, 1 home

S$544 per night

includes taxes & fees

Exceptional

(51 reviews)

GREAT DEALS , STAR WARS, HARRY POTTER, MINIONS THEMED BEDROOMS

Kissimmee, FL

8% off

for 7 nights, 1 home

S$618 per night

includes taxes & fees

Professional arcade game room inside house! No coins needed.

Exceptional

(70 reviews)

Villa 7748 - Updated Home w/ Arcade Rm! 3 mi from Disney, Pool Heat, BBQ & PS5

Kissimmee, FL

7% off

for 7 nights, 1 home

S$569 per night

includes taxes & fees

Wonderful

(24 reviews)

South Facing Lux 5bd/5ba Pool Home W/spa & Private View 2mi To Disney!

Kissimmee, FL

7% off

for 7 nights, 1 villa

S$403 per night

includes taxes & fees

Exceptional

(123 reviews)

Amazing Private Theater and Game Room! Pool/Spa & Star Wars room!

Kissimmee, FL

8% off

for 7 nights, 1 home

S$532 per night

includes taxes & fees

Large heated pool, jacuzzi, pool toys, beach towels and lounges provided!

Exceptional

(112 reviews)

5-star family home with water park, private pool/hot tub- 2 stoplights to Disney

Kissimmee, FL

8% off

for 7 nights, 1 home

S$469 per night

includes taxes & fees

Exceptional

(58 reviews)

Large Two Story Home with TWO Master Bedrooms with attached full baths.

Kissimmee, FL

7% off

for 7 nights, 1 home

S$439 per night

includes taxes & fees

Private Pool and spa enjoy after a day at the parks or spend the day relaxing

Exceptional

(46 reviews)

AWESOME 6BR/4BA Resort Private Pool/Spa - 2 mi to Disney - Game Room/Theme Rooms

Kissimmee, FL

8% off

for 7 nights, 1 home

S$513 per night

includes taxes & fees

Exceptional

(23 reviews)

Windsor Hills Resort! 6 Bedroom House, 2 miles to Disney, Private Pool & Spa🏝

Kissimmee, FL

7% off

for 7 nights, 1 home

S$432 per night

includes taxes & fees

Exceptional

(70 reviews)

😎RELAX at Windsor Hills🌴, minutes to Disney - 5 bed / 5 bath, Private Pool🌞

Kissimmee, FL

8% off

for 7 nights, 1 home

S$439 per night

includes taxes & fees

Air Conditioned Game Room - Billiards, Pinball, Multi-Arcade, Bubble Hockey

Exceptional

(220 reviews)

Villa Sonrisa - 5 Bedroom/5 Bath Luxury, Minutes To Disney In Windsor Hills

Kissimmee, FL

7% off

for 7 nights, 1 home

S$386 per night

includes taxes & fees

Exceptional

(62 reviews)

4 Masters, wifi, private pool, Ultimate gameroom, resort community, 3mi to WDW

Kissimmee, FL

7% off

for 7 nights, 1 home

S$355 per night

includes taxes & fees

Exceptional

(106 reviews)

Steps from clubhouse. "Be Our Guest" in Windsor Hills-Pool Heat Included

Kissimmee, FL

7% off

for 7 nights, 1 home

S$301 per night

includes taxes & fees

Find spaces that suit your style

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Find the best place to stay - Windsor Hills Resort

Premier Host

FREE Pool Heat - Stay in the BEST Luxury 5 bedroom villa with SOUTH facing pool

Sleeps 10 · 5 bedrooms · 5 bathrooms

Premier Host

😎RELAX at Windsor Hills🌴, minutes to Disney - 5 bed / 5 bath, Private Pool🌞

Sleeps 10 · 5 bedrooms · 5 bathrooms

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
More for less
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Windsor Hills Resort holiday rentals

Holiday rentals with weekly discounts - Windsor Hills Resort

Image gallery for Villa 7757 - 3 mi from Disney, Free Heated Pool/Spa, BBQ, Game/Theater Rm, & PS5

Villa 7757 - 3 mi from Disney, Free Heated Pool/Spa, BBQ, Game/Theater Rm, & PS5

Find spaces that suit your style

Find the best place to stay - Windsor Hills Resort

FREE Pool Heat - Stay in the BEST Luxury 5 bedroom villa with SOUTH facing pool

Peace of mind

More quality time

All the privacy of home

More for less

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