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WH_609BR Windsor Hills Paradise

WH_609BR Windsor Hills Paradise

WH_609BR Windsor Hills Paradise

WH_609BR Windsor Hills Paradise

WH_609BR Windsor Hills Paradise

WH_609BR Windsor Hills Paradise

WH_609BR Windsor Hills Paradise

WH_609BR Windsor Hills Paradise

6 guests 3 bed 3 bath 1,440 sq ft

Orlando - Windsor Hills Resort | Kissimmee

Flex30

Starting at $90 daily

AF2582 Exterior

AF2582 Game Room
Pool Table Foosball

AF2582 Family Room (Angle)
50" TV

AF2582 Family Room

AF2582 Living Room

AF2582 Dining Room

12 guests 6 bed 4 bath 2,812 sq ft

Orlando - Windsor Hills Resort | Kissimmee

Starting at $223 daily

CW7739 Pool Deck View

CW7739 Pool/Patio

CW7739 Living Room

CW7739 Kitchen (Angle)

CW7739 Dining Room

CW7739 Living Room (Angle)
65" Smart TV

CW7739 Dining Room (Angle)

8 guests 4 bed 4 bath 1,816 sq ft

Orlando - Windsor Hills Resort | Kissimmee

Starting at $255 daily

WH_608BR The Gem Villa

WH_608BR The Gem Villa

WH_608BR The Gem Villa

WH_608BR The Gem Villa

WH_608BR The Gem Villa

WH_608BR The Gem Villa

WH_608BR The Gem Villa

WH_608BR The Gem Villa

14 guests 5 bed 5 bath 2,297 sq ft

Orlando - Windsor Hills Resort | Kissimmee

Recommended Rental Flex30

5.0 (1)

Guest rating

Starting at $209 daily

WH_607BR The Castle at Windsor Hills

WH_607BR The Castle at Windsor Hills

WH_607BR The Castle at Windsor Hills

WH_607BR The Castle at Windsor Hills

WH_607BR The Castle at Windsor Hills

WH_607BR The Castle at Windsor Hills

WH_607BR The Castle at Windsor Hills

WH_607BR The Castle at Windsor Hills

12 guests 6 bed 4 bath 2,812 sq ft

Orlando - Windsor Hills Resort | Kissimmee

Recommended Rental Flex30

Starting at $195 daily

WH_604BR Windsor Charm

WH_604BR Windsor Charm

WH_604BR Windsor Charm

WH_604BR Windsor Charm

WH_604BR Windsor Charm

WH_604BR Windsor Charm

WH_604BR Windsor Charm

WH_604BR Windsor Charm

8 guests 4 bed 4 bath 1,878 sq ft

Orlando - Windsor Hills Resort | Kissimmee

Flex30

4.9 (15)

Guest rating

Starting at $145 daily

MVH_120M | Archfeld Oasis Welcome to Archfeld Oasis!

MVH_120M | Archfeld Oasis

MVH_120M | Archfeld Oasis The private pool has a screened-in lanai

MVH_120M | Archfeld Oasis

MVH_120M | Archfeld Oasis

MVH_120M | Archfeld Oasis

MVH_120M | Archfeld Oasis Sit back and relax in the living room with friends and family

MVH_120M | Archfeld Oasis Transport into the galaxy arcade for hours of fun

10 guests 5 bed 5 bath 2,342 sq ft

Orlando - Windsor Hills Resort | Kissimmee

Starting at $123 daily

WH_606BR Windsor Hills Gem

WH_606BR Windsor Hills Gem

WH_606BR Windsor Hills Gem

WH_606BR Windsor Hills Gem

WH_606BR Windsor Hills Gem

WH_606BR Windsor Hills Gem

WH_606BR Windsor Hills Gem

WH_606BR Windsor Hills Gem

6 guests 3 bed 2 bath 1,450 sq ft

Orlando - Windsor Hills Resort | Kissimmee

Flex30

Starting at $95 daily

TS7718 Two Twins Bedroom 5 Upstairs
24" Smart TV

TS7718 Game Room
Pool Table
Air Hockey
Foosball

TS7718 Pool Deck

TS7718 Family Room (Angle)

TS7718 Family Room
55" TV
Xbox

TS7718 Kitchen (Angle)

TS7718 Dining Room /Living

12 guests 6 bed 4 bath 2,812 sq ft

Orlando - Windsor Hills Resort | Kissimmee

Starting at $223 daily

MNL2696 Game Room

MNL2696 Pool & Patio

MNL2696 Family Room

MNL2696 Two Twins Bedroom 4 Upstairs
Mickey Theme

MNL2696 Exterior

MNL2696 Living Room

MNL2696 Living Room

MNL2696 Dining Room

12 guests 6 bed 4 bath 2,812 sq ft

Orlando - Windsor Hills Resort | Kissimmee

Starting at $248 daily

MVH_104M | Windsor Oasis Welcome to Windsor Oasis, a beautiful 5-bed villa in Windsor Hills | PHOTOS TAKEN: August 2021

MVH_104M | Windsor Oasis This 5-bed villa is the perfect home for you and your family

MVH_104M | Windsor Oasis The kids will love splashing around in the evenings

MVH_104M | Windsor Oasis Play all day in this custom galaxy game room.

MVH_104M | Windsor Oasis A large open floor plan throughout

MVH_104M | Windsor Oasis Relax and unwind in the living area with views of the pool area

MVH_104M | Windsor Oasis The living area features a 65-inch 4K SMART TV

MVH_104M | Windsor Oasis Make memories with your family

12 guests 5 bed 5 bath 2,297 sq ft

Orlando - Windsor Hills Resort | Kissimmee

Starting at $221 daily

AF2574 Family Room
85" Smart TV

AF2574 Family Room (Angle)

AF2574 Nook (Angle)

AF2574 Kitchen (Angle)

AF2574 Living Room

AF2574 Master King Bedroom 1 Upstairs
Attached Bathroom

12 guests 6 bed 5 bath 2,812 sq ft

Orlando - Windsor Hills Resort | Kissimmee

Starting at $185 daily

CW7713 Living Room
65" Smart TV
Blu-Ray Sound Bar

CW7713 Living Room (Angle 2)

CW7713 Kitchen (Angle)

CW7713 Living Room (Angle)

CW7713 Kitchen (Angle 2)

CW7713 Dining Room

10 guests 5 bed 5 bath 2,382 sq ft

Orlando - Windsor Hills Resort | Kissimmee

Starting at $159 daily

CW7730 Living Room (Angle) 43" TV

CW7730 Exterior

CW7730 Living Room

CW7730 Dining Room

CW7730 Dining Room (Angle)

CW7730 Master King Bedroom 1 Downstairs
Attached Bathroom-Shower

10 guests 5 bed 5 bath 2,382 sq ft

Orlando - Windsor Hills Resort | Kissimmee

Starting at $158 daily

DB2605 Family Room 75" Roku TV Electric Fireplace

DB2605 Family Room / Kitchen

DB2605 Dining Seats 8

DB2605 Dining / Living

DB2605 Kitchen Bar Seating for 2

DB2605 Kitchen Nook Seats 4

DB2605 Living Room 75" Roku TV

12 guests 6 bed 4 bath 2,812 sq ft

Orlando - Windsor Hills Resort | Kissimmee

Starting at $226 daily

AF2501 Two Twins Bedroom 5 Upstairs

AF2501 Two Twins Bedroom 4 Upstairs
Minion Theme

AF2501 Queen Bedroom 3 Upstairs

AF2501 Pool/Spa

AF2501 Family Room
55" TV 3D Blu-Ray
Sound System

AF2501 Kitchen/Nook (Angle)

AF2501 Kitchen/Nook

12 guests 6 bed 4 bath 2,812 sq ft

Orlando - Windsor Hills Resort | Kissimmee

Starting at $171 daily

MNL2702 Living Room (Angle)

MNL2702 Living Room (Angle 2)

MNL2702 Kitchen

MNL2702 Kitchen (Angle)

MNL2702 Living Room
55" TV

MNL2702 Kitchen (Angle 2)

MNL2702 Dining/Living

11 guests 5 bed 5 bath 2,382 sq ft

Orlando - Windsor Hills Resort | Kissimmee

Starting at $156 daily

TT7752 Family Room (Angle)

TT7752 Kitchen (Angle)

TT7752 Family Room
65" Smart TV

TT7752 Living Room

TT7752 Dining Room

TT7752 Living Room (Angle)

17 guests 6 bed 4 bath 2,812 sq ft

Orlando - Windsor Hills Resort | Kissimmee

Starting at $233 daily

WHC-2774AL-103 Windsor Loop (S) Vacation rental near Disney managed by Orlando rent a villa.

WHC-2774AL-103 Windsor Loop (S) Master bedroom showing king bed, bedside tables and lighting.

WHC-2774AL-103 Windsor Loop (S) Master bedroom showing king bed and en-suite entrance.

WHC-2774AL-103 Windsor Loop (S) Master en-suite bathroom showing vanity.

WHC-2774AL-103 Windsor Loop (S) Master en-suite bathroom showing toilet and shower entrance.

WHC-2774AL-103 Windsor Loop (S) Bedroom 2 showing queen bed, drawers, and ceiling fan.

WHC-2774AL-103 Windsor Loop (S) Bedroom 2 showing entrance to room, and closet.

WHC-2774AL-103 Windsor Loop (S) twin bedroom

6 guests 3 bed 2 bath 1,410 sq ft

Orlando - Windsor Hills Resort | Kissimmee

Starting at $122 daily

MVH_044M | The Magical Dream Getaway Book your stay today at The Magical Dream Getaway, a beautiful 3 bedroom Windsor Hills condo.

MVH_044M | The Magical Dream Getaway The open living space is perfect to accommodate the whole family

MVH_044M | The Magical Dream Getaway

MVH_044M | The Magical Dream Getaway This comfortable oversized condo is perfect for your Orlando family vacation

MVH_044M | The Magical Dream Getaway Dine at the formal dining table with seating for 4

MVH_044M | The Magical Dream Getaway

MVH_044M | The Magical Dream Getaway Prepare delicious meals in this fully-equipped kitchen

MVH_044M | The Magical Dream Getaway The kitchen features upgraded appliances and granite countertops

7 guests 3 bed 2 bath 1,408 sq ft

Orlando - Windsor Hills Resort | Kissimmee

Starting at $79 daily

MVH_090M | Comrow Hideout Welcome to Comrow Hideout, a 2 bedroom condo with a kids bedroom & upgraded kitchen: Photos taken: September 2021

MVH_090M | Comrow Hideout Enjoy the fantastic community pool only minutes away from your vacation rental

MVH_090M | Comrow Hideout

MVH_090M | Comrow Hideout The fully equipped kitchen offers all the basics to prepare delicious family meals

MVH_090M | Comrow Hideout The open layout is great for spending quality time together

MVH_090M | Comrow Hideout

MVH_090M | Comrow Hideout

MVH_090M | Comrow Hideout Relax on the comfortable couch with plenty of space for everyone to enjoy time together

4 guests 2 bed 2 bath 1,112 sq ft

Orlando - Windsor Hills Resort | Kissimmee

Starting at $63 daily

MVH_091M | Windsor Nook Welcome to Windsor Nook

MVH_091M | Windsor Nook Take a refreshing dip in the private pool

MVH_091M | Windsor Nook Enjoy meals as a family with seating for 6

MVH_091M | Windsor Nook The living space is modern and contemporary with sliding glass doors out to the pool

MVH_091M | Windsor Nook The updated kitchen has everything your family will need for delicious meals

MVH_091M | Windsor Nook Easy breakfast bar seating for 4

MVH_091M | Windsor Nook Kids will love having their own custom galactic bedroom!

MVH_091M | Windsor Nook The kids room has plenty of magical details

6 guests 3 bed 3 bath 1,440 sq ft

Orlando - Windsor Hills Resort | Kissimmee

Starting at $99 daily

MVH_108M | Magical Villa Welcome to Magical Villa, a 5 bedroom Windsor Hills Villa | PHOTOS TAKEN: January 2019

MVH_108M | Magical Villa A screened-in private pool and spillover spa for all to enjoy

MVH_108M | Magical Villa Sun loungers for you to catch the Florida sun

MVH_108M | Magical Villa The whole family will want to play all day in this awesome game room

MVH_108M | Magical Villa Have a meal on the outdoor dining table with seating for 6

MVH_108M | Magical Villa Sit back and relax after a long day in the theme parks in the spacious living area

MVH_108M | Magical Villa An open floor plan throughout for the whole family to hangout together

MVH_108M | Magical Villa Plenty of room for everyone on the comfortable couches

10 guests 5 bed 5 bath 2,494 sq ft

Orlando - Windsor Hills Resort | Kissimmee

Starting at $129 daily

MVH_115M | Sun n Games Villa Welcome to Sun 'n Games Villa, a modern 5 bedroom vacation home located in Windsor Hills| PHOTOS UPDATED: March 2022

MVH_115M | Sun n Games Villa Sun N Games Villa awaits your next vacation

MVH_115M | Sun n Games Villa Relax in the spillover spa or on one of the four sun loungers

MVH_115M | Sun n Games Villa Enjoy the Florida sunshine at your own private screened-in pool

MVH_115M | Sun n Games Villa Dine al fresco underneath the covered lanai with seating for 8 and two ceiling fans for those hot summer days

MVH_115M | Sun n Games Villa Go for a swim under the stars

MVH_115M | Sun n Games Villa Exterior lighting makes dining outdoors comfortable

MVH_115M | Sun n Games Villa Challenge your family members to a game of air hockey or race head to head on the NASCAR racers

12 guests 5 bed 5 bath 2,966 sq ft

Orlando - Windsor Hills Resort | Kissimmee

Starting at $168 daily

MVH_107M | Pawnall Bliss Welcome to your home away from home, Pawnall Bliss | Photos Updated: August 2026

MVH_107M | Pawnall Bliss Perfect vacation home to enjoy with your loved ones

MVH_107M | Pawnall Bliss

MVH_107M | Pawnall Bliss The super hero games room will be your favorite room in the house

MVH_107M | Pawnall Bliss

MVH_107M | Pawnall Bliss Enjoy the screened-in private pool with table seating for 6 and 4 sun loungers

MVH_107M | Pawnall Bliss Soak up the Florida sunshine at your own private screened-in pool

MVH_107M | Pawnall Bliss Your private oasis awaits

8 guests 4 bed 4 bath 1,824 sq ft

Orlando - Windsor Hills Resort | Kissimmee

Starting at $99 daily

MVH_074M | Windsor Point Welcome to Windsor Point, a luxury 6 bed Windsor Hills home with everything you will need

MVH_074M | Windsor Point Enjoy a meal outside with this large dining room set with seating for 6

MVH_074M | Windsor Point

MVH_074M | Windsor Point Disclaimer: Firepit not for guest use. Owner use only.

MVH_074M | Windsor Point Disclaimer: Firepit not for guest use. Owner use only.

MVH_074M | Windsor Point Enjoy the sunshine at your own screened-in pool

MVH_074M | Windsor Point Take a seat at the island with seating for 8

MVH_074M | Windsor Point The fully-equipped kitchen is perfect for preparing delicious family meals

12 guests 6 bed 4 bath 2,812 sq ft

Orlando - Windsor Hills Resort | Kissimmee

Starting at $131 daily

WH2618DS - Windsor Hills Retreat (G) Vacation rental near Disney managed by Orlando rent a villa with a screened in pool and spa.

WH2618DS - Windsor Hills Retreat (G) Pool area showing sun loungers.

WH2618DS - Windsor Hills Retreat (G) Pool area showing dining table seating for 6.

WH2618DS - Windsor Hills Retreat (G) Pool area

WH2618DS - Windsor Hills Retreat (G) air conditioned games room showing ping pong

WH2618DS - Windsor Hills Retreat (G) alternate view of games room showing pool table

WH2618DS - Windsor Hills Retreat (G) entryway

WH2618DS - Windsor Hills Retreat (G) living room overlooking pool area

9 guests 4 bed 4 bath 1,851 sq ft

Orlando - Windsor Hills Resort | Kissimmee

Starting at $142 daily

ALM2774-204 Living Room (Angle)
Has Sleeper Sofa

ALM2774-204 Living Room (Angle)
50" Smart TV

ALM2774-204 Balcony

ALM2774-204 Kitchen

ALM2774-204 Kitchen (Angle)

ALM2774-204 Dining Room (Angle)

ALM2774-204 Dining Room

ALM2774-204 Master King Bedroom 1
Attached Bathroom-Shower

8 guests 3 bed 2 bath 1,412 sq ft

Orlando - Windsor Hills Resort | Kissimmee

Starting at $73 daily

ALM2809-101 Two Twins Bedroom 3
32" TV
Mickey Theme

ALM2809-101 Living Room
Has a sleeper Sofa

ALM2809-101 Living Room (Angle)
52" TV
Sound System
PS3

ALM2809-101 Patio

ALM2809-101 Kitchen

ALM2809-101 Dining Room

ALM2809-101 Kitchen (Angle)

ALM2809-101 Master King Bedroom 1
Attached Bathroom

8 guests 3 bed 2 bath 1,247 sq ft

Orlando - Windsor Hills Resort | Kissimmee

Starting at $84 daily

ALM2813-403 Living Room (Angle 2)

ALM2813-403 Living Room

ALM2813-403 Living Room (Angle)
42" TV

ALM2813-403 Kitchen

ALM2813-403 Kitchen (Angle)

ALM2813-403 Dining /Living

ALM2813-403 Dining Room

ALM2813-403 Master King Bedroom 1
Attached Bathroom

6 guests 3 bed 2 bath 1,247 sq ft

Orlando - Windsor Hills Resort | Kissimmee

Starting at $73 daily

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