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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 $95 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 $195 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 $199 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 $139 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

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 $121 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 $141 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

MVH_025MDNB | Windsor Magic Welcome to Windsor Magic, a gorgeous private townhome rental in Windsor Hills Resort. | Photos updated: August 2017

MVH_025MDNB | Windsor Magic Everyone will love having their own pool to play in all day

MVH_025MDNB | Windsor Magic Take a splash in your private screened-in pool

MVH_025MDNB | Windsor Magic With a beautiful open concept living space, the whole family can gather and spend time together

MVH_025MDNB | Windsor Magic Watch favorite shows on the 50-inch SMART TV

MVH_025MDNB | Windsor Magic Plenty of space to accommodate everyone

MVH_025MDNB | Windsor Magic Enjoy a family meal at the dining room table with seating for 6

MVH_025MDNB | Windsor Magic

8 guests 3 bed 3 bath 1,440 sq ft

Orlando - Windsor Hills Resort | Kissimmee

Starting at $99 daily

MVH_044M | The Magical Dream Getaway Book your stay today at The Magical Dream Getawat, a beautiful 3 bedroom Windsor Hills condo. | PHOTOS TAKEN: September 2024

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

MVH_044M | The Magical Dream Getaway Photos taken: Sept 2024

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 Photos taken: Sept 2024

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 | PHOTOS TAKEN: December 2015

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 $138 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 TAKEN: February 2019

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

MVH_107M | Pawnall Bliss Your private oasis awaits

MVH_107M | Pawnall Bliss Relax by the pool area and soak up the Florida sun

MVH_107M | Pawnall Bliss Featuring a foosball table, pool table, gaming system and table and chairs

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

MVH_107M | Pawnall Bliss A large and open floor plan throughout

MVH_107M | Pawnall Bliss Comfortable sofa seating for you to relax after long days at the theme parks

8 guests 4 bed 4 bath 1,824 sq ft

Orlando - Windsor Hills Resort | Kissimmee

Starting at $104 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

MVH_074M | Windsor Point Welcome to Windsor Point, a luxury 6 bed Windsor Hills home with everything you will need | PHOTOS UPDATED: December 2023

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 $132 daily

MVH_121M | The Menagerie Welcome to The Menagerie | PHOTOS TAKEN: December 2025

MVH_121M | The Menagerie Enjoy the fantastic community pool only minutes away from your vacation rental

MVH_121M | The Menagerie This home away from home features magical touches throughout to enhance your vacation experience

MVH_121M | The Menagerie Sit back on the comfortable sofa and loveseat and enjoy a favorite TV show

MVH_121M | The Menagerie Step out onto the private balcony from the living room

MVH_121M | The Menagerie Gather together for meals at the dining room table that seats 6

MVH_121M | The Menagerie Prepare delicious meals in the fully equipped kitchen

MVH_121M | The Menagerie

6 guests 3 bed 2 bath 1,246 sq ft

Orlando - Windsor Hills Resort | Kissimmee

Starting at $73 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 $281 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

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 $214 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 $83 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

BNC7795 Living Room

BNC7795 Kitchen Nook

BNC7795 Kitchen

BNC7795 Living Room (Angle)
52" TV

BNC7795 Dining Room

BNC7795 Master King Bedroom 1 Downstairs
Attached Bathroom

BNC7795 Master King Bedroom 1 (Angle)
32" TV

BNC7795 Master King Bathroom 1
Downstairs
Shower

10 guests 5 bed 5 bath 2,336 sq ft

Orlando - Windsor Hills Resort | Kissimmee

5.0 (11)

Guest rating

Starting at $134 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 $142 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 $166 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 $216 daily

DVL2638 Game Room
Pool Table, Air Hockey
Has AC

DVL2638 Living Room
60" Smart TV
Sound Bar

DVL2638 Living Room (Angle)

DVL2638 Living Room (Angle 2)

DVL2638 Kitchen

DVL2638 Kitchen (Angle)

DVL2638 Nook (Angle)

10 guests 5 bed 5 bath 2,336 sq ft

Orlando - Windsor Hills Resort | Kissimmee

Starting at $172 daily

GRS7756 Family Room (Angle)
55" TV

GRS7756 Kitchen

GRS7756 Kitchen (Angle)

GRS7756 Family Room

GRS7756 Living room

GRS7756 Dining Room

GRS7756 Dining Room (Angle)

12 guests 6 bed 4 bath 2,812 sq ft

Orlando - Windsor Hills Resort | Kissimmee

Starting at $162 daily

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