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Orlando - Windsor Island Resort
WIR_1557AR Villa Moderna photo 1
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Recommended Rental Flex30
WIR_1557AR Villa Moderna
Beds 6 | Baths 5 | Guests 12 | SQ.FT 3117
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Starting At
$254.00 daily
Orlando - Windsor Island Resort
WIR_1554AR Epic Windsor Dream photo 1
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Recommended Rental Flex30
WIR_1554AR Epic Windsor Dream
Beds 6 | Baths 6 | Guests 12 | SQ.FT 4866
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Starting At
$339.00 daily
Orlando - Windsor Island Resort
WIR_1564AR Windsor Island Gem photo 1
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WIR_1564AR Windsor Island Gem The clubhouse is just a walk away!...
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Recommended Rental Flex30
WIR_1564AR Windsor Island Gem
Beds 5 | Baths 4 | Guests 10 | SQ.FT 2283
Book Now
Starting At
$162.00 daily
Orlando - Windsor Island Resort
WIR_1561AR Windsor Deluxe photo 1
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Recommended Rental Flex30
WIR_1561AR Windsor Deluxe
Beds 10 | Baths 8 | Guests 20 | SQ.FT 4477
Book Now
Starting At
$329.00 daily
Orlando - Windsor Island Resort
WIR_1562AR Windsor Gem photo 1
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Recommended Rental Flex30
WIR_1562AR Windsor Gem
Beds 10 | Baths 8 | Guests 20 | SQ.FT 4383
Book Now
Starting At
$489.00 daily
Orlando - Windsor Island Resort
WIR_1559AR The Hang Out #3 photo 1
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Recommended Rental Flex30
WIR_1559AR The Hang Out #3
Beds 10 | Baths 8 | Guests 24 | SQ.FT 4034
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Starting At
$516.00 daily
Orlando - Windsor Island Resort
WIR_1553AR Windsor Delight photo 1
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Flex30
WIR_1553AR Windsor Delight
Beds 5 | Baths 5 | Guests 10 | SQ.FT 2271
Book Now
Starting At
$174.00 daily
Orlando - Windsor Island Resort
WIR_1563AR Sunny Stays photo 1
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Recommended Rental Flex30
WIR_1563AR Sunny Stays
Beds 5 | Baths 4 | Guests 12 | SQ.FT 2504
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Starting At
$184.00 daily
Orlando - Windsor Island Resort
WIR_1560AR Windsor Luxury photo 1
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Flex30
WIR_1560AR Windsor Luxury
Beds 8 | Baths 6 | Guests 16 | SQ.FT 4034
Book Now
Starting At
$326.00 daily
Orlando - Windsor Island Resort
WIR_1556AR Windsor Island Living photo 1
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Recommended Rental Flex30
WIR_1556AR Windsor Island Living
Beds 8 | Baths 6 | Guests 16 | SQ.FT 4034
Book Now
Starting At
$320.00 daily
Orlando - Windsor Island Resort
WIR_1558AR Windsor Splendor photo 1
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Recommended Rental Flex30
WIR_1558AR Windsor Splendor
Beds 7 | Baths 6 | Guests 16 | SQ.FT 3281
Book Now
Starting At
$258.00 daily
Orlando - Windsor Island Resort
WIR_1555AR Windsor Living photo 1
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WIR_1555AR Windsor Living The clubhouse is just a walk away!...
WIR_1555AR Windsor Living photo 6
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WIR_1555AR Windsor Living photo 9
Recommended Rental Flex30
WIR_1555AR Windsor Living
Beds 5 | Baths 4 | Guests 12 | SQ.FT 2484
Book Now
Starting At
$197.00 daily
Orlando - Windsor Island Resort
WIR_1552AR Windsor Oasis photo 1
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WIR_1552AR Windsor Oasis The clubhouse is just a walk away!...
WIR_1552AR Windsor Oasis photo 4
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Flex30
WIR_1552AR Windsor Oasis
Beds 5 | Baths 4 | Guests 10 | SQ.FT 2265
Book Now
Starting At
$178.00 daily
Orlando - Windsor Island Resort
WIR_1551AR Windsor Escape photo 1
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WIR_1551AR Windsor Escape photo 3
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WIR_1551AR Windsor Escape The clubhouse is just a walk away!...
WIR_1551AR Windsor Escape photo 6
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Recommended Rental Flex30
WIR_1551AR Windsor Escape
Beds 5 | Baths 4 | Guests 10 | SQ.FT 2265
Book Now
Starting At
$192.00 daily
Orlando - Windsor Island Resort
2186LC - Villa de Rosa(P) photo 1
2186LC - Villa de Rosa(P) Screened in private pool area...
2186LC - Villa de Rosa(P) Safety fence...
2186LC - Villa de Rosa(P) Alternate view of pool and spa...
2186LC - Villa de Rosa(P) Pool and bubbling spa...
2186LC - Villa de Rosa(P) Pool area with child safety fence up....
2186LC - Villa de Rosa(P) Spa and sun loungers...
2186LC - Villa de Rosa(P) Themed space with foosball, gaming stations and arcade games. **Air hockey has been removed and will not be available...
2186LC - Villa de Rosa(P) Themed space with foosball, gaming stations and arcade games. **Air hockey has been removed and will not be available...
2186LC - Villa de Rosa(P)
Beds 10 | Baths 8 | Guests 20 | SQ.FT 4399
Book Now
Starting At
$307.00 daily
Orlando - Windsor Island Resort
4298LA - Lana Dream Villa (G) photo 1
4298LA - Lana Dream Villa (G) Front of villa near Disney...
4298LA - Lana Dream Villa (G) Upstairs loft has comfortable seating and foosball game...
4298LA - Lana Dream Villa (G) Kitchen through entry...
4298LA - Lana Dream Villa (G) Lounge area showing patio doors to pool...
4298LA - Lana Dream Villa (G) Master bedroom 2 has queen bed, wall mounted flatscreen TV...
4298LA - Lana Dream Villa (G) Bedroom 5 has a princess theme...
4298LA - Lana Dream Villa (G) Master bedroom features king size bed, wall mounted flatscreen TV and casual chair...
4298LA - Lana Dream Villa (G) Bedroom 3 has a superhero theme and twin beds...
4298LA - Lana Dream Villa (G)
Beds 5 | Baths 5 | Guests 10 | SQ.FT 1976
Book Now
Starting At
$146.00 daily
Orlando - Windsor Island Resort
2191LC - Island Luxury Manor (P) photo 1
2191LC - Island Luxury Manor (P) Screened in private pool area...
2191LC - Island Luxury Manor (P) Stay in shape and let the fun continue with Peloton bikes in the garage with fun arcade games....
2191LC - Island Luxury Manor (P) Terminator arcade game located in the garage,...
2191LC - Island Luxury Manor (P) Full on exercise room with weights so you don't have to go back home pudgy from your vacation experience. ....
2191LC - Island Luxury Manor (P) Pool view at dusk. Beautifully pristine property with gorgeous pool views....
2191LC - Island Luxury Manor (P) Loft area games. Shown is foosball and 2 arcades....
2191LC - Island Luxury Manor (P) Close up of weighted balls and dumbbells...
2191LC - Island Luxury Manor (P) Converted garage showing arcade games with Peloton bikes....
2191LC - Island Luxury Manor (P)
Beds 10 | Baths 8 | Guests 27 | SQ.FT 4383
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Starting At
$308.00 daily
Orlando - Windsor Island Resort
3545LD - Island Getaway (P) photo 1
3545LD - Island Getaway (P) Dinosaur themed movie room...
3545LD - Island Getaway (P) Alternate view of the movie room...
3545LD - Island Getaway (P) Quick look at the poolside views...
3545LD - Island Getaway (P) Shaded spa...
3545LD - Island Getaway (P) Pool view...
3545LD - Island Getaway (P) Kitchen showing breakfast bar with seating for 4...
3545LD - Island Getaway (P) Look inside this beautiful home...
3545LD - Island Getaway (P) Bright and modern dining room with a wispy leaf chandelier...
3545LD - Island Getaway (P)
Beds 9 | Baths 6 | Guests 18 | SQ.FT 4398
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Starting At
$331.00 daily
Orlando - Windsor Island Resort
2260LC - Magical Mansion (P) photo 1
2260LC - Magical Mansion (P) Front of unit near Disney...
2260LC - Magical Mansion (P) Games room showing ping pong table and arcade games...
2260LC - Magical Mansion (P) Outdoor dining table seating for 6...
2260LC - Magical Mansion (P) Pool area...
2260LC - Magical Mansion (P) Alternate view of pool area...
2260LC - Magical Mansion (P) Alternate view of games room...
2260LC - Magical Mansion (P) 3rd view of games room...
2260LC - Magical Mansion (P) Front entrance hallway showing front door...
2260LC - Magical Mansion (P)
Beds 10 | Baths 8 | Guests 22 | SQ.FT 4383
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Starting At
$324.00 daily
Orlando - Windsor Island Resort
900PDWI - Island Paradise Villa (P) photo 1
900PDWI - Island Paradise Villa (P) Drone picture of resort...
900PDWI - Island Paradise Villa (P) Front of villa near Disney...
900PDWI - Island Paradise Villa (P) Entry...
900PDWI - Island Paradise Villa (P) Entry...
900PDWI - Island Paradise Villa (P) Family seating area...
900PDWI - Island Paradise Villa (P) Family lounge area showing patio doors to pool area and wall mounted flat screen TV...
900PDWI - Island Paradise Villa (P) View from patio doors across living area...
900PDWI - Island Paradise Villa (P) Kitchen...
900PDWI - Island Paradise Villa (P)
Beds 5 | Baths 5 | Guests 10 | SQ.FT 1524
Book Now
Starting At
$146.00 daily
Orlando - Windsor Island Resort
976PD - Island Hopper Villa (P) photo 1
976PD - Island Hopper Villa (P) Front of villa near Disney...
976PD - Island Hopper Villa (P) Covered Patio for outdoordining...
976PD - Island Hopper Villa (P) Jetted Splash Pool showing accent lighting...
976PD - Island Hopper Villa (P) Entryway...
976PD - Island Hopper Villa (P) Fully equipped kitchen showing island...
976PD - Island Hopper Villa (P) Living area showing sofa...
976PD - Island Hopper Villa (P) Galley Style Kitchen with stainless appliances...
976PD - Island Hopper Villa (P) Breakfast bar seating for 4...
976PD - Island Hopper Villa (P)
Beds 5 | Baths 4 | Guests 10 | SQ.FT 1976
Book Now
Starting At
$146.00 daily
Orlando - Windsor Island Resort
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WI107-4416-5-GP
Beds 5 | Baths 5 | Guests 11
Book Now
Starting At
$176.00 daily
Orlando - Windsor Island Resort
WI110-3913-7-P photo 1
WI110-3913-7-P Enjoy a lovely evening outside by the pool!...
WI110-3913-7-P Taking the day off? Our home is located in Windsor Island Resort, where you'll get access to all of its amenities....
WI110-3913-7-P You want to stay indoors? Our game room is perfect for those days you want to relax and enjoy inside....
WI110-3913-7-P The home features multiple themed rooms, designed to create a playful atmosphere for your children!...
WI110-3913-7-P Our vacation rental offers the ideal entertainment for large groups of friends & family, featuring an extra TV room and pool table....
WI110-3913-7-P Enjoy beautiful Florida sunsets at Windsor Island Resort!...
WI110-3913-7-P Located a 20-to-30 minute drive from Orlando's most popular attracttions....
WI110-3913-7-P Each corner of the house has been carefuly decorated for your confort....
WI110-3913-7-P
Beds 7 | Baths 5 | Guests 20 | SQ.FT 3234
Book Now
Starting At
$250.80 daily
Orlando - Windsor Island Resort
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WI109-3946-5-GP
Beds 5 | Baths 4 | Guests 12
Book Now
Starting At
$154.00 daily
Orlando - Windsor Island Resort
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WI108-4198-5-GP
Beds 5 | Baths 4 | Guests 12
Book Now
Starting At
$154.00 daily
Orlando - Windsor Island Resort
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WI106-3373-5-GP
Beds 5 | Baths 5 | Guests 12
Book Now
Starting At
$214.50 daily
Orlando - Windsor Island Resort
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WI105-1836-5-GP
Beds 5 | Baths 5 | Guests 14 | SQ.FT 2621
Book Now
Starting At
$214.50 daily
Orlando - Windsor Island Resort
WI102-3705-5-P photo 1
WI102-3705-5-P Fan of Harry Potter? Enjoy a movie marathon in our Harry Potter themed TV room....
WI102-3705-5-P Rest in our high quality beds after a long day at the parks....
WI102-3705-5-P Love Ratatouille? Step into Remy's delicious world with a themed room complete with its own mini kitchen!...
WI102-3705-5-P Relax in the Florida sun by our private pool....
WI102-3705-5-P Located in Windsor Island Resort, where you get access to all its amenities....
WI102-3705-5-P Located a 20-minute drive from Orlando's most popular attractions....
WI102-3705-5-P Unwind in style and spend some quality time with your loved ones in our modern but stylish living room....
WI102-3705-5-P The house's open concept layout perfectly integrates the living room, dining room and kitchen with our outdoor space....
WI102-3705-5-P
Beds 5 | Baths 5 | Guests 13 | SQ.FT 2250
Book Now
Starting At
$168.30 daily
Orlando - Windsor Island Resort
WI101-2310-8-GP photo 1
WI101-2310-8-GP Free access to all resort amenities!...
WI101-2310-8-GP Fun for everyone in our spacious game room!...
WI101-2310-8-GP The room for your kids! (or older ones too!)...
WI101-2310-8-GP Feel yourself at home!...
WI101-2310-8-GP photo 6
WI101-2310-8-GP Game room for the kids!...
WI101-2310-8-GP photo 8
WI101-2310-8-GP Tasteful decor!...
WI101-2310-8-GP
Beds 8 | Baths 6 | Guests 17 | SQ.FT 4000
Book Now
Starting At
$264.00 daily
Orlando - Windsor Island Resort
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WI103-4178-5-GP
Beds 5 | Baths 4 | Guests 12 | SQ.FT 2749
Book Now
Starting At
$154.00 daily
Orlando - Windsor Island Resort
WI104-4408-5-GP photo 1
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WI104-4408-5-GP
Beds 5 | Baths 5 | Guests 12 | SQ.FT 2622
Book Now
Starting At
$158.40 daily
Orlando - Windsor Island Resort
WIR_1500M | Windsor Island Luxury photo 1
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WIR_1500M | Windsor Island Luxury photo 4
WIR_1500M | Windsor Island Luxury Relax with everyone after a fun day at the parks in the gathering room...
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WIR_1500M | Windsor Island Luxury
Beds 7 | Baths 6 | Guests 16 | SQ.FT 4034
Book Now
Starting At
$293.00 daily
Orlando - Windsor Island Resort
WIR_1510M | Windsor Island Dream photo 1
WIR_1510M | Windsor Island Dream photo 2
WIR_1510M | Windsor Island Dream photo 3
WIR_1510M | Windsor Island Dream photo 4
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WIR_1510M | Windsor Island Dream photo 8
WIR_1510M | Windsor Island Dream photo 9
WIR_1510M | Windsor Island Dream
Beds 5 | Baths 5 | Guests 12 | SQ.FT 2550
Book Now
Starting At
$106.00 daily
Orlando - Windsor Island Resort
WIR_1508M | Lana Paradise photo 1
WIR_1508M | Lana Paradise photo 2
WIR_1508M | Lana Paradise photo 3
WIR_1508M | Lana Paradise photo 4
WIR_1508M | Lana Paradise photo 5
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WIR_1508M | Lana Paradise photo 8
WIR_1508M | Lana Paradise photo 9
WIR_1508M | Lana Paradise
Beds 10 | Baths 8 | Guests 20 | SQ.FT 4384
Book Now
Starting At
$300.00 daily
Orlando - Windsor Island Resort
WIR_1509M | Coastal Haven photo 1
WIR_1509M | Coastal Haven photo 2
WIR_1509M | Coastal Haven photo 3
WIR_1509M | Coastal Haven photo 4
WIR_1509M | Coastal Haven photo 5
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WIR_1509M | Coastal Haven photo 8
WIR_1509M | Coastal Haven photo 9
WIR_1509M | Coastal Haven
Beds 7 | Baths 6 | Guests 14 | SQ.FT 4000
Book Now
Starting At
$383.00 daily
Orlando - Windsor Island Resort
WIR_1512M | Charming Villa photo 1
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WIR_1512M | Charming Villa photo 3
WIR_1512M | Charming Villa photo 4
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WIR_1512M | Charming Villa
Beds 6 | Baths 5 | Guests 14 | SQ.FT 3127
Book Now
Starting At
$154.00 daily
Orlando - Windsor Island Resort
LNA4353 photo 1
LNA4353 Pool / Spa Pool Faces South...
LNA4353 Dining / Kitchen / Living...
LNA4353 Windsor Island Resort...
LNA4353 Theater Room Upstairs 85
LNA4353 Living Room 75
LNA4353 Living Room 75
LNA4353 Living Room 75
LNA4353 Dining / Kitchen / Living...
LNA4353
Beds 10 | Baths 6 | Guests 28 | SQ.FT 4398
Book Now
Starting At
$499.00 daily
Orlando - Windsor Island Resort
AHB1137 photo 1
AHB1137 Theater Room (Angle) 82
AHB1137 Living Room (Angle) 70
AHB1137 Living Room...
AHB1137 Dining Room...
AHB1137 Kitchen...
AHB1137 Theater Room...
AHB1137 Master King Bedroom 2 Upstairs Attached Bathroom...
AHB1137 Master King Bedroom 2 (Angle) 65
AHB1137
Beds 5 | Baths 6 | Guests 12 | SQ.FT 2587
Book Now
Starting At
$247.20 daily
Orlando - Windsor Island Resort
PSD816 photo 1
PSD816 Two Twins Bedroom 5 Mickey Theme...
PSD816 Patio Dining Pool Faces West...
PSD816 Loft 65
PSD816 Living Room 65
PSD816 Kitchen...
PSD816 Kitchen (Angle)...
PSD816 Dining Room...
PSD816 Dining Room (Angle)...
PSD816
Beds 5 | Baths 5 | Guests 10 | SQ.FT 2263
Book Now
Starting At
$255.00 daily
Orlando - Windsor Island Resort
LLC2131 photo 1
LLC2131 Patio Dining...
LLC2131 Game Room 65
LLC2131 Two Twins Bedroom 8 Upstairs 43
LLC2131 Two Twins Suite Bedroom 2 Upstairs Attached Bathroom 43
LLC2131 Living Room / Kitchen 70
LLC2131 Living Room 70
LLC2131 Dining / Kitchen / Living...
LLC2131 Kitchen Island / Dining / Living...
LLC2131
Beds 10 | Baths 6 | Guests 25 | SQ.FT 4393
Book Now
Starting At
$499.00 daily
 

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