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Windward Cay self-catering vacation accommodation is located within a cosy and quiet community that sits remarkably close to some of Florida’s most famous attractions. For instance, Walt Disney World is only a ten-minute drive from Windward Cay self-catering villas. At this iconic resort you’ll be able to discover first-class theme parks like the Magic Kingdom and Epcot, alongside attractions to suit every age and taste. Also within easy reach of Windward Cay self-catering apartments are other top family destinations, such as Islands of Adventure, SeaWorld and Universal Studios - the theme park with a wealth of rides and shows inspired by movies. Windward Cay self-catering villas are also found at the very heart of an area famous for its spectacular array of golf courses. You’ll be able to find public pay and play courses with excellent facilities alongside some internationally renowned resorts like ChampionsGate, Reunion and Mystic Dunes, all within a short drive of apartments in Windward Cay. There are yet more top attractions to discover within an hour’s drive of self-catering holiday accommodation in Windward Cay. To the west is the high-profile theme park, Busch Gardens, which is perfect for a family day out; while to the east lies Cape Canaveral, where you’ll find the legendary Kennedy Space Center. Weather At a holiday rental in Kissimmee you’ll be able to expect warm weather from March until as late as November, while winters here tend to remain mild and sunny. Best Time to Visit If you head for a Windward Cay holiday rental in April or May you’ll find glorious weather, and slightly fewer crowds at the theme parks. Reaching Windward Cay Windward Cay self-catering villas and apartments are just 30 minutes away from the closest airport – Orlando International (MCO).

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Viewed 28 times in the last 48 hours
  • 3 BR
  • 2 BA
avg/night
Villa #8225408
1
Viewed 14 times in the last 48 hours
  • 3 BR
  • 2 BA
Wonderful! 4.8/5
(9 reviews)
avg/night
Villa #6782050
9
  • 3 BR
  • 2 BA
avg/night
Villa #4549772
1
Viewed 34 times in the last 48 hours
  • 3 BR
  • 2 BA
  • 1538 sq. ft.
avg/night
House #4675207
1
  • 3 BR
  • 2 BA
Exceptional! 5/5
(3 reviews)
avg/night
Villa #6511019
3
  • 1 BR
  • 2 BA
Exceptional! 5/5
(6 reviews)
avg/night
Villa #136384
6
  • 3 BR
  • 2 BA
avg/night
Villa #4515446
3
Viewed 5 times in the last 48 hours
  • 3 BR
  • 2 BA
avg/night
Villa #8224253
Viewed 10 times in the last 48 hours
  • 3 BR
  • 2 BA
  • Separate Toilet
avg/night
Villa #4515394
  • 3 BR
  • 2 BA
avg/night
Villa #4549250
Viewed 7 times in the last 48 hours
  • 3 BR
  • 2 BA
  • 1291 sq. ft.
Exceptional! 5/5
(14 reviews)
View details for price
Villa #6517541
14
  • 3 BR
  • 2 BA
  • Separate Toilets
  • 1506 sq. ft.
Exceptional! 5/5
(31 reviews)
avg/night
Villa #6322099
31
  • 3 BR
  • 2 BA
avg/night
Villa #8240546
  • 3 BR
  • 2 BA
  • Separate Toilet
avg/night
Villa #6511678
1
Viewed 5 times in the last 48 hours
  • 3 BR
  • 2 BA
Excellent! 4.4/5
(5 reviews)
avg/night
Villa #8077003
5
avg/night
Villa #8288297
Viewed 51 times in the last 48 hours
  • 4 BR
  • 2 BA
  • 2003 sq. ft.
avg/night
House #930981vb
3
Viewed 55 times in the last 48 hours
  • 3 BR
  • 2 BA
  • Separate Toilet
Wonderful! 4.9/5
(38 reviews)
avg/night
House #7017516
38
Viewed 76 times in the last 48 hours
  • 7 BR
  • 5 BA
  • 3500 sq. ft.
Wonderful! 4.8/5
(36 reviews)
avg/night
Villa #370387
36
Viewed 44 times in the last 48 hours
  • 3 BR
  • 2 BA
  • Separate Toilet
  • 1275 sq. ft.
Excellent! 4.5/5
(6 reviews)
avg/night
Townhome #824799vb
6
Viewed 80 times in the last 48 hours
Premier Partner
  • 5 BR
  • 4 BA
  • 2286 sq. ft.
avg/night
House #4299420
4
Viewed 43 times in the last 48 hours
  • 5 BR
  • 3 BA
Excellent! 4.7/5
(17 reviews)
avg/night
Villa #56145vb
17
Viewed 18 times in the last 48 hours
  • 5 BR
  • 4 BA
  • 2765 sq. ft.
Excellent! 4.5/5
(50 reviews)
avg/night
Villa #116960vb
50
Viewed 57 times in the last 48 hours
Premier Partner
  • 3 BR
  • 2 BA
  • Separate Toilet
  • 1392 sq. ft.
Excellent! 4.4/5
(40 reviews)
avg/night
Townhome #703142vb
40
Viewed 64 times in the last 48 hours
Premier Partner
  • 7 BR
  • 5 BA
  • Separate Toilet
  • 2836 sq. ft.
Very Good! 4.2/5
(10 reviews)
avg/night
House #4386935
10
Viewed 34 times in the last 48 hours
Premier Partner
  • 5 BR
  • 4 BA
  • 2773 sq. ft.
Wonderful! 4.8/5
(57 reviews)
avg/night
Villa #3511581
57
Viewed 12 times in the last 48 hours
Premier Partner
  • 4 BR
  • 3 BA
  • 1900 sq. ft.
avg/night
House #4458326
4
Viewed 74 times in the last 48 hours
  • 4 BR
  • 2 BA
  • 1978 sq. ft.
Wonderful! 4.8/5
(5 reviews)
avg/night
House #4588416
5
Viewed 36 times in the last 48 hours
  • 7 BR
  • 5 BA
  • 3500 sq. ft.
Wonderful! 4.9/5
(36 reviews)
avg/night
Villa #3587513
36
Viewed 31 times in the last 48 hours
Premier Partner
  • 4 BR
  • 3 BA
  • 2003 sq. ft.
Exceptional! 5/5
(70 reviews)
avg/night
House #651427vb
70
Viewed 38 times in the last 48 hours
Premier Partner
  • 7 BR
  • 4 BA
  • Separate Toilet
  • 3000 sq. ft.
Excellent! 4.5/5
(57 reviews)
avg/night
Villa #921338
57
Viewed 33 times in the last 48 hours
  • 7 BR
  • 4 BA
  • Separate Toilet
  • 3500 sq. ft.
Wonderful! 4.8/5
(12 reviews)
avg/night
Villa #3931680
12
Viewed 77 times in the last 48 hours
  • 4 BR
  • 3 BA
Excellent! 4.4/5
(12 reviews)
avg/night
House #3871706
12
Viewed 30 times in the last 48 hours
Premier Partner
  • 2 BR
  • 2 BA
  • 1250 sq. ft.
Wonderful! 4.9/5
(41 reviews)
avg/night
Condo #4654380
41
Viewed 71 times in the last 48 hours
Premier Partner
  • 5 BR
  • 4 BA
  • 2400 sq. ft.
Excellent! 4.4/5
(73 reviews)
avg/night
Villa #194591
73
Viewed 10 times in the last 48 hours
  • 4 BR
  • 3 BA
  • 2359 sq. ft.
Excellent! 4.5/5
(10 reviews)
avg/night
Villa #3818222
10
  • 3 BR
  • 2 BA
avg/night
House #1227865vb
Viewed 39 times in the last 48 hours
Premier Partner
  • 5 BR
  • 4 BA
  • 2331 sq. ft.
Wonderful! 4.9/5
(31 reviews)
avg/night
Villa #659872vb
31
Viewed 17 times in the last 48 hours
  • 7 BR
  • 4 BA
  • Separate Toilet
  • 3500 sq. ft.
Wonderful! 4.8/5
(11 reviews)
avg/night
Villa #3931699
11
Viewed 28 times in the last 48 hours
  • 6 BR
  • 5 BA
  • Separate Toilet
  • 2827 sq. ft.
Wonderful! 4.9/5
(51 reviews)
avg/night
Villa #424767
51
Viewed 109 times in the last 48 hours
  • 6 BR
  • 3 BA
  • Separate Toilet
  • 3500 sq. ft.
Exceptional! 5/5
(7 reviews)
avg/night
House #381616
7
Viewed 62 times in the last 48 hours
  • 5 BR
  • 3 BA
Very Good! 4.2/5
(5 reviews)
avg/night
House #4427988
5
Viewed 30 times in the last 48 hours
  • 7 BR
  • 5 BA
  • Separate Toilet
  • 3200 sq. ft.
Excellent! 4.3/5
(30 reviews)
avg/night
Villa #3763977
30
Viewed 142 times in the last 48 hours
  • 3 BR
  • 2 BA
  • 1300 sq. ft.
Excellent! 4.7/5
(106 reviews)
avg/night
Condo #71694
106
Viewed 9 times in the last 48 hours
  • 7 BR
  • 4 BA
  • Separate Toilet
  • 3200 sq. ft.
Wonderful! 4.9/5
(10 reviews)
avg/night
Villa #305209vb
10
Viewed 28 times in the last 48 hours
  • 4 BR
  • 3 BA
  • 1960 sq. ft.
Excellent! 4.7/5
(7 reviews)
avg/night
Villa #849656
7
  • 5 BR
  • 3 BA
  • 1950 sq. ft.
Excellent! 4.4/5
(18 reviews)
avg/night
Villa #150805
18
Viewed 36 times in the last 48 hours
  • 7 BR
  • 5 BA
  • Separate Toilet
  • 3200 sq. ft.
Excellent! 4.7/5
(45 reviews)
avg/night
Villa #385222
45
Viewed 89 times in the last 48 hours
  • 4 BR
  • 3 BA
avg/night
House #4427987
3
Viewed 13 times in the last 48 hours
  • 3 BR
  • 2 BA
Wonderful! 4.9/5
(41 reviews)
avg/night
Condo #97421vb
41

Holiday Accommodation Windward Cay (127)