Windward Cay Villas

Windward Cay Villas

Shops Nearby Restaurants Nearby
★ Walmart and shops close by on US192
★ Restaurants nearby on US192
★ Lake Buena Vista Factory Stores and Premium Outlets (10-25 mins)
★ Walt Disney World Resort (10-25 mins), Seaworld (25-40 mins) and Universal Studios (25-55 mins)
Villas in Windward Cay
Distances to the Attractions
Nearby Villa Communities

Walt Disney World Resort and the Lake Buena Vista area are very much one in the same. This is the area south-east of the Walt Disney World Resort and towards Kissimmee and highway US192. Rental communities will be established and offer a great location, especially with the many nearby restaurants, shops and supermarkets. For a fun day out visit Old Town Fun Spot or for an evening with a difference visit the Medieval Times dinner show with knights and horses.

#387  'Lakeside Haven' South Facing Pool, Spa and Stunning Lakeside Views

Kissimmee Windward Cay
3 Bedrooms, sleeps 6
• 1 Ensuite, 1 Double and 1 Twin
• 2 Bathrooms
• Private Pool with Spa / Hot Tub
• Barbecue
• Games Room
• Lake Views
Villa Facilities & Amenities
Private Pool Spa / Hot Tub Ownership Verified Wi-Fi Internet Games Room Barbecue Grill Cot and Stroller 360° Video Tour Shops Nearby Restaurants Nearby Payment accepted in Sterling
Book this villa
From £107 per night

#321  Windward Cay 'Another Attractive 3 bed Villa with Large Pool Deck Area'.

Kissimmee Windward Cay
10 July 2026 - 10 September 2026 — FREE Welcome Pack
3 Bedrooms, sleeps 6
• 1 Ensuite, 1 Double and 1 Twin
• 2 Bathrooms
• Private Pool
Villa Facilities & Amenities
Private Pool Ownership Verified Wi-Fi Internet Cot and Stroller Shops Nearby Restaurants Nearby Payment accepted in Sterling
Book this villa
From £114 per night

#234  Attractive 3 Bed Vacation Home - '36ft' SOUTH facing Pool with Lake view.

Kissimmee Windward Cay
10 July 2026 - 18 September 2026 — FREE Welcome Pack
3 Bedrooms, sleeps 8
• 1 Ensuite, 1 Double and 1 Twin
• 2 Bathrooms
• Private Pool with Spa / Hot Tub
• Lake Views
Villa Facilities & Amenities
Private Pool Spa / Hot Tub Ownership Verified Wi-Fi Internet Cot and Stroller Shops Nearby Restaurants Nearby Payment accepted in Sterling
Book this villa
From £111 per night

#186  Florida Lets A Dream! With WIFI

Kissimmee Windward Cay
3 Bedrooms, sleeps 8
• 1 Ensuite, 1 Double and 1 Twin
• 2 Bathrooms
• Private Pool
Villa Facilities & Amenities
Private Pool Ownership Verified Wi-Fi Internet Cot and Stroller Shops Nearby Restaurants Nearby Payment accepted in Sterling
Book this villa
From £111 per night

#113  Splendid 3 Bed Villa On Windward Cay

Kissimmee Windward Cay
9 July 2026 - 9 September 2026 — FREE Welcome Pack
3 Bedrooms, sleeps 6
• 1 Ensuite, 1 Double and 1 Twin
• 2 Bathrooms
• Private Pool
Villa Facilities & Amenities
Private Pool Ownership Verified Wi-Fi Internet Cot and Stroller Shops Nearby Restaurants Nearby Payment accepted in Sterling
Book this villa
From £114 per night

#482  4 bed villa with 'South' facing pool in Windward Cay & WIFI

Kissimmee Windward Cay
10 July 2026 - 1 September 2026 — School Holidays Deal
4 Bedrooms, sleeps 10
• 1 Ensuite, 1 Double and 2 Twin
• 2 Bathrooms
• Private Pool
Villa Facilities & Amenities
Private Pool Ownership Verified Wi-Fi Internet Cot and Stroller Shops Nearby Restaurants Nearby Payment accepted in Sterling
Book this villa
From £114 per night

BOOKING A VILLA: Where you are flexible with your dates, check dates either side for potentially more villas and a better deal. Filter villas by the number of bedrooms you need and any preferences. Shortlist those villas which are ideal for your holiday, so that you can compare availability, location, amenities and price. Adding a villa to your shortlist will not contact the owners of a villa. For more information or to book a specific villa, simply enquire. You can send an enquiry to a specific villa owner, multiple villas and even to all villas to check availability. The villa owners will respond with the price for your dates and provide you more details about booking. You are under no obligation to book a villa which you enquire about.

If you have rented a Florida villa in the past five years then you will know prices have increased. Florida has seen above inflation price increases since re-opening after the US Travel Ban in 2021, which have resulted in villa owner costs increasing considerably. Such increases have seen many villas sold, so the demand for villas at peak periods now exceeds availability. However with no service fee to pay when booking through this website, you will not find the same villa cheaper on other websites. Private holiday villas still offer fantastic value and will work out cheaper than booking multiple hotel rooms. Not forgetting your private pool and privacy of your own bedroom.