Owner Direct Vacation
Rentals in Windward Cay

The Best Owner Direct Vacation Rentals in Windward Cay. Explore thousands of vacation home rentals, large cabins, and villas near Windward Cay

Explore the Best Windward Cay Vacation Homes

Looking for the perfect place to stay in Windward Cay? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Windward Cay character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.

  • vacation rentals
  • luxury villas
  • beachfront homes
  • pet-friendly rentals
  • condos

Why Travelers Love Using
Owner Direct to
Find Windward Cay Vacation Rentals

What makes our vacation homes stand out?

check-mark

Verified Properties

Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.

check-mark

Value You Can Trust

Compare a range of properties and find fair, transparent pricing—no hidden fees.

check-mark

Endless Variety

From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.

Thursday Jan 22

Windward Cay, Kissimmee

Thu
icon
18.3°C
Fri
icon
20.3°C
Sat
icon
19.9°C
Sun
icon
22.5°C
Mon
icon
18.8°C
Tue
icon
7.8°C
Wed
icon
10.0°C

Common Vacation Rental Amenities Typical Vacation Rental Amenities

What sort of amenities will be available at your stay?

Our Windward Cay vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.

Indoor Amenities

  • indoor-amenities-kitchenFully equipped kitchens
  • indoor-amenities-living-areaSpacious living areas with streaming TVs
  • indoor-amenities-wifiComplimentary Wi-Fi
  • indoor-amenities-acAir conditioning and heating
  • indoor-amenities-washerIn-unit washer and dryer
  • indoor-amenities-bedPlush bedding and comfortable furniture

Outdoor Amenities

  • outdoor-amenities-balconyBalconies or patios with coastal views
  • outdoor-amenities-poolPrivate or shared pools
  • outdoor-amenities-bbqBBQ grills and outdoor dining areas
  • outdoor-amenities-parkingOn-site parking
  • outdoor-amenities-beachEasy access to beaches and attractions

How to Reserve Your Windward Cay Vacation Rental

Booking Made Simple

Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.

search-icon

SEARCH PROPERTIES

Use filters for location, amenities, and budget.

compare-icon

VIEW DETAILS

Check photos, reviews, and features for your top picks.

bed-icon

BOOK SECURELY

Confirm your stay safely through our trusted travel partners.

Windward Cay Vacation Rental FAQs

1. What are the top vacation rentals in Windward Cay?

2. Which vacation homes in Windward Cay are best for families?

If you are looking for a family-friendly vacation home in Windward Cay, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Windward Cay:

3. How many vacation rentals are available in Windward Cay?

Currently, the total number of properties listed in 2026 is over 33 in the Windward Cay area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Windward Cay.