A golf course with a large hotel and residential area.

Windward Cay Vacations from $513

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Your Windward Cay Vacation

Take all the hassle out of organizing your next break with a Windward Cay vacation package. Soak in the sights and sounds of this captivating neighborhood and enjoy what it has to offer. Kick start your trip to Windward Cay by checking out nearby attractions such as Old Town, Give Kids the World Village and Medieval Times. Expedia can help you turn your ideal Windward Cay vacation into reality, whatever your budget or travel plans.

The Latest Windward Cay Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A deck with lounge chairs and tables overlooking a beach with palm trees and ocean waves.
    Jan 25 - Jan 29

    Westgate Cocoa Beach Resort + Flight

    Cocoa Beach
    4 nights
    4.0 star property
    8.6/10 - Excellent (578 reviews)
    "The beaches across the street. The pools are nice however I had a room right next to the pool and they play music up until 9:00pm at night. So if you just trying to rest that will not happen. The music just kept playing all day long."
    Reviewed November 8, 2026
    Roundtrip • Philadelphia (PHL) - Orlando (MCO)
    PHL - MCO • Nonstop MCO - PHL • Nonstop
    $992
    $513
    per traveler
    found 18 hours ago
    Westgate Cocoa Beach Resort
  • An outdoor pool area with red umbrellas, chairs, and a view of a body of water.
    Jan 10 - Jan 16

    Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive + Flight

    International Drive District
    6 nights
    3.0 star property
    7.8/10 - Good (639 reviews)
    "The place is nice and the rooms were very clean, but the breakfast was horrible. They had no bacon or sausage. The fruits were stale apples and oranges and they had only hard-boiled eggs. It was literally the worst breakfast for a decent hotel that I have ever seen all they had was bread and they didn’t even have the good cereal they were just being cheap."
    Reviewed November 8, 2026
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    $933
    $553
    per traveler
    found 1 day ago
    Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
  • A coastal area with dense vegetation and a pathway leading to the beach.
    Jan 25 - Jan 29

    The Resort on Cocoa Beach + Flight

    Cocoa Beach
    4 nights
    3.5 star property
    9.4/10 - Exceptional (684 reviews)
    Roundtrip • Philadelphia (PHL) - Orlando (MCO)
    PHL - MCO • Nonstop MCO - PHL • Nonstop
    Save 100% on your flight
    $958
    $576
    per traveler
    found 18 hours ago
    The Resort on Cocoa Beach
  • A swimming pool with multiple water features, surrounded by palm trees and hotel buildings.
    Jan 17 - Jan 23

    Magical Moment Vacation Condos + Flight

    International Drive District
    6 nights
    4.5 star property
    6.4/10 - (10 reviews)
    "La propiedad está muy, pero muy bien ubicada, cerca de todo lo principal en Orlando y muchos restaurantes alrededor, el complex es muy bonito, la piscina es grande y el personal es muy amable, el gimnasio es extremadamente sencillo. Los apartamentos vienen equipados con cocina, lavadora, secadora, pero si tú buscas cocinar tus comidas como yo y mi familia, vas a sufrir porque la cocina casi no tienen utensilios, solo un sartén, una olla pequeña, un cuchillo para cortar y por supuesto platos y..."
    Reviewed October 25, 2026
    Roundtrip • New York (EWR) - Orlando (MCO)
    EWR - MCO • Nonstop MCO - EWR • 1 stop
    $1,211
    $732
    per traveler
    found 3 hours ago
    Magical Moment Vacation Condos
  • A modern hotel lobby with a pool table, seating area, and a staircase.
    Jan 16 - Jan 22

    Riviere 2BR Apartment Pet Friendly Oasis Sleeps 6 Close to Epic Universe Pool & Gym + Flight

    International Drive District
    6 nights
    4.0 star property
    Roundtrip • New York (NYC) - Orlando (MCO)
    LGA - MCO • Nonstop MCO - LGA • Nonstop
    $1,146
    $711
    per traveler
    found 1 day ago
    Riviere 2BR Apartment Pet Friendly Oasis Sleeps 6 Close to Epic Universe Pool & Gym

Where to stay in Windward Cay

Find the best Windward Cay areas and neighborhoods for the activities you enjoy most.
The entrance to the Hollywood Studios area with a large sign and distinctive architecture.
Photo by Gary Burke
Open Photo by Gary Burke

Bay Lake

Home to all four Walt Disney World Resort theme parks and one water park, this city offers endless entertainment, including Disney's Fort Wilderness Resort & Campground and Magnolia and Palm Golf Courses.

A large Ferris wheel with blue lights, surrounded by a cityscape with illuminated buildings and a tall green tower.

International Drive District

Adventure activities, iconic attractions, shopping and world-class dining destinations make this famous street one of Orlando’s most popular tourist attractions.

A roller coaster at Universal Orlando Resort, featuring a tall palm tree and a clear blue sky.
Photo by Peter Sutton
Open Photo by Peter Sutton

Florida Center

While visiting Florida Center, you might make a stop by sights like Universal Orlando Resort and Universal Studios Florida.

A large Ferris wheel with blue lighting, surrounded by a parking lot and buildings.

Champions Gate

Abundant dining options and pristine golf courses are well-reviewed features of Champions Gate. Make a stop by top sights like ChampionsGate Golf Club while you're exploring the area.

A golf course with bunkers, water hazards, and a large lake.

Reunion

The waterparks and pristine golf courses are top of the list for many visitors to Reunion. A stop by Reunion Resort Golf Course or Jack Nicklaus Course might round out your trip.

Windward Cay Hotel Deals

A spacious restaurant with high ceilings, hanging pendant lights, and a variety of seating arrangements.

Embassy Suites by Hilton Orlando Lake Buena Vista South

Embassy Suites by Hilton Orlando Lake Buena Vista South
4.0 star property
1.9 mi from Windward Cay
9.6 out of 10, Exceptional, (1,688 reviews)
"Ok"
$118 nightly
The price is $134
Nov 16 - Nov 17
Total with taxes and fees
Embassy Suites by Hilton Orlando Lake Buena Vista South
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
See all properties in Windward Cay
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.