Find hotels in Windward Cay, Orlando from NT$1,510

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Jul 8 - Jul 9
Tomorrow
Jul 9 - Jul 10
This weekend
Jul 11 - Jul 13
Next weekend
Jul 18 - Jul 20

Filter by

Guest rating
Guest rating
Star rating

Discover 52,436 Windward Cay hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

The Delaney Hotel
Terrace/patio

The Delaney Hotel

3.5 star property
9.6 out of 10, Exceptional, (1000)
"Excellent all around place and stay "
The Delaney Hotel
Hyatt House Orlando International Drive
In-room safe, individually decorated, individually furnished, desk

Hyatt House Orlando International Drive

4.0 star property
9.2 out of 10, Wonderful, (585)
"Super clean hotel, recommend it!"
The price is NT$2,533
NT$2,849 total
includes taxes & fees
Aug 3 - Aug 4
Hyatt House Orlando International Drive
Rosen Plaza on International Drive
Meeting facility

Rosen Plaza on International Drive

4.0 star property
9.2 out of 10, Wonderful, (1612)
"Great place to stay & enjoy the weekend "
The price is NT$3,230
NT$3,723 total
includes taxes & fees
Jul 27 - Jul 28
Rosen Plaza on International Drive
Rosen Shingle Creek
4 outdoor pools, open 5:30 AM to midnight, cabanas (surcharge)

Rosen Shingle Creek

4.5 star property
9.4 out of 10, Exceptional, (3866)
"Nice large resort with plenty of restaurants and pools."
The price is NT$3,462
NT$3,894 total
includes taxes & fees
Jul 18 - Jul 19
Rosen Shingle Creek
SPOT X Hotel Orlando/Intl Dr by The Red Collection
Front of property - evening/night

SPOT X Hotel Orlando/Intl Dr by The Red Collection

3.0 star property
8.8 out of 10, Excellent, (2606)
"Loved staying here "
The price is NT$2,197
NT$2,472 total
includes taxes & fees
Jul 28 - Jul 29
SPOT X Hotel Orlando/Intl Dr by The Red Collection
Bryan’s Spanish Cove
Lake

Bryan’s Spanish Cove

3.0 star property
9.4 out of 10, Exceptional, (1004)
"Great place for a vacation "
The price is NT$3,670
NT$4,619 total
includes taxes & fees
Aug 3 - Aug 4
Bryan’s Spanish Cove
Wyndham Garden Orlando Universal / I Drive
Comfort Room, 2 Double Beds, Accessible (Mobility) | Living area | 45-inch flat-screen TV with digital channels, TV

Wyndham Garden Orlando Universal / I Drive

3.0 star property
9.4 out of 10, Exceptional, (2179)
"Amazing hotel great location.! "
The price is NT$3,185
NT$3,583 total
includes taxes & fees
Jul 27 - Jul 28
Wyndham Garden Orlando Universal / I Drive
Ramada by Wyndham Suites Orlando Airport
Premium bedding, in-room safe, desk, blackout drapes

Ramada by Wyndham Suites Orlando Airport

3.0 star property
8.2 out of 10, Very Good, (4590)
"Excellent location, service and rooms!!"
The price is NT$2,295
NT$2,581 total
includes taxes & fees
Jul 10 - Jul 11
Ramada by Wyndham Suites Orlando Airport
Holiday Inn Resort Orlando - Lake Buena Vista by IHG
Lobby

Holiday Inn Resort Orlando - Lake Buena Vista by IHG

3.5 star property
8.4 out of 10, Very Good, (3361)
"Good for a weekend stay and visit to the parks."
The price is NT$1,952
NT$3,176 total
includes taxes & fees
Jul 28 - Jul 29
Holiday Inn Resort Orlando - Lake Buena Vista by IHG
Candlewood Suites Orlando - Lake Buena Vista by IHG
1 bedroom, premium bedding, desk, laptop workspace

Candlewood Suites Orlando - Lake Buena Vista by IHG

2.5 star property
9.0 out of 10, Wonderful, (1919)
"Love this place we stay her frequently great for families too."
The price is NT$2,293
NT$2,871 total
includes taxes & fees
Jul 13 - Jul 14
Candlewood Suites Orlando - Lake Buena Vista by IHG
Holiday Inn Express And Suites Clermont Se West Orlando by IHG
Property amenity

Holiday Inn Express And Suites Clermont Se West Orlando by IHG

2.5 star property
8.2 out of 10, Very Good, (672)
"Nice hotel and helpful stuff"
The price is NT$2,054
NT$2,715 total
includes taxes & fees
Aug 6 - Aug 7
Holiday Inn Express And Suites Clermont Se West Orlando by IHG
Drury Plaza Hotel Orlando - Disney Springs Area
Outdoor pool, sun loungers

Drury Plaza Hotel Orlando - Disney Springs Area

3.0 star property
9.8 out of 10, Exceptional, (4381)
"Great position and lovely hotel"
The price is NT$3,949
NT$4,443 total
includes taxes & fees
Jul 14 - Jul 15
Drury Plaza Hotel Orlando - Disney Springs Area
Parkway International Resort
Outdoor pool, sun loungers

Parkway International Resort

3.0 star property
9.4 out of 10, Exceptional, (1913)
"Great place"
The price is NT$3,317
NT$4,259 total
includes taxes & fees
Jul 30 - Jul 31
Parkway International Resort
Sonesta ES Suites Orlando - International Drive
Exterior

Sonesta ES Suites Orlando - International Drive

3.5 star property
9.0 out of 10, Wonderful, (1005)
"I love the location and the rooms are always clean. "
The price is NT$2,913
NT$3,832 total
includes taxes & fees
Jul 19 - Jul 20
Sonesta ES Suites Orlando - International Drive
Palazzo Lakeside Hotel
1 bedroom, in-room safe, laptop workspace, blackout drapes

Palazzo Lakeside Hotel

3.0 star property
8.2 out of 10, Very Good, (5115)
"Great stay "
Palazzo Lakeside Hotel
Westgate Lakes Resort & Spa Universal Studios Area
7 outdoor pools, cabanas (surcharge), pool umbrellas

Westgate Lakes Resort & Spa Universal Studios Area

4.0 star property
8.2 out of 10, Very Good, (5096)
"Excellent would recommend to anybody to stay here "
The price is NT$2,999
NT$4,223 total
includes taxes & fees
Aug 3 - Aug 4
Westgate Lakes Resort & Spa Universal Studios Area
Orbit One Vacation Villas
Lobby sitting area

Orbit One Vacation Villas

3.0 star property
9.4 out of 10, Exceptional, (1413)
"We love staying here when visiting Orlando"
The price is NT$3,317
NT$4,589 total
includes taxes & fees
Jul 14 - Jul 15
Orbit One Vacation Villas
Holiday Inn Orlando International Dr-ICON by IHG
Exterior

Holiday Inn Orlando International Dr-ICON by IHG

3.0 star property
9.0 out of 10, Wonderful, (2074)
"Great property.staff was excellent "
The price is NT$2,300
NT$3,023 total
includes taxes & fees
Jul 13 - Jul 14
Holiday Inn Orlando International Dr-ICON by IHG
Hilton Vacation Club Grande Villas Orlando
2 outdoor pools, a heated pool, cabanas (surcharge)

Hilton Vacation Club Grande Villas Orlando

3.5 star property
9.2 out of 10, Wonderful, (3047)
"Very nice and comfortable place to stay."
The price is NT$2,834
NT$3,841 total
includes taxes & fees
Jul 29 - Jul 30
Hilton Vacation Club Grande Villas Orlando
Hotel Landy Orlando Universal Blvd., a Tribute Portfolio Hotel
Outdoor pool, open 7:00 AM to 11:00 PM, pool umbrellas, sun loungers

Hotel Landy Orlando Universal Blvd., a Tribute Portfolio Hotel

4.0 star property
8.6 out of 10, Excellent, (928)
"Great hotel, greatly staff ! "
The price is NT$2,439
NT$3,180 total
includes taxes & fees
Jul 31 - Aug 1
Hotel Landy Orlando Universal Blvd., a Tribute Portfolio Hotel
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.

Where to stay in Windward Cay

Find the best Windward Cay areas and neighborhoods for the activities you enjoy most.
International Drive showing landscape views
International Drive map

International Drive

1 out of top 10 points of interest in this area

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

Universal Studios Orlando featuring signage, a city and night scenes
Florida Center map

Florida Center

2 out of top 10 points of interest in this area

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

Magic Kingdom® Park showing rides and interior views as well as a couple
Photo by ©Disney
Open Photo by ©Disney
Bay Lake map

Bay Lake

3 out of top 10 points of interest in this area

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.

Downtown Orlando
Downtown Orlando map

Downtown Orlando

Orlando's historic core boasts art galleries, retail, restaurants, and nightclubs, with attractions like Lake Eola Park, Linton E. Allen Memorial Fountain, and performing arts theaters, all accessible via public transportation.

Windsor Hills map

Windsor Hills

If you're looking for some top things to see and do in Windsor Hills and surrounding area, you can visit Mystic Dunes Golf Club and Island H2O Live!.

Frequently asked questions

What's it like in Windward Cay?

Travelers to the Windward Cay neighborhood in Kissimmee will be sure to enjoy their stay.

What's a favorite place to stay in Windward Cay?

For your stay in Windward Cay, Windward Cay 4707 is one of the top choices based on our traveler data. Another good option for your stay in the area is Peaceful Windward Cay 3 Bedroom Home by Redawning.

How many hotels will I find in Windward Cay?

Expedia has 28 hotels and other accommodations in Windward Cay to choose from, making this an ideal home base for exploring the greater Kissimmee area.

If I need to cancel my hotel reservation in Windward Cay, will I receive a refund?

Yes, most hotel reservations are refundable provided that you cancel before the hotel’s cancellation deadline, which in most cases is within 24 or 48 hours of your check-in date. If you booked a non-refundable reservation, you might be able to still cancel and be given a refund within a 24-hour period of booking. Plug in your dates, click on "Search", then use the "fully refundable" filter to get the best deals available in Windward Cay.

Where can I learn more about changing or cancelling my trip to Windward Cay?

For more information about changing or cancelling your trip to Windward Cay, click here.

What is there to do around this Kissimmee neighborhood?

A few places to visit in the area around Windward Cay include Old Town, Medieval Times, and Wat Florida Dhammaram. While you're out sightseeing, Kissimmee Go-Karts and Capone's Dinner Show are a couple of additional sights to visit in Kissimmee.