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29 Aug - 30 Aug
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Top Trending Hotels Near Windward Cay, Orlando

Our top choices for Windward Cay hotels

Palazzo Lakeside Hotel
1 bedroom, in-room safe, laptop workspace, blackout curtains

Palazzo Lakeside Hotel

3.0 star property
8.2 out of 10, Very good, (5181)
"Great hotel!"
The price is 1.044.433 ₫
2.082.590 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Palazzo Lakeside Hotel
Kompose Boutique Resort at Theme Parks
Suite, 1 King Bed with Sofa bed, Balcony | 1 bedroom, premium bedding, minibar, in-room safe

Kompose Boutique Resort at Theme Parks

3.0 star property
9.4 out of 10, Exceptional, (1150)
"Great stay"
The price is 1.608.626 ₫
2.142.903 ₫ total
includes taxes & fees
29 Sept - 30 Sept
Kompose Boutique Resort at Theme Parks
CoCo Key Hotel and Water Resort 
Water park

CoCo Key Hotel and Water Resort 

3.5 star property
7.8 out of 10, Good, (3558)
"Great location and the water park was a blast. "
The price is 2.065.185 ₫
3.656.950 ₫ total
includes taxes & fees
22 Sept - 23 Sept
CoCo Key Hotel and Water Resort 
Magic Moment Resort and Kids Club
Royal Room, 2 Queen Beds, Pool View | Pool | Outdoor pool, a heated pool, open 9 AM to 9:00 PM, free pool cabanas

Magic Moment Resort and Kids Club

3.0 star property
8.4 out of 10, Very good, (2480)
"We loved our stay. The best stay for the money. "
Magic Moment Resort and Kids Club
Drury Plaza Hotel Orlando - Disney Springs Area
Outdoor pool, pool loungers

Drury Plaza Hotel Orlando - Disney Springs Area

3.0 star property
9.8 out of 10, Exceptional, (4828)
"AMAZING place to stay "
The price is 3.582.657 ₫
4.030.489 ₫ total
includes taxes & fees
8 Sept - 9 Sept
Drury Plaza Hotel Orlando - Disney Springs Area
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
8.6 out of 10, Excellent, (2698)
"Had a nice stay"
The price is 1.792.514 ₫
2.016.578 ₫ total
includes taxes & fees
30 Sept - 1 Oct
SPOT X Hotel Orlando/Intl Dr by The Red Collection
The Grove Resort & Water Park Orlando
Aerial view

The Grove Resort & Water Park Orlando

4.0 star property
8.0 out of 10, Very good, (8449)
"Our family had a great stay! "
The price is 3.925.405 ₫
5.601.605 ₫ total
includes taxes & fees
8 Sept - 9 Sept
The Grove Resort & Water Park Orlando
Rosen Shingle Creek
4 outdoor pools, open 5:30 AM to midnight, pool cabanas (surcharge)

Rosen Shingle Creek

4.5 star property
9.4 out of 10, Exceptional, (3991)
"Great stay!"
The price is 2.718.804 ₫
3.058.655 ₫ total
includes taxes & fees
7 Sept - 8 Sept
Rosen Shingle Creek
Rosen Inn Lake Buena Vista
View from room

Rosen Inn Lake Buena Vista

3.5 star property
8.6 out of 10, Excellent, (5388)
"Nice place to stay."
The price is 2.001.957 ₫
2.252.235 ₫ total
includes taxes & fees
2 Sept - 3 Sept
Rosen Inn Lake Buena Vista
Caribe Royale Orlando
Sports court

Caribe Royale Orlando

4.5 star property
9.2 out of 10, Wonderful, (4392)
"Great place to stay"
The price is 4.190.604 ₫
5.841.148 ₫ total
includes taxes & fees
31 Aug - 1 Sept
Caribe Royale Orlando
Ramada by Wyndham Suites Orlando Airport
Premium bedding, in-room safe, desk, blackout curtains

Ramada by Wyndham Suites Orlando Airport

3.0 star property
8.2 out of 10, Very good, (4801)
"Enjoyed our stay "
The price is 2.133.945 ₫
2.400.689 ₫ total
includes taxes & fees
31 Aug - 1 Sept
Ramada by Wyndham Suites Orlando Airport
Legacy Vacation Resorts - Kissimmee/Orlando
4 outdoor pools

Legacy Vacation Resorts - Kissimmee/Orlando

3.5 star property
7.8 out of 10, Good, (2673)
"This resort is my favorite it quite and it’s close to things that the kids enjoy "
The price is 1.614.716 ₫
2.221.189 ₫ total
includes taxes & fees
4 Sept - 5 Sept
Legacy Vacation Resorts - Kissimmee/Orlando
Rosen Inn International
Front of property – evening/night

Rosen Inn International

3.0 star property
8.4 out of 10, Very good, (5768)
"Great location"
The price is 2.082.124 ₫
2.342.521 ₫ total
includes taxes & fees
27 Sept - 28 Sept
Rosen Inn International
Baymont by Wyndham Orlando/International Dr/Universal Blvd
Lobby

Baymont by Wyndham Orlando/International Dr/Universal Blvd

2.5 star property
7.0 out of 10, Good, (1799)
"Great service and good breakfast."
The price is 1.657.100 ₫
2.012.559 ₫ total
includes taxes & fees
29 Sept - 30 Sept
Baymont by Wyndham Orlando/International Dr/Universal Blvd
Wingate by Wyndham - Orlando International Airport
Pillow-top beds, in-room safe, desk, blackout curtains

Wingate by Wyndham - Orlando International Airport

3.0 star property
8.8 out of 10, Excellent, (3586)
"Nice hotel,good staff, great location"
The price is 1.920.550 ₫
2.160.619 ₫ total
includes taxes & fees
2 Sept - 3 Sept
Wingate by Wyndham - Orlando International Airport
Home2 Suites by Hilton Orlando at Flamingo Crossings
Outdoor pool, open 9:00 AM to 10:00 PM, pool umbrellas, pool loungers

Home2 Suites by Hilton Orlando at Flamingo Crossings

3.0 star property
9.2 out of 10, Wonderful, (4576)
"Great place to stay. "
The price is 2.888.729 ₫
3.249.820 ₫ total
includes taxes & fees
8 Sept - 9 Sept
Home2 Suites by Hilton Orlando at Flamingo Crossings
The Delaney Hotel
Terrace/patio

The Delaney Hotel

3.5 star property
9.6 out of 10, Exceptional, (1011)
"great restaurant and even better rooms!"
The Delaney Hotel
Galleria Palms Hotel
Property entrance

Galleria Palms Hotel

2.5 star property
8.8 out of 10, Excellent, (3585)
"Great place to stay!! "
Galleria Palms Hotel
La Quinta Inn & Suites by Wyndham Orlando - IDrive Theme Parks
Front of property – evening/night

La Quinta Inn & Suites by Wyndham Orlando - IDrive Theme Parks

3.0 star property
8.6 out of 10, Excellent, (2185)
"A clean place for family stay"
The price is 2.253.438 ₫
2.535.118 ₫ total
includes taxes & fees
22 Sept - 23 Sept
La Quinta Inn & Suites by Wyndham Orlando - IDrive Theme Parks
Avanti International Resort
View from property

Avanti International Resort

4.0 star property
7.8 out of 10, Good, (4086)
"Nice stay"
Avanti International Resort
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.
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Where to stay in Windward Cay

Find the best Windward Cay areas for the activities you enjoy most.

International Drive District

1 out of top 10 points of interest in this area

Visitors to International Drive District rave about its breathtaking beach views, exciting theme parks and popular shops. You might also want to make some time to see Aquatica or The Orlando Eye at ICON Park while you're exploring the neighbourhood.

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

Bay Lake

4 out of top 10 points of interest in this area

Exciting theme parks plentiful wildlife and top sights from Epcot® to Walt Disney World® Resort – discover Bay Lake, a destination also famous for its entertainment.

Downtown Orlando

Ample dining options, great live music, and fantastic lake views are just a few top things to explore in Downtown Orlando. A visit to The Social or Church Street Station might round out your trip, and you can jump aboard the metro at Church Street Station or Lynx Central Station to get around town.

Universal Studios Florida® featuring night scenes, a city and signage

Florida Center

2 out of top 10 points of interest in this area

If you're spending some time in Florida Center, Universal Orlando Resort and Universal Studios Florida are top sights worth seeing.

Reunion

The top golf courses and fun-filled water parks 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.

Top Windward Cay Hotel Reviews

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

What's it like in Windward Cay?

Travellers to the Windward Cay neighbourhood in Kissimmee will be sure to enjoy their stay.

How many hotels will I be able to find in Windward Cay?

Expedia has 28 hotels and other accommodation options 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! The majority of hotel reservations are fully refundable if you cancel before the hotel’s cancellation deadline, which often is within 24-48 hours of your arrival date. If you have a non-refundable reservation, it might still be possible to cancel it and receive a refund within a 24-hour period of booking. Put your dates in and click on "Search", then you can filter by "fully refundable" to review the best options available in Windward Cay.

What is there to do around this Kissimmee neighbourhood?

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.