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Our top choices for Windward Cay hotels

Exterior
La Quinta Inn & Suites by Wyndham Orlando Airport North

La Quinta Inn & Suites by Wyndham Orlando Airport North

La Quinta Inn & Suites by Wyndham Orlando Airport North
3.0 star property
22.8 km from Windward Cay
7.4 out of 10, Good, (847)
"nice and clean staff was great also"
United States
sumatran
The price is 2.083.514 ₫
2.343.954 ₫ total
includes taxes & fees
17 Dec - 18 Dec
La Quinta Inn & Suites by Wyndham Orlando Airport North
Reception
Seasons Florida Resort

Seasons Florida Resort

Seasons Florida Resort
2.0 star property
1.6 km from Windward Cay
8.8 out of 10, Excellent, (3300)
"Excellent location and value, very clean and friendly check in"
United States
Jason
The price is 1.598.150 ₫
1.813.901 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Seasons Florida Resort
Lobby
Country Inn & Suites by Radisson, Orlando Airport, FL

Country Inn & Suites by Radisson, Orlando Airport, FL

Country Inn & Suites by Radisson, Orlando Airport, FL
3.0 star property
22.9 km from Windward Cay
7.8 out of 10, Good, (4306)
"Friendly staff and good breakfast!"
United States
wendy
The price is 2.190.321 ₫
2.464.440 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Country Inn & Suites by Radisson, Orlando Airport, FL
Outdoor banquet area
Rosen Shingle Creek

Rosen Shingle Creek

Rosen Shingle Creek
4.5 star property
13.4 km from Windward Cay
9.4 out of 10, Exceptional, (4359)
"Great resort "
United States
Camille
The price is 2.925.338 ₫
3.291.004 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Rosen Shingle Creek
Lobby
Hyatt House Orlando International Drive

Hyatt House Orlando International Drive

Hyatt House Orlando International Drive
4.0 star property
17.1 km from Windward Cay
9.4 out of 10, Exceptional, (1360)
"The staff was really friendly and the property was nice and cozy "
United States
curtis
The price is 3.104.226 ₫
3.492.255 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Hyatt House Orlando International Drive
In-room safe, laptop workspace, blackout curtains, iron/ironing board
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel
3.0 star property
2.7 km from Windward Cay
8.2 out of 10, Very good, (5153)
"Overall good experience would stay again"
United States
Jacquelyn
The price is 718.244 ₫
1.710.697 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Palazzo Lakeside Hotel
Outdoor pool, pool umbrellas, pool loungers
Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center
3.5 star property
16.5 km from Windward Cay
7.4 out of 10, Good, (3897)
"Room was good hotel was nice and clean"
United States
Amy
The price is 1.639.189 ₫
2.376.805 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Wyndham I-Drive Avanti Resort & Conference Center
Exterior
Holiday Inn Resort Kissimmee by the Parks by IHG

Holiday Inn Resort Kissimmee by the Parks by IHG

Holiday Inn Resort Kissimmee by the Parks by IHG
3.5 star property
11.8 km from Windward Cay
8.4 out of 10, Very good, (1043)
"Great place - hardworking staff!"
United States
Theodore
The price is 1.841.490 ₫
2.612.548 ₫ total
includes taxes & fees
16 Dec - 17 Dec
Holiday Inn Resort Kissimmee by the Parks by IHG
Lobby lounge
Aloft Orlando Lake Buena Vista

Aloft Orlando Lake Buena Vista

Aloft Orlando Lake Buena Vista
3.0 star property
9.5 km from Windward Cay
8.8 out of 10, Excellent, (1907)
"Great stay"
United States
Gerard
The price is 2.051.946 ₫
2.308.440 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Aloft Orlando Lake Buena Vista
Exterior
Hampton Inn & Suites Orlando Airport @ Gateway Village

Hampton Inn & Suites Orlando Airport @ Gateway Village

Hampton Inn & Suites Orlando Airport @ Gateway Village
3.0 star property
22.8 km from Windward Cay
9.4 out of 10, Exceptional, (2453)
"Great location to airport and food choices. "
United States
Aliza
The price is 2.718.039 ₫
3.057.795 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Hampton Inn & Suites Orlando Airport @ Gateway Village
Lobby
Embassy Suites by Hilton Orlando Lake Buena Vista South

Embassy Suites by Hilton Orlando Lake Buena Vista South

Embassy Suites by Hilton Orlando Lake Buena Vista South
4.0 star property
3 km from Windward Cay
9.4 out of 10, Exceptional, (1237)
"Nice place very good"
United States
Hugo
The price is 2.998.472 ₫
3.403.266 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Embassy Suites by Hilton Orlando Lake Buena Vista South
Fitness facility
Wyndham Garden Orlando Airport

Wyndham Garden Orlando Airport

Wyndham Garden Orlando Airport
3.0 star property
20 km from Windward Cay
9.0 out of 10, Wonderful, (4009)
"Very clean hotel and easy experience checking in and out "
United States
Arielle
The price is 2.209.788 ₫
2.486.012 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Wyndham Garden Orlando Airport
Free daily on-the-go breakfast
Tru By Hilton Orlando Convention Center Area, FL

Tru By Hilton Orlando Convention Center Area, FL

Tru By Hilton Orlando Convention Center Area, FL
3.5 star property
12.2 km from Windward Cay
9.0 out of 10, Wonderful, (3656)
"Great location clean rooms "
United States
Erika
The price is 2.083.514 ₫
2.343.953 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Tru By Hilton Orlando Convention Center Area, FL
View from room
Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando
3.0 star property
13.8 km from Windward Cay
8.6 out of 10, Excellent, (5402)
"Room very clean and amazing location."
United States
Mehilin
The price is 2.130.604 ₫
2.396.831 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Rosen Inn at Pointe Orlando
Poolside Family Suite - Exterior Entry (Includes Early Park Admission*) | View from room
Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort
3.5 star property
17.5 km from Windward Cay
9.0 out of 10, Wonderful, (5735)
"Great stay "
Canada
Marjorie
The price is 3.498.831 ₫
3.936.184 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Universal's Cabana Bay Beach Resort
Exterior
Ramada by Wyndham Kissimmee Gateway

Ramada by Wyndham Kissimmee Gateway

Ramada by Wyndham Kissimmee Gateway
3.0 star property
11.4 km from Windward Cay
8.0 out of 10, Very good, (3913)
"Always great to stay there "
United States
Giandre
The price is 1.325.873 ₫
2.042.317 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Ramada by Wyndham Kissimmee Gateway
Terrace/patio
Hyatt House Orlando Airport

Hyatt House Orlando Airport

Hyatt House Orlando Airport
3.5 star property
22.7 km from Windward Cay
9.6 out of 10, Exceptional, (2788)
"Great stay close to airport and plenty of dining available "
United States
Lonnie
The price is 2.998.998 ₫
3.373.872 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Hyatt House Orlando Airport
Restaurant
Wingate by Wyndham - Orlando International Airport

Wingate by Wyndham - Orlando International Airport

Wingate by Wyndham - Orlando International Airport
3.0 star property
23.5 km from Windward Cay
8.8 out of 10, Excellent, (3750)
"Beautiful property, excellent staff and love the shuttle service to the airport!"
United States
Robert
The price is 2.059.838 ₫
2.317.384 ₫ total
includes taxes & fees
16 Dec - 17 Dec
Wingate by Wyndham - Orlando International Airport
Business centre
Spark by Hilton Orlando near Universal

Spark by Hilton Orlando near Universal

Spark by Hilton Orlando near Universal
2.5 star property
19.7 km from Windward Cay
9.0 out of 10, Wonderful, (430)
"The rooms and breakfast were lovely"
United States
MacKenzie Rose
The price is 2.311.333 ₫
2.600.249 ₫ total
includes taxes & fees
13 Jan - 14 Jan 2026
Spark by Hilton Orlando near Universal
Lobby
Fairfield Inn By Marriott Orlando Airport

Fairfield Inn By Marriott Orlando Airport

Fairfield Inn By Marriott Orlando Airport
3.5 star property
23.4 km from Windward Cay
9.2 out of 10, Wonderful, (2344)
"Clean great staff , good breakfast "
United States
Paul Douglas
The price is 2.437.344 ₫
2.742.013 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Fairfield Inn By Marriott Orlando Airport
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

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 Pointe Orlando or Aquatica 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

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.

Champions Gate

Ample dining options and top 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.

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

Florida Center

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

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 Orlando City Hall might round out your trip, and you can jump aboard the metro at Church Street Station or Lynx Central Station to get around town.

Top Windward Cay Hotel Reviews

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 Kissimmee Go-Karts. While you're out sightseeing, Capone's Dinner Show and Pirate's Island Adventure Golf are a couple of additional sights to visit in Kissimmee.