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Check prices for these dates

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28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

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Our top choices for Windward Cay hotels

A modern hotel lobby with a reception desk, a round coffee table, a sofa, and a large window with curtains.

1. Seasons Florida Resort

Seasons Florida Resort
2.0 star property
1.6 km from Windward Cay
9.0 out of 10, Wonderful, (3,833 reviews)
"Nice and a good place to stay."
United States
Joel
The price is Rp942.864
Rp1.070.151 total
includes taxes & fees
20 Sept - 21 Sept
Seasons Florida Resort
A hotel room with a large bed, a smaller bed, a desk, and a chair. There is a decorative item on the bed and a rug on the floor.

2. Palazzo Lakeside Hotel

Palazzo Lakeside Hotel
3.0 star property
2.7 km from Windward Cay
8.4 out of 10, Very good, (5,293 reviews)
"The hotel was beautiful, we had a great time."
United States
LILLIAN
The price is Rp379.653
Rp1.034.265 total
includes taxes & fees
1 Sept - 2 Sept
Palazzo Lakeside Hotel
An outdoor patio area with seating, a bar, and a fire feature.

3. Hyatt House Orlando Airport

Hyatt House Orlando Airport
3.5 star property
22.7 km from Windward Cay
9.6 out of 10, Exceptional, (2,964 reviews)
"Clean and comfortable, restaurants choices were excellent and close to hotel. would stay here again."
United States
Armando
The price is Rp2.091.314
Rp2.352.729 total
includes taxes & fees
6 Sept - 7 Sept
Hyatt House Orlando Airport
A hotel atrium with a central fountain, palm trees, and a circular seating area.

4. Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport
4.0 star property
21.3 km from Windward Cay
9.4 out of 10, Exceptional, (4,414 reviews)
"Will definitely stay again!"
United States
William
The price is Rp3.172.775
Rp3.569.461 total
includes taxes & fees
7 Sept - 8 Sept
Hyatt Regency Orlando International Airport
A spacious restaurant with high ceilings, hanging pendant lights, and a variety of seating arrangements.

5. 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
9.6 out of 10, Exceptional, (1,539 reviews)
"Excellent service and breakfast"
United States
Ivandra
The price is Rp2.020.068
Rp2.292.777 total
includes taxes & fees
7 Sept - 8 Sept
Embassy Suites by Hilton Orlando Lake Buena Vista South
A swimming pool with a blue slide, surrounded by palm trees and a fenced area.

6. Radisson Hotel Orlando Lake Buena Vista South

Radisson Hotel Orlando Lake Buena Vista South
3.5 star property
3 km from Windward Cay
8.8 out of 10, Excellent, (3,887 reviews)
"Love staying at this place. They do need to get more floaties for the lazy river besides that love being here"
United States
Soraida
The price is Rp764.873
Rp1.270.443 total
includes taxes & fees
7 Sept - 8 Sept
Radisson Hotel Orlando Lake Buena Vista South
An outdoor patio area with a fire pit, yellow and blue seating, and a covered section with a pergola.

7. Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings
3.0 star property
16.2 km from Windward Cay
9.4 out of 10, Exceptional, (5,985 reviews)
"Great place to stay with the family for Disney vacation! Very clean, great breakfast, close to all the parks and a fun pool!"
United States
Alicia
The price is Rp1.656.746
Rp1.863.840 total
includes taxes & fees
7 Sept - 8 Sept
Home2 Suites by Hilton Orlando at Flamingo Crossings
A hotel with a large pool, palm trees, and a waterfall feature.

8. Caribe Royale Orlando, WorldHotels Elite

Caribe Royale Orlando, WorldHotels Elite
4.5 star property
5.7 km from Windward Cay
9.2 out of 10, Wonderful, (5,256 reviews)
"Great place to stay!"
United States
Carnesha
The price is Rp2.995.187
Rp4.127.332 total
includes taxes & fees
30 Aug - 31 Aug
Caribe Royale Orlando, WorldHotels Elite
A modern gym with treadmills, stationary bikes, and elliptical machines.

9. Wyndham Garden Orlando Airport

Wyndham Garden Orlando Airport
3.0 star property
19.9 km from Windward Cay
9.0 out of 10, Wonderful, (4,172 reviews)
"Great place to stay"
United States
Gabriel
The price is Rp1.488.732
Rp1.674.824 total
includes taxes & fees
9 Sept - 10 Sept
Wyndham Garden Orlando Airport
A modern living room with a large flat-screen TV, a white sofa, and a coffee table.

10. Magic Moment Resort & Kids Club, Dazzler Select by Wyndham

Magic Moment Resort & Kids Club, Dazzler Select by Wyndham
3.0 star property
3.2 km from Windward Cay
8.6 out of 10, Excellent, (3,215 reviews)
"Little gem in a great location"
United Kingdom
Owen
The price is Rp319.014
Rp965.372 total
includes taxes & fees
31 Aug - 1 Sept
Magic Moment Resort & Kids Club, Dazzler Select by Wyndham
An outdoor seating area with green chairs and umbrellas, a fire pit, and a building with large windows in the background.

11. 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, (2,836 reviews)
"Very clean hotel, not too far from the airport, great coffee and breakfast!!"
United States
Katherine
The price is Rp1.511.588
Rp1.700.537 total
includes taxes & fees
31 Aug - 1 Sept
Hampton Inn & Suites Orlando Airport @ Gateway Village
A modern hotel room with a large bed, a nightstand, a drawer, a wall-mounted light, and a window with a view of trees.

12. Ramada by Wyndham Suites Orlando Airport

Ramada by Wyndham Suites Orlando Airport
3.0 star property
22.9 km from Windward Cay
8.4 out of 10, Very good, (6,065 reviews)
"we loved the proximity to the airport, nice restaurants. staff were very friendly and breakfast was nice"
United States
Dwayne
The price is Rp1.401.003
Rp1.576.127 total
includes taxes & fees
13 Sept - 14 Sept
Ramada by Wyndham Suites Orlando Airport
A spacious lobby with a wooden staircase, a reception desk, and a large wall clock.

13. Country Inn & Suites by Radisson, Orlando Airport, FL

Country Inn & Suites by Radisson, Orlando Airport, FL
3.0 star property
22.8 km from Windward Cay
7.8 out of 10, Good, (4,949 reviews)
"Fantastic stay."
United States
Adley
The price is Rp1.370.874
Rp1.542.232 total
includes taxes & fees
3 Sept - 4 Sept
Country Inn & Suites by Radisson, Orlando Airport, FL
A breakfast bar with various food dispensers, a seating area with a table and chairs, and large windows with a view of greenery.

14. Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
3.0 star property
16.4 km from Windward Cay
9.4 out of 10, Exceptional, (5,463 reviews)
"Great location, breakfast was extensive, and the rooms were nice and large."
United States
Andrea
The price is Rp1.491.390
Rp1.677.813 total
includes taxes & fees
3 Sept - 4 Sept
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
A modern hotel with a sign reading "SPOT X HOTEL" and the number "12235" on the entrance.

15. SPOT X Hotel Orlando/Intl Dr by The Red Collection

SPOT X Hotel Orlando/Intl Dr by The Red Collection
3.0 star property
9 km from Windward Cay
8.6 out of 10, Excellent, (3,656 reviews)
"Everything great including location!"
United States
Travis
The price is Rp829.436
Rp1.251.951 total
includes taxes & fees
30 Aug - 31 Aug
SPOT X Hotel Orlando/Intl Dr by The Red Collection
A modern restaurant with multiple dining tables and chairs, a bar area, and a television mounted on the wall.

16. Wingate by Wyndham - Orlando International Airport

Wingate by Wyndham - Orlando International Airport
3.0 star property
23.4 km from Windward Cay
8.8 out of 10, Excellent, (4,211 reviews)
"Great place"
United States
Ronda
The price is Rp1.175.168
Rp1.322.064 total
includes taxes & fees
21 Sept - 22 Sept
Wingate by Wyndham - Orlando International Airport
A spacious lobby with a high ceiling, wooden beams, and a central round table surrounded by chairs. There are potted plants, a reception desk, and a wall with a welcome sign.

17. Hilton Vacation Club Polynesian Isles Kissimmee

Hilton Vacation Club Polynesian Isles Kissimmee
3.0 star property
3.9 km from Windward Cay
9.6 out of 10, Exceptional, (1,947 reviews)
"Nice room and friendly staff"
United States
Bridget
The price is Rp1.642.922
Rp2.267.029 total
includes taxes & fees
3 Sept - 4 Sept
Hilton Vacation Club Polynesian Isles Kissimmee
A modern indoor patio with a fire pit table, seating, a bar area, and large windows.

18. SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista

SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista
3.0 star property
9.5 km from Windward Cay
8.8 out of 10, Excellent, (3,603 reviews)
"Breakfast was amazing room was clean for the price everything was great!"
United States
Anabel
The price is Rp1.364.671
Rp1.535.254 total
includes taxes & fees
3 Sept - 4 Sept
SpringHill Suites by Marriott Orlando Theme Parks/Lake Buena Vista
A large hotel with multiple floors, a central courtyard, and a reflective water feature.

19. Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
3.0 star property
16.3 km from Windward Cay
9.6 out of 10, Exceptional, (2,247 reviews)
"Location was really close to all the parks, the breakfast was really nice to have before heading out to enjoy the great city of orlando"
Canada
harman
The price is Rp1.461.261
Rp1.643.920 total
includes taxes & fees
15 Sept - 16 Sept
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
A hotel pool area with lounge chairs and umbrellas, surrounded by tall buildings and a sunset sky.

20. Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area
4.0 star property
8.4 km from Windward Cay
9.8 out of 10, Exceptional, (6,008 reviews)
"Great hotel"
United States
Mohammed
The price is Rp2.636.119
Rp2.965.635 total
includes taxes & fees
7 Sept - 8 Sept
Drury Plaza Hotel Orlando - Disney Springs Area
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.
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

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.

The entrance to Aquatica with colorful signage and a water slide.

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

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.

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

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

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

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.

Top Windward Cay Hotel Reviews

Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent
"Great breakfast and the Kickback snacks and drinks really saved us money"
Michael 9-night trip
Posted less than an hour ago
Drury Plaza Hotel Orlando - Disney Springs Area

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 32 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, Pioneer Village at Shingle Creek and 192 Flea Market are a couple of additional sights to visit in Kissimmee.