The Best Hotels in Windward Cay, Orlando - 2026 Updated Prices

A golf course with a large hotel and residential area.

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Property	Property class	Guest rating
Embassy Suites by Hilton Orlando Lake Buena Vista South	4.0 star property	9.6 Exceptional 1,694 reviews	View
Drury Plaza Hotel Orlando - Disney Springs Area	4.0 star property	9.8 Exceptional 6,250 reviews	View
Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort	2.0 star property	9.0 Wonderful 4,116 reviews	View
Radisson Hotel Orlando Lake Buena Vista South	3.5 star property	8.8 Excellent 3,731 reviews	View
Club Sevilla	3.5 star property	9.0 Wonderful 1,010 reviews	View

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.

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.

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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.

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A roller coaster at Universal Orlando Resort, featuring a tall palm tree and a clear blue sky.

Florida Center

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

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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.

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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.

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Top Windward Cay Hotel Reviews

Holiday Inn Resort Orlando Suites - Waterpark by IHG

10/10 Excellent

"Everything was great until Frontier and their new baggage rules, where only Groups 1–3 get free carry ons! Then the hotel we wish they had cameras in the hallways. Our groceries were stolen right from outside our door, and unfortunately, there was no way to find out who took them. Other than those two issues, we had a great time! ❤️"

Universal's Cabana Bay Beach Resort

8/10 Good

"This is our 5th stay at Cabana Bay Beach resort. For the most part the hotel is a good value. Some issues this time, 1. Many guests were purchasing the souvenir drink cup with free refills. Numerous problems w the length of stay their staff was entering and refills would not work. Staff was carefree, didn't matter to them. 2. Music in the pool area usually shuts off at 10pm, last night it was on past 1am and workers at the front desk (called 2x) weren't interested in addressing it. I am not sure I will stay here again any time soon. Sitting on the fence....."

Fairfield Inn & Suites Lake Buena Vista in Marriott Village

8/10 Good

"The hotel offers free breakfast they post the times where the lines are not busy then they’re busy and then they die down again so make sure the first day you test it out hopeful staff clean room housekeeping was every day. Not sure if there’s an airport shuttle that was my mistake not looking into it too much, but I did take Uber from the airport to the hotel and the hotel staff advised if you take Lyft it’s much cheaper because Disney World has a contract with Lyft so the rides will be cheaper. Sometimes it might take a little longer, but the price is worth it. I would definitely stay back at this hotel if I had a choice to stay off property of Disney was close to the outlets close to Target Ross dress for less in case you need to buy a new suitcase I advise you go to raw stressful less. There’s a steakhouse in the back. There is golden corral in the back. There is also a Mexican Bahama breeze of Bahamas something restaurant in the back there’s a Disney gift shop that sometimes has some awesome sales. Walmart is not too far by Lyft or Uber and the outlets are close by as well."

Evermore Orlando Resort

10/10 Excellent

"We came to celebrate my husband's 60th birthday, just the two of us, and stayed in a beautiful four-bedroom flat. At check-in, I had booked the Bayfront online and initially received a city view we didn't understand the mishap., however the staff let us know there was a complimentary upgrade to the Bayfront, which was wonderful💕 My husband was delighted with the experience. We did need some air freshener in the apartment but otherwise it was clean.👌 The service was excellent. 🥰The staff made my husband feel amazing. surprising him with champagne, and a few appetizers.. They were all so kind and made us feel special. We will definitely return.🌟💕❤️💕"

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 33 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.

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Our top choices for Windward Cay hotels

1. Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

2. Marriott's Grande Vista

3. Kompose Boutique Resort at Theme Parks

4. Westgate Lakes Resort & Spa Universal Studios Area

5. Universal's Cabana Bay Beach Resort

6. Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

7. Caribe Royale Orlando, WorldHotels Elite

8. Holiday Inn Resort Orlando Suites - Waterpark by IHG

9. The Grove Resort & Water Park Orlando

10. Vacation Village Orlando, Celebration

11. Drury Plaza Hotel Orlando - Disney Springs Area

12. Evermore Orlando Resort

13. Lake Buena Vista Resort Village & Spa

14. Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort

15. Rosen Inn Lake Buena Vista

16. Walt Disney World Dolphin

17. Embassy Suites by Hilton Orlando Lake Buena Vista South

18. Palazzo Lakeside Hotel

19. Holiday Inn Resort Orlando - Lake Buena Vista by IHG

20. Radisson Hotel Orlando Lake Buena Vista South

Compare popular hotels in Windward Cay

Where to stay in Windward Cay

Bay Lake

International Drive District

Florida Center

Champions Gate

Reunion

Top Windward Cay Hotel Reviews

Holiday Inn Resort Orlando Suites - Waterpark by IHG

Frequently asked questions

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