Windward Cay Hotels, Orlando

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2 Oct - 3 Oct
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53739 Cheap Hotels in Windward Cay - Specials, Reviews, & Last Minute Deals

The Delaney Hotel
Terrace/patio

The Delaney Hotel

3.5 star property
9.6 out of 10, Exceptional, (1004)
"great restaurant and even better rooms!"
The Delaney Hotel
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, (4920)
"Awesome hotel!"
The price is AU$135
includes taxes & fees
19 Oct - 20 Oct
Ramada by Wyndham Suites Orlando Airport
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, (3676)
"My stay was very comfortable, I enjoyed the continental breakfast very much."
The price is AU$131
includes taxes & fees
7 Oct - 8 Oct
Wingate by Wyndham - Orlando International Airport
Ramada by Wyndham Hotel & Water Park
Water park

Ramada by Wyndham Hotel & Water Park

3.0 star property
7.2 out of 10, Good, (1484)
"Excellent place for familys"
The price is AU$105
includes taxes & fees
14 Oct - 15 Oct
Ramada by Wyndham Hotel & Water Park
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, (8569)
"Great place to stay!!!"
The price is AU$356
includes taxes & fees
22 Oct - 23 Oct
The Grove Resort & Water Park Orlando
Holiday Inn Express & Suites Clermont Se West Orlando by IHG
Property amenity

Holiday Inn Express & Suites Clermont Se West Orlando by IHG

2.5 star property
8.4 out of 10, Very good, (961)
"Had a great experience this weekend at the hotel and the free breakfast was good and very convenient for the family and kids. "
The price is AU$137
includes taxes & fees
9 Oct - 10 Oct
Holiday Inn Express & Suites Clermont Se West Orlando by IHG
Country Inn & Suites by Radisson, Orlando Airport, FL
Exterior

Country Inn & Suites by Radisson, Orlando Airport, FL

3.0 star property
7.8 out of 10, Good, (4089)
"Property was just what we needed, clean and very pleasant staff."
The price is AU$104
includes taxes & fees
16 Oct - 17 Oct
Country Inn & Suites by Radisson, Orlando Airport, FL
Kompose Boutique Resort at Theme Parks
Suite, 1 King Bed with Sofa bed, Balcony

Kompose Boutique Resort at Theme Parks

3.0 star property
9.4 out of 10, Exceptional, (1443)
"clean rooms, great staff, family friendly"
The price is AU$124
includes taxes & fees
28 Oct - 29 Oct
Kompose Boutique Resort at Theme Parks
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, (2766)
"Great property to stay with family while visiting the parks"
The price is AU$129
includes taxes & fees
29 Oct - 30 Oct
SPOT X Hotel Orlando/Intl Dr by The Red Collection
Wyndham Garden Orlando Airport
Outdoor pool, pool loungers

Wyndham Garden Orlando Airport

3.0 star property
9.0 out of 10, Wonderful, (3835)
"Great stay!"
The price is AU$136
includes taxes & fees
6 Oct - 7 Oct
Wyndham Garden Orlando Airport
Lake Nona Wave Hotel
Outdoor pool, open 8:00 AM to 10:00 PM, pool loungers

Lake Nona Wave Hotel

4.0 star property
9.6 out of 10, Exceptional, (1000)
"Love this place!"
The price is AU$411
includes taxes & fees
5 Oct - 6 Oct
Lake Nona Wave Hotel
La Quinta Inn & Suites by Wyndham Orlando Airport North
Dining

La Quinta Inn & Suites by Wyndham Orlando Airport North

3.0 star property
7.6 out of 10, Good, (424)
"Clean room close to airport and many good restaurants "
The price is AU$123
includes taxes & fees
5 Oct - 6 Oct
La Quinta Inn & Suites by Wyndham Orlando Airport North
DoubleTree by Hilton at the Entrance to Universal Orlando
Outdoor pool

DoubleTree by Hilton at the Entrance to Universal Orlando

4.0 star property
8.4 out of 10, Very good, (6691)
"It was an amazing stay! "
The price is AU$152
includes taxes & fees
2 Nov - 3 Nov
DoubleTree by Hilton at the Entrance to Universal Orlando
Orlando Palms Hotel
Outdoor pool, open 9 AM to 10 PM, pool loungers

Orlando Palms Hotel

2.5 star property
7.6 out of 10, Good, (2079)
"Great stay!!!"
The price is AU$79
includes taxes & fees
9 Oct - 10 Oct
Orlando Palms Hotel
The Eo Inn - Downtown
Front of property

The Eo Inn - Downtown

3.0 star property
8.0 out of 10, Very good, (1000)
"The room was perfect for what I needed and I felt incredibly safe in my room and with the staff!"
The price is AU$204
includes taxes & fees
3 Oct - 4 Oct
The Eo Inn - Downtown
Seasons Florida Resort
Property grounds

Seasons Florida Resort

2.0 star property
8.8 out of 10, Excellent, (3166)
"Great place to stay. "
The price is AU$85
includes taxes & fees
6 Oct - 7 Oct
Seasons Florida Resort
Tru By Hilton Orlando Convention Center Area, FL
Exterior

Tru By Hilton Orlando Convention Center Area, FL

3.5 star property
9.0 out of 10, Wonderful, (3347)
"It was a great stay!"
The price is AU$143
includes taxes & fees
30 Oct - 31 Oct
Tru By Hilton Orlando Convention Center Area, FL
Hyatt Regency Orlando
2 outdoor pools, pool cabanas (surcharge), pool umbrellas

Hyatt Regency Orlando

4.5 star property
9.2 out of 10, Wonderful, (1778)
"Great place to stay "
The price is AU$288
includes taxes & fees
4 Oct - 5 Oct
Hyatt Regency Orlando
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, (2127)
"Excellent stay"
The price is AU$122
includes taxes & fees
5 Oct - 6 Oct
Candlewood Suites Orlando - Lake Buena Vista by IHG
Fairfield Inn By Marriott Orlando Airport
Terrace/patio

Fairfield Inn By Marriott Orlando Airport

3.5 star property
9.2 out of 10, Wonderful, (2330)
"Very convenient close to the airport friendly staff "
The price is AU$150
includes taxes & fees
22 Oct - 23 Oct
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.
View all properties

Our guide on where to stay in Windward Cay

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

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.

Magic Kingdom® Theme Park featuring rides and interior views 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.

Universal Studios Florida® which includes a city, night scenes 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

One of the most popular neighborhoods in Florida, this bustling area is full of art galleries, shops, bars and restaurants.

Windsor Hills

While there might not be top attractions in Windsor Hills, you can explore the larger area and discover places like Mystic Dunes Golf Club and Island H2O Live!.

Top Windward Cay Hotel Reviews

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

10/10 Excellent
"Great for families "
jordan 2-night trip
Posted 1 day ago
Universal's Cabana Bay Beach Resort

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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia