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17 Aug - 18 Aug
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Top Trending Hotels Near Windward Cay, Orlando

The Delaney Hotel
Terrace/patio

The Delaney Hotel

3.5 star property
9.6 out of 10, Exceptional, (1002)
"Excelente, buen hotel"
The Delaney Hotel
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, (3557)
"The hotel was very clean, the staff were friendly and knowledgeable about the hotel and area"
The price is Rp1.207.824
Rp1.358.801 total
includes taxes & fees
18 Aug - 19 Aug
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, (1430)
"Excellent place for familys"
The price is Rp840.788
Rp1.413.171 total
includes taxes & fees
21 Aug - 22 Aug
Ramada by Wyndham Hotel & Water Park
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, (815)
"Great stay and relaxing "
The price is Rp1.220.436
Rp1.354.684 total
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn Express & Suites Clermont Se West Orlando by IHG
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, (4725)
"Perfect spot to stay close to the airport!"
The price is Rp1.440.658
Rp1.620.942 total
includes taxes & fees
18 Aug - 19 Aug
Ramada by Wyndham Suites Orlando Airport
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, (8351)
"Was an amazing stay definitely would recommend it"
The price is Rp2.247.491
Rp3.256.033 total
includes taxes & fees
18 Aug - 19 Aug
The Grove Resort & Water Park Orlando
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, (3994)
"Great stay!!"
The price is Rp1.234.180
Rp1.388.451 total
includes taxes & fees
1 Sept - 2 Sept
Country Inn & Suites by Radisson, Orlando Airport, FL
Wyndham Garden Orlando Airport
Outdoor pool, pool loungers

Wyndham Garden Orlando Airport

3.0 star property
9.0 out of 10, Wonderful, (3776)
"I enjoy really enjoyed the stay staff was friendly restaurant food was really good"
The price is Rp1.484.314
Rp1.669.854 total
includes taxes & fees
2 Sept - 3 Sept
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, (1010)
"Amazing stay!"
The price is Rp3.542.951
Rp4.021.248 total
includes taxes & fees
24 Aug - 25 Aug
Lake Nona Wave Hotel
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, (6538)
"Nice, friendly, and comfortable place to stay "
The price is Rp1.499.190
Rp1.686.589 total
includes taxes & fees
10 Sept - 11 Sept
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, (1995)
"Staff was super friendly, cost was amazing, and very close to the airport"
The price is Rp714.023
Rp803.276 total
includes taxes & fees
21 Aug - 22 Aug
Orlando Palms Hotel
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, (2671)
"It was a very pleasant stay"
The price is Rp1.222.376
Rp1.375.173 total
includes taxes & fees
21 Aug - 22 Aug
SPOT X Hotel Orlando/Intl Dr by The Red Collection
La Quinta Inn & Suites by Wyndham Orlando Airport North
Dining

La Quinta Inn & Suites by Wyndham Orlando Airport North

3.0 star property
7.8 out of 10, Good, (7252)
"Wonderful stay. "
The price is Rp1.346.878
Rp1.515.239 total
includes taxes & fees
19 Aug - 20 Aug
La Quinta Inn & Suites by Wyndham Orlando Airport North
Holiday Inn Club Vacations at Orange Lake Resort by IHG
7 outdoor pools, pool cabanas (surcharge), pool umbrellas

Holiday Inn Club Vacations at Orange Lake Resort by IHG

4.0 star property
8.6 out of 10, Excellent, (2337)
"Great place to stay can’t wait to go back"
The price is Rp1.600.731
Rp2.512.259 total
includes taxes & fees
18 Aug - 19 Aug
Holiday Inn Club Vacations at Orange Lake Resort by IHG
Avanti International Resort
View from property

Avanti International Resort

4.0 star property
7.8 out of 10, Good, (4060)
"Great location "
Avanti International Resort
Holiday Inn Resort Orlando Suites - Waterpark by IHG
Exterior

Holiday Inn Resort Orlando Suites - Waterpark by IHG

3.5 star property
7.0 out of 10, Good, (3990)
"Second time staying here and both times were great. "
The price is Rp1.083.323
Rp2.401.177 total
includes taxes & fees
19 Aug - 20 Aug
Holiday Inn Resort Orlando Suites - Waterpark by IHG
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, (3207)
"The common area and bar and breakfast was very nice "
The price is Rp1.360.621
Rp1.530.698 total
includes taxes & fees
26 Aug - 27 Aug
Tru By Hilton Orlando Convention Center Area, FL
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, (3972)
"Great stay!"
The price is Rp1.668.641
Rp1.877.222 total
includes taxes & fees
7 Sept - 8 Sept
Rosen Shingle Creek
Hyatt Regency Grand Cypress
3 outdoor pools, open 7 AM to 10:00 PM, pool cabanas (surcharge)

Hyatt Regency Grand Cypress

4.0 star property
9.2 out of 10, Wonderful, (2222)
"Amazing place to stay "
The price is Rp2.085.801
Rp3.256.113 total
includes taxes & fees
25 Aug - 26 Aug
Hyatt Regency Grand Cypress
Caribe Royale Orlando
Sports court

Caribe Royale Orlando

4.5 star property
9.2 out of 10, Wonderful, (4342)
"Great stay "
The price is Rp2.570.871
Rp3.583.535 total
includes taxes & fees
31 Aug - 1 Sept
Caribe Royale Orlando
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.

Where to stay in Windward Cay

Find the best Windward Cay areas for the activities you enjoy most.
International Drive District map

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 map

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 map

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 map

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 map

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

DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent
"I liked the breakfast bar !"
Annabell 4-night trip
Posted 15 hours ago
DoubleTree by Hilton at the Entrance to Universal Orlando

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.

What's a favourite hotel to stay in Windward Cay?

For your stay in Windward Cay, Windward Cay 4707 is one of the top choices based on our traveller data. Another good option for your stay in the area is Peaceful Windward Cay 3 Bedroom Home by Redawning.

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.