Hotels in Windward Cay

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Top 10 Hotels in Windward Cay

Seasons Florida Resort
Property grounds

Seasons Florida Resort

2.0 star property
8.8 out of 10, Excellent, (2334)
"Have stayed here numerous times now and it is truly enjoyable being at this hotel. The location is great and the room is spacious and comfortable. I feel treated less like a guest and more like a family member. All aspects of this stay was great, and I look forward to being back there again soon."
The price is S$85
includes taxes & fees
13 Jan - 14 Jan,2025
Seasons Florida Resort
Econo Lodge Inn & Suites Maingate Central
Lobby

Econo Lodge Inn & Suites Maingate Central

2.5 star property
5.8 out of 10, (1005)
"Worth every penny "
The price is S$84
includes taxes & fees
9 Jan - 10 Jan,2025
Econo Lodge Inn & Suites Maingate Central
Hotel MonteCarlo
In-room safe, desk, blackout curtains, iron/ironing board

Hotel MonteCarlo

2.0 star property
8.4 out of 10, Very good, (280)
"Very clean room and quiet"
The price is S$112
includes taxes & fees
26 Jan - 27 Jan,2025
Hotel MonteCarlo
El Sol
Outdoor pool

El Sol

2.0 star property
7.4 out of 10, Good, (29)
"Brand new "
The price is S$96
includes taxes & fees
3 Jan - 4 Jan,2025
El Sol
Sunshine Inn
Lobby

Sunshine Inn

2.0 star property
7.6 out of 10, Good, (197)
"Hotel was very modern and chic. Wasn’t expecting microwave, addtl sink and area to store groceries if needed "
The price is S$108
includes taxes & fees
2 Jan - 3 Jan,2025
Sunshine Inn
Club Sevilla
Property entrance

Club Sevilla

2.0 star property
8.8 out of 10, Excellent, (1000)
"I liked everything about my stay. From the staff to my room. Everything was completely acceptable. The only thing that I didn't like was not having shampoo to wash my hair, I had to use soap. Hotels need to be consistant so that travelers know what they need to bring."
The price is S$100
includes taxes & fees
12 Jan - 13 Jan,2025
Club Sevilla
Home 1 Suites Extended Stay - Kissimmee
Outdoor pool, open 9 AM to 10:00 PM, pool umbrellas, pool loungers

Home 1 Suites Extended Stay - Kissimmee

2.5 star property
6.8 out of 10, (1000)
"Cleanliness of the room. Room space. "
The price is S$100
includes taxes & fees
5 Jan - 6 Jan,2025
Home 1 Suites Extended Stay - Kissimmee
Park Royal Orlando
Exterior

Park Royal Orlando

2.5 star property
7.8 out of 10, Good, (1005)
"Excellent hotel! Even though I only used it to sleep, since my trip was an emergency to be close to the hospital where my brother was, everything was very pleasant, including the staff, who behaved very well despite the circumstances."
The price is S$114
includes taxes & fees
26 Jan - 27 Jan,2025
Park Royal Orlando
Sevilla Inn - Near Medieval Times
Front of property – evening/night

Sevilla Inn - Near Medieval Times

2.0 star property
5.6 out of 10, (880)
"Close to Disney & other attractions."
The price is S$104
includes taxes & fees
9 Jan - 10 Jan,2025
Sevilla Inn - Near Medieval Times
Ambassador Inn
Outdoor pool

Ambassador Inn

2.0 star property
4.4 out of 10, (775)
"Okay to stay "
The price is S$93
includes taxes & fees
1 Jan - 2 Jan,2025
Ambassador Inn
Days Inn by Wyndham Kissimmee West
Exterior

Days Inn by Wyndham Kissimmee West

2.5 star property
5.8 out of 10, (1001)
"Not bad but needs so upkeep, latch lock on broken, bathroom door wouldn't close"
The price is S$116
includes taxes & fees
1 Jan - 2 Jan,2025
Days Inn by Wyndham Kissimmee West
Free Resort Access 4 Bedroom Near Disney with Themed Rooms
Exterior

Free Resort Access 4 Bedroom Near Disney with Themed Rooms

5.0 star property
9.2 out of 10, Wonderful, (31)
"Perfect location for 192, All Disney and Universal. 20 mins max. Pool fab, local restaurants and services perfect. Easy slept 2 families. Good facilities throughout the Villa. "
Free Resort Access 4 Bedroom Near Disney with Themed Rooms
The Keys
Lobby

The Keys

2.5 star property
4.2 out of 10, (600)
"I enjoyed my stay "
The price is S$99
includes taxes & fees
1 Jan - 2 Jan,2025
The Keys
Splendid 5Bd Close to Disney at Storey Lake 4251
Water park

Splendid 5Bd Close to Disney at Storey Lake 4251

5.0 star property
9.2 out of 10, Wonderful, (5)
"Everything from the house to the property was amazing!!! the only downside is entering the property. cars were backed up for at least half a mile and it took a long time to get in every time we returned from an outing. My husband had an argument with the security guard because his pass was not scanning so he was told he could not come in. They really need to come up with a better check in system."
Splendid 5Bd Close to Disney at Storey Lake 4251
Maple Leaf Inn & Suites
Front of property

Maple Leaf Inn & Suites

2.5 star property
7.0 out of 10, Good, (59)
"Not nearly as nice as advertised. Appeared to have long term tenants. Owner was nice. All of the cats outside were cute."
The price is S$108
includes taxes & fees
2 Jan - 3 Jan,2025
Maple Leaf Inn & Suites
RW Hotel
Outdoor pool

RW Hotel

2.5 star property
6.6 out of 10, (193)
"Hotel and room were clean, bed was comfortable and staff was friendly and helpful. "
The price is S$131
includes taxes & fees
3 Jan - 4 Jan,2025
RW Hotel
Marvelous 5Bd w/ Pool Close to Disney @ Storey Lake 2629
Private pool

Marvelous 5Bd w/ Pool Close to Disney @ Storey Lake 2629

5.0 star property
10.0 out of 10, Exceptional, (1)
"Es muy bonita y limpia y segura mi familia y yo disfrutamos mucho."
Marvelous 5Bd w/ Pool Close to Disney @ Storey Lake 2629
Seven Dwarfs Vacations Resort
Front of property – evening/night

Seven Dwarfs Vacations Resort

2.5 star property
7.4 out of 10, Good, (16)
"I loved everything about my experience! Mrs Linda is so kind and motherly. She was very prompt with every phone conversation. My family and I will most definitely stay again! "
Seven Dwarfs Vacations Resort
Marvelous 4Bd with Pool at Storey Lake Resort 2601
Water park

Marvelous 4Bd with Pool at Storey Lake Resort 2601

5.0 star property
10.0 out of 10, Exceptional, (2)
Marvelous 4Bd with Pool at Storey Lake Resort 2601
Gorgeous 4Bd with Pool @ Storey Lake Resort 4475
Water park

Gorgeous 4Bd with Pool @ Storey Lake Resort 4475

5.0 star property
9.0 out of 10, Wonderful, (2)
Gorgeous 4Bd with Pool @ Storey Lake Resort 4475
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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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 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 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.