Windward Cay holiday rentals
We found 1,362 holiday rentals — enter your dates for availability
Discover a selection of 17 homes, 10 villas and holiday rentals in Windward Cay that are perfect for your trip. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll find the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a washer and dryer. Whatever you're looking for, you'll find a property to rent for everyone's needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Windward Cay
Showing deals for:17 Oct - 24 Oct
Image gallery for FULLY REMODELED!!3BDR/2BTH Villa near Disney World UNIT B
9.89.8 out of 10 rating
Exceptional
(11 reviews)
FULLY REMODELED!!3BDR/2BTH Villa near Disney World UNIT B
Kissimmee, FL
7% off
Price is S$1,309
S$1,309
S$187 per night
includes taxes & fees
Image gallery for Discover Orlando charm, just a short drive to Disney
1010 out of 10 rating
Exceptional
(19 reviews)
Discover Orlando charm, just a short drive to Disney
Kissimmee, FL
14% off
Price is S$1,168
S$1,168
S$167 per night
includes taxes & fees
Image gallery for Fully Remodeled stylish 3/2 condo, close to the parks
9.69.6 out of 10 rating
Exceptional
(17 reviews)
Fully Remodeled stylish 3/2 condo, close to the parks
Kissimmee, FL
7% off
Price is S$1,250
S$1,250
S$179 per night
includes taxes & fees
Image gallery for Your home away from home.
9.69.6 out of 10 rating
Exceptional
(34 reviews)
Your home away from home.
Kissimmee, FL
6% off
Price is S$3,048
S$3,048
S$435 per night
includes taxes & fees
Image gallery for JUST REMODELED!! 3BR/2BR Chic Villa Near Disney UNIT A
9.69.6 out of 10 rating
Exceptional
(116 reviews)
JUST REMODELED!! 3BR/2BR Chic Villa Near Disney UNIT A
Kissimmee, FL
7% off
Price is S$1,309
S$1,309
S$187 per night
includes taxes & fees
Image gallery for UNBEATABLE LOCATION THEMATIC HOUSE with HEATED POOL OPTION 8 miles to Disney
9.09.0 out of 10 rating
Wonderful
(41 reviews)
UNBEATABLE LOCATION THEMATIC HOUSE with HEATED POOL OPTION 8 miles to Disney
Kissimmee, FL
7% off
Price is S$2,499
S$2,499
S$357 per night
includes taxes & fees
Image gallery for Mickey’s Magic Retreat at Terra Verde Resort
1010 out of 10 rating
Exceptional
(14 reviews)
Mickey’s Magic Retreat at Terra Verde Resort
Kissimmee, FL
7% off
Price is S$1,122
S$1,122
S$160 per night
includes taxes & fees
Image gallery for 139 Stunning 3BD Home Inside Disney Area!
8.68.6 out of 10 rating
Excellent
(7 reviews)
139 Stunning 3BD Home Inside Disney Area!
Kissimmee, FL
6% off
Price is S$1,802
S$1,802
S$257 per night
includes taxes & fees
Image gallery for Luxury Modern Upgraded 7/4.5 Villa On 5 Stars Terra Verde Resort Near Disney
9.29.2 out of 10 rating
Wonderful
(19 reviews)
Luxury Modern Upgraded 7/4.5 Villa On 5 Stars Terra Verde Resort Near Disney
Kissimmee, FL
8% off
Price is S$3,519
S$3,519
S$503 per night
includes taxes & fees
Image gallery for Close to all Orlando theme Parks and fully refurbished in 2024.
9.69.6 out of 10 rating
Exceptional
(105 reviews)
Close to all Orlando theme Parks and fully refurbished in 2024.
Kissimmee, FL
7% off
Price is S$1,740
S$1,740
S$249 per night
includes taxes & fees
Image gallery for CYBER WEEK WAS 180 NOW 175 Near Disney World: 4BR/2BA Pool Home + Free Internet
9.89.8 out of 10 rating
Exceptional
(144 reviews)
CYBER WEEK WAS 180 NOW 175 Near Disney World: 4BR/2BA Pool Home + Free Internet
Kissimmee, FL
12% off
Price is S$1,440
S$1,440
S$206 per night
includes taxes & fees
Image gallery for Lake View Villa with Private Pool/Games Rm/WiFi/HD TV - 10% Discount on 2025/26
9.69.6 out of 10 rating
Exceptional
(100 reviews)
Lake View Villa with Private Pool/Games Rm/WiFi/HD TV - 10% Discount on 2025/26
Kissimmee, FL
7% off
Price is S$2,431
S$2,431
S$347 per night
includes taxes & fees
Image gallery for 15-20 minutes from all Disney World Parks.
9.89.8 out of 10 rating
Exceptional
(8 reviews)
15-20 minutes from all Disney World Parks.
Kissimmee, FL
6% off
Price is S$1,724
S$1,724
S$246 per night
includes taxes & fees
Image gallery for 3BR Bella Vida Resort BBQ Near Parks
8.48.4 out of 10 rating
Very good
(7 reviews)
3BR Bella Vida Resort BBQ Near Parks
Kissimmee, FL
7% off
Price is S$1,612
S$1,612
S$230 per night
includes taxes & fees
Image gallery for Relaxing 3 bed pool home 7 miles from Disney and 5 minutes from Midevil times
8.88.8 out of 10 rating
Excellent
(8 reviews)
Relaxing 3 bed pool home 7 miles from Disney and 5 minutes from Midevil times
Kissimmee, FL
7% off
Price is S$1,568
S$1,568
S$224 per night
includes taxes & fees
Image gallery for Set in the beautiful Bellavida Resort with own South West Facing Pool
9.89.8 out of 10 rating
Exceptional
(41 reviews)
Set in the beautiful Bellavida Resort with own South West Facing Pool
Kissimmee, FL
6% off
Price is S$2,106
S$2,106
S$301 per night
includes taxes & fees
Image gallery for Experience Kissimmee living near vibrant Old Town
9.49.4 out of 10 rating
Exceptional
(38 reviews)
Experience Kissimmee living near vibrant Old Town
Kissimmee, FL
7% off
Price is S$1,964
S$1,964
S$281 per night
includes taxes & fees
Image gallery for Luxury Townhome 4 bed + 3 bath + Private Pool in front of the Clubhouse Resort!
1010 out of 10 rating
Exceptional
(14 reviews)
Luxury Townhome 4 bed + 3 bath + Private Pool in front of the Clubhouse Resort!
Kissimmee, FL
6% off
Price is S$2,021
S$2,021
S$289 per night
includes taxes & fees
Image gallery for Sunny Dream Home near Disney with Pool and Spa on Terra Verde Resort
9.69.6 out of 10 rating
Exceptional
(44 reviews)
Sunny Dream Home near Disney with Pool and Spa on Terra Verde Resort
Kissimmee, FL
8% off
Price is S$3,519
S$3,519
S$503 per night
includes taxes & fees
Image gallery for Relaxing 4BR Pool Home in Gated Resort - 12 Min to Disney!
9.29.2 out of 10 rating
Wonderful
(52 reviews)
Relaxing 4BR Pool Home in Gated Resort - 12 Min to Disney!
Kissimmee, FL
8% off
Price is S$2,586
S$2,586
S$369 per night
includes taxes & fees
Image gallery for Gorgeous Family Home! Sleeps 28
9.29.2 out of 10 rating
Wonderful
(5 reviews)
Gorgeous Family Home! Sleeps 28
Kissimmee, FL
6% off
Price is S$4,858
S$4,858
S$694 per night
includes taxes & fees
Image gallery for 4-Bedroom Vacation Home with Pool
9.49.4 out of 10 rating
Exceptional
(45 reviews)
4-Bedroom Vacation Home with Pool
Kissimmee, FL
7% off
Price is S$2,039
S$2,039
S$291 per night
includes taxes & fees
Image gallery for Upstay: Resort-Style 12BR Villa—Bella Vida Resort
8.88.8 out of 10 rating
Excellent
(14 reviews)
Upstay: Resort-Style 12BR Villa—Bella Vida Resort
Kissimmee, Florida
7% off
Price is S$5,366
S$5,366
S$767 per night
includes taxes & fees
Image gallery for Upstay Luxury Resort Home w Private Pool & Hot Tub
9.09.0 out of 10 rating
Wonderful
(9 reviews)
Upstay Luxury Resort Home w Private Pool & Hot Tub
Kissimmee, Florida
7% off
Price is S$4,552
S$4,552
S$650 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Windward Cay
Showing deals for: 13 Oct - 16 Oct
Beautiful, modern, salt water pool home close to Disney!!
Sleeps 8 · 3 bedrooms · 2 bathrooms
The current price is S$1,170
S$1,170
for 3 nights, 1 home
S$390 per night
includes taxes & fees
Relaxing 3 bed pool home 7 miles from Disney and 5 minutes from Midevil times
Sleeps 9 · 3 bedrooms · 2 bathrooms
8.88.8 out of 10
Excellentexcellent
8 reviews(8 reviews)
The current price is S$886
S$886
for 3 nights, 1 home
S$295 per night
includes taxes & fees
Kissimmee entire home near Disney, Walmart shopping Entertainment, Resturants
Sleeps 8 · 3 bedrooms · 2 bathrooms
7.07.0 out of 10
Goodgood
10 reviews(10 reviews)
The current price is S$1,108
S$1,108
for 3 nights, 1 home
S$369 per night
includes taxes & fees
4716 Windwood Magic Villa & pool
Sleeps 9 · 4 bedrooms · 2 bathrooms
9.29.2 out of 10
Wonderfulwonderful
The current price is S$948
S$948
for 3 nights, 1 home
S$316 per night
includes taxes & fees
Contemporary pool home with private pool and extended deck
Sleeps 6 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
The current price is S$1,104
S$1,104
for 3 nights, 1 home
S$368 per night
includes taxes & fees
NEW LISTING Stunning Villa - Amazing Value - Lake Berkley
Sleeps 10 · 5 bedrooms · 3 bathrooms
9.09.0 out of 10
Wonderfulwonderful
6 reviews(6 reviews)
The current price is S$1,188
S$1,188
for 3 nights, 1 home
S$396 per night
includes taxes & fees
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of holiday rental accommodation in Windward Cay?
According to our research, villas are the most in-demand type of property in Windward Cay. But as you might expect, everyone's idea of an epic stay can differ. Vrbo has holiday homes in a variety of sizes and shapes, so you're sure to discover your ideal match.
How much does it cost to rent a holiday rental in Windward Cay?
The average price for a holiday rental in Windward Cay is determined by a number of factors, like length of stay, property type and season. Whether you prefer a sprawling villa with lots of bedrooms or a quaint cabin for you and your other half, just add your travel dates to discover stays that offer great value.
How much does it cost to rent a beach house in Windward Cay?
Prices for beach houses in Windward Cay can differ depending on the size and style of the property and when you're travelling. Just enter your travel dates into Vrbo and how many guests to view your rental options and prices. From there you can use the filters to narrow down your search by nearby activities, ratings, amenities and more.
Are there pet-friendly holiday rentals in Windward Cay?
Yes. You can pick from 24 holiday rentals that cater to pets in Windward Cay. Lots of our pet-friendly holiday rentals even have an area outdoors for your four-legged pal to play around in, doggie beds, complimentary treats and proximity to parks or green space. Apply the "Pets allowed" filter to find your pawfect holiday home on Vrbo.
Can I rent a house with a pool in Windward Cay?
Pack your swimwear and inflatable flamingo, because there are 23 houses with a private pool in Windward Cay. Unwind at one of these terrific holiday rentals and every day will be a pool day. Simply enter your travel dates into Vrbo, then check the "pool" filter to find the perfect place to make a splash!
What are popular rental amenities in Windward Cay?
The most popular rental amenities people look for in Windward Cay include nearby museums, a barbecue grill and a lake view. Whether you're on a trip with family, your besties or even pets, Vrbo holiday homes include the best amenities for hanging out with the people you love.
Are there large group holiday rentals in Windward Cay?
Take your pick of 17 Vrbo properties in Windward Cay that can host five or more guests. You'll enjoy all the privacy and room you need to kick back with your nearest and dearest --- and no one else.
Are there holiday rentals in Windward Cay that welcome kids?
Windward Cay has 24 family-friendly holiday homes. And tracking down a stay that welcomes children is a cinch with Vrbo's "Properties good for families" filter. On top of having the entire place to yourselves, you'll get access to perks and conveniences like bunk beds, kitchens and private pools.
What are the top attractions for families in Windward Cay?
Keeping the kids occupied during your stay in Windward Cay is a breeze with these exciting family-friendly attractions:
- Fun Spot America
- Island H2O Live!
- Kissimmee Go-Karts
Are there holiday rentals with WiFi in Windward Cay?
Whether you'd like to keep up with the headlines, send some emails or update your social media, there are seven holiday homes with WiFi in Windward Cay. Check the "WiFi" box when searching on Vrbo and stay connected on your getaway.
How can I find holiday rentals with air conditioning in Windward Cay?
Windward Cay has 23 holiday rentals where you can chill out in air-conditioned comfort. To find a stay on Vrbo that comes with this perk, enter your desired travel dates and use the handy filter tool to select the "air conditioning" box.
How old do you have to be to rent a holiday rental in Windward Cay?
You'll need to check with the Windward Cay holiday home you're looking at on Vrbo as age restrictions differ. However, generally it's 16, 18 or 21.
How long can I rent a holiday rental in Windward Cay for?
The amount of time you can stay in a Windward Cay holiday rental for differs depending on the property. Simply enter your preferred travel dates to browse available options that offer extended stays. They feature all the things you need to make your extended getaway more enjoyable and convenient, like kitchens and air conditioning. Some holiday homes might also offer weekly or monthly discounted prices, so you can have a longer stay for less.