Windward Cay holiday rentals
We found 1,356 holiday rentals — enter your dates for availability
Discover a selection of 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:20 Nov - 27 Nov
Exceptional
(127 reviews)
All the comforts of home!
Kissimmee
AU$2,342
for 7 nights, 1 villa
AU$335 per night
includes taxes & fees
Exceptional
(35 reviews)
Your home away from home.
Kissimmee
AU$3,869
for 7 nights, 1 home
AU$553 per night
includes taxes & fees
Very good
(31 reviews)
Renovated 4BR Villa with Private Pool Spa in Bellavida Resort Near Disney
Kissimmee
AU$3,192
for 7 nights, 1 villa
AU$456 per night
includes taxes & fees
Exceptional
(9 reviews)
Fully Renovated, Quiet, Spacious Disney Themed Pool Home with Office
Kissimmee
AU$2,573
for 7 nights, 1 home
AU$368 per night
includes taxes & fees
Exceptional
(18 reviews)
FULLY REMODELED!!3BDR/2BTH Villa near Disney World UNIT B
Kissimmee
AU$1,575
for 7 nights, 1 villa
AU$225 per night
includes taxes & fees
Very good
(24 reviews)
Garden View 6BR Escape with Pool, Hot Tub & Games
Kissimmee
AU$5,214
for 7 nights, 1 home
AU$745 per night
includes taxes & fees
Wonderful
(40 reviews)
6-Bed Villa, Private Pool & Hot Tub! Game Room | Gated Resort near Disney
Kissimmee
AU$4,122
for 7 nights, 1 home
AU$589 per night
includes taxes & fees
Very good
(18 reviews)
Bella Vida House with Pool and Games - Near Disney!
Kissimmee
AU$4,129
for 7 nights, 1 home
AU$590 per night
includes taxes & fees
Wonderful
(23 reviews)
Upstay - Resort Home w Cinema, Pool & Lake View
Kissimmee
AU$4,388
for 7 nights, 1 home
AU$627 per night
includes taxes & fees
Very good
(8 reviews)
Sunsation Destination!! First Floor One Bedroom Villa in Runaway Beach Resort!!!
Kissimmee
AU$1,512
for 7 nights, 1 villa
AU$216 per night
includes taxes & fees
Exceptional
(5 reviews)
Home Away From Home in charming Kissimmee with AC, WiFi. Enjoy your stay!
Kissimmee
AU$2,440
for 7 nights, 1 home
AU$349 per night
includes taxes & fees
Exceptional
(98 reviews)
Helen's Disney Dream Home - Chatham Park
Kissimmee
AU$2,049
for 7 nights, 1 home
AU$293 per night
includes taxes & fees
Wonderful
(7 reviews)
Spacious 4BR Family Townhouse—Private Pool & BBQ
Kissimmee
AU$2,603
for 7 nights, 1 home
AU$372 per night
includes taxes & fees
Exceptional
(28 reviews)
4BR Disney Oasis: Private Screened Pool + FREE Pool Heat! (20 Min to Parks)
Kissimmee
AU$2,589
for 7 nights, 1 home
AU$370 per night
includes taxes & fees
Exceptional
(138 reviews)
South‑facing private pool/spa for all‑day sunshine. Equipped interior games room
Kissimmee
AU$3,287
for 7 nights, 1 home
AU$470 per night
includes taxes & fees
Wonderful
(27 reviews)
Destination Disney!!! Three Bedroom Villa That Sleeps 10 - Two Heated Pools
Kissimmee
AU$2,037
for 7 nights, 1 villa
AU$291 per night
includes taxes & fees
Exceptional
(8 reviews)
3BR Townhome Near Disney I Resort Pool, Hot Tub & Disney-Themed Room
Kissimmee
AU$2,354
for 7 nights, 1 home
AU$336 per night
includes taxes & fees
Exceptional
(21 reviews)
Gorgeous Luxury 2 Bedroom Resort Condo Close to Disney
Kissimmee
AU$2,212
for 7 nights, 1 apartment
AU$316 per night
includes taxes & fees
Exceptional
(10 reviews)
Sweet Main Floor Home in Sweetwater
Kissimmee
AU$1,300
for 7 nights, 1 apartment
AU$186 per night
includes taxes & fees
Exceptional
(210 reviews)
Clean, Comfortable, Family Friendly Condo, EXCELLENT Location! Mins to DISNEY!!
Kissimmee
AU$1,649
for 7 nights, 1 apartment
AU$236 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
Kissimmee Family Vacation Home
Sleeps 6 · 3 bedrooms · 2 bathrooms
Bright contemporary home, recently renovated, private south facing pool, movie room
Sleeps 8 · 4 bedrooms · 2 bathrooms
Cosy Kissimmee Pool Home w/Games Room in secluded community. Near Disney
Sleeps 6 · 3 bedrooms · 2 bathrooms
Per friendly for September only. 3BR Pool Home Near Theme Parks.
Sleeps 9 · 3 bedrooms · 2 bathrooms
Luxurious 4 Bedroom/3.5 Bathroom Home, Perfectly Located with Private Conservation View Pool & Game Room
Sleeps 8 · 4 bedrooms · 3 bathrooms
kissimmee entire home ,NEAR DISNEY ,AND ALL . 2208
Sleeps 8 · 3 bedrooms · 2 bathrooms
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 home 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. Stayz 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 home in Windward Cay?
The average price for a holiday home 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 Stayz and how many guests to view your home 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 homes in Windward Cay?
Yes. You can pick from 24 holiday homes that cater to pets in Windward Cay. Lots of our pet-friendly holiday homes 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 Stayz.
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 homes and every day will be a pool day. Simply enter your travel dates into Stayz, then check the "pool" filter to find the perfect place to make a splash!
What are popular home amenities in Windward Cay?
The most popular home 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, Stayz holiday homes include the best amenities for hanging out with the people you love.
Are there large group holiday homes in Windward Cay?
Take your pick of 17 Stayz 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 homes 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 Stayz'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 homes 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 Stayz and stay connected on your getaway.
How can I find holiday homes with air conditioning in Windward Cay?
Windward Cay has 23 holiday homes where you can chill out in air-conditioned comfort. To find a stay on Stayz 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 home in Windward Cay?
You'll need to check with the Windward Cay holiday home you're looking at on Stayz as age restrictions differ. However, generally it's 16, 18 or 21.
How long can I rent a holiday home in Windward Cay for?
The amount of time you can stay in a Windward Cay holiday home 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.
More holiday ideas
- Golden Oak Holiday Rentals
- Bonnet Creek Holiday Rentals
- Oakwater Holiday Rentals
- Falcon's Fire Golf Club Holiday Rentals
- Celebration Holiday Rentals
- Disney SpringsTM Holiday Rentals
- Little Lake Bryan Holiday Rentals
- Kissimmee Holiday Rentals
- Lake Berkley Holiday Rentals
- Villas at Somerset Holiday Rentals
- Runaway Beach Club Holiday Rentals
- Seasons Holiday Rentals
- Regal Oaks Holiday Rentals
- Grand Beach Vacation Resort Holiday Rentals
- Fantasy World Resort Holiday Rentals
- Crystal Cove Holiday Rentals
- Cumbrian Lakes Holiday Rentals
- Vacation Village at Parkway Holiday Rentals
- Silver Lake Resort Holiday Rentals
- Storey Lake Resort Holiday Rentals
- Worldquest Holiday Rentals
- Sheraton Vistana Resort Villas Holiday Rentals
- Villas at Seven Dwarfs Lane Holiday Rentals
- Windsor Hills Holiday Rentals
- Hideaway Bay Holiday Rentals
- Disney's Maingate East Holiday Rentals
- Lake Bryan Holiday Rentals
- Villas at Shadow Bay Holiday Rentals
- Chatham Park Holiday Rentals
- Eagle Pointe South Holiday Rentals
- Villa rentals in Kissimmee
- Apartments in Kissimmee
- House rentals in Kissimmee
- Resort rentals in Orlando
- Villa rentals in Orlando
- Rentals with pool in Orlando
- House rentals in Mount Dora
- Townhouse rentals in Windsor Hills Resort
- House rentals in Regal Palms