Windward Cay holiday rentals
We found 1,406 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:15 Jan - 22 Jan

Very good
(31 reviews)
Renovated 4BR Villa with Private Pool Spa in Bellavida Resort Near Disney
Kissimmee
AU$3,099
for 7 nights, 1 villa
AU$443 per night
includes taxes & fees

Exceptional
(145 reviews)
Luxury 6BR / 3.5 Bathroom villa near Disney. Pool, Hot Tub, Games Room, etc.
Kissimmee
AU$3,460
for 7 nights, 1 villa
AU$494 per night
includes taxes & fees

Exceptional
(21 reviews)
Gorgeous Luxury 2 Bedroom Resort Condo Close to Disney
Kissimmee
AU$1,742
for 7 nights, 1 apartment
AU$249 per night
includes taxes & fees

Wonderful
(5 reviews)
Your Orlando Getaway Lakefront Villa with Pool, Only 15min to Disney @TerraVerde
Kissimmee
AU$2,216
for 7 nights, 1 home
AU$317 per night
includes taxes & fees

Exceptional
(127 reviews)
All the comforts of home!
Kissimmee
AU$2,406
for 7 nights, 1 villa
AU$344 per night
includes taxes & fees

Exceptional
(35 reviews)
Your home away from home.
Kissimmee
AU$4,244
for 7 nights, 1 home
AU$606 per night
includes taxes & fees

Wonderful
(7 reviews)
Spacious 4BR Family Townhouse—Private Pool & BBQ
Kissimmee
AU$2,256
for 7 nights, 1 home
AU$322 per night
includes taxes & fees

Very good
(10 reviews)
290 LF - BellaVida Cozy 6BR Pool Home
Kissimmee
AU$1,991
for 7 nights, 1 home
AU$284 per night
includes taxes & fees

Exceptional
(5 reviews)
Home Away From Home in charming Kissimmee with AC, WiFi. Enjoy your stay!
Kissimmee
AU$2,104
for 7 nights, 1 home
AU$301 per night
includes taxes & fees

Very good
(15 reviews)
Family Resort Home—Game Room, Cinema & Theme Rooms
Kissimmee
AU$3,762
for 7 nights, 1 home
AU$537 per night
includes taxes & fees

Wonderful
(54 reviews)
Relaxing 4BR Pool Home in Gated Resort - 12 Min to Disney!
Kissimmee
AU$2,908
for 7 nights, 1 home
AU$415 per night
includes taxes & fees

Wonderful
(24 reviews)
Upstay - Resort Home w Cinema, Pool & Lake View
Kissimmee
AU$2,941
for 7 nights, 1 home
AU$420 per night
includes taxes & fees

Very good
(35 reviews)
Family Home with Pool, BBQ & Cinema Near Disney
Kissimmee
AU$3,245
for 7 nights, 1 home
AU$464 per night
includes taxes & fees

Exceptional
(8 reviews)
3BR Townhome Near Disney I Resort Pool, Hot Tub & Disney-Themed Room
Kissimmee
AU$1,935
for 7 nights, 1 home
AU$276 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Windward Cay

Bright contemporary home, recently renovated, private south facing pool, movie room
Sleeps 8 · 4 bedrooms · 2 bathrooms

Kissimmee Family Vacation Home
Sleeps 6 · 3 bedrooms · 2 bathrooms

MAGIC 5* LAKE VIEW VILLA HEATED POOL&HOT SPA, near DISNEY, 10 Guests
Sleeps 11 · 4 bedrooms · 3 bathrooms

Luxurious 4 Bedroom/3.5 Bathroom Home, Perfectly Located with Private Conservation View Pool & Game Room
Sleeps 8 · 4 bedrooms · 3 bathrooms

3BR Pool Home Near Theme Parks.
Sleeps 9 · 3 bedrooms · 2 bathrooms

Cosy Kissimmee Pool Home w/Games Room in secluded community. Near Disney
Sleeps 6 · 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
When is the best time to visit Windward Cay for a holiday rental?
The best time to visit Windward Cay for a holiday rental is during the summer months, particularly in July, when the area is buzzing with activity. This peak season, spanning from June to August, invites travellers to indulge in the warm sun and the stunning beaches along Florida's coast. With temperatures typically ranging from 25 to 33 degrees Celsius, July offers ideal conditions for swimming, sunbathing, and enjoying water sports.During this vibrant time, you can also participate in local festivals and events that showcase the unique culture of the region. The lively option is great for families looking to create lasting memories while soaking in the sunshine.If you're seeking a more tranquil experience, consider visiting in October, which is a fantastic option for those who prefer to avoid crowds. The weather remains pleasantly warm, and you'll find great value in holiday rentals as prices tend to be lower outside the peak season. October is also a lovely time to explore the natural beauty of the area with fewer tourists around, allowing for a more relaxed pace to enjoy the local attractions.
What are the top attractions in Windward Cay, Florida, United States of America?
In Windward Cay, Florida, visitors can enjoy a variety of attractions that highlight the area's charm. The nearby Walt Disney World® Resort is a major draw, offering a multitude of theme parks, including Magic Kingdom and Epcot, making it a great destination for families. Just a short drive away, the vibrant shops and restaurants of the Lake Buena Vista area provide ample dining options and entertainment.For those interested in nature, the nearby Shingle Creek Regional Park offers beautiful walking trails and opportunities for kayaking, showcasing Florida's natural beauty.
Are all fees included in the Windward Cay holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Windward Cay holiday homes with parking?
Stayz offers a wide selection of holiday homes in Windward Cay with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Windward Cay holiday homes?
You can find great discounts on holiday homes in Windward Cay on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Windward Cay holiday home booking on Stayz?
To find Windward Cay holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Windward Cay?
A long-stay holiday home in Windward Cay is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Windward Cay holiday home?
Book your Windward Cay holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Windward Cay?
Prices for holiday homes in Windward Cay vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Windward Cay to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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