Windward Cay holiday lettings

We found 1,365 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 May - 22 May

Image gallery for 8BR/5BA pool home,Near Disney,SeaWorld,Convention Center

8br/5ba 3680sqft pool villa
9.0 out of 10, Wonderful, (15 reviews)
Wonderful
(15 reviews)

8BR/5BA pool home,Near Disney,SeaWorld,Convention Center

Kissimmee

22% off
Price is £1,396
for 7 nights, 1 home
£199 per night
includes taxes & fees
8BR/5BA pool home,Near Disney,SeaWorld,Convention Center

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

What is the most popular type of holiday rental in Windward Cay?
In Windward Cay, holiday houses are the most popular type of rental, with around 15 options available throughout the area. These houses typically feature spacious interiors with multiple bedrooms, fully equipped kitchens, and private outdoor areas such as gardens or patios, ideal for enjoying the pleasant Florida weather. Additionally, there are several villas and apartments available, offering a variety of amenities that cater to different needs. Villas often come with luxurious features like private pools and entertainment areas, making them suitable for larger groups or families seeking a more upscale experience.
Are there any beach house rentals in Windward Cay?
In Windward Cay, Florida, there are several beach house rentals available, suiting travellers looking for a coastal getaway. These properties are typically situated close to popular attractions like the Walt Disney World Resort and various shopping centres. Most beach houses come equipped with amenities such as private pools, spacious living areas, and fully stocked kitchens, making them ideal for families or groups. Many also feature outdoor patios or decks, superb for enjoying the warm Florida weather after a day of exploring.
How much does it cost to rent a holiday home in Windward Cay?
Prices for holiday rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Windward Cay to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Windward Cay holiday house rentals?
You can find great discounts on house rentals in Windward Cay on Vrbo, 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.
Are there any Windward Cay holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 on Vrbo 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.
Can I find long-stay holiday rentals in Windward Cay?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there any remote work holiday rentals in Windward Cay?
In Windward Cay, Florida, there are numerous remote work holiday rentals available, with around 23 options to choose from. This area is particularly suitable for those looking to combine work and leisure, as many properties come equipped with essential amenities tailored for remote work. Expect to find features such as high-speed Wi-Fi, dedicated workspaces with desks and chairs, and even additional conveniences like computer monitors and safes for securing valuables. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Windward Cay holiday rental?
Book your Windward Cay holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Windward Cay home rental booking on Vrbo?
To find Windward Cay holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Windward Cay holiday rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

More holiday ideas