Windsor Hills holiday rentals
We found 2,734 holiday rentals — enter your dates for availability
Select from 170 houses, 61 flats and other holiday rentals to find the perfect place for your stay in Windsor Hills. Whether you’re travelling with friends, family or just with your pet, holiday rentals have the amenities that you expect for your stay, such as air conditioning and Wi-Fi. You'll be able to choose a property to rent for everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts – Windsor Hills
Showing deals for:18 Dec - 25 Dec

Very good
(35 reviews)
A Perfect Holiday House Waitting U at Windsor Palms Resort close to Disney World
Kissimmee
AU$4,587
for 7 nights, 1 home
AU$655 per night
includes taxes & fees

Exceptional
(8 reviews)
Luxury Themed home close to Disney
Kissimmee
AU$2,494
for 7 nights, 1 home
AU$356 per night
includes taxes & fees

Exceptional
(25 reviews)
Welcome to The Windsor Treasure with Professional Arcade Room! Brand New 2024!
Kissimmee
AU$8,647
for 7 nights, 1 villa
AU$1,235 per night
includes taxes & fees

Exceptional
(143 reviews)
Mickey Pool Villa - 10 minutes to Disney
Kissimmee
AU$5,423
for 7 nights, 1 villa
AU$775 per night
includes taxes & fees

Exceptional
(138 reviews)
Cinderella Pool Villa - 10 minutes from Disney
Kissimmee
AU$5,740
for 7 nights, 1 villa
AU$820 per night
includes taxes & fees

Exceptional
(90 reviews)
😎RELAX at Windsor Hills🌴, minutes to Disney - 5 bed / 5 bath, Private Pool🌞
Kissimmee
AU$3,491
for 7 nights, 1 home
AU$499 per night
includes taxes & fees

Exceptional
(96 reviews)
Harry Potter Villa - 10 Mins to Disney
Kissimmee
AU$6,997
for 7 nights, 1 villa
AU$1,000 per night
includes taxes & fees

Exceptional
(6 reviews)
Mickey’s Vacation Villa-Premium- Minutes from Disney World with private pool!
Kissimmee
AU$5,914
for 7 nights, 1 home
AU$845 per night
includes taxes & fees

Exceptional
(16 reviews)
Theme Parks, Heated Pool, Theater, Arcades, Mario Kart Bedroom
Kissimmee
AU$6,577
for 7 nights, 1 home
AU$940 per night
includes taxes & fees

Exceptional
(73 reviews)
Extrended Pool Deck/No Rear Neighbors/Windsor Hills Resort, 3 Miles to Disney®!
Kissimmee
AU$8,974
for 7 nights, 1 home
AU$1,282 per night
includes taxes & fees

Exceptional
(136 reviews)
Luxury Pool Home Steps to Disney, 2 Master Suites, Gated, Game Rm, BBQ Free WiFi
Kissimmee
AU$3,265
for 7 nights, 1 home
AU$466 per night
includes taxes & fees

Exceptional
(19 reviews)
Luxary villa close to disney
Kissimmee
AU$2,670
for 7 nights, 1 villa
AU$381 per night
includes taxes & fees

Exceptional
(57 reviews)
NEW Immersive Luxury Experience- 2 miles from Disney. Game Room, 3 en-suites
Kissimmee
AU$3,637
for 7 nights, 1 home
AU$520 per night
includes taxes & fees

Exceptional
(127 reviews)
3BR, 2BA, ground floor condo, just steps away from the pool and clubhouse.
Kissimmee
AU$1,466
for 7 nights, 1 apartment
AU$209 per night
includes taxes & fees

Exceptional
(104 reviews)
Monorail Silver | Near Disney & ESPN | Private Pool | No Rear Neighbors
Kissimmee
AU$4,196
for 7 nights, 1 home
AU$599 per night
includes taxes & fees

Exceptional
(33 reviews)
OW006 3bedroom 2bath main floor Closest to the Pool
Kissimmee
AU$2,119
for 7 nights, 1 home
AU$303 per night
includes taxes & fees

Exceptional
(79 reviews)
2 bed, 2 bath condo close to Disney and other theme parks Orlando
Kissimmee
AU$1,382
for 7 nights, 1 apartment
AU$197 per night
includes taxes & fees

Wonderful
(45 reviews)
Casa Mickey 3-bed Townhome on Windsor Hills near Disney with private Splash Pool
Kissimmee
AU$1,887
for 7 nights, 1 home
AU$270 per night
includes taxes & fees

Excellent
(171 reviews)
Mickey's Hangout - Quiet but close to Clubhouse & Pool - Under NEW MANAGEMENT
Kissimmee
AU$2,083
for 7 nights, 1 apartment
AU$298 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Windsor Hills

Fabulous Lake View/South Facing Pool Home- Game room -2 Miles to Disney!
Sleeps 10 · 5 bedrooms · 5 bathrooms

🌴Beautiful home in Windsor Hills Resort -Disney 2.5 miles 🌴
Sleeps 7 · 3 bedrooms · 3 bathrooms

WINNER:TOP VACATION RENTAL , CERTIFICATE OF EXCELLENCE
Sleeps 6 · 3 bedrooms · 3 bathrooms

FREE Pool Heat - Stay in the BEST Luxury 5 bedroom villa with SOUTH facing pool
Sleeps 10 · 5 bedrooms · 5 bathrooms

Windsor Hills Town Home! So Close You Can Feel the Magic!
Sleeps 8 · 3 bedrooms · 3 bathrooms

Spacious 5BR Home | Private Pool | 2 Miles to Disney | Windsor Hills Resort | Save on Long Stays
Sleeps 10 · 5 bedrooms · 5 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 Windsor Hills for a holiday rental?
The best time to visit Windsor Hills for a holiday rental is during the peak season, which runs from January to March. This period is particularly popular among families and adventure seekers looking to enjoy the warm Florida weather while exploring the nearby attractions of Disney World and other theme parks. With average temperatures ranging from 15 to 25 degrees Celsius, visitors can comfortably engage in outdoor activities, making it an ideal time for both relaxation and adventure.January is a standout month, as it marks the beginning of the year with fewer crowds compared to later months. This allows for a more relaxed experience at the parks, with shorter wait times for rides and attractions. Additionally, the pleasant climate makes it great for enjoying leisurely strolls around the community and local shops.For those looking for a more budget-friendly option, November is a great time to visit. While it may be considered the low season, visitors can still enjoy pleasant weather and fewer tourists. This month is fantastic for exploring the natural beauty of the area, including nearby state parks, without the hustle and bustle of peak tourist traffic.
What are the top attractions in Windsor Hills, Florida, United States of America?
Windsor Hills is a popular resort community located near Orlando, making it an ideal base for exploring several attractions. Just a short drive away, visitors can easily access the iconic Walt Disney World® Resort, including Magic Kingdom, Epcot, and Disney's Hollywood Studios. The proximity to these theme parks makes Windsor Hills particularly attractive for families.Additionally, the area is conveniently located near other attractions such as the exciting Universal Orlando Resort, which features Universal Studios and Islands of Adventure, offering thrilling rides and entertainment. For those looking for a bit of outdoor fun, the nearby Lake Louisa State Park provides opportunities for hiking, fishing, and enjoying the natural beauty of Florida.
Are all fees included in the Windsor Hills 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 Windsor Hills holiday homes with parking?
Stayz offers a wide selection of holiday homes in Windsor Hills 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 Windsor Hills holiday homes?
You can find great discounts on holiday homes in Windsor Hills 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 Windsor Hills holiday home booking on Stayz?
To find Windsor Hills 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 Windsor Hills?
A long-stay holiday home in Windsor Hills 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 Windsor Hills holiday home?
Book your Windsor Hills 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 Windsor Hills?
Prices for holiday homes in Windsor Hills 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 Windsor Hills 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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