Windsor Island Resort holiday lettings

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Holiday rentals with weekly discounts – Windsor Island Resort

Showing deals for:8 Jan - 15 Jan

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Pool
9.6 out of 10, Exceptional, (47 reviews)
Exceptional
(47 reviews)

SPECIAL OFFER! Get UP TO 20% off Weekly Rental with complementary Pool Heating!

Davenport

7% off
Price is £2,585
for 7 nights, 1 villa
£369 per night
includes taxes & fees
SPECIAL OFFER! Get UP TO 20% off Weekly Rental with complementary Pool Heating!

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Why visit Windsor Island Resort

  • Luxurious accommodation: Enjoy spacious private villas and condos, perfect for families and groups seeking comfort.
  • Exceptional amenities: Relax at the stunning clubhouse and refreshing pool, ideal for leisure and recreation.
  • Recreational activities: Access a theme park and golf course, providing entertainment for all ages.
  • Picturesque lakes: Unwind by serene lakes, offering a tranquil setting for relaxation and outdoor experiences.
  • State-of-the-art fitness centre: Stay active and fit with modern facilities available within the resort.

Popular types of accommodation around Windsor Island Resort

Welcome to Windsor Island Resort, a delightful retreat in Four Corners, Florida, where you can enjoy a range of houses, villas, and condos. This enchanting resort features exceptional amenities, including a stunning clubhouse, a refreshing pool, and recreational facilities. Experience the comfort of spacious bedroom villas, perfect for families or groups seeking a memorable Florida getaway. Discover the charm and relaxation that awaits you at Windsor Island Resort, your home away from home.

  • Houses: Enjoy the luxury of spacious private homes that offer a home-like atmosphere, ideal for families or groups.
  • Villas: Experience upscale living in elegant villas, often featuring private pools and stunning views, perfect for a lavish getaway.
  • Condos: Stay in modern condominiums that provide convenience and comfort, often located near local attractions.
  • Apartments: Opt for fully furnished apartments, offering a blend of practicality and homely charm for shorter stays.
  • Cottages: Choose quaint cottages for a cosy retreat, surrounded by nature and tranquil settings.**

Top attractions near Windsor Island Resort

Windsor Island Resort in Four Corners, Florida, offers a delightful blend of attractions for families and outdoor enthusiasts alike. Within the resort, visitors can enjoy various leisure activities, including access to a theme park and a golf course, perfect for those seeking entertainment and recreation. Additionally, the resort's serene lakes provide a picturesque setting for relaxation and outdoor experiences, making it an ideal destination for a memorable holiday.

  • Walt Disney World® Resort: Experience the magic at this iconic theme park, featuring enchanting attractions, thrilling rides, and family-friendly entertainment that create unforgettable memories.
  • ChampionsGate Golf Club: Enjoy a round of golf at this beautiful course, known for its family-friendly atmosphere, stunning landscapes, and welcoming staff, making it perfect for both beginners and experienced players.
  • Lake Davenport: Relax by the serene waters of Lake Davenport, offering picturesque scenery, outdoor activities, and a romantic setting that’s ideal for a leisurely day by the beach.

Things to do recommended for couples

For a romantic getaway near Windsor Island Resort, indulge in a sunset picnic at Lake Louisa State Park, just a short drive away. Explore the charming boutiques in Celebration or enjoy a candlelit dinner at a local restaurant, creating unforgettable memories together.

Things to do recommended for families

Families will love exploring the thrilling rides at nearby Disney World, experiencing wildlife at the Central Florida Zoo, or enjoying the splash pads and playgrounds at Lake Eva Park. For a unique adventure, consider a day trip to the enchanting Bok Tower Gardens.

Things to do recommended for groups

Explore the scenic beauty of Lake Louisa State Park, only a short drive away, where your group can hike, picnic, or enjoy water sports. Alternatively, visit the nearby fun-filled attractions of Kissimmee for thrilling amusement park adventures.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Windsor Island Resort

If you're travelling with a group, family, pets, or planning for extended stays, be sure to use the appropriate filters to match your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Windsor Island Resort with a group: Think about the number of bedrooms you'll require, along with features like a fully equipped kitchen or outdoor space for group activities. Thankfully, you can easily apply filters for all of these options, and more, on Vrbo.
  • Traveling to Windsor Island Resort with young kids: Travelling with young children can be quite demanding. It’s essential to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about your closeness to family-friendly attractions.
  • Taking your pets with you to Windsor Island Resort: For many, a family holiday isn’t truly fulfilling without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds to ensure that everyone feels completely at home.
  • Planning for a long term stay visiting Windsor Island Resort: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Windsor Island Resort

Windsor Island Resort in Four Corners, Florida, is a luxurious haven for families seeking a memorable holiday experience. With its state-of-the-art fitness centre and a plethora of recreational activities, guests can unwind and stay active. The resort's stunning amenities, coupled with its proximity to the enchanting Disney World, make it an ideal vacation spot. Enjoy the friendly atmosphere and indulge in the ultimate relaxation that Windsor Island Resort has to offer.

  • Orlando: Orlando is a vibrant metropolis known for its family-friendly atmosphere and entertainment options. Situated a short drive from Windsor Island Resort, it boasts a plethora of theme parks, including the renowned Walt Disney World and Universal Studios. Visitors can indulge in shopping at various malls, explore the arts at local centres, and enjoy the dynamic nightlife. With beautiful parks and beaches nearby, Orlando offers a perfect blend of leisure and adventure, making it an ideal destination for families and business travellers alike.
  • Four Corners: Four Corners is a quaint village that serves as a gateway to some of Florida’s most exciting attractions. Located near Windsor Island Resort, it is ideal for families and outdoor enthusiasts seeking a mix of relaxation and fun. The area features several golf courses and resorts, making it perfect for leisurely days out. With easy access to theme parks and sports facilities, Four Corners offers visitors a chance to experience the thrill of Florida's outdoor lifestyle while enjoying a peaceful retreat away from the hustle and bustle.
  • Tuscan Hills: Tuscan Hills is a charming neighbourhood located a mere half-mile from Windsor Island Resort. This community is highly sought after for its outdoor activities and entertainment offerings, making it a favourite among families. Visitors can enjoy golf courses and local parks, providing ample opportunity for recreation. Its close proximity to major theme parks and film studios adds to the allure, making Tuscan Hills a wonderful spot for those looking to immerse themselves in the excitement of Florida while enjoying a tranquil, community feel.

Best time to go to Windsor Island Resort

If you're planning a trip to Windsor Island Resort, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs in February to March and July, while off-peak times, like August to October tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January60.6°F (15.9°C)Light RainMostly SunnyAverageAverage
February64.4°F (18.0°C)Light RainMostly SunnySlightly HighSlightly Low
March67.6°F (19.8°C)Light RainMostly SunnySlightly HighAverage
April72.7°F (22.6°C)Light RainMostly SunnyAverageAverage
May77.2°F (25.1°C)Light RainMostly SunnyAverageAverage
June81.1°F (27.3°C)Light RainMostly SunnyAverageSlightly High
July82.4°F (28.0°C)Moderate RainMostly SunnySlightly HighSlightly High
August82.6°F (28.1°C)Moderate RainMostly SunnySlightly LowAverage
September80.4°F (26.9°C)Moderate RainMostly SunnySlightly LowSlightly Low
October75.2°F (24.0°C)Light RainMostly SunnySlightly LowSlightly Low
November68.5°F (20.3°C)Light RainMostly SunnyAverageAverage
December64.4°F (18.0°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is a breeze

Are you hoping to save on your next getaway? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you can achieve considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a convenient platform to plan new journeys, pick up where you last paused, or keep track of your arrangements. You can easily access properties you've previously saved or booked under Potential, Upcoming, or Current Trips. To explore Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What are the best holiday rentals near Windsor Island Resort?
The best holiday rentals near Windsor Island Resort are typically located within the Four Corners area, offering convenient access to the resort's attractions. You will find a wide array of private holiday houses and luxurious villas available, many situated within gated communities. If you are willing to drive a bit further, renting in nearby areas can be an affordable option for finding larger properties. You can choose from a range of styles to find the best holiday rentals near Windsor Island Resort.

Many of these properties offer fantastic amenities so you can have a comfortable stay, such as private or shared pools, laundry facilities, and access to fitness facilities. These homes are ideal for families or large groups visiting the area, providing ample space and comfort.
Are there any cheap holiday rentals near Windsor Island Resort?
There are several affordable holiday rentals near Windsor Island Resort, especially if you are flexible with location and travel dates. Budget-friendly stays typically start around £150 per night. Some stays even drop below £100 per night in September during the off-season, making it a great option for guests looking to experience the area without overspending. These rentals often include amenities such as free WiFi, complimentary toiletries, and free self-parking, and can range from cosy villas to modest private homes, providing a clean, comfortable base for adventure.

To get the best value, consider staying slightly outside major hubs. If you're willing to drive a bit further, renting around nearby areas can be an affordable option. With a little planning, it is absolutely possible to find a comfortable stay near Windsor Island Resort while keeping costs down.

*Pricing data are based on past 12 months data.
What are the best pet-friendly holiday rentals near Windsor Island Resort?
There are over 1,800 pet-friendly holiday rentals near Windsor Island Resort, primarily private holiday houses and villas, making it simple to bring your furry companions along. These properties are found in the Four Corners area and often feature amenities such as dog exercise areas, food and water bowls, and some even allow pets to stay free. Guests can enjoy comfortable living spaces while their pets have dedicated areas to play and relax.

To find the best pet-friendly holiday rentals near Windsor Island Resort, always review the specific house rules regarding pet size, breed restrictions, and any additional fees. While Windsor Island Resort itself may have specific regulations for pets, nearby green spaces and public parks in the Four Corners area, such as Lake Louisa State Park, offer ample opportunities for pets to enjoy the outdoors on paved paths or designated trails.
What are the top holiday rentals with pools near Windsor Island Resort?
There are over 10,730 holiday rentals near Windsor Island Resort that include access to swimming pools, with both private and shared options available. Properties are concentrated within Windsor Island Resort itself and nearby areas, offering a variety of layouts from private holiday houses to spacious villas. Many of these homes come fully equipped with amenities such as full kitchens, Wi-Fi, and comfortable living areas, making them ideal for families or groups seeking a relaxing stay.

When selecting your ideal home, consider the benefits of different pool types. Private pools offer seclusion for families, while shared pools often include access to additional features like waterslides or poolside bars, enhancing the communal experience. For cooler months, look for heated or indoor pool options to ensure year-round enjoyment.
What are the best family holiday rentals near Windsor Island Resort?
There are over 8,700 family-friendly holiday homes near Windsor Island Resort, offering a vast selection for groups of all sizes. These properties, predominantly private holiday houses and villas, provide ample space with multiple bedrooms and bathrooms, full kitchens for meal preparation, and comfortable living areas. Many also feature essential amenities like outdoor play areas, yards, or patios, as well as entertainment options such as video games and HDTVs, ensuring a comfortable stay for everyone.

When selecting the ideal holiday rental, look for properties that offer separate spaces for adults and children to unwind, and prioritise homes with practical utilities like a well-appointed kitchen. Staying close to Windsor Island Resort means less travel time and more opportunities to enjoy the area's attractions.
Are there any luxury holiday rentals near Windsor Island Resort?
Near Windsor Island Resort, guests can find several luxury holiday rentals that offer modern comfort. These properties often feature amenities such as private heated pools, private outdoor hot tubs, deep soaking bathtubs, designer toiletries, and premium bedding. Some homes also boast resort views or offer access to golf courses on-site, providing a truly upscale experience.

These homes are ideal for families or larger groups, ensuring a comfortable stay with features like air conditioning and efficient climate control. Many of these top-tier stays are managed by highly rated Vrbo hosts, promising a professional and premium experience.
How much is a holiday rental near Windsor Island Resort?
Holiday rental prices near Windsor Island Resort start from £185 per night, offering a variety of home styles to suit your needs. Budget-friendly properties, such as simple apartments, or explore mid-range rentals, including private homes with standard amenities, which are generally around £185 per night. For those seeking a more luxurious experience, upscale options can cost £275 or more per night, especially for larger homes with premium features like private pools and extensive living space.

Enter your destination, travel dates, and number of guests on search to see the best options. You can use filters to set a minimum and maximum nightly price range along with other preferences. Rates may vary based on the season and specific amenities, but with a little planning, guests can find a rental that perfectly balances convenience and value.

*Pricing data are based on past 12 months data.
Where should I stay when visiting Windsor Island Resort?
When visiting Windsor Island Resort, there are several excellent areas for holiday rentals that offer convenient access and a great base for your stay.

The immediate vicinity of Four Corners provides numerous large holiday homes, many with private pools, making them ideal for families and larger groups. These properties are a short drive from Windsor Island Resort, offering convenient access to local attractions and amenities.

For those seeking a slightly different setting, the Kissimmee area, a little further east, also offers a wide array of holiday rentals. This area is known for its diverse range of properties, from spacious villas to comfortable apartments, and provides easy routes to Windsor Island Resort and the wider Orlando theme parks.
What is the cheapest month to stay near Windsor Island Resort?
The cheapest time to find holiday rentals near Windsor Island Resort is typically during the late Autumn (late August to September) and late Winter (January to early February), excluding major holiday periods like Christmas, New Year's, and Spring Break. January is frequently the single cheapest month, often providing lower rates on properties. Guests can often find various savings during these months, with rates often 15-25% less compared to peak season.
Are there any lakefront holiday rentals near Windsor Island Resort
Lakefront holiday rentals near Windsor Island Resort are available, primarily found on nearby lakes such as Lake Davenport and some of the smaller, interconnected natural lakes in the area. These properties are a short drive from Windsor Island Resort, offering convenient access to water activities like kayaking, fishing, swimming, or relaxing by the shore.

These homes often feature spacious decks, fire pits, hot tubs, and full kitchens, making them ideal for families and larger groups. Guests can enjoy watersports, observe local wildlife, and unwind in peaceful surroundings.
Are there any monthly holiday rentals near Windsor Island Resort?
Vrbo offers excellent options for monthly holiday rentals near Windsor Island Resort, making it a great choice for those who want to combine work and adventure. Monthly rentals often feel like a true home away from home, with fully furnished properties equipped with essential amenities like high-speed Wi-Fi, full kitchens, and comfortable workspaces, perfect for remote work or a summer holiday with the family. With flexible monthly rental options, Vrbo is a convenient and comfortable choice for extended stays near Windsor Island Resort.
Are there any last-minute holiday rentals near Windsor Island Resort?
Vrbo makes it simple to find last-minute holiday rentals near Windsor Island Resort that blend comfort, style, and great value. Vrbo offers plenty of options for guests ready to pack up and go. Families and groups will find these deals especially appealing. Many spacious homes, complete with full kitchens, private pools, and multiple bedrooms, often become available when hosts want to fill open dates on their calendars.

Finding these stays is easy. Just enter your destination and travel dates, then use Vrbo's "Last Minute" or "Discounts" filter to uncover the best offers. You'll see reduced rates in the listings. Vrbo's last-minute rentals are a smart way to save while you explore. Whether you're planning a quick trip or a weekend getaway with friends, your last-minute escape is waiting, you just have to decide where to go next.
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 favourites, and build the perfect itinerary together.

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