Planning a family trip to Florida is exciting, but choosing the right resort can make a huge difference to your holiday experience. For many British travellers, the decision often comes down to two popular communities near Orlando: Windsor Hills and Windsor Island.
Both resorts offer spacious accommodation, excellent facilities, and easy access to Florida’s world-famous attractions. However, they cater to slightly different types of travellers. If you’re deciding where to stay during your next UK family holiday or Florida adventure, understanding the differences can help you get the best value for your money.
At Chillax Inn, we regularly help British travellers compare these two highly sought-after communities as they plan their Orlando getaway. In this guide, we’ll compare accommodation options, amenities, location, family-friendly features, and overall value to help you choose between Windsor Hills holiday rentals and Windsor Island.
Why UK Families Love Orlando Resort Communities
Many British visitors prefer staying in resort communities rather than hotels. The reasons are simple:
- More space for families
- Better value for longer stays
- Full kitchens for self-catering
- Private swimming pools
- Multiple bedrooms
- Access to resort facilities
Unlike traditional hotel rooms, holiday homes allow families to relax after busy theme park days while enjoying the comforts of home.
Among the many Florida holiday resorts, Windsor Hills and Windsor Island consistently rank among the most popular choices for international visitors.
An Overview of Windsor Hills
Located in Kissimmee, Windsor Hills has become one of the most recognised resort communities near Walt Disney World.
The resort has earned a strong reputation thanks to its excellent location and extensive range of accommodation options. Many UK travellers specifically search for Windsor Hills holiday rentals because of the resort’s close proximity to Disney parks and family-friendly atmosphere.
Key Features of Windsor Hills
- Located approximately 10 minutes from Disney World
- Gated entrance with 24-hour security
- Large lagoon-style swimming pool
- Water park and splash zone
- Cinema room
- Tennis courts
- Basketball courts
- Children’s playgrounds
- Games rooms in many villas
The resort offers a mixture of:
- Condominiums
- Townhouses
- Large family villas
- Luxury private pool villas
Because the community has been established for many years, visitors enjoy a mature, well-maintained environment with plenty of repeat guests returning year after year.
An Overview of Windsor Island
Windsor Island is one of Orlando’s newer resort communities and has quickly become a favourite among families seeking modern accommodation and upgraded amenities.
Located in the Davenport area, the resort offers larger homes and impressive leisure facilities designed for today’s holidaymakers.
Key Features of Windsor Island
- Contemporary holiday homes
- Resort-style clubhouse
- Lazy river
- Water slides
- Fitness centre
- Mini golf
- Sports courts
- Children’s splash areas
- Outdoor dining spaces
Many travellers looking for Windsor Island holiday homes Orlando are attracted by the newer properties and resort atmosphere.
The homes are generally larger and often feature modern interior designs, open-plan living spaces, and upgraded furnishings.
Location Comparison: Which Resort Is Closer to Disney?
Location is often the deciding factor for UK families visiting Orlando.
Windsor Hills
One of the biggest advantages of Windsor Hills is its exceptional Disney location.
Guests staying in Windsor Hills holiday rentals can often reach Disney property within 10 to 15 minutes, depending on traffic and the specific park being visited.
This shorter travel time offers several benefits:
- Less time driving
- Easier mid-day breaks
- Reduced fuel costs
- More flexibility for park hopping
For families with younger children, this convenience can be invaluable. Many travellers consider Windsor Hills to be the best Orlando resort for UK families because of this unmatched accessibility.
Windsor Island
Windsor Island is located slightly further away in Davenport.
Typical driving times include:
- Disney World: 20 to 30 minutes
- Universal Orlando: 35 to 45 minutes
- SeaWorld: 25 to 35 minutes
While still convenient, guests should expect slightly longer journeys to Orlando’s main attractions.
Winner: Windsor Hills
If Disney World proximity is your top priority, Windsor Hills clearly has the advantage.
Accommodation Comparison
Windsor Hills Accommodation
The variety of Windsor Hills holiday rentals is one of the resort’s strongest selling points.
Accommodation options range from:
- Two-bedroom condos
- Three-bedroom townhouses
- Six-bedroom villas
This flexibility makes the resort suitable for:
- Couples
- Small families
- Large multi-generational groups
Many villas include:
- Games rooms
- Home cinemas
- Heated pools
- Outdoor dining areas
Windsor Island Accommodation
Windsor Island focuses primarily on larger family homes.
Many properties feature:
- Five to ten bedrooms
- Open-plan layouts
- Modern kitchens
- Stylish interiors
- Large swimming pools
For larger families or groups travelling together, Windsor Island may offer more contemporary accommodation.
Winner: Depends on Group Size
- Smaller families: Windsor Hills
- Large family groups: Windsor Island
Resort Amenities Comparison
Amenities play a major role in choosing between these two communities.
Windsor Hills Amenities
The resort offers:
- Lagoon pool
- Water slides
- Splash park
- Cinema room
- Sports courts
- Children’s playgrounds
Many guests spend rest days entirely within the resort.
Windsor Island Amenities
Windsor Island takes the resort experience a step further.
Highlights include:
- Lazy river
- Water slides
- Poolside cabanas
- Fitness centre
- Mini golf
- Modern clubhouse
The newer facilities appeal to families who enjoy spending significant time at the resort itself.
Winner: Windsor Island
Its newer facilities provide a more luxurious resort experience.
Which Resort Offers Better Value?
Value isn’t simply about nightly rates.
You should also consider:
- Location
- Property size
- Resort facilities
- Transportation costs
Windsor Hills Value
Although some villas command premium prices due to their location, guests often save money on fuel, parking, and travel time. For many families, Windsor Hills holiday rentals represent excellent value because they maximise time spent enjoying Orlando’s attractions.
Windsor Island Value
Windsor Island often provides larger homes, newer interiors, and premium amenities. Families seeking luxury accommodation may find Windsor Island offers better overall value despite the longer drive.
Winner: Tie
The best value depends entirely on your holiday priorities.
Self-Catering Convenience for UK Families
Many British travellers prefer self-catering accommodation during Florida holidays, and both resorts excel in this area.
Benefits of Kissimmee Self-Catering
At Windsor Hills, guests enjoy easy access to:
- Supermarkets
- Restaurants
- Convenience stores
- Takeaway options
The availability of Kissimmee self-catering accommodation allows families to save money by preparing meals at home while maintaining flexibility throughout their stay.
Self-Catering at Windsor Island
Windsor Island properties also feature fully equipped kitchens, often with larger layouts suitable for extended family gatherings.
Both resorts make it easy to prepare breakfasts before park visits, cook family dinners, and store snacks and drinks.
Security and Peace of Mind
Security is an important consideration for overseas visitors.
Windsor Hills
As a long-established gated community Orlando destination, Windsor Hills offers controlled access, security personnel, and well-maintained communal areas.
Windsor Island
Windsor Island also operates as a secure gated community Orlando resort with modern entry systems and monitored access.
Winner: Tie
Both resorts provide excellent security standards.
Which Resort Is Best for Families with Young Children?
Young children often mean earlier bedtimes and less tolerance for long journeys.
In this scenario, Windsor Hills gains a significant advantage. The shorter drive to Disney allows families to return for naps, take afternoon breaks, and avoid lengthy evening journeys.
Many parents specifically choose Windsor Hills holiday rentals for this reason alone.
Winner: Windsor Hills
The Disney location makes family logistics much easier.
Which Resort Is Best for Large Family Groups?
For extended families travelling together, space becomes increasingly important.
Windsor Island’s larger homes offer more bedrooms, additional bathrooms, larger communal areas, and modern entertainment spaces.
If grandparents, cousins, or multiple families are travelling together, Windsor Island may be the better fit.
Winner: Windsor Island
Its larger properties suit bigger groups exceptionally well.
Comparing Private Pool Villas
One of the biggest attractions of staying in either resort is the availability of private pool villas.
Windsor Hills Pools
Many villas include:
- Heated pools
- Spillover spas
- Pool safety fencing
- Covered lanais
Windsor Island Pools
Because many homes are newer and larger, pools often feature:
- Extended deck areas
- Contemporary designs
- Larger outdoor entertaining spaces
Families who prioritise villa quality may prefer Windsor Island, while those focused on location often choose Windsor Hills.
Which Resort Should UK Families Choose?
The answer depends on the type of holiday you’re planning.
Choose Windsor Hills holiday rentals if:
- Disney is your main priority
- You have young children
- You want shorter driving times
- You prefer staying close to attractions
- You want a proven resort with years of positive reviews
Choose Windsor Island holiday homes Orlando if:
- You want newer accommodation
- Resort facilities are important to you
- You’re travelling with a large family group
- You plan to spend significant time relaxing at the resort
- You prefer larger modern homes
For most first-time visitors planning a major UK family holiday in Florida, Windsor Hills often edges ahead because of its unbeatable location near Disney World. This is why many travellers consider it the best Orlando resort for UK families.
However, families seeking a luxury resort atmosphere may find Windsor Island provides a more contemporary holiday experience.
Both remain among the best Florida holiday resorts available to British travellers, offering spacious accommodation, excellent amenities, and everything needed for an unforgettable Orlando adventure.
Whether you choose Windsor Hills holiday rentals or Windsor Island, you’ll enjoy the privacy, comfort, and flexibility that make Orlando villa holidays so popular with UK families year after year.
Frequently Asked Questions
Is Windsor Hills closer to Disney than Windsor Island?
Yes. Windsor Hills is typically around 10 to 15 minutes from Walt Disney World, while Windsor Island is generally 20 to 30 minutes away depending on traffic.
Are Windsor Hills holiday rentals suitable for large families?
Absolutely. The resort offers a wide selection of villas with multiple bedrooms, private pools, games rooms, and family-friendly amenities suitable for both small and large groups.
Which is the best Orlando resort for UK families?
Many British travellers choose Windsor Hills for its proximity to Disney World and established reputation. However, Windsor Island appeals to families looking for larger homes and more modern resort facilities.
Do both resorts offer private pool villas?
Yes. Both communities feature a wide range of private pool villas, making them excellent choices for families seeking extra privacy and space during their Orlando holiday.
Book Your Orlando Villa with Chillax Inn
Whether you’re looking for Windsor Hills holiday rentals close to Disney or spacious Windsor Island holiday homes Orlando, Chillax Inn can help you find the perfect base for your Florida adventure.
Our carefully selected holiday homes combine comfort, convenience, and exceptional locations, helping UK families make the most of every moment in Orlando.
Browse our available villas today and secure your ideal accommodation for an unforgettable UK family holiday Florida experience.
Contact Chillax Inn today and start planning your dream Florida family holiday.
