Windsor Cay vs. Island vs. Westside: Which Is Best for 5-7BR Homes?

Choosing the right Orlando resort for a large group vacation or a short-term rental (STR) investment can feel overwhelming. The “Windsor” brand by Pulte Homes, including Windsor at Westside, Windsor Island, and the brand-new Windsor Cay, represents the gold standard for amenity-rich communities near Disney World. But when it comes to spacious 5–7 bedroom homes, which resort offers the best value, experience, and return on investment?

Whether you’re an investor scouting your next high-yield property or a family planning an unforgettable multi-generational trip, this guide breaks down everything you need to know.

Windsor Cay: The Newest and Most Modern

As the latest addition to the Windsor family, Windsor Cay Resort in Clermont is designed to impress. Construction began in 2023, meaning every home features the latest designs, technology, and finishes. For travelers and investors wanting that brand-new feel, this is the place to be.

Homes and Booking Options

Windsor Cay offers a fresh inventory of 5-bedroom townhomes and single-family homes with up to 7 bedrooms. Because the resort is new, booking availability is currently strong across platforms like VRBO and Airbnb. Investors have a unique opportunity here, as early buyers often receive booking incentives and closing cost credits. Themed rooms and private game rooms are common, appealing directly to the family vacation market.

Amenities

The amenities at Windsor Cay are state-of-the-art and a major draw. The Aloha Clubhouse is the centerpiece, featuring:

• A massive zero-entry resort pool and lazy river
• Dual water slides and a children’s splash playground
• A 9-hole mini-golf course
• Full-service tavern, cafe, and ice cream shop
• Fitness center, sports courts, and a fire pit

Every home also includes a private screened-in pool, and the HOA fee covers high-speed internet, cable, and daily trash pickup, adding value for both owners and guests.

Pricing and Location

Being the newest resort, Windsor Cay commands premium pricing. A 5-bedroom home can range from $220 to $350 per night during the off-season, jumping to $400–$600 during peak times. The larger 7-bedroom homes can reach $700+ on holiday weeks.

Located 8-9 miles from Walt Disney World, the drive is a convenient 10-15 minutes. While some minor construction may continue into late 2025, the primary amenities are fully operational. Early guest reviews are overwhelmingly positive, praising the pristine homes and modern facilities.

Best for:

• Investors seeking the highest potential for future returns.
• Travelers who want the “first-to-experience” luxury of a brand-new resort.
• Groups that prioritize modern design and the latest amenities.

Windsor Island: The Amenity-Packed Fan Favorite

Windsor Island Resort has quickly become the benchmark for Orlando vacation communities. Fully completed and operational, it boasts a comprehensive set of amenities and a vibrant, family-focused atmosphere that keeps guests coming back. For those looking for a proven winner, Windsor Island is a top contender.

Homes and Booking Options

With over 1,000 homes, the resort has a huge inventory of 5–7 bedroom properties. You can find listings on major sites like Booking.com and directly through dozens of property managers, which creates healthy price competition. Themed bedrooms (Disney, Star Wars, Marvel) and elaborate game rooms are extremely common in the Windsor Island Resort 7-bedroom homes, making them a hit with families.

Amenities

Windsor Island is famous for its resort-style water features, which are often cited as a key reason for its popularity.

• A massive lagoon-style heated pool with zero entry
• An extensive lazy river, perfect for relaxing
• Dual water slides and a large children’s splash park
• A 9-hole mini-golf course and sports courts
• Poolside tiki bar and restaurant

The clubhouse offers a fitness center, arcade, and lounge, ensuring there’s something for everyone. Like its sister resorts, every home has its own private pool.

Pricing and Location

Pricing is competitive, reflecting its high demand. A 5-bedroom home typically costs $210–$350 per night off-peak, while a 7-bedroom home can range from $350–$900 depending on the season. Its location in the Four Corners/Davenport area is just 8-9 miles from Disney (a 15-18 minute drive) and offers easy access to the US-192 tourist corridor, packed with restaurants and shops.

Best for:

• Families and large groups are looking for the best Orlando resort for large groups with maximum amenities.
• Investors who want a reliable property with high occupancy rates and outstanding guest reviews.
• Travelers who want a complete, resort-centric vacation experience.

Windsor at Westside: The Established Value Choice

As the oldest of the three, Windsor at Westside offers a proven track record of guest satisfaction and a fantastic value proposition. While it may not have the “newest” tag, its mature landscaping and comprehensive amenities make it a reliable choice for budget-conscious groups who don’t want to compromise on quality or location.

Homes and Booking Options

Windsor at Westside features a large selection of 5–9 bedroom homes, making it another great option for large groups. These homes are widely available on platforms like Trip.com and VRBO. With years of operation, there’s a huge volume of guest reviews available, giving bookers and buyers confidence in their choice.

Amenities

The amenities at Windsor at Westside set the standard for modern Orlando resorts and remain impressive today.

• A 10,000+ sq. ft. clubhouse with a full-service restaurant and bar
• A massive zero-entry resort pool and a winding lazy river
• A dedicated water slide and kids’ splash area
• Tennis, basketball, and volleyball courts
• A tiki bar and cabanas for poolside relaxation

The resort’s Mediterranean-style architecture and lush, established greenery give it a distinct, tranquil atmosphere that many guests prefer.

Pricing and Location

This is where Windsor at Westside truly shines. Prices for a Windsor at Westside 6-bedroom home are generally 10-20% lower than at the newer resorts. A 5-bedroom home might cost $180–$275 off-peak, while larger homes range from $270–$600+. This makes it an excellent option for stretching a vacation budget further without sacrificing space or fun. Its location is also a major plus, sitting just 8 miles (a quick 10–15 minute drive) from Disney World.

Best for:

• Value-focused travelers and investors who prioritize affordability and location.
• Large groups that need more space and bedrooms for their budget.
• Guests who prefer a resort with mature landscaping and a proven reputation.

The Head-to-Head Comparison: Which Windsor is Right for You?

Find Your Perfect Orlando Vacation Home

Whether you’re investing or planning a trip, choosing between these Kissimmee Davenport vacation home resorts depends entirely on your priorities.

• Windsor Cay is the top choice for those who want the newest homes and amenities and are willing to pay a premium for that luxury.
• Windsor Island offers the best all-around experience, with a perfect blend of amazing amenities, stellar reviews, and high-quality homes.
• Windsor at Westside delivers unbeatable value, offering a fantastic resort experience at a more accessible price point.

If you’re ready to find the perfect 5–7 bedroom vacation home near Disney World or need guidance on maximizing your rental income, let’s talk.

Start your Orlando investment journey. Schedule a free 15-minute consultation with me, Mike Chen, and let’s find a home you’ll love.

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