Windsor Hills vs Windsor Island: Which Resort Is Better for Your Disney Stay?

Windsor Hills vs Windsor Island – Quick Overview

Planning a Disney vacation is exciting, but let’s be honest, it can also be overwhelming. You’re comparing ticket prices, park strategies, and, of course, where to stay. Two names that keep popping up are Windsor Hills Resort and Windsor Island Resort. Both are incredible vacation communities near Disney World. Both promise comfort, luxury, and convenience.

So the big question is, Windsor Hills vs Windsor Island: which resort is better for your Disney stay?

Let’s dive in and compare them side by side. We’ll look at location, amenities, water parks, family features, and overall value. By the end, you’ll know exactly which resort fits your Disney vacation style.

1. Overview: Windsor Hills vs Windsor Island

Before getting into the details, here’s a quick snapshot of both resorts.

Windsor Hills Resort (Orlando, Florida)

• Established, family-favorite community
• Located in Kissimmee, just 2.5 miles from Disney World
• Known for its unbeatable proximity and excellent amenities
• Popular for family groups and repeat visitors

Windsor Island Resort (Davenport, Florida)

• Newer resort, opened in 2021
• About 8.5 miles from Disney World
• Offers upgraded, modern homes and high-end amenities
• Gaining popularity fast with luxury-seeking travelers

So if you’re comparing Windsor Hills vs Windsor Island Resort, the difference is evident from the start. Windsor Hills wins for location and convenience, while Windsor Island shines for its newness and luxury.

2. Location & Distance to Disney World

The first thing most travelers ask is, “How far are these resorts from Disney?”

Windsor Hills Resort: Closer to the Magic

Windsor Hills sits in Kissimmee, just 2.5 miles from the gates of Walt Disney World. It’s one of the closest off-site vacation communities you can stay in without being on Disney property.
Driving to Disney’s Animal Kingdom takes roughly 10 minutes, while Magic Kingdom and EPCOT are around 15 minutes away.

This proximity means less time in traffic, quicker mid-day returns for naps or swims, and more overall park time.

Windsor Island Resort: Slightly Farther, but Still Convenient

Windsor Island is in Davenport, about 8.5 miles from Disney World. It’s a straight shot along Highway 192 and US-27. Expect around 20 to 25 minutes to reach most Disney parks.

While that’s a little farther, many guests don’t mind the extra distance since the resort’s amenities make up for it.

Verdict

If being close to Disney is your top priority, Windsor Hills Resort wins this round.
If you’re fine with a slightly longer drive in exchange for newer luxury homes, Windsor Island could be your pick.

3. Amenities & Water Park Comparison

When comparing Windsor Hills vs Windsor Island, amenities are where the differences really show.

Windsor Hills Resort Amenities

Windsor Hills has long been known for offering some of the best community amenities in the Disney area. Despite being more established, it continues to hold its own.

You’ll find:

• Massive lagoon-style pool with water slides
• Splash pad and water park area for kids
• Hot tub, sun deck, and loungers for adults
• Clubhouse with a movie theater, arcade, and gym
• On-site marketplace for snacks, drinks, and souvenirs
• Tennis, basketball, and volleyball courts
• Playgrounds and picnic areas

The Windsor Hills Resort water park is a major highlight. Families love the tropical theme, zero-entry pool, and safe play structures, making it ideal for young children.

Windsor Island Resort Amenities

Since it’s newer, Windsor Island steps up the game with a next-generation water park and resort layout.

Here’s what you get:

• Huge resort-style pool with lazy river and splash zone
• Water slides and splash pad
• Mini golf course
• Hammock garden
• Sports courts for basketball, volleyball, and more
• Tiki bar and dining area
• Event space and fire pits
• Brand-new clubhouse with modern decor

The Windsor Island Resort water park feels more like a small theme park than a water park. It’s one of the most impressive in the Orlando area.

Verdict

If you want tried-and-true family fun with everything you need, Windsor Hills delivers.
If you want sleek, modern, and wow-factor pool amenities, Windsor Island takes the win.

4. Family-Friendly Features

Both resorts cater to families, but their experiences differ slightly. Let’s break it down.

Windsor Hills Resort: Perfect for Younger Families

Because of its proximity to Disney, Windsor Hills is ideal for families with small children. You can pop back from the parks easily, enjoy the pool mid-day, and rest before fireworks.

The resort’s community design feels cozy, safe, and walkable. Many homes have themed kids’ rooms like Star Wars, Frozen, or Toy Story, and private splash pools for little ones.

The proximity of Windsor Hills Resort to Disney is a huge bonus for families who want easy logistics and less driving.

Windsor Island Resort: Great for Larger Families and Teens

Windsor Island homes are bigger, newer, and more modern. They often feature themed game rooms, theater spaces, and high-end kitchens.

The community amenities are designed for multi-generational fun, from toddlers to grandparents. Teens love the lazy river and sports courts.

If you’re traveling with extended family or a large group, Windsor Island Resort in Davenport, Florida, offers more space and style.

Verdict

For smaller families who value closeness and convenience, Windsor Hills is the winner.
For larger families or those wanting a newer, resort-style vibe, Windsor Island takes the edge.

5. Accommodation Types & Design

Both resorts offer short-term vacation rentals ranging from condos to large villas. The main difference is age and design style.

Windsor Hills Resort Homes

• Built between 2005 and 2015, recently updated by many owners
• Range from 2-bedroom condos to 6-bedroom pool homes
• Classic Florida-style decor
• Private pools, full kitchens, and themed rooms are common
• Excellent value for the price

Windsor Island Resort Homes

• Newly built homes with modern layouts and designs
• Range from 5 to 10 bedrooms
• Sleek interiors, open-concept spaces, and smart home tech
• Private pools, spas, and entertainment rooms standard
• More high-end finishes

Verdict

If you want modern luxury, Windsor Island Resort is the clear winner.
If you prefer affordability and proven comfort, Windsor Hills Resort delivers excellent value.

6. Price & Value for Money

Here’s where most families make their decision: budget.

Windsor Hills Resort Pricing

Because it’s more established, Windsor Hills tends to be more affordable.
You can find condos starting around $130–$180 per night and homes around $200–$350 per night, depending on season and size.

Given its location just minutes from Disney, it’s easily one of the best value-for-money resorts in the area.

Windsor Island Resort Pricing

As a newer and more luxurious resort, Windsor Island homes start a bit higher.
Expect to pay $250–$500 per night for multi-bedroom homes with premium finishes and large pools.

You’re paying for newness, upgraded amenities, and larger homes.

Verdict

If you’re price-conscious but still want proximity and fun, Windsor Hills wins on value.
If you’re after luxury and don’t mind spending more, Windsor Island earns its price tag.

Resort Atmosphere & Vibe

Windsor Hills Resort

Windsor Hills feels warm and family-centered. The community is always buzzing with kids riding bikes, parents relaxing by the pool, and families walking back from the playground.

It’s laid-back, friendly, and feels like home.

Windsor Island Resort

Windsor Island feels more like a full-scale resort. The design is sleek, the landscaping manicured, and the amenities feel new and polished.

It attracts travelers who want a vacation resort feel, something a little more exclusive and contemporary.

Verdict

Windsor Hills equals family comfort and familiarity.
Windsor Island equals upscale, resort-luxury experience.

Community Access & Security

Both resorts offer gated security and 24-hour monitoring so that you can feel safe at either.

Windsor Hills benefits from being an established neighborhood, so traffic flows smoothly, and check-in is smooth.
Windsor Island uses a similar gate system but adds smart access features and digital codes for convenience.

Verdict: Both are equally secure and well-managed.

Windsor Hills vs Windsor Island: Water Park & Clubhouse Showdown

If your family loves pool days, this section is for you.

Windsor Hills Pool and Clubhouse

The Windsor Hills Resort water park includes:

• Lagoon-style pool with two water slides
• Zero-entry pool is great for kids
• Separate splash pad
• Sun loungers and shaded cabanas
• Snack bar and café

It’s not massive but feels intimate and family-friendly.

Windsor Island Pool and Clubhouse

The Windsor Island Resort pool is bigger and more advanced:

• Large central pool
• Lazy river and water slides
• Kids’ splash zone
• Full-service bar
• Cabanas, fire pits, and an event lawn

It’s perfect for those “non-park days” when you want to relax by the water.

Verdict:
Windsor Island wins on scale and features. Windsor Hills wins on family comfort and simplicity.

Which Resort Has Better Reviews?

Looking at guest feedback helps round out the Windsor Hills vs Windsor Island debate.

• Windsor Hills Resort reviews consistently highlight its location, value, and family atmosphere. Guests love how close it is to Disney and the ease of returning mid-day.
• Windsor Island Resort reviews praise the modern homes, clean design, and luxury vibe, though some mention the slightly longer drive.

Both earn high satisfaction scores, but Windsor Hills edges out in repeat visitors due to convenience.

Which Resort Offers Better Value Overall?

If we’re talking overall value, you can’t ignore the location advantage of Windsor Hills.

It offers:

• Excellent amenities
• Lower nightly rates
• Quick Disney access
• Proven reputation

Windsor Island’s newer homes and luxury touches appeal to travelers who prioritize modern comfort over proximity.

Verdict:
For overall value and convenience, Windsor Hills Resort is the winner.
For luxury and wow-factor amenities, Windsor Island Resort wins.

Best Resort for Disney Family Vacations

If your goal is a family-friendly Disney vacation, both options deliver, but in different ways.

Choose Windsor Hills if:

• You want to be close to Disney World
• You prefer an affordable, family-oriented vibe
• You’re traveling with young kids
• You love the idea of walking to the pool or playground

Choose Windsor Island if:

• You want brand-new, modern accommodations
• You have a large family or multi-generational group
• You’re planning rest days to enjoy the resort itself
• You appreciate luxury touches and bigger spaces

There’s no wrong choice here. It all comes down to what kind of Disney vacation you want.

Windsor Hills vs Windsor Island: Quick Comparison Chart

Windsor Hills vs Windsor Island Resort

Let’s wrap it up.

If you want the closest resort to Disney World with proven comfort, family vibes, and unbeatable value, Windsor Hills Resort is your best bet.

If you’d rather enjoy modern luxury, bigger homes, and an authentic resort-style feel, Windsor Island Resort is the way to go.

Both are among the best resorts near Disney World for families, offering stays full of fun, relaxation, and Florida sunshine.

No matter which one you pick, you’ll be surrounded by the magic of Orlando, minutes from the parks, and guaranteed to create unforgettable memories.

If you’re ready to experience the perfect Disney area, book your stay with Chillax Inn today!