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Windsor Hills Resort Villas, Orlando

Dan Houston (Luxury Villa Specialist) Benefit from our personal service & experience Orlando experts like Dan can guide you through booking a villa for your next vacation. You can email, call, make an enquiry or book online.
  • Travel guide

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Windsor Hills Resort Travel Guide

What's on your wish list for a dream Orlando vacation? Choose from amazing luxury villas with stunning pool and spa areas, games rooms, beautiful dining areas and much more. Many of the luxury villas in Windsor Hills Resort were built in only 2009, giving them a fresh and modern feel for every visitor. You'll be amazed with everything these luxurious private homes have to offer.

Disney on your doorstep

Windsor Hills is located just 3 miles from Disney, making it perfect for families who prefer to be close to the action.

Lots to see and do

The club house is at the heart of this exclusive community, which means you'll never be short of ways to entertain your family. Offering you more facilities than most resorts, Windsor Hills offers you:

  • Impressive clubhouse with games room
  • Water park complex with a double Olympic sized heated pool
  • State of the art gym
  • Grocery shops
  • Restaurants
  • Movie theatre
  • Flood lit tennis court
  • Basket Ball court
  • Sand volleyball court
  • Golf putting green
  • A castle theme children's play area
  • Picnic and BBQ area
  • 24-hour gated and guarded entrance
  • Shuttle bus service to shops and parks (local charges apply)
  • DVD rental service

Windsor Hills also offers guests a shuttle to one of the many Orlando championship golf courses. In fact, Mystic Dunes golf course is right next door!

Only guests at Windsor Hills gain free access to the resorts facilities. A Guest Card can be obtained from the clubhouse.

You'll soon forget that you're a stone's throw from Disney. The manned gatehouse at Windsor Hills Resort leads into a stunning oasis - a welcome retreat after a day of sight-seeing. Windsor Hills is beautifully landscaped and overlooks impressive woodlands.

You won't regret choosing a Windsor Hills luxury villa for your next vacation.

Windsor Hills Resort Overview

Our fantastic range of modern villas and vacation rentals in 5 star Windsor Hills Resort offer luxury combined with home-from-home comfort to compliment your vacation experience. You'll become so accustomed to the luxurious, high tech amenities and space that our villas offer that you won't want to go home:

  • Stunning pools
  • Jacuzzis/Hot Tubs
  • Spa areas
  • Beautiful dining areas
  • Gourmet kitchens
  • Large entertaining spaces
  • Games rooms
  • High Definition TVs/DVDs/VCRs with satellite television
  • High-Speed WIFI Internet Access

Windsor Hills Resort activities

Windsor Hills resort offers more facilities than most resorts and has a great communal area with a clubhouse at the heart of it:

  • Impressive clubhouse with games arcade featuring video games, billiards, table tennis
  • Water park complex with slides, waterfalls, fountains, lagoon spa and double Olympic sized heated pool
  • State of the art gym
  • Grocery shops
  • Movie theatre with high definition and surround sound
  • Flood lit tennis court
  • Basket Ball court
  • Sand volleyball court
  • Golf putting green
  • A castle theme children's play area
  • Picnic and BBQ area
  • Shuttle bus service to shops and parks (local charges apply)
  • DVD rental service

Windsor Hills Resort Dining

There is a vast range of restaurants, diners and cafes in the immediate vicinity including family favourites and well known chains to cater for everyone's taste. Here are just a few of them:

  • Red Lobster - 1.5 miles
  • Taste of China - 1.5 miles
  • TGI Friday's - 1.5 miles
  • Fiorino New York Pizza - 1.5 miles
  • Burger King - 1.5 miles
  • Take Japanese Restaurant - 1.5 miles
  • Giordano's - 1.5 miles
  • McDonalds - 1.5 miles
  • Taco Bell - 1.5 miles
  • Outback Steak House - 1.5 miles
  • Passage to India - 1.5 miles
  • Key W Kool's - 1.5 miles
  • Dairy Queen - 1.6 miles
  • Subway - 1.6 miles
  • Cracker Barrel Restaurant - 1.6 miles

Safety in Windsor Hills Resort

The safety of guests is a priority at Windsor Hills Resort. The community is guarded and gated 24hours a day, so only resort guests are able to enter and use the facilities.

Special extras at Windsor Hills Resort

Windsor Hills Resort offers a free shuttle service directly to the Disney theme parks and one of the many Orlando championship golf courses. Mystic Dunes Golf Course is also located next door to Windsor Hills Resort.

We can arrange any additional services including flights, car hire, limousine hire, airport transfers, theme park tickets, daily housekeeping and private chefs and catering.

We believe you will thoroughly enjoy your stay in a luxury villa rental at Windsor Hills Resort with its exceptional facilities and close proximity to all the popular Orlando attractions.

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Thought about owning your own vacation home?

Find out more
Top Villas home Point of interest (e.g. Walt Disney)

2 miles from Disney, this 6 bedroom luxury home includes a games room, private pool and spa

Windsor Hills Resort 68 in Windsor Hills Resort

6 Bedrooms, Sleeps 12
4 Bathrooms, 2,812 sq.ft

/per week$2,331

Fabulous 6 bedroom vacation home just 2 miles from Disney with a fantastic pool and spa

Windsor Hills Resort 69 in Windsor Hills Resort

6 Bedrooms, Sleeps 12
3.5 Bathrooms, 3,073 sq.ft

/per week$2,331

With spectacular lakeside views-6 bedroom villa, 2 miles from Disney includes stunning pool

Windsor Hills Resort 71 in Windsor Hills Resort

6 Bedrooms, Sleeps 12
4 Bathrooms

/per week$2,331

Thought about owning your own vacation home?

2 miles from Disney, this gorgeous 6 bedroom home with beautiful pool area and games room

Windsor Hills Resort 74 in Windsor Hills Resort

6 Bedrooms, Sleeps 12
4 Bathrooms, 2,812 sq.ft

/per week$2,331

Lovely 6 bedroom villa with cosy living space, games room, and private pool- 2 miles to Disney

Windsor Hills Resort 82 in Windsor Hills Resort

6 Bedrooms, Sleeps 12
4 Bathrooms

/per week$2,331

Gorgeous and modern 6 bedroom vacation rental includes a private pool and games room

Windsor Hills Resort 86 in Windsor Hills Resort

6 Bedrooms, Sleeps 12
3.5 Bathrooms, 3,073 sq.ft

/per week$2,331

A homely, lovely 5 bedroom vacation home just 2 miles to Disney includes a private pool

Windsor Hills Resort 93 in Windsor Hills Resort

5 Bedrooms, Sleeps 10
5 Bathrooms

/per week$2,072

Incredible 5 bedroom Windsor Hills home includes a private pool and games room

Windsor Hills Resort 120 in Windsor Hills Resort

5 Bedrooms, Sleeps 10
5 Bathrooms

/per week$2,072
Windsor Hills Resort homeowner?
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Need a better management company? We can provide comprehensive property management services to meet the needs of both homeowners and tenants.

This 5 bedroom Windsor Hills vacation rental offers a luxury private pool and games room

Windsor Hills Resort 122 in Windsor Hills Resort

5 Bedrooms, Sleeps 10
5 Bathrooms

/per week$2,072

Stunning 6 bedroom Windsor Hills home includes a private pool and spa only 3 miles to Disney

Windsor Hills Resort 27 in Windsor Hills Resort

6 Bedrooms, Sleeps 14
4 Bathrooms, 3,000 sq.ft

/per week$1,795

5 en-suite bedroom villa, is perfect for sunset lake views and offers a private pool and hot tub

Windsor Hills Resort 21 in Windsor Hills Resort

5 Bedrooms, Sleeps 11
5 Bathrooms, 3,000 sq.ft

/per week$1,694

With lake front views and 3 miles to Disney, this 6 bedroom villa features a private pool and spa

Windsor Hills Resort 10 in Windsor Hills Resort

6 Bedrooms, Sleeps 12
4.5 Bathrooms, 3,600 sq.ft

/per week$1,650

Beautiful 5 bedroom Windsor Hills villa, 3 miles from Disney with private pool and spa

Windsor Hills Resort 12 in Windsor Hills Resort

5 Bedrooms, Sleeps 10
5 Bathrooms, 2,800 sq.ft

/per week$1,611

5 Bedroom Windsor Hills luxury home offering a private pool and spa close to Disney

Windsor Hills Resort 13 in Windsor Hills Resort

5 Bedrooms, Sleeps 10
5 Bathrooms, 2,800 sq.ft

/per week$1,611

2 miles from Disney with a games room and private pool is this stunning 5 bedroom villa

Windsor Hills Resort 1 in Windsor Hills Resort

5 Bedrooms, Sleeps 12
5 Bathrooms, 2,382 sq.ft

/per week$1,611

Luxury 5 en suite bedroom villa featuring a games room and private pool with spa

Windsor Hills Resort 3 in Windsor Hills Resort

5 Bedrooms, Sleeps 12
5 Bathrooms, 3,000 sq.ft

/per week$1,611

This Windsor Hills home has 6 lovely bedrooms and a private pool with spa, located near Disney

Windsor Hills Resort 4 in Windsor Hills Resort

6 Bedrooms, Sleeps 12
4 Bathrooms, 3,000 sq.ft

/per week$1,611

1.5 miles to Disney, 6 bedroom beautiful home includes a private pool and games room

Windsor Hills Resort 214 in Windsor Hills Resort

6 Bedrooms, Sleeps 14
3.5 Bathrooms

/per week$1,596
Need assistance?

We're available 24/7 to offer help and advice, just call 1-866-341-8086 or contact us another way.

Luxurious 6 bedroom vacation rental featuring a private pool and located 3 miles to Disney

Windsor Hills Resort 35 in Windsor Hills Resort

6 Bedrooms, Sleeps 12
4 Bathrooms, 2,800 sq.ft

/per week$1,575

A private pool, spa and garage are some of the features offered by this stunning 6 bedroom home

Windsor Hills Resort 36 in Windsor Hills Resort

6 Bedrooms, Sleeps 12
4 Bathrooms, 2,800 sq.ft

/per week$1,575

Fantastic 6 bedroom, 4 bathroom villa featuring fully equipped games room and private pool

Windsor Hills Resort 299 in Windsor Hills Resort

6 Bedrooms, Sleeps 12
4 Bathrooms

/per week$1,575

Close to Disney,this fabulous 5 en suite bedroom vacation home has a games room and private pool

Windsor Hills Resort 6 in Windsor Hills Resort

5 Bedrooms, Sleeps 10
5 Bathrooms, 2,800 sq.ft

/per week$1,565

6 Bedroom home with themed bedrooms,private pool, games room- 3 miles to Disney

Windsor Hills Resort 34 in Windsor Hills Resort

6 Bedrooms, Sleeps 14
4 Bathrooms, 3,534 sq.ft

/per week$1,505

Fantastic 6 bedroom villa with private pool and games room

Windsor Hills Resort 313 in Windsor Hills Resort

6 Bedrooms, Sleeps 12
4 Bathrooms

/per week$1,369

3 miles from Disney, luxury 5 bedroom Windsor Hills home includes a pool and games room

Windsor Hills Resort 20 in Windsor Hills Resort

5 Bedrooms, Sleeps 12
5 Bathrooms, 2,800 sq.ft

/per week$1,347

Traditional 6 bedroom villa with luxurious private pool and spa area

Windsor Hills Resort 314 in Windsor Hills Resort

6 Bedrooms, Sleeps 12
4 Bathrooms

/per week$1,328

Fabulous, sophisticated and large 6 bedroom, 4 bathroom home with stunning west facing pool

Windsor Hills Resort 297 in Windsor Hills Resort

6 Bedrooms, Sleeps 12
4 Bathrooms, 3,534 sq.ft

/per week$1,323

Disney themed kid's Rooms, Perfect family home with Pool, Games Room, 2 Miles to Disney

Windsor Hills Resort 305 in Windsor Hills Resort

6 Bedrooms, Sleeps 14
4 Bathrooms, 3,212 sq.ft

/per week$1,323

Wonderful 6 bedroom luxury villa with 2 Disney kid's bedrooms, Large Pool, Games Room

Windsor Hills Resort 309 in Windsor Hills Resort

6 Bedrooms, Sleeps 12
4 Bathrooms

/per week$1,323

Located 3 miles from Disney, this 5 bedroom luxury home offers a double garage and private pool

Windsor Hills Resort 30 in Windsor Hills Resort

5 Bedrooms, Sleeps 10
5 Bathrooms, 2,800 sq.ft

/per week$1,272

Windsor Hills

Windsor Hills Resort is a luxury family-friendly villa community located just 2 miles from Walt Disney World. The guard-gated community is home to an impressive range of rentals in Windsor Hills with full access to the resort’s amenities including a double sized lagoon-style pool with fountains, waterslide, spa and hot tub. The resort also boasts a splendid clubhouse, games room, movie theatre, fitness centre, billiards tables, sundry shops and outdoor recreation facilities. Set within beautiful natural wetlands Windsor Hills offers plenty of outdoor activities including table tennis, a stunning pool, kid’s playground, and sand volleyball, basketball and tennis courts. There is also a shuttle bus service to Disney World, Sea World and Universal Studios available.

Windsor Hills Amenities

Villas in Windsor Hills Resort offer superior accommodation complete with luxury pool and spa areas, games rooms, sumptuous dining areas and access to the resort’s excellent amenities. These include:

  • Olympic sized heated community pool
  • Tiki bar
  • Vast clubhouse
  • Games arcade with billiards, table tennis and video games
  • Gymnasium
  • Movie theatre
  • Lit tennis courts
  • Basketball court
  • Sand volleyball
  • Golf putting green
  • Castle themed play area
  • Grocery shops
  • Picnic and BBQ area
  • 24-hour gated and guarded entrance
  • Shuttle bus service to shops and parks
  • DVD rental service
  • Nearby restaurants

Windsor Hills Pool

Designed with pleasure in mind, Windsor Hills’ community swimming pool is double the size of an Olympic pool and features a water park area for little ones. Kids can splash in the water park complete with slides, fountain and kids play amenities, while adults chill out and relax by the main lagoon-style pool. The pool also features a bubbling hot tub plus easy access to the clubhouse and resort amenities.

Windsor Hills Clubhouse

Located in the heart of the resort is an impressive clubhouse jam-packed with things to do. For fitness lovers the clubhouse offers a gymnasium equipped state-of-the-art weight training and cardiovascular equipment. The clubhouse is also home to a movie theatre, a games room, video arcade, billiards table, shops and outdoor recreation facilities.

Windsor Hills Activities

Set within stunning natural wetlands the resort boasts plenty of outdoor activities including table tennis, a stunning pool, kid’s playground, volleyball, basketball and tennis courts. Windsor Hills villa rentals are located in Kissimmee, adjacent to Mystic Dunes Golf course and 5 minutes from the main street shops and restaurants on US Highway 192. A shuttle bus service operates from the resort to Disney World, Sea World and Universal Studios.

Dining at Windsor Hills Resort

Dine in the comfort of your own villa equipped with everything you need for a family meal or dinner party, or take a trip to the nearby Windsor Hills village where you’ll find a medley of restaurants, cafes and diners to enjoy including:

  • Red Lobster - Serving a delicious selection of American seafood with New England themed décor – just 1.5 miles away.
  • T.G.I Fridays – Everyone’s favourite American restaurant and cocktail bar – 1.5 miles away.
  • Outback Steakhouse – A lively Australian themed chain restaurant serving steaks, seafood and more – 1.5 miles away.
  • Giordano’s – Famous for its deep-dish pizzas this Italian chain restaurant is just 1.5 miles away.
  • Subway - The ideal place to grab a quick snack and go – 1.6 miles away.
  • Plus many more!
Book with confidence

You can expect the highest standard of service when booking with us. We are members of, and regulated by, ABTA. We adhere to ABTA's strict code of conduct in order to, as an ABTA member (no. Y6259), guarantee you the best booking experience and peace of mind.

ABTA member