Sign up for deals & updates!

Site navigation

Windsor Hills Magic Retreat

Discover the enchantment of Windsor Hills Magic Retreat in the prestigious Windsor Hills

Need help deciding
Mon-Sun 9:00am-7:00pm

  • Magic Retreat
     Photo date: Sep 2019   
  • Pool and Spa
     Photo date: Sep 2019   
  • Shaded Lanai
     Photo date: Sep 2019   
  • Florida Lifestyle
     Photo date: Sep 2019   
  • Welcome!
     Photo date: Sep 2019   
  • Dining Table
     Photo date: Sep 2019   
  • Family Room
     Photo date: Sep 2019   
  • Gather Together
     Photo date: Sep 2019   
  • Spacious Living
     Photo date: Sep 2019   
  • Breakfast Nook
     Photo date: Sep 2019   
  • Kitchen Bar
     Photo date: Sep 2019   
  • Complimentary amenities pack
     Photo date: Mar 2022   
  • Open Kitchen
     Photo date: Sep 2019   
  • Games Room
     Photo date: Sep 2019   
  • Family Fun
     Photo date: Sep 2019   
  • Bedroom 1
     Photo date: Sep 2019   
  • King Bedroom
     Photo date: Sep 2019   
  • En-suite Bathroom
     Photo date: Sep 2019   
  • Bedroom 2
     Photo date: Sep 2019   
  • Queen Bedroom
     Photo date: Sep 2019   
  • En-suite Bathroom
     Photo date: Sep 2019   
  • Bedroom 3
     Photo date: Sep 2019   
  • Minion Themed
     Photo date: Sep 2019   
  • Shared Bathroom
     Photo date: Sep 2019   
  • Bedroom 4
     Photo date: Sep 2019   
  • King Bedroom
     Photo date: Sep 2019   
  • Shared Bathroom
     Photo date: Sep 2019   
  • Bedroom 5
     Photo date: Sep 2019   
  • Twin Bedroom
     Photo date: Sep 2019   
  • Disney Themed
     Photo date:   
  • Shared Bathroom
     Photo date: Mar 2017   
  • Windsor Hills
     Photo date: Mar 2018   
  • Clubhouse Amenities
     Photo date: Nov 2021   
  • Ariel Views
     Photo date: Nov 2021   
  • Sports Courts
     Photo date: Nov 2021   
  • Tennis Courts
     Photo date: Nov 2021   
  • Beach Volleyball
     Photo date: Nov 2021   
  • Waterslide
     Photo date: Nov 2021   
  • Splash Zone
     Photo date: Nov 2021   
  • Lagoon Pool
     Photo date: Nov 2021   
  • Poolside Loungers
     Photo date: Nov 2021   
  • Mega Chair
     Photo date: Nov 2021   
  • Outdoor Ping Pong
     Photo date: Nov 2021   
  • Kid's Castle
     Photo date: Nov 2021   
  • Checkers
     Photo date: Nov 2021   
  • Playground
     Photo date: Nov 2021   
  • Resort Clubhouse
     Photo date: Nov 2021   
  • Sundry Shop
     Photo date: Jun 2018   
  • Game Room
     Photo date: Jun 2018   
  • Arcade Games
     Photo date: Mar 2018   
  • Fitness Center
     Photo date: Mar 2018   
  • Movie Theater
     Photo date: Nov 2021   
Reservation Quote
Enter dates to check availability.
Click to see if home is available.

Availability Price

The from to price is a guide to the nightly base price depending on season of travel. The quoted price is worked out on a nightly basis so if a stay spans to seasons the total base price may have different nightly rates.

Availability Price

The from to price is a guide to the nightly base price depending on season of travel. The quoted price is worked out on a nightly basis so if a stay spans to seasons the total base price may have different nightly rates.

Fully inclusive price

The fully inclusive price is the total price for your stay, these price including all applicable taxes, adminstration fees, cleaning and Accidental damage waiver protection (security fee) You will have the option to add extra items like pool heat, vacation cancellation protection at the booking stage.

positive review we rent every year and have never been disappointed!!!! but fantasy villa could use bigger televisions.....and a new fridge!!!

Deborah Etheridge

Amazing customer service!!!!! I had to make 1 call to maintenance and they arrived within an hour of my phone call.
The house is absolutely all we imagined!
Will definitely book again through them for next year.

Nicole Quickle


Property type Vacation Home
Floor plan (sq. ft.) 2382
Bedrooms 5
Bathrooms 5
Sleeps 11
Community Windsor Hills
Check-in time 4:00 pm
Check-out time 10:00 am
Escape to the enchanting Windsor Hills Magic Retreat, a luxurious vacation villa within the prestigious Windsor Hills Resort. This captivating villa boasts five bedrooms and five bathrooms and comfortably accommodates up to 11 guests, making it perfect for large families or groups.

Step into your private oasis as you discover the south-facing pool with a raised spa, where you can soak up the sun or unwind in the soothing waters. For added convenience, optional pool and spa heating are available at an additional cost. Relax on the sundeck or seek shade under the lanai, creating the ideal space for outdoor enjoyment.

Inside, the villa exudes contemporary elegance with its stylish furnishings and decor. The fully equipped kitchen invites culinary adventures, while the deep-cushioned leather sofas provide a cozy retreat for relaxation. Stay connected with loved ones and share your vacation memories with complimentary high-speed Wi-Fi internet access.

Indulge in endless entertainment options within the family games room, featuring a pool table and an air hockey game. With a laundry room equipped with a washer and dryer, you can pack light and keep your clothes fresh throughout your stay.

Your safety and security are paramount, so the villa has a digital entry/lock system. Each guest receives a unique and private code, ensuring peace of mind throughout your vacation.

Experience the magic of Windsor Hills Resort and make unforgettable memories at Windsor Hills Magic Retreat. Book your stay today and immerse yourself in the ultimate vacation experience in Orlando.

Property Summary
|| South-facing pool with raised spa (not a hot tub)
|| Optional pool and spa heating available (additional charges apply)
|| Sundeck and shaded lanai
|| Contemporary furnishings and decor
|| Fully equipped kitchen
|| Deep cushioned leather sofas
|| Laundry with washer and dryer
|| Family games room with pool table and an air hockey game
|| FREE Wi-Fi high-speed internet (500 Mbps)
|| Digital entry/lock system with unique, private code

Windsor Hills Resort
Welcome to the prestigious Windsor Hills Resort, a premier destination for an unforgettable vacation in Orlando. Nestled just minutes away from the enchantment of Walt Disney World, this exceptional resort offers a world-class experience that will exceed every expectation.

Immerse yourself in a tropical paradise as you enter the gates of Windsor Hills Resort. Lush greenery, palm trees, and manicured landscapes create a serene ambiance that sets the stage for a relaxing getaway. The Resort boasts a variety of luxurious amenities designed to cater to all ages and interests.

Indulge in leisurely afternoons at the Resort's expansive lagoon-style pool, with a thrilling water slide for the little ones and a tranquil hot tub for the adults. Lounge on the sun deck and soak up the warm Florida sunshine, or retreat to the shaded areas and find respite from the heat. The children's playground offers endless fun for the little adventurers, while the fitness center allows you to maintain your active lifestyle.

Sports enthusiasts will delight in the various recreational activities at Windsor Hills Resort. Challenge your family and friends to a tennis, basketball, or volleyball game on the well-maintained courts. For those seeking friendly competition, the putting green and golf practice area is perfect for honing your skills. Stay connected with the community at the clubhouse, where you can socialize, relax in the lounge area, or catch up on work at the business center.

Windsor Hills Resort also caters to the youngest members of your family. The interactive water fountains and splash pad provide hours of excitement, while the on-site arcade offers many games and entertainment. With a 40-seat movie theater showcasing the latest films, you can gather for a memorable movie night with loved ones.

Convenience is key at Windsor Hills Resort. A sundry shop provides essential items and snacks, ensuring you have everything you need during your stay. Additionally, the Resort offers a shuttle service to major attractions, allowing you to explore the wonders of Orlando hassle-free.

With its prime location near world-renowned theme parks, championship golf courses, and shopping destinations, Windsor Hills Resort places you in the heart of all the excitement and adventure Orlando offers. Whether you're seeking relaxation, family fun, or thrilling experiences, Windsor Hills Resort is the ultimate destination for an unforgettable vacation.

Community Summary
|| Resort clubhouse with lagoon pool
|| Resort children's adventure playgrounds (3)
|| Resort putting green
|| Resort volleyball court
|| Resort tennis courts
|| Resort basketball press courts
|| Poolside spa and hot tub
|| Poolside kid's water slide
|| Poolside shaded pergolas
|| Clubhouse 58-seat cinema
|| Clubhouse video arcade
|| Clubhouse games room
|| Clubhouse fitness center
|| Clubhouse Sundry shop
|| Clubhouse Wi-Fi
|| Manned gated resort entry

Guest Amenities
VillaDirect also provides a range of amenities in the property for the start of each guest stay - including coffee, milk, sugar, salt, pepper, soaps, body wash, shampoo, conditioner, sponges, dishwasher tabs, washing detergent pods, liquid soap, extra trash bags, a roll of toilet tissue in each bathroom and more. We are always interested in feedback about what additional amenities could benefit guests who stay in our homes. It is expected that guests will need to replenish some items and supply personal toiletries during their stay, and that items are only provided as a "starter pack" of amenities. Just so you know, amenities may be changed without notice due to supply constraints.

Offers a wide selection of the highest quality vacation homes in Orlando. We are accredited by Walt Disney World Resort and can guarantee that your vacation property will be within easy reach of all theme parks and attractions. Book your perfect Florida family vacation getaway today.

|| Inspected and approved by Walt Disney World Resort
|| Part of the Vacation Rental Home Connection program
|| Professionally managed, inspected, and cleaned by VillaDirect Vacation Homes
|| VillaDirect is rated A-Plus by the Better Business Bureau
|| Serving and delighting guests since 1997
|| Local Guest Services Team available 24/7, 365 days
|| Authorized Disney and Universal Studios discount tickets center

Whether traveling for pleasure or business, your accommodations are ideally located to easily access Orlando's must-see attractions. You can enjoy the nearby theme park destinations such as Magic Kingdom, Epcot, Hollywood Studios, Animal Kingdom, Universal Studios, Islands of Adventure, Sea World, Legoland, Aquatica, Discovery Cove, H20 Water Park, Typhoon Lagoon and Blizzard Beach.

Being in the heart of the number one family travel destination, you will always be able to enjoy world-class entertainment, outlet mall shopping, championship golf courses, great museums, and world-renowned dining from places such as City Walk, Disney Springs, International Drive, or the Orange County Convention Center.

Bed Types

Room Level Bed types Sleeps En-suite?
Bedroom 1 Ground Floor King Bed 2
Bedroom 2 Ground Floor Queen Bed 2
Bedroom 3 Ground Floor Bunk bed Full/Twin (x 1) 3
Bedroom 4 1 Floor Above Ground Twin Bed
Twin Bed
Bedroom 5 1 Floor Above Ground King Bed 2
       Sleeps 11 2 En-suites

Floor Plan


Property Amenities
All linens and towelsAir conditioningPool and spa (heating optional)
Pool safety fenceShaded lanaiCable or satellite TV
DVD player(s)Games consoleEquipped kitchen
WasherIron and boardHairdryer(s)
Games room7ft pool tableAir hockey
Free use of community/resort amenities50-inch flat screen TVWi-fi
Flat-screen TVs in bedroomSecurePASS electronic lockBlu-Ray DVD player
Range/cookerFridge/freezerCoffee maker
ToasterKitchenwareDeck loungers
Community/Resort Amenities
Manned gatehouseClubhousePool
Sundry shopPicnic/BBQ areaCinema
PlaygroundFitness centerGames room
Tennis courtVolleyball courtBasketball court
Hot-tubCabanaNature / walking trails
Nearby supermarket(s)Nearby restaurant(s)Video arcade
Gathering loungesChildren's Splash PadWater park
DVD Rental


April 2024
  1 2 3 4 5 6
7 8 9 10 11 12 13
14 15 16 17 18 19 20
21 22 23 24 25 26 27
28 29 30        
May 2024
      1 2 3 4
5 6 7 8 9 10 11
12 13 14 15 16 17 18
19 20 21 22 23 24 25
26 27 28 29 30 31  
June 2024
2 3 4 5 6 7 8
9 10 11 12 13 14 15
16 17 18 19 20 21 22
23 24 25 26 27 28 29

Quotes are calculated by using the seasonal rate for each night of your stay.
For a fully inclusive price for your stay, please click the quote button.
The prices advertised reflect the quality, amenities and age of the property you select.
A 20% deposit is required to secure this property.
Reservations made within 60 days of arrival require full payment.
Pool heat is recommended from the 31st-Oct to the 31st-Mar.
Pool heat is an additional $35.00 per night for this property.
If requested, a minimum of 4 nights pool heat is chargeable on all reservations.
A cleaning surcharge applies to all stays in this home.


8 May 2022

We had a great time! Fabulous house - maybe a little more light needed... but the pool is a dream. The clubhouse water park was a daily hit with the kids. We will be back again next year.

Julia R

Hi Julia

We were delighted to read that you had such a good stay and hope to welcome you back again to this home or one of our pool homes on Windsor Hills next year too.

Guest Services 
25 March 2022

We stayed in Windsor Hills in Kissimmee. We had 10 guests in this house and everyone felt they had lots of space.

We had a couple of problems with the TV and internet but we called and the managers resolved it quickly.

The house pool and the clubhouse water park were excellent. We were close to Disney and Universal and spent a day at each.

Very good experience and the price was good compared to other properties in the area.

Danielle J

Hi Danielle

We're very pleased that you had such a good stay and that you enjoyed the house, the resort and the nearby parks during your visit.

We hope that you'll all come back to visit soon and we look forward to welcoming you again.

Guest Services 
11 March 2022

Great house - shame about the guard house, which is why I marked it down - otherwise it would have been a 5 star review.

The house was a wonderful break for our family and we enjoyed every minute of being there and especially the pool area.

Unfortunately, some of the enjoyment got spoiled by the treatment from the guards at the gate.

But we'd come back if the resort fixed the attitude - maybe it was just a bad week for the guards!

Dewar S

Hi Dewar

We were happy to read that you enjoyed the house and the pool.

We are sorry that you had any problems with the guards at the gate house. Unfortunately, we have little to no influence over the guards that the resort employs, but we will pass on your feedback, as it's such a pity that your vacation was marred by their service.

We hope that you will come back to Orlando soon and book with VillaDirect. We have a number of other resorts for you to choose from if you would prefer.

Guest Services 


No video at this time.

© 2024 Orlando vacation rentals, homes, villas, condos near Disney Kissimmee All Rights Reserved Developed by VRS Software.
Translate »