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Disney Dreaming

Dream of a Paradise Found in Windsor Island Resort!

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Mon-Sun 9:00am-7:00pm

  • Disney Dreaming
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  • Relax Poolside
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  • Family Fun
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  • Games Room
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  • Gaming Station
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  • Themed Bedrooms
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  • Modern Home
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  • Home Entrance
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  • Disney Inspired
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  • Welcome!
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  • Beautifully Appointed
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  • Open Floor Plan
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  • Family Room
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  • Kitchen Bar
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  • Large Kitchen
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  • High-end Appliances
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  • Amenties Provided
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  • Stainless Steel
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  • Dining Suite
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  • Gather Together
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  • Private Pool
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  • Shaded Spa
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  • Spillover
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  • Florida Lifestyle
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  • Shaded Lanai
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  • Outdoor Dining
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  • Game Room
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  • Shuffleboard
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  • Ping Pong
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  • Foosball
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  • Bedroom 1
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  • King Bedroom
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  • En-suite Bathroom
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  • Double Vanity
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  • Starter Amenities
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  • Soaking Tub
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  • Glassdoor Shower
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  • Pool Access
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  • Bedroom 2
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  • Beach House
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  • Double Bedroom
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  • En-suite Bathroom
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  • Upstairs Loft
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  • Poker Table
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  • Bedroom 3
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  • King Bedroom
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  • En-suite Bathroom
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  • Bedroom 4
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  • Double Bedroom
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  • Shared Bathroom
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  • Jack and Jill
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  • Bedroom 5
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  • King Bedroom
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  • Bedroom 6
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  • King Bedroom
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  • En-suite Bathroom
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  • Starter Amenities
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  • Bedroom 7
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  • Twin Bedroom
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  • En-suite Bathroom
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  • Bedroom 8
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  • King Bedroom
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  • En-suite Bathroom
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  • Bedroom 9
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  • Twin Bedroom
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  • Shared Bathroom
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  • Bedroom 10
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  • Twin Bedroom
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  • Windsor Island
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  • Clubhouse
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  • Community Pool
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  • Waterpark
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  • Games
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  • Shaded Lanais
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  • Waterpark
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  • Lazy River
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  • Tiki Bar
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  • Volleyball Court
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  • Basketball Court
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  • Firepit
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  • Mini Golf
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  • Game Zone
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  • Loungers
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Reservation Quote
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836
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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.

My aunt came down to visit and loved her house. The customer service was samazing and very helpful

Dallas Walpole
9/23/2015

5 star ratingEverything was great. The condo was clean. We were there for 12 days. It was our home away from home.
An maintenence man came in to change a couple of light bulbs. He was very pleasant and polite. We will stay with VillaDirect again.

Debbie B.
2/20/2019

Overview

Property type Vacation Home
Floor plan (sq. ft.) 4383
Bedrooms 10
Bathrooms 8
Sleeps 24
Community Windsor Island
Check-in time 4:00 pm
Check-out time 10:00 am
Come and stay in this luxurious, spacious 10-bedroom, 8-bathroom vacation home in the enchanting Windsor Island Resort. Boasting 4383 square feet of coastal charm and elegance, this stunning property comfortably accommodates up to 24 guests, making it an ideal choice for large family gatherings, group getaways, or special celebrations.

Upon entering, you'll be greeted by a Beach House-inspired decor, that radiates a soothing coastal color palette, instantly immersing you in a relaxed and tropical atmosphere.

The heart of this vacation home lies in its welcoming gathering room, where you'll find a wall-mounted 65-inch UHD Smart TV, perfect for hosting memorable movie nights with loved ones. The dining area provides ample seating for up to 16 guests, with 12 at the elegant dining table and four at the kitchen counter. For those who prefer al fresco, the outdoor dining area accommodates 6, providing a delightful setting to savor delicious meals in the Florida breeze.

One of this dream vacation homes highlights is the screened pool, complete with a raised bubbling spa (not a hot tub), where you can relax and unwind while soaking up the warm Florida sunshine. Optional electric pool and spa heating are available for an additional charge, ensuring year-round comfort. A sundeck with comfortable loungers and a shaded lanai with a dining table offer further opportunities to enjoy the outdoors.

There are many indoor entertainment options too, with an air-conditioned games room featuring shuffleboard and table-soccer games and a pool table and ping-pong table to keep everyone entertained. The vacation home also features additional entertainment areas, including a 50-inch UHD Smart TV in the main bedroom, a 60-inch UHD Smart TV in the family loft area, and a Game Zone complete with two 43-inch TVs and an X-Box gaming console.

The modern, fully equipped kitchen boasts granite countertops and stainless-steel appliances, making meal preparation a breeze. A laundry area with a washer and dryer adds convenience for guests during their stay.

Bedroom Layouts
The primary bedroom suite is on the first floor and treats you to a restful king bed and a lavish en-suite bathroom for the ultimate spa-like retreat. Bedroom 2 is also on the first floor and offers the convenience of two full beds. All other bedrooms are located on the second floor.

Bedroom 3 spoils you, with another king-size bed, a UHD Smart TV and a private en-suite bathroom. Bedroom 4 features two full beds, ensuring ample sleeping space for all. Bedroom 5 features a plush king-size bed, providing both comfort and style and Bedroom 6 continues the theme with yet another king bed, sharing a bathroom with Bedroom 7, which hosts two twin beds with a jungle theme decor. Bedroom 8 adds a touch of luxury with a king bed and a well-appointed en-suite bathroom. Bedrooms 9 and 10 cater to guests with two twin beds each and share a bathroom, offering a cozy and charming space for younger travelers or friends.

Each bedroom comes equipped with a flat-screen HDTV for personal entertainment, and high-speed Wi-Fi is provided free of charge throughout the home, allowing guests to stay connected during their stay.

With its splendid amenities, tasteful decor, and ample space for guests, this vacation home in Windsor Island Resort promises an unforgettable and rejuvenating retreat, ensuring that you and your loved ones will create cherished memories that will last a lifetime.

Property Summary
|| Screened pool with raised, bubbling spa (not a hot tub)
|| Optional electric pool and spa heating available (additional charges apply)
|| Outdoor living includes a sundeck with loungers and a shaded lanai with a dining table
|| Beach house/Coastal furnishings and decor
|| Spacious, open-plan modern family gathering room
|| Full kitchen with granite counters and stainless appliances
|| Laundry with washer and dryer
|| Air-conditioned games room with shuffle-board and table soccer game
|| Games room pool table and ping-pong
|| 65-inch UHD Smart TV in the family room
|| 50-inch UHD Smart TV in the master bedroom
|| 60-inch UHD Smart TV in the family loft area
|| Game Zone with 2 x 43-inch TVs and X-Box
|| Flat screen HDTV in every bedroom
|| Wi-Fi high speed internet provided FREE
|| Digital entry/lock system with unique, private code

Please note: Guests should refer to the Beds section (click on the beds button/tab above) for an accurate description of the beds in each room. The room numbers correspond to those shown on the floorplan (click floorplan in the tabs above).

Windsor Island Resort
Welcome to Windsor Island Resort, a breathtaking oasis nestled in the heart of Kissimmee, Florida. This luxurious resort offers a perfect blend of comfort, convenience, and indulgence, making it an ideal destination for unforgettable vacations.

As you step into Windsor Island Resort, you'll be captivated by its charming and inviting atmosphere. The resort's central location places you just minutes away from the world-renowned theme parks of Orlando, including Walt Disney World, Universal Studios, and SeaWorld, ensuring an exciting and magical adventure for guests of all ages. Additionally, Windsor Island Resort offers easy access to shopping, dining, golf courses, and many other entertainment options, making it a convenient and sought-after destination for travelers.

Within the resort, you'll discover an array of fantastic amenities designed to enhance your stay. The outdoor spaces provide the perfect setting for relaxation and fun under the Florida sun, from lush tropical landscapes to sparkling pools and bubbling spas. Immerse yourself in the resort's inviting ambiance as you bask in the warmth of the poolside, enjoying moments of serenity and leisure.

Windsor Island Resort boasts an impressive array of activities for those seeking entertainment and recreation. From well-equipped fitness centers to sports courts, guests can stay active and engaged. Additionally, children will delight in the resort's play areas and dedicated kids' zones, providing them with endless opportunities for play and laughter.

Windsor Island Resort also offers a variety of community spaces where guests can come together to socialize and create cherished memories. Whether gathering in cozy lounges, meeting neighbors at communal barbecues, or participating in organized events, the resort's sense of community and camaraderie adds a special touch to your vacation experience.

With its idyllic location, modern amenities, and warm hospitality, Windsor Island Resort promises an unforgettable escape for families, friends, and couples alike. Come and experience the magic of Kissimmee, Florida, as you make cherished memories and create moments that will last a lifetime. Welcome to Windsor Island Resort, where paradise awaits.

Community Summary
|| Resort-style community pool with dual water slides
|| Lazy river and hot tub
|| Splash pad area for kids
|| 24-hour manned security entrance
|| Video Arcade
|| Firepit area
|| Poolside miniature golf course
|| Basketball court
|| Soccer field
|| Tennis Court
|| Clubhouse with an outdoor bar and dining area

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. Please note amenities may be changed without notice due to supply constraints.

VillaDirect
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
|| 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 strategically located to access Orlando's must-see attractions easily. 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 Full Bed
Full Bed
2
2
Bedroom 3 1 Floor Above Ground King Bed 2
Bedroom 4 1 Floor Above Ground Full Bed
Full Bed
2
2
Bedroom 5 1 Floor Above Ground King Bed 2
Bedroom 6 1 Floor Above Ground King Bed 2
Bedroom 7 1 Floor Above Ground Twin Bed
Twin Bed
1
1
Bedroom 8 1 Floor Above Ground King Bed 2
Bedroom 9 1 Floor Above Ground Twin Bed
Twin Bed
1
1
Bedroom 10 1 Floor Above Ground Twin Bed
Twin Bed
1
1
       Sleeps 24 7 En-suites

Floor Plan

Amenities

Property Amenities
All linens and towelsAir conditioningPool and spa (heating optional)
Pool safety fenceShaded lanaiThemed kids bedrooms
Games consoleCeiling fansEquipped kitchen
MicrowaveDishwasherDryer
WasherIron and boardHairdryer(s)
Games room7ft pool tableAir hockey
Table soccer/FoosballKids gamesFree use of community/resort amenities
Fiber optic pool lightingTiled floorsPing-Pong/table tennis
50-inch flat screen TVWi-fiStainless appliances
Flat-screen TVs in bedroomSecurePASS electronic lockAir conditioned games room
Shuffle boardGranite or quartz countertops46-inch flat screen TV
70-inch flat screen TVVacuumBlender
Range/cookerFridge/freezerCoffee maker
ToasterKitchenware40-inch flat screen TV
Deck loungersSmart TV, Roku or Fire stick
 
Community/Resort Amenities
Lazy riverClubhousePool
Spa poolFitness centerGame room
Tennis courtBasketball courtSoccer field
Hot-tubCabana(s)Nearby supermarket(s)
Nearby restaurant(s)Water slide(s)Video arcade
Poolside tiki barRestaurant(s)Children's splash zone
Water parkConcierge serviceMini-Golf

Availability

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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.
This home is equipped with a spa-pool. Please note that this is not a hot-tub. The spa-pool can only be heated to the same temperature as the main pool.
A cleaning surcharge applies to all stays in this home.

Reviews

6 September 2024

When we walked through the door we were stunned. This house had everything - and more - that we could wish for. The pictures on the advert simply don't do justice to the space and luxury that we made the most of when we stayed. We couldn't get enough of the pool and deck... so much so that we even skipped a park day to relax. We WILL DEFINITELY be back!!!!!

Karen D
OH USA

Thanks for leaving such a lovely review - we appreciate it. Be sure to book direct with us n your next stay to get your returning guest discount!

Guest Services 
11 August 2024

Our family recently stayed at the beautiful Disney Dreaming home at Windsor Island Resort. We had such a great time! They provided us with everything we needed, the pool was very relaxing, the game room was so much fun, and the resort was everything we could have hoped for. The home itself exceeded our expectations. We cannot wait to stay there again! We've already booked our next trip to Orlando and will be staying at Disney Dreaming.

Ali H
NJ USA

Hi Ali - Thanks for leaving a review. We're delighted that you had such a great time - and we can't wait to welcome you back again soon!

Guest Services 
27 March 2024

We brought our daughter and her team to the Disney tournament and we stayed here for a week. Everything was just perfect. The check-in was easy and the booking agent was really helpful. We've already booked again for 2025.

Allison A
PA USA

Hey Allison - We hope your daughter's team did well in the tourney! We all look forward to welcoming you back as guests again next year.

Guest Services 
27 November 2023

Thanks for providing such a fabulous house to stay in! Our family came for Thanksgiving and the house gave us all lots of room and plenty to do. We spent most of our time either in the pool or relaxing together in the loft or the game room. The kids had a blast. Thanks again!

Mitchell M
FL USA

Hi Mitchell - We were delighted to read that you had such a great time. We hope you'll bring the family back again soon so we can welcome you as returning guests.

Guest Services 
27 August 2023

What a great place to stay this turned out to be - to visit and take the family to Disney and to relax after the parks. We plan to be back soon!

Sofie B
WI USA

Hi Sofie - Thanks for leaving a review. We're all happy that you had such a great time and hope to welcome you back again soon.

Guest Services 

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