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Charming Retreat – 5 Bed 4 Bath Sleeps 11 – from $239

,
Kissimmee, Windsor Island
|
5 Bed
|
Windsor Island
11 Guests| 5 Bedrooms| 4 Baths
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Description

🏡 Overview

5 bed villa Windsor Island welcomes you to Charming Retreat — your charming escape in the heart of Windsor Island Resort. This elegant yet cozy 5 bed villa Windsor Island is designed for families who want the best of Florida sunshine with a sprinkle of Disney magic.

Step inside and enjoy the spacious open-concept layout. The fully equipped kitchen features modern appliances and a breakfast bar, perfect for casual family breakfasts. The dining area comfortably seats six for shared meals and laughter.

After days of adventure, unwind in your beautifully decorated living space, filled with warm, inviting touches that make you feel right at home.

👉 Want to see more family villas? Check out our Windsor Island vacation homes.


🛏️ Bed Configuration

  • Master Suite: King Bed for ultimate comfort

  • Bedroom #2: Queen Bed

  • Bedroom #3: Queen Bed

  • Bedroom #4: Minnie Mouse-Themed Room with Twin Beds

  • Bedroom #5: Mickey Mouse-Themed Room with Twin Beds

Each room is thoughtfully designed with fresh linens and plenty of space. The kids will love drifting off to dreamland in their magical Disney-themed bedrooms!


🎮 Entertainment

When you’re not exploring the parks, relax in the bright, open living area — perfect for movie nights and family games. The Mickey and Minnie rooms add extra fun for little ones!

Ready for more adventure? Nearby attractions like Walt Disney World® and Universal Orlando Resort™ are just a short drive away.


🌴 Outdoor Space

Step outside to your private oasis. The covered glass lanai surrounds the sparkling pool for peaceful swims and sunny lounging. Enjoy outdoor meals with seating for six, all while soaking up the Florida breeze.

When you’re ready to explore, Windsor Island Resort offers incredible amenities:

  • Thrilling waterpark and splash pad

  • Relaxing lazy river

  • Fitness center and sports courts

  • Playgrounds and picnic areas

Learn more about all the resort perks on our Windsor Island Resort overview.


🧺 Additional Features

  • Fully equipped kitchen with breakfast bar

  • Dining for six indoors and outdoors

  • Air conditioning and ceiling fans for comfort

  • Smoke-free and pet-free home

  • Complimentary high-speed Wi-Fi

  • Fresh towels and linens included

  • Full laundry room with washer and dryer

Book Charming Retreat today! Discover why this 5 bed villa Windsor Island is the perfect family escape for magical memories in the Sunshine State.

Book Now

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Rates
Property protection fee: $ 149
Cleaning fee: $ 260
Pool and Spa Heat per night (optional): $ 25
Rates
Price per night
Price per night (7n+)
Price per night (30n+)
Minimum Night Stay
Extra price per guest
Price per night in weekends
Booking starts only on
Booking starts/ends only on
From 24-08-2024 To 29-08-2024
$ 230
-
-
3
-
$ 230
All
All
From 30-08-2024 To 05-09-2024
$ 246
-
-
4
-
$ 246
All
All
From 06-09-2024 To 22-11-2024
$ 230
-
-
3
-
$ 230
All
All
From 23-11-2024 To 02-12-2024
$ 327
-
-
4
-
$ 327
All
All
From 03-12-2024 To 18-12-2024
$ 250
-
-
3
-
$ 250
All
All
From 19-12-2024 To 03-01-2025
$ 411
-
-
5
-
$ 411
All
All
From 04-01-2025 To 23-02-2025
$ 230
-
-
3
-
$ 230
All
All
From 24-02-2025 To 28-03-2025
$ 304
-
-
4
-
$ 304
All
All
From 29-03-2025 To 10-04-2025
$ 239
-
-
3
-
$ 239
All
All
From 11-04-2025 To 25-04-2025
$ 420
-
-
5
-
$ 420
All
All
From 26-04-2025 To 22-05-2025
$ 239
-
-
3
-
$ 239
All
All
From 23-05-2025 To 27-05-2025
$ 255
-
-
4
-
$ 255
All
All
From 28-05-2025 To 15-06-2025
$ 239
-
-
3
-
$ 239
All
All
From 16-06-2025 To 20-08-2025
$ 313
-
-
4
-
$ 313
All
All
From 21-08-2025 To 28-08-2025
$ 239
-
-
3
-
$ 239
All
All
From 29-08-2025 To 03-09-2025
$ 255
-
-
4
-
$ 255
All
All
From 04-09-2025 To 23-11-2025
$ 239
-
-
3
-
$ 239
All
All
From 24-11-2025 To 01-12-2025
$ 336
-
-
4
-
$ 336
All
All
From 02-12-2025 To 21-12-2025
$ 239
-
-
3
-
$ 239
All
All
From 22-12-2025 To 03-01-2026
$ 420
-
-
5
-
$ 420
All
All
From 04-01-2026 To 28-02-2026
$ 239
-
-
3
-
$ 239
All
All
From 01-03-2026 To 25-03-2026
$ 313
-
-
4
-
$ 313
All
All
From 26-03-2026 To 15-04-2026
$ 420
-
-
5
-
$ 420
All
All
From 16-04-2026 To 22-05-2026
$ 239
-
-
3
-
$ 239
All
All
From 23-05-2026 To 27-05-2026
$ 255
-
-
4
-
$ 255
All
All
From 28-05-2026 To 20-06-2026
$ 239
-
-
3
-
$ 239
All
All
From 21-06-2026 To 15-08-2026
$ 313
-
-
4
-
$ 313
All
All
From 16-08-2026 To 03-09-2026
$ 239
-
-
3
-
$ 239
All
All
From 04-09-2026 To 08-09-2026
$ 255
-
-
4
-
$ 255
All
All
From 09-09-2026 To 23-11-2026
$ 239
-
-
3
-
$ 239
All
All
From 24-11-2026 To 30-11-2026
$ 336
-
-
4
-
$ 336
All
All
From 01-12-2026 To 21-12-2026
$ 239
-
-
3
-
$ 239
All
All
From 22-12-2026 To 02-01-2027
$ 420
-
-
5
-
$ 420
All
All
Period
From 24-08-2024 To 29-08-2024
Price per night
$ 230
Price per night (7n+)
-
Price per night (30n+)
-
Minimum Night Stay
3
Extra price per guest
-
Price per night in weekends
$ 230
Booking starts only on
All
Booking starts/ends only on
All
Period
From 30-08-2024 To 05-09-2024
Price per night
$ 246
Price per night (7n+)
-
Price per night (30n+)
-
Minimum Night Stay
4
Extra price per guest
-
Price per night in weekends
$ 246
Booking starts only on
All
Booking starts/ends only on
All
Period
From 06-09-2024 To 22-11-2024
Price per night
$ 230
Price per night (7n+)
-
Price per night (30n+)
-
Minimum Night Stay
3
Extra price per guest
-
Price per night in weekends
$ 230
Booking starts only on
All
Booking starts/ends only on
All
Period
From 23-11-2024 To 02-12-2024
Price per night
$ 327
Price per night (7n+)
-
Price per night (30n+)
-
Minimum Night Stay
4
Extra price per guest
-
Price per night in weekends
$ 327
Booking starts only on
All
Booking starts/ends only on
All
Period
From 03-12-2024 To 18-12-2024
Price per night
$ 250
Price per night (7n+)
-
Price per night (30n+)
-
Minimum Night Stay
3
Extra price per guest
-
Price per night in weekends
$ 250
Booking starts only on
All
Booking starts/ends only on
All
Period
From 19-12-2024 To 03-01-2025
Price per night
$ 411
Price per night (7n+)
-
Price per night (30n+)
-
Minimum Night Stay
5
Extra price per guest
-
Price per night in weekends
$ 411
Booking starts only on
All
Booking starts/ends only on
All
Period
From 04-01-2025 To 23-02-2025
Price per night
$ 230
Price per night (7n+)
-
Price per night (30n+)
-
Minimum Night Stay
3
Extra price per guest
-
Price per night in weekends
$ 230
Booking starts only on
All
Booking starts/ends only on
All
Period
From 24-02-2025 To 28-03-2025
Price per night
$ 304
Price per night (7n+)
-
Price per night (30n+)
-
Minimum Night Stay
4
Extra price per guest
-
Price per night in weekends
$ 304
Booking starts only on
All
Booking starts/ends only on
All
Period
From 29-03-2025 To 10-04-2025
Price per night
$ 239
Price per night (7n+)
-
Price per night (30n+)
-
Minimum Night Stay
3
Extra price per guest
-
Price per night in weekends
$ 239
Booking starts only on
All
Booking starts/ends only on
All
Period
From 11-04-2025 To 25-04-2025
Price per night
$ 420
Price per night (7n+)
-
Price per night (30n+)
-
Minimum Night Stay
5
Extra price per guest
-
Price per night in weekends
$ 420
Booking starts only on
All
Booking starts/ends only on
All
Period
From 26-04-2025 To 22-05-2025
Price per night
$ 239
Price per night (7n+)
-
Price per night (30n+)
-
Minimum Night Stay
3
Extra price per guest
-
Price per night in weekends
$ 239
Booking starts only on
All
Booking starts/ends only on
All
Period
From 23-05-2025 To 27-05-2025
Price per night
$ 255
Price per night (7n+)
-
Price per night (30n+)
-
Minimum Night Stay
4
Extra price per guest
-
Price per night in weekends
$ 255
Booking starts only on
All
Booking starts/ends only on
All
Period
From 28-05-2025 To 15-06-2025
Price per night
$ 239
Price per night (7n+)
-
Price per night (30n+)
-
Minimum Night Stay
3
Extra price per guest
-
Price per night in weekends
$ 239
Booking starts only on
All
Booking starts/ends only on
All
Period
From 16-06-2025 To 20-08-2025
Price per night
$ 313
Price per night (7n+)
-
Price per night (30n+)
-
Minimum Night Stay
4
Extra price per guest
-
Price per night in weekends
$ 313
Booking starts only on
All
Booking starts/ends only on
All
Period
From 21-08-2025 To 28-08-2025
Price per night
$ 239
Price per night (7n+)
-
Price per night (30n+)
-
Minimum Night Stay
3
Extra price per guest
-
Price per night in weekends
$ 239
Booking starts only on
All
Booking starts/ends only on
All
Period
From 29-08-2025 To 03-09-2025
Price per night
$ 255
Price per night (7n+)
-
Price per night (30n+)
-
Minimum Night Stay
4
Extra price per guest
-
Price per night in weekends
$ 255
Booking starts only on
All
Booking starts/ends only on
All
Period
From 04-09-2025 To 23-11-2025
Price per night
$ 239
Price per night (7n+)
-
Price per night (30n+)
-
Minimum Night Stay
3
Extra price per guest
-
Price per night in weekends
$ 239
Booking starts only on
All
Booking starts/ends only on
All
Period
From 24-11-2025 To 01-12-2025
Price per night
$ 336
Price per night (7n+)
-
Price per night (30n+)
-
Minimum Night Stay
4
Extra price per guest
-
Price per night in weekends
$ 336
Booking starts only on
All
Booking starts/ends only on
All
Period
From 02-12-2025 To 21-12-2025
Price per night
$ 239
Price per night (7n+)
-
Price per night (30n+)
-
Minimum Night Stay
3
Extra price per guest
-
Price per night in weekends
$ 239
Booking starts only on
All
Booking starts/ends only on
All
Period
From 22-12-2025 To 03-01-2026
Price per night
$ 420
Price per night (7n+)
-
Price per night (30n+)
-
Minimum Night Stay
5
Extra price per guest
-
Price per night in weekends
$ 420
Booking starts only on
All
Booking starts/ends only on
All
Period
From 04-01-2026 To 28-02-2026
Price per night
$ 239
Price per night (7n+)
-
Price per night (30n+)
-
Minimum Night Stay
3
Extra price per guest
-
Price per night in weekends
$ 239
Booking starts only on
All
Booking starts/ends only on
All
Period
From 01-03-2026 To 25-03-2026
Price per night
$ 313
Price per night (7n+)
-
Price per night (30n+)
-
Minimum Night Stay
4
Extra price per guest
-
Price per night in weekends
$ 313
Booking starts only on
All
Booking starts/ends only on
All
Period
From 26-03-2026 To 15-04-2026
Price per night
$ 420
Price per night (7n+)
-
Price per night (30n+)
-
Minimum Night Stay
5
Extra price per guest
-
Price per night in weekends
$ 420
Booking starts only on
All
Booking starts/ends only on
All
Period
From 16-04-2026 To 22-05-2026
Price per night
$ 239
Price per night (7n+)
-
Price per night (30n+)
-
Minimum Night Stay
3
Extra price per guest
-
Price per night in weekends
$ 239
Booking starts only on
All
Booking starts/ends only on
All
Period
From 23-05-2026 To 27-05-2026
Price per night
$ 255
Price per night (7n+)
-
Price per night (30n+)
-
Minimum Night Stay
4
Extra price per guest
-
Price per night in weekends
$ 255
Booking starts only on
All
Booking starts/ends only on
All
Period
From 28-05-2026 To 20-06-2026
Price per night
$ 239
Price per night (7n+)
-
Price per night (30n+)
-
Minimum Night Stay
3
Extra price per guest
-
Price per night in weekends
$ 239
Booking starts only on
All
Booking starts/ends only on
All
Period
From 21-06-2026 To 15-08-2026
Price per night
$ 313
Price per night (7n+)
-
Price per night (30n+)
-
Minimum Night Stay
4
Extra price per guest
-
Price per night in weekends
$ 313
Booking starts only on
All
Booking starts/ends only on
All
Period
From 16-08-2026 To 03-09-2026
Price per night
$ 239
Price per night (7n+)
-
Price per night (30n+)
-
Minimum Night Stay
3
Extra price per guest
-
Price per night in weekends
$ 239
Booking starts only on
All
Booking starts/ends only on
All
Period
From 04-09-2026 To 08-09-2026
Price per night
$ 255
Price per night (7n+)
-
Price per night (30n+)
-
Minimum Night Stay
4
Extra price per guest
-
Price per night in weekends
$ 255
Booking starts only on
All
Booking starts/ends only on
All
Period
From 09-09-2026 To 23-11-2026
Price per night
$ 239
Price per night (7n+)
-
Price per night (30n+)
-
Minimum Night Stay
3
Extra price per guest
-
Price per night in weekends
$ 239
Booking starts only on
All
Booking starts/ends only on
All
Period
From 24-11-2026 To 30-11-2026
Price per night
$ 336
Price per night (7n+)
-
Price per night (30n+)
-
Minimum Night Stay
4
Extra price per guest
-
Price per night in weekends
$ 336
Booking starts only on
All
Booking starts/ends only on
All
Period
From 01-12-2026 To 21-12-2026
Price per night
$ 239
Price per night (7n+)
-
Price per night (30n+)
-
Minimum Night Stay
3
Extra price per guest
-
Price per night in weekends
$ 239
Booking starts only on
All
Booking starts/ends only on
All
Period
From 22-12-2026 To 02-01-2027
Price per night
$ 420
Price per night (7n+)
-
Price per night (30n+)
-
Minimum Night Stay
5
Extra price per guest
-
Price per night in weekends
$ 420
Booking starts only on
All
Booking starts/ends only on
All
Property Address
Address: 1811 Summer Drive
City:
State: Florida
Zip: 33897
Country: United States
Bed Configuration
Property Name:
83577
Property Size: 2,496 ft2
Bedrooms: 5
Bathrooms: 4
King : 1
Queen : 2
Sets Of Bunk Beds: 1
Full: 2
Features and Amenities
Private Pool
Themed Bedrooms
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Florida Premier Rentals
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What's Nearby

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(7.1 miles)Disney's Art of Animation Resort
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Beauty & Spas

Food

The Wharf at Sunset Walk
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Hokusai Ramen And Izakaya
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Cowboy Chicken
(3.67 miles)Cowboy Chicken

Restaurants

The Wharf at Sunset Walk
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(3.72 miles)Lazy Dog Restaurant & Bar

Shopping

Celebration Factory Outlet
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Availability

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Customer Reviews

Florida Premier Rentals

Customer Reviews

Justina White 06/15/2025

Best Stay Ever!
The family and I enjoyed our stay; the house was large enough for 3 families; we all had our own space to spread out. The house was very comfortable and well stocked with all the essentials. Never once did w

Lauren McCann 22/06/2025

Wonderful experience. Beautiful home, great location.

Joe Rebman 06/03/2024

We attended a 4 day business conference at the Gaylord Palms and opted to stay here instead of paying for multiple rooms at the Gaylord. With 5 bedrooms and 5 bathrooms and the pool and hot tub, this spot was awesome and saved us $$! Everything was great!

Kim Gordon 06/03/2025

This was a great house with plenty of room. The pool was a great way to unwind after a long day of fun. We really enjoyed the games in the house as well. There was so much room that we all had plenty of privacy. We would definitely stay there again.

jeffrey corrao 07/06/2025

Great location. Easy access to the parks. Great place to stay.

Stephanie Rook 07/01/2025

Great condo and location. We would recommend it and we’re planning to go back!

Deena Harris 07/06/2025

Wonderful home! Had everything for the family! Plenty of room, beautifully decorated! The garage with ping pong table, air hockey, basketball and games was a hit! The beds were comfortable and the backyard was great! It’s a 15 minute drive to Disney, no shuttles. I have nothing negative to say! The house was perfect!

Ashley Young 05/05/2025

Awesome family vacation. Everything was great for our family of five including an almost 2, 4, and 7yo, and a set of grandparents. Plenty of space and great resort amenities and location.

John Cooper 04/24/2025

Fun Experience, This was a fantastic property. The house was great. The only negative was we couldn't get the pool or hot tub to work properly, but the management company refunded our money. Florida Premiere Rentals is a 1st class company and they did what was right. Thank you.

Martin Wolfe 03/23/2025

Disney trip
Convenient spacious clean. Well appointed. Kids loved the pool and were in it on off days. All in all excellent place to stay.
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