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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

Arts & Entertainment

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

Food

The Wharf at Sunset Walk
(3.59 miles)The Wharf at Sunset Walk
Hokusai Ramen And Izakaya
(4.35 miles)Hokusai Ramen And Izakaya
Osaka Bay Buffet
(4.32 miles)Osaka Bay Buffet

Restaurants

The Wharf at Sunset Walk
(3.59 miles)The Wharf at Sunset Walk
Adega Gaucha
(3.89 miles)Adega Gaucha
Rock & Brews - Kissimmee
(3.63 miles)Rock & Brews - Kissimmee

Shopping

Celebration Factory Outlet
(7.95 miles)Celebration Factory Outlet
Sunset Walk
(3.75 miles)Sunset Walk
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(3.33 miles)Target

Availability

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Customer Reviews

Florida Premier Rentals

Customer Reviews

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.

Angela Griffith 03/24/2025

Great location to spend while in Orlando, relaxing!
This property was absolutely perfect for our family of 6 and we could have hosted more for sure!

Tina Antolik 03/29/2025

Amazing Disney Family Vacation Home
The property was exactly as described. Management was very responsive. We had a great time.

Kathy Herzog 04/04/2025

House was great, but not really set up for toddlers with the glass top tables. The Moana room was a big hit for the kids. The playground and splash pad were wonderful!

Gregory Abbink 04/02/2025

Clean, spacious and great location!
We truly enjoyed our stay- it provided lots of room for everyone and we were pleased with the cleanliness and functionality. We also felt very safe in the gated community.

Jo-Anne Perkins 03/18/2025

We really enjoyed this VRBO unit and thought it was well appointed, clean and in a good location.Staff were easy to communicate with and responsive.Definately rent this unit again, thanks!

Bob Murphy 02/28/25

Very Nice Home for a Family Stay
The home is spacious, and very well appointed. We enjoyed our stay here very much.

Sharleen Koepp 02/16/2025

It was amazing
Our family loved the private pool & hot tub. Would be nice to have float tubes and a ball especially for kids. Loved the large living/entertainment spaces & 4 bedrooms.Kitchen could have basic spices in the cupboard. Our toaster wasn’t working so called to report it & they promptly delivered a new one. Great place, close to Disney. Highly recommend.
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