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Skyline Retreat – 5 Bed 5.5 Bath Sleeps 10 – from $239

,
Kissimmee, Windsor Island
, , |
5 Bedroom Vacation Homes Orlando, Communal Pool, Private Pool
|
Windsor Island
10 Guests| 5 Bedrooms| 5.5 Baths
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Description


🏡 Overview

Welcome to Skyline Retreat, an elegant and tranquil Orlando villa for rent nestled in the peaceful Windsor Island Resort. Designed to be a serene escape from the hustle and bustle, this 5-bedroom, 5.5-bathroom home offers a perfect mix of comfort, style, and relaxation. Whether you’re planning a quiet getaway or a laid-back family holiday, Skyline Retreat is the ideal home base for your Florida vacation.

Inside, you’ll find a bright and airy open-plan layout with modern finishes and sophisticated furnishings. The living area features plush seating and a sleek flat-screen TV, while the adjacent dining space accommodates six for memorable meals together. The stylish kitchen—highlighted by warm wooden cabinetry and a four-seat breakfast island—is fully equipped for everything from quick snacks to full family dinners.

Every detail of this villa has been designed for both comfort and beauty, providing the peaceful escape you’ve been waiting for.


🛏️ Bedrooms

This stunning home offers flexible sleeping arrangements across five beautifully designed bedrooms, each with its own en-suite bathroom for added privacy. The layout includes:

  • Five tranquil bedrooms upstairs, each featuring tasteful dĂ©cor and calming tones

  • En-suite bathrooms in every bedroom, offering convenience and luxury

  • An additional half bath downstairs for guests

The clean and simple design creates an atmosphere of calm that promotes deep rest—perfect after long days exploring the Orlando area.


🎮 Entertainment

Skyline Retreat is ideal for travelers seeking a peaceful yet luxurious vacation. While it doesn’t include a traditional game room, guests will love:

  • A large smart TV in the main living area, perfect for streaming your favorite shows

  • High-speed Wi-Fi throughout the home for entertainment and connectivity

  • Comfortable indoor and outdoor spaces for socializing and unwinding

If you’re looking for more active fun, the Windsor Island Resort clubhouse is just a short stroll away and packed with family-friendly amenities.


🌴 Outdoor Living

Step outside to discover a relaxing north-facing private pool area, where peace and comfort meet Florida sunshine:

  • Covered lanai with open sky views for true serenity

  • Outdoor dining area perfect for al fresco meals

  • Sparkling private pool to cool off after sun-soaked days

  • Loungers for enjoying quiet afternoons or stargazing at night

Whether you’re sipping morning coffee by the pool or dining beneath the stars, this outdoor area offers pure relaxation.


🏰 Windsor Island Resort

Your stay at Skyline Retreat comes with access to one of Orlando’s most desirable vacation communities—Windsor Island Resort. Just minutes from Disney World and other top attractions, this gated resort offers something for every guest:

  • Lagoon-style resort pool with lazy river and waterslides

  • Splash pad for younger children

  • Fully equipped fitness center and arcade

  • Basketball, volleyball, and mini-golf facilities

  • Clubhouse with lounge, on-site dining, and a convenience store

Whether you’re soaking up the sun or heading out for adventure, Windsor Island Resort makes every stay unforgettable.

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Rates
Property protection fee: $ 150
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 15-10-2024 To 22-11-2024
$ 230
-
-
3
-
$ 230
All
All
From 23-11-2024 To 04-12-2024
$ 430
-
-
4
-
$ 430
All
All
From 05-12-2024 To 18-12-2024
$ 230
-
-
3
-
$ 230
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 15-10-2024 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 04-12-2024
Price per night
$ 430
Price per night (7n+)
-
Price per night (30n+)
-
Minimum Night Stay
4
Extra price per guest
-
Price per night in weekends
$ 430
Booking starts only on
All
Booking starts/ends only on
All
Period
From 05-12-2024 To 18-12-2024
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 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: 3421 Lilac Way
City:
State: Florida
Zip: 33897
Country: United States
Bed Configuration
Property Name:
83527
Property Size: 2,622 ft2
Bedrooms: 5
Bathrooms: 5.5
King : 1
Queen : 3
Full: 2
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Availability

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Customer Reviews

Florida Premier Rentals

Customer Reviews

Jesse Phillips 22/12/2025

Great place to stay and very close to the theme parks.

Rodney Rael 21/12/2025

Thank you for the great experience!

Sean Burke 02/12/2025

House was well laid out for multiple generations to be comfortable. Very clean and well kept. 25-30 minute drive to Disney World.

Jon Slodysko 29/11/2025

Great communication, clean, easy to work with more than enough amenities!

Tim Young 29/11/2025

The heated pool was perfect to soak away the tired aches and pains of big days at Disney . Lots of room and very well equipped . We would come back with a big group in a heart beat !

Lauren McKenna 20/11/2025

Loved the pool and game room!

Mary Redmond 10/11/2025

They so flexible to allow us to check in early and get jumpstart to our vacation!

Tony esposito 01/11/2025

The house was great, location was great, rooms were great , and the kid friendly entertainment and bedrooms made it perfect.

Steffen Nizinski 09/22/2025

Beautiful property! We will definitely be coming back! Perfect for a family Disney vacation!

Joshua Hembrough 09/03/2025

Beautiful and modern home that is great for large families! The kids loved the Harry Potter Room and the game room! We enjoyed having space and loved having access to the resort's pool club. The drive is only 15 minutes from Disney Parks, which was the main reason we chose this location. Highly recommend this place and we will be back in the future!
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