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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

Jennifer DeLeonardis

07/07/2025
Beautiful property. The pool and game room were definitely the best part of the whole stay! The pool was very clean, someone came twice in the week we were there to clean it. The kids had a blast in the game room! There was plenty of room for everyone. The property manager was quick to respond to all our questions. We will definitely come back. We made a lot of memories with the other family we were with!

David Procious 07/13/2025

The house was incredible , the pool and hot tub was a warm and cool sensation , the bedrooms were as the pictures showed. Extremely comfortable and charming for the kids. The game room was an extra touch and very nice for family entertainment. The kids enjoyed the house and pool as much as Disney World.

Stefany Foster 07/06/2025

Great! Clean and quite close to everything. Thank you!

Kahea Tomberlin

07/23/2025
Perfect place for our family
The house was exactly as described in the listing. Lots of room for 7 of us. Well equipped kitchen for cooking. Very clean. We loved using the pool after the long days at Disney and Universal Parks. Great location to restaurants and grocery stores. The game room was a family favorite! We loved our stay and would definitely recommend our family and friends to book this house.

Ashley Law 07/21/2025

The home we stayed in was very clean. Great communication! Will be staying again!

David Perez 07/22/2025

Everything was wonderful. We could not have stayed in better place.

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!
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