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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

๐Ÿก Overview

Welcome to Skyline Retreat, a peaceful Luxury Windsor Island Resort Vacation Rental designed for guests seeking comfort, relaxation and resort-style living. Located within the beautiful Windsor Island Resort, just minutes from Walt Disney World Resort, this elegant five-bedroom vacation home offers stylish interiors, spacious living areas and a private pool, making it the perfect choice for families and friends visiting Central Florida.

Whether you’re spending your days exploring Orlando’s famous attractions or simply unwinding by the pool, Skyline Retreat provides the ideal setting for a memorable Florida getaway.


๐Ÿ›๏ธ Bed Configuration

Skyline Retreat comfortably accommodates families and groups across five beautifully furnished bedrooms and five-and-a-half bathrooms.

First Floor

๐Ÿ‘‘ Five spacious bedrooms, each with its own private en-suite bathroom

๐Ÿšฟ Additional downstairs half bathroom for guest convenience

Every bedroom has been thoughtfully designed with calming dรฉcor, comfortable bedding and Smart TVs, creating a peaceful retreat after exciting days exploring Orlando.


๐ŸŽฎ Entertainment

Skyline Retreat has been designed for relaxation and quality family time.

๐Ÿ›‹๏ธ Spacious open-plan living area with comfortable seating

๐Ÿ“บ Large Smart TV in the family room

๐Ÿ“ถ Complimentary high-speed Wi-Fi throughout the home

๐Ÿฝ๏ธ Fully equipped modern kitchen with breakfast bar seating for four

๐Ÿฅž Dining table seating for six guests

The peaceful atmosphere makes Skyline Retreat the perfect place to relax after busy days at the parks, while Windsor Island Resort’s clubhouse and entertainment facilities are just a short walk away.


๐ŸŒด Outside Space

Relax in your own private outdoor oasis.

๐ŸŠ Private north-facing screened swimming pool

๐Ÿฝ๏ธ Covered lanai with outdoor dining area

โ˜€๏ธ Comfortable loungers for enjoying the Florida sunshine

๐ŸŒด Quiet outdoor space perfect for morning coffee or relaxing evenings

Whether you’re cooling off in the pool or enjoying dinner outdoors, the private lanai offers a peaceful escape throughout your stay.


๐ŸŒŸ Windsor Island Resort

Guests staying at Skyline Retreat enjoy full access to Windsor Island Resort’s exceptional amenities, including a resort-style swimming pool, lazy river, water slides, splash park, clubhouse, fitness centre, mini golf, arcade, sports courts, children’s play areas and on-site dining. Conveniently located just minutes from Walt Disney World Resort, Windsor Island is one of Orlando’s newest and most desirable gated vacation communities.

๐Ÿ”— Internal Links

  • /listings/windsor-island-resort/
  • /5-bedroom-orlando-vacation-homes/

๐ŸŒ External Links

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Rates
Property protection fee: $ 150
Cleaning fee: $ 260
Pool and Spa Heat per night (optional): $ 30
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
Features and Amenities
Private Pool
Communal Tennis Courts
Communal Gym
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Availability

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Customer Reviews

Florida Premier Rentals

Customer Reviews

Carol Crout 05/04/2026

Clean and home friendly.Made some beautiful memories with our family. All was exceptional. We would love to return in a few years.

Cicily Shaull 22/03/2026

Love home and great location. Management responded quickly when we decided to have the pool heated! The home was well stocked with kitchen items to cook with. We truly enjoyed our time there!

Kenneth Keller 19/03/2026

Great location! Very spacious and clean. Was exactly as pictured. Would definitely stay here again.

Melissa Brye 01/11/2026

Our family had an exceptional stay here. We traveled with my husband, our four children, and my parents, and the home truly accommodated all ages comfortably. From the moment we arrived, it was clear the property is very well cared for. The decor is beautiful, and the home was spotless, creating an inviting and relaxing environment.The amenities truly set this property apart. The playroom and movie room were huge highlights for the kids, while the pool quickly became the center of our stay for everyone. In fact, there were multiple days during our Orlando trip, even with Disney and Universal planned, when the kids chose to stay at the house to swim and play instead. That alone speaks to how enjoyable the home was.There were genuinely activities for every age group, which made traveling as a multi-generational family easy and enjoyable.The location was very convenient, with attractions, games, and entertainment nearby whenever we decided to go out.Communication from the hosts was excellent from check-in through departure. They were kind, responsive, and proactive, making the entire process seamless and stress-free.If visiting during the winter months, I strongly recommend opting for the heated pool. It made a significant difference and was absolutely worth it.We cannot recommend this property highly enough. It provided a memorable experience for our family, and we would gladly stay again.

Mark Lucero 01/28/2026

The host was very helpful, the house was beautiful and very comfortable. Thank you!

Jane Sauther 01/28/2026

Clean, comfortable, spacious home, perfect for our large family trip to Disney. Location was perfect, pool was a hit, kitchen was well appointed for large groups, and beds were comfy. We highly recommend this property.

Dita Lawson 01/25/2026

We had the best time ever! House is really beautiful, clean and cozy. You can feel the homy vibes. Pool was clean too and super warm so we could enjoy it after long day in Disney! Location is also very convenient. We really loved our stay here!!! Thank you!!!

Joseph McFarland 01/25/2026

This home was perfect! Great accommodations, amazing community with a lot of amenities and close to all Orlando attractions. Rental agency was wonderful to work with and very responsive!

susie fisher 02/10/2026

Yvonne was wonderful in communicating with us and any questions we had.

Michael Faletto 02/09/2026

House as advertised and was amazing. Absolutely great communication with the host team, and the home was beautiful. An excellent stay for the 8 of us! Will definitely book again if we come back - GREAT location and easy ride shares to the parks!
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