Reset Password

click to see all images

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
Check Availability

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.

đź”— View More Orlando Villas for Rent
đź”— Explore All Florida Premier Rentals

Book Now

Pool Heat

Add to Favorites
Contact Us
Share
Your search results
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
Submit your review
1
2
3
4
5
Submit
     
Cancel

Create your own review

Florida Premier Rentals
Average rating:  
 0 reviews
What's Nearby

Arts & Entertainment

Osceola County Library System
(19.01 miles)Osceola County Library System
Orlando Kings Tattoo
(19.73 miles)Orlando Kings Tattoo
Our Kids Count
(19.46 miles)Our Kids Count

Beauty & Spas

Food

Taco Fiesta
(19.83 miles)Taco Fiesta
Flavors of Jamaica
(18.54 miles)Flavors of Jamaica
empanadas serrano
(18.64 miles)empanadas serrano

Restaurants

Taino's Bakery & Deli
(19.65 miles)Taino's Bakery & Deli
Taco Fiesta
(19.83 miles)Taco Fiesta
Flavors of Jamaica
(18.54 miles)Flavors of Jamaica

Shopping

Walmart Neighborhood Market
(20.44 miles)Walmart Neighborhood Market
dd's DISCOUNTS
(18.29 miles)dd's DISCOUNTS
Avalon
(24.63 miles)Avalon

Availability

March 2026
M T W T F S S
 1
2345678
9101112131415
16171819202122
23242526272829
3031  
April 2026
M T W T F S S
 12345
6789101112
13141516171819
20212223242526
27282930  
past
today
booked

Customer Reviews

Florida Premier Rentals

Customer Reviews

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!

Andrea 01/02/2026

Thank you so much for the kind words! We’re really glad you enjoyed the space, the location, and felt well looked after during your stay. It was a pleasure hosting you, and you’re welcome back anytime.

Marcy Allison 01/19/2026

Absolutely wonderful stay! The house was perfect for our family. It was clean and offered so many fun options for the whole family - pool, game room, media room. Could not recommend it more!! We will definitely book again if we return to the area.

Gregory Sather 01/19/2026

Fantastic house! Pool, hot tub, games room were all additional amenities not found everywhere. Host was extremely responsive to our needs and made sure we were satisfied with our stay. Parking for more than 3 vehicles was easily accessed just a few feet away and the location was still close enough to the parks, bars, restaurants. Plenty of beds and baths for large groups/families. Very enjoyable stay!
Read more...