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Legends Lounge at Windsor at Westside

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The loft theater area is ideal for epic movie nights at home​
The sophisticated kitchen is well equipped for an unforgettable getaway​
Make a splash in your very own sparkling pool​
Lounge the day away in the sunshine at one of the spacious community pools​
Soak your cares away in the community’s winding lazy river​

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8 bedrooms6 bathroomsSleeps 184041 sq ft

Popular amenities

  • Pool
  • Hot tub
  • Kitchen
  • Washer
  • Dryer
  • Air conditioning

Explore the area

View in a map
Kissimmee, Florida
  • Place, Northeast Regional Park
    ‪3 min drive‬
  • Place, Lake Davenport
    ‪4 min drive‬
  • Place, Highland Reserve Golf Club
    ‪6 min drive‬
  • Airport, Orlando, FL (MCO-Orlando Intl.)
    ‪43 min drive‬

Rooms & beds

8 bedrooms (sleeps 18)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 King Bed

Bedroom 4

1 Double Bed and 1 Twin Bed

Bedroom 5

1 Double Bed and 1 Twin Bed

Bedroom 6

1 Double Bed

Bedroom 7

1 King Bed

Bedroom 8

1 King Bed

6 bathrooms

Bathroom 1

Bathtub · Toilet · Shower only

Bathroom 2

Bathtub · Toilet · Shower only

Bathroom 3

Bathtub · Toilet · Shower only

Bathroom 4

Bathtub · Toilet · Shower only

Bathroom 5

Bathtub · Toilet · Shower only

Bathroom 6

Bathtub · Toilet · Shower only

Spaces

Kitchen
Office
Balcony
Garden

About this property

Legends Lounge at Windsor at Westside

Summary:

Legends Lounge at Windsor at Westside delivers a true resort-style escape just minutes from Orlando’s top attractions—and only a 3-minute walk to the main clubhouse. Spend your days floating along the lazy river, lounging by the resort pool, or enjoying the on-site restaurant, tiki bar, fitness center, and sports courts. This gated community blends the excitement of a full-service resort with the comfort and privacy of your own home, making it the perfect base for both relaxation and adventure.



The Space:

You’re welcomed by a thoughtfully designed entry featuring a mud room with built-in storage and bench seating—perfect for dropping off beach bags and theme park gear. The home opens into a bright, inviting living space where an L-shaped couch and smart TV create the ideal spot to unwind, with oversized sliding glass doors leading straight out to your private lanai. The kitchen is both stylish and functional, showcasing black granite countertops, stainless steel appliances, a cozy nook for two, and an oversized island with seating for three. Just beyond, a large dining table for 11 brings everyone together for memorable meals and late-night conversations.



The fun continues throughout the home, starting with a fully loaded garage game room featuring air hockey, pool, foosball, and a high-top table for friendly competition. Upstairs, the loft transforms into an entertainment haven with a wraparound sofa, smart TV, Xbox streaming setup, dual sit-down arcade game, and bold Marvel-themed décor that adds an immersive, playful vibe. Outside, your private oasis awaits—an oversized, fully enclosed lanai with a sparkling pool and spa that overflows into the water, surrounded by a brick paver patio, dining table for six, and four chaise loungers. With added privacy fencing and open green space nearby, Legends Lounge at Windsor at Westside is the perfect blend of excitement, comfort, and laid-back Florida luxury.



This home comfortably sleeps 18 guests between 8 private bedrooms.



Bedroom #1 includes a king size bed, a smart TV also equipped with cable TV, patio access, and an ensuite bathroom with a dual vanity, a soaking tub, and a walk-in shower.



Bedroom #2 is a queen size bed and a smart TV.



Bedroom #3 includes a king size bed, a smart TV, and an ensuite bathroom with a dual vanity and a walk-in shower.



Bedroom #4 is Star Wars themed and includes a twin size bed, a full size bed, and a smart TV.



Bedroom #5 is Mickey themed and includes a twin size bed, a full size bed, and a smart TV also equipped with cable.



Bedroom #6 includes a full size bed, a smart TV, and a Jack-and-Jill bathroom with a single vanity and a shower/tub combo, shared with bedroom #7.



Bedroom #7 includes a king size bed, a smart TV, and a Jack-and-Jill bathroom shared with bedroom #6.



Bedroom #8 includes a king size bed, a smart TV, and an ensuite bathroom with a dual vanity and a walk-in shower.



This home also includes 2 additional full guest bathrooms; one with a single vanity and a walk-in shower, and another with a dual vanity and a walk-in shower.



THINGS TO NOTE:

• Washer and dryer in home.

• Driveway and street parking for 2 vehicles available.

• Guests renting homes on Gobi Dr, Bengal Ct, and will need to stop at the Lima Ave 24/7 manned guardhouse upon entry and provide the booking confirmation for the home that clearly shows the address, check in, and check out dates for the stay. Guests will be issued a proxy card that will remain active throughout their stay, allowing them to enter through the gates quickly, without having to stop and speak with the guard attendant again.

o It is important to note that all proxy cards will shut down at 10AM on the day of check out. If guests have a late check out scheduled and leave the property with the intent to return after 10am on their check out day, they will need to stop at the guardhouse with proof of the late check out information to leave.

o Upon check out, all cards will automatically become inactive. There will be collection boxes at each exit gate so guests can dispose of their proxy cards.

• Miscellaneous fee(s):

o Optional pool heating is available for an additional fee of $29 per night — please note that a minimum of 48 hours advance notice is required. Pool heat must be added for the entirety of the stay — partial pool heating is not available due to the high cost of bringing the temperature up.

o Your home may have a BBQ grill installed on the patio — please note that use of the grill is subject to a $95 fee and must be requested prior to arrival, as grills are kept locked when not in use.

• This home is equipped with one (1) external Ring security camera, located at the entryway and monitoring the exterior entryway walkway.

• A standard crib, portable crib, and high chair are provided for guests traveling with little ones.



Visiting the Kissimmee and Orlando area means stepping into one of the most exciting and family-friendly travel destinations in the country. From world-famous theme parks—including Walt Disney World®, Universal Orlando, and SeaWorld®—to outlet shopping, championship golf, waterparks, and dinner shows, there’s never a shortage of things to do. Between the thrills, travelers can explore charming Old Town Kissimmee, stroll lakefront boardwalks, enjoy nature preserves, or savor everything from casual bites to celebrity-chef restaurants. Whether you’re planning theme park magic, outdoor adventures, or simply a warm-weather escape, this region makes it effortless to fill your days with fun and return home with unforgettable memories.
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Pool
Hot Tub
Kitchen
Washer
Dryer
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 21
Check out before 10:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
- This property is non-smoking — violators will be fined $500 plus mitigation costs. - Pets are not allowed — violators will be fined $500 plus cle...

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room

About the neighborhood

Kissimmee

Located in Kissimmee, this vacation home is in the city center and near theme parks. ChampionsGate Golf Club and Mystic Dunes Golf Club are worth checking out if an activity is on the agenda, while those in the mood for shopping can visit Old Town and Disney Springs™. Traveling with kids? Make time for Walt Disney World® Resort, or check out an event or a game at ESPN Wide World of Sports Complex.
Map
Kissimmee, Florida

What's nearby

  • Northeast Regional Park - 3 min drive - 2.7 km
  • Lake Davenport - 4 min drive - 2.8 km
  • Four Corners FC - 6 min drive - 5.1 km
  • Highland Reserve Golf Club - 6 min drive - 4.0 km
  • Orange Lake Golf - 8 min drive - 8.5 km

Getting around

  • Kissimmee Station - 30 min drive
  • Kissimmee, FL (ISM-Kissimmee Gateway) - 40 min drive

Restaurants

  • ‪McDonald's - ‬5 min drive
  • ‪7-Eleven - ‬17 min walk
  • ‪Circle K - ‬6 min drive
  • ‪Dutch Bros Coffee - ‬6 min drive
  • ‪Twistee Treat Berry Town - ‬5 min drive

Frequently asked questions

Does Legends Lounge at Windsor at Westside have a pool?

Yes, this property has a pool.

How much does it cost to stay at Legends Lounge at Windsor at Westside?

As of Apr 24, 2026, prices found for a 1-night stay for 2 adults at Legends Lounge at Windsor at Westside on May 31, 2026 start from $454, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Legends Lounge at Windsor at Westside pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Legends Lounge at Windsor at Westside?

Check-in begins at 4:00 PM.

What time is check-out at Legends Lounge at Windsor at Westside?

Check-out is at 10:00 AM.

Where is Legends Lounge at Windsor at Westside located?

This family-friendly vacation home is located in the city center, within 3 mi (5 km) of Highland Reserve Golf Club, Four Corners FC, and Lake Davenport. Surfari Water Park and Island H2O Live! are also within 6 mi (10 km).

About the host

Hosted by Grand Welcome Orlando

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