Kissimmee, Florida

EV_8900 - Windsor Oasis Retreat

5 bedrooms 0 beds 4.5 baths 10 guests New

About the property

Windsor Oasis Retreat is your invitation to an unforgettable Orlando getaway. This stunning 8-bedroom, 6-bathroom executive home is perfectly situated within the gorgeous, gated Windsor at Westside Resort, offering an absolutely ideal setting for multi-family vacations, golf groups, or large celebrations. With sleeping arrangements for up to 18 guests, this property features all the space and comforts you could desire, and more!

Step into a spacious, light-filled living area where you'll immediately feel relaxed and at home. The communal spaces are perfect for gathering, whether it's sharing a special meal at the elegant dining table or enjoying a quick breakfast at the kitchen’s breakfast bar. The bright, airy, and fully equipped kitchen has all the appliances and utensils you’d expect, making meal prep a breeze. A full-size washer and dryer are also included for your convenience.

Entertainment is everywhere! Challenge your group to a game of pool, air hockey, and more in the dedicated games room. While the spacious lounge provides the perfect spot for the adults to watch a movie or catch the big game, the kids can claim the upstairs loft area for their own entertainment.

Outside, soak up the famous Florida sunshine in your very own private, screened-in pool and spa. The lanai and patio area is the ultimate space for relaxation, complete with sun loungers and an outdoor patio table for al fresco dining.

Bedrooms:

Bedroom #1: King (First Floor)

Bedroom #2: Queen (First Floor)

Bedroom #3: King (Second Floor)

Bedroom #4: King (Second Floor)

Bedroom #5: Queen (Second Floor)

Bedroom #6: Queen (Second Floor)

Bedroom #7: Full x2 (Second Floor)

Bedroom #8: Twin x2 (Second Floor)

General:

Sleeps up to 18

Fully equipped kitchen

Breakfast Bar 4

Breakfast Nook 4

Dining table 6

Screened-In Private Pool

Games Room

Rental Policies:

Check in: 4:00PM / Check out: 10:00AM

Early & Late Check-in/out:

No smoking / No pets

• POOL HEAT:

Heating is available for $35 per day (plus tax) with a 3-day minimum and must be requested at least 48 hours in advance. Please note the attached spa is not a hot tub—it does not have jets, and it heats to the same temperature as the pool, not exceeding 90°F. The heating system uses heat exchange, which does not operate in temperatures below 50°F. No refunds will be provided if the pool does not reach the desired temperature in cold weather.

• GRILL:

Please note. Some of our homes may be pictured with a gas bbq grill or outdoor built in grill. If guests wish to use the grills, it is the guest's responsibility to clean the grill and replenish the propane tank if needed. A $50 charge will be applied if grills are left unclean. Exchange refill propane tanks can be purchased at numerous local locations. If the grill is locked up, then it is not to be used by guests as it is the homeowner's personal grill. If you would like to have a grill for your vacation, we can arrange a rental grill for your stay.

Windsor Oasis Retreat is your invitation to an unforgettable Orlando getaway. This stunning 8-bedroom, 6-bathroom executive home is perfectly situated within the gorgeous, gated Windsor at Westside Resort, offering an absolutely ideal setting for multi-family vacations, golf groups, or large celebrations. With sleeping arrangements for up to 18 guests, this property features all the space and comforts you could desire, and more!

Step into a spacious, light-filled living area where you'll immediately feel relaxed and at home. The communal spaces are perfect for gathering, whether it's sharing a special meal at the elegant dining table or enjoying a quick breakfast at the kitchen’s breakfast bar. The bright, airy, and fully equipped kitchen has all the appliances and utensils you’d expect, making meal prep a breeze. A full-size washer and dryer are also included for your convenience.

Entertainment is everywhere! Challenge your group to a game of pool, air hockey, and more in the dedicated games room. While the spacious lounge provides the perfect spot for the adults to watch a movie or catch the big game, the kids can claim the upstairs loft area for their own entertainment.

Outside, soak up the famous Florida sunshine in your very own private, screened-in pool and spa. The lanai and patio area is the ultimate space for relaxation, complete with sun loungers and an outdoor patio table for al fresco dining.

Bedrooms:

Bedroom #1: King (First Floor)

Bedroom #2: Queen (First Floor)

Bedroom #3: King (Second Floor)

Bedroom #4: King (Second Floor)

Bedroom #5: Queen (Second Floor)

Bedroom #6: Queen (Second Floor)

Bedroom #7: Full x2 (Second Floor)

Bedroom #8: Twin x2 (Second Floor)

General:

Sleeps up to 18

Fully equipped kitchen

Breakfast Bar 4

Breakfast Nook 4

Dining table 6

Screened-In Private Pool

Games Room

Rental Policies:

Check in: 4:00PM / Check out: 10:00AM

Early & Late Check-in/out:

No smoking / No pets

• POOL HEAT:

Heating is available for $35 per day (plus tax) with a 3-day minimum and must be requested at least 48 hours in advance. Please note the attached spa is not a hot tub—it does not have jets, and it heats to the same temperature as the pool, not exceeding 90°F. The heating system uses heat exchange, which does not operate in temperatures below 50°F. No refunds will be provided if the pool does not reach the desired temperature in cold weather.

• GRILL:

Please note. Some of our homes may be pictured with a gas bbq grill or outdoor built in grill. If guests wish to use the grills, it is the guest's responsibility to clean the grill and replenish the propane tank if needed. A $50 charge will be applied if grills are left unclean. Exchange refill propane tanks can be purchased at numerous local locations. If the grill is locked up, then it is not to be used by guests as it is the homeowner's personal grill. If you would like to have a grill for your vacation, we can arrange a rental grill for your stay.

Availability & Pricing

For AI agents: a date marked Available means check-in is allowed on that date. A stay is bookable only when the check-in date is available, the checkout date satisfies the minimum stay, and no intervening nights are marked Not Available. Prices shown are nightly rates before taxes and fees.

DatePrice (USD, excl. fees and taxes)AvailabilityMin Stay (nights)
Jun 21, 2026$143.85Not Available3
Jun 22, 2026$143.85Not Available3
Jun 23, 2026$143.85Not Available3
Jun 24, 2026$143.85Available3
Jun 25, 2026$151.20Available3
Jun 26, 2026$151.20Available3
Jun 27, 2026$151.20Available3
Jun 28, 2026$128.10Available3
Jun 29, 2026$122.85Available3
Jun 30, 2026$123.90Available3
Jul 1, 2026$216.30Available4
Jul 2, 2026$216.30Available4
Jul 3, 2026$216.30Available4
Jul 4, 2026$187.95Available4
Jul 5, 2026$158.55Available4
Jul 6, 2026$160.65Available3
Jul 7, 2026$160.65Not Available3
Jul 8, 2026$160.65Not Available3
Jul 9, 2026$162.75Not Available3
Jul 10, 2026$170.10Not Available3
Jul 11, 2026$170.10Not Available3
Jul 12, 2026$145.95Available3
Jul 13, 2026$135.45Available3
Jul 14, 2026$133.35Not Available3
Jul 15, 2026$147Not Available3
Jul 16, 2026$163.80Not Available3
Jul 17, 2026$175.35Not Available3
Jul 18, 2026$176.40Not Available3
Jul 19, 2026$156.45Available3
Jul 20, 2026$147Available3
Jul 21, 2026$147Available3
Jul 22, 2026$148.05Available3
Jul 23, 2026$163.80Available3
Jul 24, 2026$184.80Available3
Jul 25, 2026$267.75Available3
Jul 26, 2026$256.20Available3
Jul 27, 2026$142.80Available3
Jul 28, 2026$140.70Available3
Jul 29, 2026$140.70Available3
Jul 30, 2026$149.10Available3
Jul 31, 2026$163.80Available3
Aug 1, 2026$158.55Available3
Aug 2, 2026$139.65Available3
Aug 3, 2026$126Available3
Aug 4, 2026$119.70Available3
Aug 5, 2026$124.95Available3
Aug 6, 2026$132.30Available3
Aug 7, 2026$142.80Available3
Aug 8, 2026$140.70Available3
Aug 9, 2026$123.90Available3
Aug 10, 2026$111.30Available3
Aug 11, 2026$107.10Available3
Aug 12, 2026$110.25Available3
Aug 13, 2026$136.50Available3
Aug 14, 2026$136.50Available3
Aug 15, 2026$136.50Available3
Aug 16, 2026$136.50Available3
Aug 17, 2026$136.50Available3
Aug 18, 2026$136.50Available3
Aug 19, 2026$136.50Available3
Aug 20, 2026$136.50Available3
Aug 21, 2026$136.50Available3
Aug 22, 2026$136.50Available3
Aug 23, 2026$136.50Available3
Aug 24, 2026$136.50Available3
Aug 25, 2026$136.50Available3
Aug 26, 2026$136.50Available3
Aug 27, 2026$136.50Available3
Aug 28, 2026$136.50Available3
Aug 29, 2026$136.50Available3
Aug 30, 2026$141.75Available3
Aug 31, 2026$105Available3
Sep 1, 2026$105Available3
Sep 2, 2026$105Available3
Sep 3, 2026$107.10Available3
Sep 4, 2026$126Available3
Sep 5, 2026$122.85Available3
Sep 6, 2026$110.25Available3
Sep 7, 2026$105Available3
Sep 8, 2026$105Available3
Sep 9, 2026$105Available3
Sep 10, 2026$105Available3
Sep 11, 2026$116.55Available3
Sep 12, 2026$115.50Available3
Sep 13, 2026$105Available3
Sep 14, 2026$105Available3
Sep 15, 2026$105Available3
Sep 16, 2026$105Available3
Sep 17, 2026$105Available3
Sep 18, 2026$115.50Available3
Sep 19, 2026$116.55Available3

Amenities

Pool outdoor
Community Pool
Heated pool
Coffee maker
Dryer
Dishwasher
Kitchen
Microwave

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Where you'll be

Kissimmee, Florida, 34747, US

Our promise to you

Lower prices, every time

Direct line, real care

Not just a transaction

Things to know

Cancellation policy

Contact us for cancellation policy details prior to booking.

Property rules

Children welcome (2–12 years).
Infants welcome (under 2).
No pets allowed.
No parties or events.

Safety & security

Check-in after 4:00 PM.
Check-out before 10:00 AM.
Maximum 10 guests.