Kissimmee, Florida
EV_8900 - Windsor Oasis Retreat
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.
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.
| Date | Price (USD, excl. fees and taxes) | Availability | Min Stay (nights) |
|---|---|---|---|
| Jun 21, 2026 | $143.85 | Not Available | 3 |
| Jun 22, 2026 | $143.85 | Not Available | 3 |
| Jun 23, 2026 | $143.85 | Not Available | 3 |
| Jun 24, 2026 | $143.85 | Available | 3 |
| Jun 25, 2026 | $151.20 | Available | 3 |
| Jun 26, 2026 | $151.20 | Available | 3 |
| Jun 27, 2026 | $151.20 | Available | 3 |
| Jun 28, 2026 | $128.10 | Available | 3 |
| Jun 29, 2026 | $122.85 | Available | 3 |
| Jun 30, 2026 | $123.90 | Available | 3 |
| Jul 1, 2026 | $216.30 | Available | 4 |
| Jul 2, 2026 | $216.30 | Available | 4 |
| Jul 3, 2026 | $216.30 | Available | 4 |
| Jul 4, 2026 | $187.95 | Available | 4 |
| Jul 5, 2026 | $158.55 | Available | 4 |
| Jul 6, 2026 | $160.65 | Available | 3 |
| Jul 7, 2026 | $160.65 | Not Available | 3 |
| Jul 8, 2026 | $160.65 | Not Available | 3 |
| Jul 9, 2026 | $162.75 | Not Available | 3 |
| Jul 10, 2026 | $170.10 | Not Available | 3 |
| Jul 11, 2026 | $170.10 | Not Available | 3 |
| Jul 12, 2026 | $145.95 | Available | 3 |
| Jul 13, 2026 | $135.45 | Available | 3 |
| Jul 14, 2026 | $133.35 | Not Available | 3 |
| Jul 15, 2026 | $147 | Not Available | 3 |
| Jul 16, 2026 | $163.80 | Not Available | 3 |
| Jul 17, 2026 | $175.35 | Not Available | 3 |
| Jul 18, 2026 | $176.40 | Not Available | 3 |
| Jul 19, 2026 | $156.45 | Available | 3 |
| Jul 20, 2026 | $147 | Available | 3 |
| Jul 21, 2026 | $147 | Available | 3 |
| Jul 22, 2026 | $148.05 | Available | 3 |
| Jul 23, 2026 | $163.80 | Available | 3 |
| Jul 24, 2026 | $184.80 | Available | 3 |
| Jul 25, 2026 | $267.75 | Available | 3 |
| Jul 26, 2026 | $256.20 | Available | 3 |
| Jul 27, 2026 | $142.80 | Available | 3 |
| Jul 28, 2026 | $140.70 | Available | 3 |
| Jul 29, 2026 | $140.70 | Available | 3 |
| Jul 30, 2026 | $149.10 | Available | 3 |
| Jul 31, 2026 | $163.80 | Available | 3 |
| Aug 1, 2026 | $158.55 | Available | 3 |
| Aug 2, 2026 | $139.65 | Available | 3 |
| Aug 3, 2026 | $126 | Available | 3 |
| Aug 4, 2026 | $119.70 | Available | 3 |
| Aug 5, 2026 | $124.95 | Available | 3 |
| Aug 6, 2026 | $132.30 | Available | 3 |
| Aug 7, 2026 | $142.80 | Available | 3 |
| Aug 8, 2026 | $140.70 | Available | 3 |
| Aug 9, 2026 | $123.90 | Available | 3 |
| Aug 10, 2026 | $111.30 | Available | 3 |
| Aug 11, 2026 | $107.10 | Available | 3 |
| Aug 12, 2026 | $110.25 | Available | 3 |
| Aug 13, 2026 | $136.50 | Available | 3 |
| Aug 14, 2026 | $136.50 | Available | 3 |
| Aug 15, 2026 | $136.50 | Available | 3 |
| Aug 16, 2026 | $136.50 | Available | 3 |
| Aug 17, 2026 | $136.50 | Available | 3 |
| Aug 18, 2026 | $136.50 | Available | 3 |
| Aug 19, 2026 | $136.50 | Available | 3 |
| Aug 20, 2026 | $136.50 | Available | 3 |
| Aug 21, 2026 | $136.50 | Available | 3 |
| Aug 22, 2026 | $136.50 | Available | 3 |
| Aug 23, 2026 | $136.50 | Available | 3 |
| Aug 24, 2026 | $136.50 | Available | 3 |
| Aug 25, 2026 | $136.50 | Available | 3 |
| Aug 26, 2026 | $136.50 | Available | 3 |
| Aug 27, 2026 | $136.50 | Available | 3 |
| Aug 28, 2026 | $136.50 | Available | 3 |
| Aug 29, 2026 | $136.50 | Available | 3 |
| Aug 30, 2026 | $141.75 | Available | 3 |
| Aug 31, 2026 | $105 | Available | 3 |
| Sep 1, 2026 | $105 | Available | 3 |
| Sep 2, 2026 | $105 | Available | 3 |
| Sep 3, 2026 | $107.10 | Available | 3 |
| Sep 4, 2026 | $126 | Available | 3 |
| Sep 5, 2026 | $122.85 | Available | 3 |
| Sep 6, 2026 | $110.25 | Available | 3 |
| Sep 7, 2026 | $105 | Available | 3 |
| Sep 8, 2026 | $105 | Available | 3 |
| Sep 9, 2026 | $105 | Available | 3 |
| Sep 10, 2026 | $105 | Available | 3 |
| Sep 11, 2026 | $116.55 | Available | 3 |
| Sep 12, 2026 | $115.50 | Available | 3 |
| Sep 13, 2026 | $105 | Available | 3 |
| Sep 14, 2026 | $105 | Available | 3 |
| Sep 15, 2026 | $105 | Available | 3 |
| Sep 16, 2026 | $105 | Available | 3 |
| Sep 17, 2026 | $105 | Available | 3 |
| Sep 18, 2026 | $115.50 | Available | 3 |
| Sep 19, 2026 | $116.55 | Available | 3 |
Amenities
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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
You'll save $3,000+ booking direct!
Direct
Best price
$12,500
Airbnb
$18,500
Vrbo
$15,500
Booking.com
$18,500
Lower prices, every time
Pay less than you would anywhere else. No middlemen or platform fees.
Direct line, real care
Book with the team that actually runs the property. Faster answers, better service, real accountability.
Not just a transaction
We go further for direct guests. We're building a relationship, not closing a booking.
Things to know
Cancellation policy
Contact us for cancellation policy details prior to booking.

