Kissimmee, Florida

5 Bedroom/4.5 Bathroom Windsor Westside (2444 DS)

5 bedrooms 5 beds 5 baths 12 guests New

About the property

• Community: Windsor At Westside • 5 Bedrooms/ 4.5 Bathrooms/ Sleeps 12 • Disney (6.7 mi) SeaWorld (16.1 mi) Legoland (27.2 mi) • Convention Center (10.5 mi) Universal Studios (19.9 mi) • Location: Dubai Street, Kissimmee FL 34747 DETAILS • Central AC • Washer & Dryer • Gated Community • Free Cable TV & WIFI • Fully Equipped Kitchen • Towels & Linens Provided • Washcloths Are Not Provided • Family Room with Flat Screen TV • Hair Dryers, Iron & Ironing Board • Private Door Code for Each Guest Stay • Outdoor Patio Furniture with Sun Loungers • Pack 'n play/ High Chair (Free Upon Request) • Private Screened-in Pool + Child Safety Pool Fence - BEDROOM SETUP FIRST FLOOR • Bedroom 1: 1 Queen Bed + Bathroom In Hallway + Half Bathroom In Pool Area SECOND FLOOR • Bedroom 2: 1 Bunk Bed (Twin Over Full) • Bedroom 3: 1 Bunk Bed (Twin Over Full) + Shared Bathroom Between Bedrooms 2 & 3 • Bedroom 4: 1 King Bed (Private Bathroom) • Bedroom 5: 1 Queen Bed (Private Bathroom) - USEFUL INFORMATION • CHECKING IN AND OUT - Check-in after 4:00 PM - Checkout before 10:00 AM • WINDSOR AT WESTSIDE PARKING - Parking is free. - Maximum of 3 Vehicles. Vehicles exceeding the limit will not be permitted entry and must arrange for offsite parking. - Commercial vehicles, RV's, trailers, buses, golf carts, recreational vehicles or watercraft is not permitted at Windsor At Westside. There is a $50 fee violation. • THIS HOME IS SELF-CATERING We do provide a small welcome kit to get you started. Please stop by the nearest supermarket to gather any additional items you may need for the duration of your stay. • POOL HEAT - OPTIONAL 1-Cost: $35 per day. 2-Minimum: 2 consecutive days. 3-Temperature will not exceed 95F. 4-Must be requested 48h in advance. 5-Attached spa is NOT a jacuzzi. It does not have jets. It can only be heated if the entire pool is heated. They both will have the same temperature. 6-Heater works through HEAT EXCHANGE and WILL NOT WORK in cold weather. If you still would like to heat the pool during cold conditions and it does not reach the desired temperature, we will not be able to offer a refund. Our pool heater pumps have a safety system that prevents overheating of the element when the pump is working overtime in cold weather conditions. This way causes a temporary shut off of services automatically until the pump can regain its functionality efficiently. This is optional and may not be available at times. • BBQ RENTAL - OPTIONAL - Cost: $75 All Stay • TRASH DISPOSAL Please dispose the trash daily in the plastic bench or dumpster to keep a clean home. • HOUSEKEEPING There is no daily housekeeping service provided in the rental rate. Before check-in, the unit will be thoroughly cleaned and inspected by a professional cleaning company. Mid-stay cleaning services during your stay can be requested for an additional fee. • ONLINE PURCHASE If the online seller uses USPS, it will not get delivered as the Post Office does not recognize vacation homes as regular addresses and the package will be returned back to the sender. Only UPS, DHL and FEDEX delivers them. In some resorts the packages are delivered to the clubhouse. Fees may apply. Some resorts may not accept them. Keep in mind we are not responsible for unexpected issues with your online purchases. If you have any questions, please contact us. WINDSOR AT WESTSIDE RESORT AMENITIES • Extraordinary 5000 sq.ft. clubhouse • Lounge • Lake Pier • Lazy River • Water Slide • Sundry Shop • Games Room • Video Arcade • Fitness Center • Kids Play Area • Pool Side Tiki Bar • On-site sundries shop • Huge Resort-Style Pool • Gated with 24h Attendant • Tennis and Basketball Courts • Volleyball Court And Soccer Field PLEASE NOTE: Additional charges apply when the owner has to fix something or pay for additional cleaning if not complied.

• Community: Windsor At Westside • 5 Bedrooms/ 4.5 Bathrooms/ Sleeps 12 • Disney (6.7 mi) SeaWorld (16.1 mi) Legoland (27.2 mi) • Convention Center (10.5 mi) Universal Studios (19.9 mi) • Location: Dubai Street, Kissimmee FL 34747 DETAILS • Central AC • Washer & Dryer • Gated Community • Free Cable TV & WIFI • Fully Equipped Kitchen • Towels & Linens Provided • Washcloths Are Not Provided • Family Room with Flat Screen TV • Hair Dryers, Iron & Ironing Board • Private Door Code for Each Guest Stay • Outdoor Patio Furniture with Sun Loungers • Pack 'n play/ High Chair (Free Upon Request) • Private Screened-in Pool + Child Safety Pool Fence - BEDROOM SETUP FIRST FLOOR • Bedroom 1: 1 Queen Bed + Bathroom In Hallway + Half Bathroom In Pool Area SECOND FLOOR • Bedroom 2: 1 Bunk Bed (Twin Over Full) • Bedroom 3: 1 Bunk Bed (Twin Over Full) + Shared Bathroom Between Bedrooms 2 & 3 • Bedroom 4: 1 King Bed (Private Bathroom) • Bedroom 5: 1 Queen Bed (Private Bathroom) - USEFUL INFORMATION • CHECKING IN AND OUT - Check-in after 4:00 PM - Checkout before 10:00 AM • WINDSOR AT WESTSIDE PARKING - Parking is free. - Maximum of 3 Vehicles. Vehicles exceeding the limit will not be permitted entry and must arrange for offsite parking. - Commercial vehicles, RV's, trailers, buses, golf carts, recreational vehicles or watercraft is not permitted at Windsor At Westside. There is a $50 fee violation. • THIS HOME IS SELF-CATERING We do provide a small welcome kit to get you started. Please stop by the nearest supermarket to gather any additional items you may need for the duration of your stay. • POOL HEAT - OPTIONAL 1-Cost: $35 per day. 2-Minimum: 2 consecutive days. 3-Temperature will not exceed 95F. 4-Must be requested 48h in advance. 5-Attached spa is NOT a jacuzzi. It does not have jets. It can only be heated if the entire pool is heated. They both will have the same temperature. 6-Heater works through HEAT EXCHANGE and WILL NOT WORK in cold weather. If you still would like to heat the pool during cold conditions and it does not reach the desired temperature, we will not be able to offer a refund. Our pool heater pumps have a safety system that prevents overheating of the element when the pump is working overtime in cold weather conditions. This way causes a temporary shut off of services automatically until the pump can regain its functionality efficiently. This is optional and may not be available at times. • BBQ RENTAL - OPTIONAL - Cost: $75 All Stay • TRASH DISPOSAL Please dispose the trash daily in the plastic bench or dumpster to keep a clean home. • HOUSEKEEPING There is no daily housekeeping service provided in the rental rate. Before check-in, the unit will be thoroughly cleaned and inspected by a professional cleaning company. Mid-stay cleaning services during your stay can be requested for an additional fee. • ONLINE PURCHASE If the online seller uses USPS, it will not get delivered as the Post Office does not recognize vacation homes as regular addresses and the package will be returned back to the sender. Only UPS, DHL and FEDEX delivers them. In some resorts the packages are delivered to the clubhouse. Fees may apply. Some resorts may not accept them. Keep in mind we are not responsible for unexpected issues with your online purchases. If you have any questions, please contact us. WINDSOR AT WESTSIDE RESORT AMENITIES • Extraordinary 5000 sq.ft. clubhouse • Lounge • Lake Pier • Lazy River • Water Slide • Sundry Shop • Games Room • Video Arcade • Fitness Center • Kids Play Area • Pool Side Tiki Bar • On-site sundries shop • Huge Resort-Style Pool • Gated with 24h Attendant • Tennis and Basketball Courts • Volleyball Court And Soccer Field PLEASE NOTE: Additional charges apply when the owner has to fix something or pay for additional cleaning if not complied.

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) AvailabilityMin Stay (nights)
May 19, 2026$105Not Available1
May 20, 2026$105Not Available1
May 21, 2026$105Available1
May 22, 2026$171.15Not Available1
May 23, 2026$186.90Not Available1
May 24, 2026$164.85Not Available2
May 25, 2026$114.45Not Available2
May 26, 2026$106.05Not Available2
May 27, 2026$107.10Not Available2
May 28, 2026$120.75Not Available2
May 29, 2026$149.10Not Available3
May 30, 2026$148.05Not Available3
May 31, 2026$117.60Not Available3
Jun 1, 2026$122.85Not Available3
Jun 2, 2026$117.60Not Available3
Jun 3, 2026$139.65Not Available4
Jun 4, 2026$149.10Not Available4
Jun 5, 2026$137.55Available1
Jun 6, 2026$165.90Not Available4
Jun 7, 2026$136.50Not Available3
Jun 8, 2026$127.05Not Available3
Jun 9, 2026$149.10Not Available3
Jun 10, 2026$132.30Not Available4
Jun 11, 2026$150.15Not Available4
Jun 12, 2026$211.05Not Available4
Jun 13, 2026$206.85Not Available4
Jun 14, 2026$142.80Not Available3
Jun 15, 2026$153.30Not Available3
Jun 16, 2026$182.70Not Available3
Jun 17, 2026$198.45Not Available4
Jun 18, 2026$181.65Not Available4
Jun 19, 2026$164.85Available1
Jun 20, 2026$201.60Available4
Jun 21, 2026$170.10Available3
Jun 22, 2026$163.80Available3
Jun 23, 2026$176.40Available3
Jun 24, 2026$177.45Available4
Jun 25, 2026$196.35Available4
Jun 26, 2026$253.05Available4
Jun 27, 2026$231Available4
Jun 28, 2026$166.95Available3
Jun 29, 2026$155.40Available3
Jun 30, 2026$162.75Available3
Jul 1, 2026$181.65Available4
Jul 2, 2026$267.75Available4
Jul 3, 2026$299.25Available4
Jul 4, 2026$303.45Available4
Jul 5, 2026$177.45Available3
Jul 6, 2026$164.85Available3
Jul 7, 2026$185.85Available3
Jul 8, 2026$180.60Available2
Jul 9, 2026$164.85Available1
Jul 10, 2026$248.85Not Available4
Jul 11, 2026$231Not Available4
Jul 12, 2026$151.20Not Available3
Jul 13, 2026$142.80Not Available3
Jul 14, 2026$117.60Available1
Jul 15, 2026$155.40Available4
Jul 16, 2026$182.70Available4
Jul 17, 2026$234.15Available4
Jul 18, 2026$279.30Available4
Jul 19, 2026$182.70Available3
Jul 20, 2026$171.15Available3
Jul 21, 2026$173.25Available3
Jul 22, 2026$211.05Available4
Jul 23, 2026$218.40Available4
Jul 24, 2026$290.85Available4
Jul 25, 2026$286.65Available4
Jul 26, 2026$202.65Available3
Jul 27, 2026$166.95Available3
Jul 28, 2026$199.50Available3
Jul 29, 2026$199.50Available4
Jul 30, 2026$203.70Available4
Jul 31, 2026$252Available4
Aug 1, 2026$244.65Available4
Aug 2, 2026$170.10Available3
Aug 3, 2026$157.50Available3
Aug 4, 2026$158.55Available3
Aug 5, 2026$166.95Available4
Aug 6, 2026$182.70Available4
Aug 7, 2026$207.90Available4
Aug 8, 2026$199.50Available4
Aug 9, 2026$152.25Available3
Aug 10, 2026$160.65Available3
Aug 11, 2026$164.85Available3
Aug 12, 2026$151.20Available4
Aug 13, 2026$164.85Available4
Aug 14, 2026$175.35Available4
Aug 15, 2026$173.25Available4
Aug 16, 2026$136.50Available3
Aug 17, 2026$135.45Available3

Where you'll sleep

Amenities

Pool outdoor
Gym
BBQ Area
Microwave
Shower
High chair
Wifi
Hair dryer

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Where you'll be

Kissimmee, Florida, 34747, United States

Experience the vibrant energy of Kissimmee, where world-class entertainment and Florida’s natural beauty converge in one of the world’s most sought-after destinations. Disney’s Animal Kingdom Theme Park is minutes away, offering immersive wildlife encounters and legendary storytelling, while Margaritaville Resort Orlando and The Grove Resort & Water Park Orlando provide endless aquatic adventures a short drive from your door. For everyday

Things to know

Cancellation policy

Contact us for cancellation policy details prior to booking.

Property rules

Not suitable for children (2–12 years).
Not suitable for infants (under 2).
No pets allowed.
No parties or events.

Safety & security

Check-in after 4:00 PM.
Check-out before 10:00 AM.
Maximum 12 guests.