• A cozy living room, stream your favorites on the smart TV & patio access
    A cozy living room, stream your favorites on the smart TV & patio access
  • Poolside retreat under the lanai, complete with inviting lounge chairs
    Poolside retreat under the lanai, complete with inviting lounge chairs
  • This cozy queen bedroom includes a smart TV & closet storage
    This cozy queen bedroom includes a smart TV & closet storage
  • Cozy loft vibes with a smart TV and classic Pac-Man
    Cozy loft vibes with a smart TV and classic Pac-Man
  • This luxe king suite boasts a private ensuite & smart TV and a cozy chair
    This luxe king suite boasts a private ensuite & smart TV and a cozy chair
  • Welcome to Windsor Grand Retreat!
    Welcome to Windsor Grand Retreat!
  • The updated kitchen offers loads of space & all the comforts of home
    The updated kitchen offers loads of space & all the comforts of home
  • The updated kitchen offers loads of space & all the comforts of home
    The updated kitchen offers loads of space & all the comforts of home
  • The updated kitchen offers loads of space & all the comforts of home
    The updated kitchen offers loads of space & all the comforts of home
  • Sip morning coffee or grab a bite at the coastal counter, seating 4
    Sip morning coffee or grab a bite at the coastal counter, seating 4
  • Gather for meals together at the dining table, with space for 6
    Gather for meals together at the dining table, with space for 6
  • Gather for meals together at the dining table, with space for 6
    Gather for meals together at the dining table, with space for 6
  • A cozy living room, stream your favorites on the smart TV & patio access
    A cozy living room, stream your favorites on the smart TV & patio access
  • A cozy living room, stream your favorites on the smart TV & patio access
    A cozy living room, stream your favorites on the smart TV & patio access
  • Enjoy a meal or drink in the outdoor seating by the Pool
    Enjoy a meal or drink in the outdoor seating by the Pool
  • Poolside retreat under the lanai, complete with inviting lounge chairs
    Poolside retreat under the lanai, complete with inviting lounge chairs
  • Poolside retreat under the lanai, complete with inviting lounge chairs
    Poolside retreat under the lanai, complete with inviting lounge chairs
  • Poolside retreat under the lanai, complete with inviting lounge chairs
    Poolside retreat under the lanai, complete with inviting lounge chairs
  • This cozy queen bedroom includes a smart TV & closet storage
    This cozy queen bedroom includes a smart TV & closet storage
  • Convenient half bath just steps from the pool
    Convenient half bath just steps from the pool
  • This shared bathroom contains a single vanity & shower/tub combo
    This shared bathroom contains a single vanity & shower/tub combo
  • Cozy loft vibes with a smart TV and classic Pac-Man
    Cozy loft vibes with a smart TV and classic Pac-Man
  • Cozy loft vibes with a smart TV and classic Pac-Man
    Cozy loft vibes with a smart TV and classic Pac-Man
  • Private laundry available for your stay in loft closet
    Private laundry available for your stay in loft closet
  • The queen suite boasts a private ensuite & smart TV
    The queen suite boasts a private ensuite & smart TV
  • The queen suite boasts a private ensuite & smart TV
    The queen suite boasts a private ensuite & smart TV
  • The queen suite boasts a private ensuite & smart TV
    The queen suite boasts a private ensuite & smart TV
  • Bedroom ensuite with single vanity and walk-in shower
    Bedroom ensuite with single vanity and walk-in shower
  • This luxe king suite boasts a private ensuite & smart TV and a cozy chair
    This luxe king suite boasts a private ensuite & smart TV and a cozy chair
  • Wash up in this queen ensuite, with a double vanity & walk-in shower
    Wash up in this queen ensuite, with a double vanity & walk-in shower
  • Take a snooze in this twin over full bunkbed room, with smart TV
    Take a snooze in this twin over full bunkbed room, with smart TV
  • Take a snooze in this twin over full bunkbed room, with smart TV
    Take a snooze in this twin over full bunkbed room, with smart TV
  • Freshen up in this shared full bathroom, featuring a shower/tub combo
    Freshen up in this shared full bathroom, featuring a shower/tub combo
  • This cozy bedroom retreat features a comfortable queen-size bed & smart TV
    This cozy bedroom retreat features a comfortable queen-size bed & smart TV
  • This cozy bedroom retreat features a comfortable queen-size bed & smart TV
    This cozy bedroom retreat features a comfortable queen-size bed & smart TV
  • Windsor at Westside
    Windsor at Westside
  • Windsor at Westside
    Windsor at Westside
  • Resort clubhouse
    Resort clubhouse
  • Resort tennis court
    Resort tennis court
  • Resort volley ball
    Resort volley ball
  • Resort Sweet Shoppe
    Resort Sweet Shoppe
  • Bar & Lounge
    Bar & Lounge
  • Bar & Lounge
    Bar & Lounge
  • Build your Buddy
    Build your Buddy
  • Resort arcade
    Resort arcade
  • Resort arcade
    Resort arcade
  • Resort arcade
    Resort arcade
  • Resort fitness center
    Resort fitness center
  • Resort lake
    Resort lake
  • Resort lake
    Resort lake
  • Resort lake
    Resort lake
  • Resort dock
    Resort dock
  • Aerial View
    Aerial View
  • Aerial View
    Aerial View
  • Aerial View
    Aerial View
  • Aerial View
    Aerial View
  • Aerial View
    Aerial View
  • Aerial View
    Aerial View
  • Resort pool
    Resort pool
  • Resort pool
    Resort pool
  • Resort pool seating
    Resort pool seating
  • Resort pool seating
    Resort pool seating
  • Resort pool
    Resort pool
  • Resort pool seating
    Resort pool seating
  • Resort pool lounges
    Resort pool lounges
  • Resort pool
    Resort pool
  • Resort pool lounges
    Resort pool lounges
  • Resort pool
    Resort pool
  • Resort pool
    Resort pool
  • Resort pool
    Resort pool
  • Resort volley ball
    Resort volley ball
  • Resort playground
    Resort playground
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Windsor Grand Retreat

Kissimmee, FL

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Townhouse

11 Guests

5 Bedrooms

6 Beds

5 Bathrooms

Experience comfort and convenience at Windsor Grand Retreat within Windsor at Westside Resort. Located near Orlando’s top attractions, this home offers a peaceful escape with resort-style amenities, such as a clubhouse, fitness center, and a community pool with a children’s play area, while keeping you close to the action. Whether you're planning a family vacation, a romantic retreat, or a getaway with friends, you’ll find everything you need for a relaxing stay.

With its prime location, Windsor Grand Retreat offers the perfect blend of relaxation and adventure. Just minutes from Orlando’s world-renowned attractions, including Walt Disney World and Universal Studios, you’ll have endless entertainment options right at your fingertips. When you're ready to explore beyond the parks, nearby shopping at Orlando Vineland Premium Outlets and dining at local favorites in Celebration provide even more to discover. After a day of excitement, return to the comfort and luxury of Windsor Grand Retreat, where resort-style amenities and thoughtfully designed spaces await.

Step inside to a welcoming and stylish living area, featuring two spacious sofas surrounding a smart TV—ideal for movie nights or unwinding after a day of adventure. From the living room, walk out to the lanai, where seating for six invites you to sip your morning coffee while soaking in the Florida breeze or enjoy a sunset dinner in the fresh air. Wrap up your evenings with a dip in the private pool or lounge poolside with a cocktail in hand while the kids have some friendly competition in the loft with an arcade table game, Pac man, and a smart TV.

Along with an outdoor grill, the fully equipped kitchen features sleek dark wood cabinets and ample stone countertops with an oversized island. Whether you're preparing a quick breakfast before heading out to the parks or cooking a full meal, you’ll have everything you need at your fingertips. The kitchen also offers counter seating for four, perfect for a casual snack or chatting while meals are being prepared. Just beyond, the dining table comfortably seats six, making it easy to gather for home-cooked meals or takeout from one of the area’s fantastic restaurants. Windsor Grand Retreat is the perfect home base for an unforgettable Orlando getaway.

This home comfortably sleeps 11 guests between 5 private bedrooms.

Bedroom #1 includes a queen size bed and a smart TV.

Bedroom #2 includes a queen size bed, a smart TV, and an ensuite bathroom with a single vanity and a walk-in shower.

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 includes a full size bed, a twin size bed, and a smart TV.

Bedroom #5 includes a queen size bed and a smart TV.

This home also includes an outdoor half bathroom and two additional full bathrooms, one with a single vanity and a walk-in shower, another with a dual vanity and a shower/tub combo.

THINGS TO NOTE:
• Washer and dryer in home.
• Lot parking available for 3 vehicles.
• Portable crib and high chair provided.
• Required stairs.

• Patio grills. Your home might have a BBQ grill installed on the patio. If you decide to use the grill, there is a $95 fee. You should request to use the BBQ grill prior to your arrival as we have locks on the grills. After each checkout and before any arrival, our operations team checks the grills by taking pictures and/or videos. If it is determined that you or your guests used the grill, you will receive communication from our guest services team advising you that your card will be charged. BBQ grill fees are non-refundable. If there is not a BBQ on site one MIGHT be able to be added depending on availably and HOA regs. Cost to rent a BBQ off site is $150/week and cannot be guaranteed.

• Pool can be heated for an additional fee of $29 per night. Please contact our customer service after you have booked your stay for further payment.
- Please be advised that the pool heat is not included in your reservation cost. Charges for pool heat are non-refundable unless the heating system is experiencing issues. Pools need a minimum of 48 hours to heat properly. Pool heat is added for the whole stay or none of the stay. There is no partial pool heat allowed due to the high costs to bring up the temperature in the home.
Note: cold fronts in the winter months (<60 degrees) can cause the electric pool equipment not to function; this does not constitute mechanical failure and refunds for pool heat will not be issued. Home with heat pumps can only pull heat from the ambient air, and generally only 15-20 degrees above ambient is the temp the pools can get to.

Note: cold fronts in the winter months (<60 degrees) can cause the electric pool equipment not to function; this does not constitute mechanical failure and refunds for pool heat will not be issued. Home with heat pumps can only pull heat from the ambient air, and generally only 15-20 degrees above ambient is the temp the pools can get to.
• Community amenities such as pools and hot tubs are subject to weather, repairs and availability per the HOA. Orlando does get lightning, hurricanes, hail storms, wind and a variety of other weather extremes. We cannot guarantee availability with HOA amenities. Please call us if you are concerned if a community amenity is available or under repair.

Located just a short drive from Walt Disney World, Universal Studios, and SeaWorld, this resort in Kissimmee, Florida provides easy access to thrilling theme parks and entertainment. For those looking to explore beyond the parks, nearby activities include championship golf courses, scenic airboat tours through the Everglades, and shopping at premium outlets. Dining options range from casual eateries to fine dining, with vibrant nightlife and entertainment at Disney Springs and Old Town Kissimmee. Whether you’re seeking adventure or relaxation, Windsor at Westside Resort offers the perfect home base for an unforgettable Central Florida getaway.

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Where you'll sleep

Bedroom 1

3 Queen

Bedroom 2

1 King

Bedroom 3

1 Twin

Bedroom 4

1 Full


Amenities

  • Air Conditioning
  • Arcade
  • BBQ
  • Blender
  • Body Soap
  • Call to Book
  • Carbon Monoxide Detector
  • Ceiling Fan
  • Close to ATM/Bank
  • Close to Aquarium
  • Close to Biking Trails
  • Close to Downtown
  • Close to Equipment Rentals
  • Close to Golf
  • Close to Groceries
  • Close to Gym
  • Close to Hiking Trails
  • Close to Mail Services
  • Close to Medical Services
  • Close to Movie Theater
  • Close to Museums
  • Close to Park
  • Close to Rec Center
  • Close to Restaurants
  • Close to Shopping
  • Close to Shuttle
  • Close to Theme Parks
  • Close to Town
  • Close to Water Parks
  • Close to Zoo
  • Clubhouse
  • Coffee Maker
  • Communal Pool
  • Cookware
  • Dining Room
  • Dining Table
  • Dishes & Silverware
  • Dishwasher
  • Dryer
  • Essentials
  • Fitness Room
  • Foosball
  • Full Kitchen
  • Garden View
  • Guest House
  • Hair Dryer
  • Heating
  • High Chair
  • Hiking
  • Hot Tub
  • Hot Water
  • Internet
  • Iron Board
  • Lanai
  • Laptop Workspace
  • Linens Provided
  • Loft
  • Long Term Stays
  • Microwave
  • Oven
  • Pack and Play
  • Parking
  • Parking Info
  • Parking Lot Parking
  • Pool Table
  • Private Entrance
  • Private Pool
  • Refrigerator
  • Required Stairs
  • Shampoo/Conditioner
  • Smoke Detector
  • Stove
  • Television
  • Toaster
  • Washer
  • Wineware

House rules

  1. This property is non-smoking. You will be fined $500 plus mitigation costs
  2. Pets of any kind are not allowed. You will be fined $500 plus cleaning costs
  3. Do not exceed the maximum number of cars or occupants
  4. Do not park automobiles in the grass, as you will be towed/ticketed
  5. Always observe quiet hours after 9PM, as there are neighbors close by
  6. Failure to follow these rules/procedures and the rules/procedures stated in the agreed upon rental agreement could result in fines, forfeit of the security deposit, and in some cases being asked to leave without a refund

Book with Confidence

Our policy is simple and transparent. Read our cancellation policy >

Enhanced Cleaning Protocols

Your safety is our priority. Our professional housekeepers are going above and beyond to provide your family with a clean stay.

Local Support

Our customer care department is available round-the-clock to assist you with any queries or concerns you may have. Additionally, our local office is open during normal business hours to serve you. In case of emergencies outside of business hours, please contact our after-hours support team.


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March 2025
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June 2025
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July 2025
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$197
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$146
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$172
   
August 2025
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$234
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$227
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$169
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$146
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$169
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$203
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$193
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$146
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$133
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$129
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$151
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$181
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$172
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$137
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$149
           
September 2025
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$119
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October 2025
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November 2025
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$135
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$119
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$126
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$142
           
December 2025
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$131
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January 2026
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$130
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$155
February 2026
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$133
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$122
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$123
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$119
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$137
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$128
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March 2026
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$194
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$178
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$165
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$165
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$189
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$247
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$240
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$251
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$259
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$210
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$255
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$212
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$191
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