Townhouse - Rating 4.8 (28)

Windsor Grand Retreat - 11ppl!

As low as $119.00 / night + taxes & fees

  • Location: Kissimmee
  • Type: Townhouse
  • View: Garden View

Bedroom 5 bedrooms
Bathroom 4 baths
Half Bathroom 1 half bath
Guests 11 guests
Pets Not Allowed Pets Not Allowed

Summary Summary
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.
Description Description
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.
• 3 Portable crib’s, 2 high chairs and 1 stroller provided.
• Required stairs.

• Please note that our community has implemented updated security and access procedures. Gate codes have been permanently deactivated, and all guests must now stop at the Tripoli Ct. guardhouse upon arrival. Access is granted with a proxy card, which will be issued upon presentation of a valid ID and booking confirmation (including property address and stay dates). A one-time $20 vehicle use fee will apply per vehicle starting August 1, 2025 . Each home has a maximum number of allowed vehicles, Any additional vehicles must be parked off-site. These new procedures are designed to enhance security and ensure a smooth experience for all guests.

• 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.
• 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.

- Due to the high incidence of theft and damage, we do not provide wash cloths for bathing. If you need wash cloths, you will want to bring your own. However, bath towels and hand towels are provided.

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.

For all reservations made through our official website, guests will be required to complete a secure verification process through our third-party partner, Autohost. This process helps us ensure the safety and integrity of all stays. Our full privacy policy, which explains how your information is handled and protected, is available upon request prior to booking.

This property is non-smoking. You will be fined $500 plus mitigation costs
Pets of any kind are not allowed. You will be fined $500 plus cleaning costs
Do not exceed the maximum number of cars or occupants
Do not park automobiles in the grass, as you will be towed/ticketed
Always observe quiet hours after 9PM, as there are neighbors close by
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

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Bedding Bedding
Queen Bed icon
3 QUEEN BEDS
King Bed icon
1 KING BED
Full Bed icon
1 DOUBLE BED
Twin Bed icon
1 SINGLE BED

Amenities 54 Amenities
  • Air conditioning
  • BBQ grill
  • Bed linens
  • Blender
  • Body soap
  • Carbon monoxide detector
  • Ceiling fan
  • Coffee maker
  • Communal pool
  • Conditioner
  • Cookware
  • Dining table
  • Dishes and silverware
  • Dishwasher
  • Downtown
  • Dryer
  • Essentials
  • Foosball table
  • Free parking on premises
  • Garden View
  • Golf - Optional
  • Gym
  • Hair dryer
  • Heating
  • High chair
  • Hot tub
  • Hot water
  • Internet
  • Iron
  • Kitchen
  • Laptop friendly workspace
  • Long term stays allowed
  • Microwave
  • Museums
  • Outdoor pool
  • Oven
  • Pack ’n Play/travel crib
  • Private entrance
  • Private pool
  • Refrigerator
  • Shampoo
  • Shopping
  • Smoke detector
  • Stove
  • Suitable for children (2-12 years)
  • Suitable for infants (under 2 years)
  • Theme Parks
  • Toaster
  • Town
  • TV
  • Washer
  • Water Parks
  • Wine glasses
  • Wireless Internet

Location Location

Reviews Rating 4.8 (28) Reviews
Rating 5
todo muy bien. resolvieron todo de la mejor forma. muy contentos
Anonymous - Posted: 2/7/2026
Thank you so much, Yago, for your kind review! We’re very happy to hear that everything went well and that you were pleased with how things were handled during your stay. It was a pleasure hosting you, and we truly appreciate your support. We hope to welcome you back again soon!
Grand Welcome staff
Posted: 2/16/2026
Rating 3
We enjoyed aspects of our stay, but there were a few issues worth noting for future guests. There was maintenance at the property prior to our arrival, which we were not notified about ahead of time. We also paid for a heated pool; however, due to outdoor temperatures, the pool was still quite cold and not really usable despite the added cost. The community center is about an 11-minute walk from the property. Inner tubes are not provided by either the host or the community center for the lazy river, and we were unable to locate any pool toys at the property. Additionally, the trash barrel on the porch had a significant number of fruit flies, which made their way into the house—likely while the maintenance crew had the door open. Lastly, checkout is at 10:00 a.m. We were in the process of wheeling our suitcases out right at 10:00, and the host rang the doorbell at that exact time, which felt a bit rushed.
Anonymous - Posted: 1/27/2026
Rating 5
We had a great stay! I came with a group of eight people, and there was more than enough space for everyone. The house was very clean and comfortable. The only small thing I would suggest improving is the curtains in the bedrooms—they don’t fully cover the blinds, so it gets extremely bright in the morning and can make sleeping in a bit difficult. Other than that, everything was excellent and we really enjoyed our stay and hope to book again soon!
Anonymous - Posted: 1/20/2026
Rating 5
Muy buen lugar, cómodo, accesible.
Anonymous - Posted: 1/13/2026
Thank you, Yomirla, for your kind words and valuable feedback! We're glad you found our place comfortable. We're appreciate your insights and hope to welcome you back soon!
Grand Welcome staff
Posted: 1/18/2026
Rating 5
Excellent place to stay Neat and clean rooms Adequate essential supplies for bathroom and kitchen Great location We wish we had more time to spend there
Anonymous - Posted: 12/22/2025
Thank you, Farooq! We're thrilled you enjoyed your stay and appreciate your kind words. Your feedback is valuable to us, and we’ll certainly look into it. We look forward to welcoming you and your family back for a longer visit!
Grand Welcome staff
Posted: 12/29/2025
Rating 5
Easy To Find Nice Neighborhood Easy Instructions Would Recommend To Others And Would Definitely Use Again If Needed In The Future
Anonymous - Posted: 12/1/2025
Thank you, Justin! We're thrilled you enjoyed your stay and found everything to your liking. Your recommendation means a lot to us. We look forward to welcoming you back in the future!
Grand Welcome staff
Posted: 12/8/2025
Rating 5
This property was amazing! Incredibly clean, great location, the hosts were very attentive and easy to reach. Will definitely recommend!
Anonymous - Posted: 11/19/2025
Thank you, Veronica! We're thrilled to hear you enjoyed your stay and found everything to your satisfaction. Your recommendation means so much to us. We look forward to welcoming you back soon!
Grand Welcome staff
Posted: 11/29/2025
Rating 4
Thank you for the stay. The only issue I would say about the location is the temperature change and limited trash bags. Regardless we had planned for this and enjoyed our time.
Anonymous - Posted: 10/27/2025
Thank you, Jennifer, for your thoughtful feedback! We're glad to hear you enjoyed your stay despite the minor challenges. We appreciate your insights and look forward to welcoming you back for another great experience!
Grand Welcome staff
Posted: 11/10/2025
Rating 5
Beautiful house and great value! We loved that we were just 15 minutes away from the Disney Parks in a quiet beautiful neighborhood. The house felt like it was brand new!
Anonymous - Posted: 10/25/2025
Thank you, Michael! We’re so glad you enjoyed your stay and found our home beautiful and conveniently located. Your feedback is much appreciated, and we’ll look into it. We can’t wait to welcome you back for another great visit!
Grand Welcome staff
Posted: 11/3/2025
Rating 5
This place was an amazing place to stay. It was very homey and clean. I would definitely stay here again if I ever find myself in the area.
Anonymous - Posted: 10/14/2025
Thank you, Giovanni! We're thrilled to hear you found our place homey and clean. Your kind words mean a lot to us, and we can't wait to welcome you back on your next visit!
Grand Welcome staff
Posted: 11/10/2025
Rating 5
Our 2 families had excellent stay at this Airbnb. We had travelled from Australia to visit the parks so it was nice to spread out and use the multiple bathrooms. Unfortunately we didn’t have time to utilise the resort facilities but they looked great.
Anonymous - Posted: 10/12/2025
Thank you, Anita! We're thrilled to hear that you and your families enjoyed your stay and found the space accommodating. We appreciate your feedback and will certainly take it into account for future guests. We’d love to welcome you back anytime!
Grand Welcome staff
Posted: 10/14/2025
Rating 5
Very nice place. We had plenty of room and it was clean. We enjoyed our stay there.
Anonymous - Posted: 10/8/2025
Rating 5
Nuestra estadía fue excelente. El lugar es tal como se muestra en las fotos: limpio, cómodo y muy bien equipado. La ubicación está muy bien, con todo lo necesario a pocos minutos. La comunicación con el anfitrión fue rápida y clara en todo momento, siempre atento a cualquier consulta. Sin duda, hizo que nuestro viaje fuera mucho más fácil y agradable. Recomendamos totalmente este alojamiento y sin duda volveríamos en el futuro.
Anonymous - Posted: 9/24/2025
Thank you so much, Fran, for your wonderful review! We’re thrilled to hear that you found the home clean, comfortable, and well-equipped, and that the location worked out so well for your trip. It’s also great to know our communication helped make your stay easier and more enjoyable—that’s always our goal. We truly appreciate your kind recommendation and would be delighted to welcome you back anytime in the future.
Grand Welcome staff
Posted: 10/6/2025
Rating 5
My family and I enjoyed the home down to the community resort area. The bartender was very cool she had us very comfortable. The home fit us all and we even enjoyed the personal pool. Really chill and relaxed stay we had no issues.
Anonymous - Posted: 9/10/2025
Thank you, Kelisea! I'm thrilled to hear you and your family enjoyed your stay and felt comfortable. It’s wonderful that you loved the home and the community amenities. We look forward to welcoming you back for another relaxing getaway!
Grand Welcome staff
Posted: 9/22/2025
Rating 5
had an amazing stay at this Airbnb! The place was spotless, comfortable, and exactly as described. The host was very responsive, friendly, and made the check-in process super easy. The home had all the amenities to make my stay comfortable, and I really appreciated the thoughtful touches. I would definitely stay here again and highly recommend it to anyone looking for a great Airbnb experience!
Anonymous - Posted: 9/10/2025
Rating 5
We didn’t have any questions throughout our stay so no need for communication. Everything was explained thoroughly! Only thing I would recommend is switching the white sheets and towels. There were stains on them both which made me not utilize them but everything else was perfect! Would recommend 1000 times!
Anonymous - Posted: 8/26/2025
Rating 5
It was amazing It felt like home and they was always checking on me I must say I would definitely stay there again
Anonymous - Posted: 8/20/2025
Thank you, Shandrika! We're thrilled to hear you felt at home during your stay and appreciated our attention. Your kind words mean so much to us. We can't wait to welcome you back for another amazing visit!
Grand Welcome staff
Posted: 8/23/2025
Rating 5
We loved our stay, the kids loved the community pool area. The food at the pool was pretty good as well. Overall our stay was comfortable. We will stay again!
Anonymous - Posted: 8/14/2025
Rating 5
Windsor Grand Retreat – 5 Stars! We stayed Aug 2–8 and loved everything! Spacious condo with comfy beds, TVs in every bedroom, and plenty of bathrooms. The fridge’s ice maker saved us money for daily adventures. The pool was perfect—loved the sitting ledge and the convenient outdoor bathroom. Patio furniture was cozy, living room was spacious, and having a washer/dryer was a big plus. Kids enjoyed the basketball court, water park and extra pool that was available in the retreat. Gated community and great communication with the owners. We’ll definitely rent again!
Anonymous - Posted: 8/9/2025
Rating 5
Overall, we had a great stay and would definitely come again! The house was clean and perfect for our needs. The private pool was a huge hit with the kids, especially after long days at the parks. The clubhouse pool was also a great bonus—clean, fun, and relaxing. Check-in to the house itself was easy, but the experience at the security gate was frustrating. The guard on duty was short with us, seemed irritated, and didn’t make us feel very welcome. It was an unpleasant start to an otherwise great trip, and we hope the property management team addresses this for future guests. The floors in the home left a bit of a sticky residue, but everything appeared clean overall. Again, despite the rough start, we really enjoyed our stay and would happily return!
Anonymous - Posted: 8/2/2025
Thank you, Tanner, for your kind words! We're thrilled to hear you enjoyed your stay and the kids loved the pool. We sincerely apologize for the experience at the security gate—your feedback is important, and we’ll be sure to share it with the appropriate team so it can be improved for future guests. We also appreciate your note on the floors and will have our cleaning team take extra care. We’re happy you had a wonderful stay and are thrilled to know you’d return—we’d love to host you again!
Grand Welcome staff
Posted: 8/17/2025
Rating 5
Great place to stay if you have a big family. The kids enjoyed the pool. Very clean and spacious. Would come again on my next vacation
Anonymous - Posted: 7/29/2025
Thank you, Karen! We’re thrilled to hear your family enjoyed the spaciousness and pool. Your feedback is invaluable, and we can’t wait to welcome you back for your next vacation!
Grand Welcome staff
Posted: 8/11/2025
Rating 5
Loved our stay !
Anonymous - Posted: 7/28/2025
Thank you, Yesleen! We're thrilled to hear you loved your stay. Your feedback means so much to us, and we can't wait to welcome you back for another wonderful experience!
Grand Welcome staff
Posted: 8/11/2025
Rating 5
My family and I enjoyed our stay and were very pleased with the cleanliness of the house and all the rooms. The place was easy to find and close enough to the parks, perfect to fit our very large family :) The hosts were very accommodating and responsive, it was a wonderful experience!
Anonymous - Posted: 7/14/2025
Thank you, Lismary! We’re so happy to hear that you and your family had such a wonderful experience. Your kind words about our home and hospitality mean a lot to us. We can’t wait to welcome you back for another stay!
Grand Welcome staff
Posted: 7/17/2025
Rating 5
My family enjoyed our stay here very clean and lots of space in a safe area. We enjoyed the personal pool as well!
Anonymous - Posted: 6/24/2025
Thank you so much, Ivan! We truly appreciate you choosing our home and are delighted to hear that you and your family enjoyed your stay. It means a lot to us that you loved the space, cleanliness, and especially the personal pool. We can’t wait to welcome you back for another wonderful experience!
Grand Welcome staff
Posted: 6/30/2025
Rating 4
Very nice place. Just wish more was put into the cleaning of the place before we arrived but overall lovely place! Enjoyed our time there for sure
Anonymous - Posted: 6/19/2025
Rating 5
Beautiful house nice location the owner are friendly I’ll recommend it
Anonymous - Posted: 6/17/2025
Thank you for your kind words! We’re so glad you enjoyed the house and location. It was a pleasure hosting you, and we truly appreciate your recommendation. We hope to welcome you back again soon!
Grand Welcome staff
Posted: 6/20/2025
Rating 5
absolutely beautiful and a great place to stay!! would love to come back and enjoy another vacation !!! :)
Anonymous - Posted: 5/30/2025
Rating 5
Great place to stay, Everything was perfect! I wish that there were ceiling fans though because the a/c only went as low as 70 degrees and we like it cooler than that. Otherwise PERFECT!
Anonymous - Posted: 5/14/2025
Thank you so much for your wonderful review! We're thrilled to hear everything was perfect for you. We appreciate your feedback about the ceiling fans and cooler temperature preferences— our team will definitely consider these options to enhance future stays. We’d love to welcome you back anytime!
Grand Welcome staff
Posted: 6/13/2025
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