2821 Windsor Hills

2 BR
2 Baths
Sleeps 6

Located minutes from Walt Disney World ® Property, this beautifully renovated single-story, second-floor condo in the Windsor Hills Resort features a freshly painted interior and brand-new flooring throughout. This second-story condo is accessible by stairs or one of 2 elevators in the building. Enjoy the convenience of stainless steel appliances, smart televisions, and stylish furniture (and new pillow top mattresses)!

This 2-bedroom, 2-bathroom condo has been thoughtfully remodeled from top to bottom. The open floor plan seamlessly integrates the living, dining, and kitchen areas, making it easy for everyone to stay connected and enjoy the space together. Step onto the fully screened-in patio to savor your morning coffee or an evening drink. The fully equipped kitchen boasts major and small appliances, dinnerware, cookware, and newly installed granite countertops paired with stainless steel appliances. The dining area comfortably seats six, perfect for shared meals and lively conversations. Both bedrooms are furnished with beautiful new pieces, pillow-top mattresses, and flat-screen TVs. Subtle theming adds a playful touch to your Central Florida stay.


• Queen MasterBedroom w/En-Suite Bath, Flat Screen TV & Walk In Closet

• En-suite bathroom to Queen Bedroom w/Walk In Shower

• Guest Bedroom w/Two Full Beds, Flat Screen TV & Walk In Closet

• Shared Bath w/Shower & Tub Combination


• Contactless Free check-in and Check-out

• Free Cable, Wi-Fi, and Streaming Television

• Beautiful LVP Flooring Throughout; no carpet!

• All New Furniture Throughout the Home

• New Bedding, Towels & Linens

• Laundry Area w/Full Size Washer & Dryer

• Smart TVs Throughout the Home

• Pack N Play and High Chair

• Patio Furniture

• Free Parking for 3 vehicles

• Gated, secure community with 24-hour security

• Fully stocked kitchen (dishes, silverware, bakeware, cookware, appliances large and small!)

• Clothes hangers, ironing board, and clothes iron

• Supply starter kit

• Televisions in every room

• Valet Trash service picked up daily

• Free access to the amazing Windsor Hills Community Amenities including a large beach entry pool, water park, hot tub, playground, and more!


• Once booked, our team will connect to assist with the resort's required gate registration process. A valid government ID will be required.

• Resort parking is limited to 3 vehicles only

• Resort amenities are managed by the Resort HOA and hours and availability may vary.

• During the month of September 2024, the Resort main pool will be closed


5 Stars - The check in process was so easy, as soon as we got here we were able to check in and we checked in about an hour early. Everything has been superb and Windsor Hills is amazing. Will definitely stay here again. Alissa I.

5 Stars - Good. Jose S.

4 Stars - Great location, beautiful surrounding atmosphere. Lovely and great first impression of the condo upon walk in. Everything about the condo was exceptional. It was clean, stylish, and roomy. The rooms were well equipped and comfortable. I was very pleased with my stay. I hope to be back for a longer visit in the future. Tachemie G.

2821 Almaton Loop, 202 Kissimmee, FL 34747

Sleeping Arrangements

Master Bedroom Queen
Guest Bedroom Full (2)

Bathroom Configuration

Master En-Suite Bathroom: Toilet, Shower
Guest Bathroom: Toilet, Combo Tub Shower

Property Rules

Check In: After 4pm
Check Out: Before 10am
Smoking: Not Allowed


Air Conditioning
Bed Linens
Big Screen TV
Carbon Monoxide Detector
Children Welcome
Clothes Dryer
Coffee Maker
Communal Pool
Cooking Basics
Deadbolt Lock
Dishes And Silverware
Enhanced Cleaning
Fire Extinguisher
Fitness Room
Hair Dryer
High Chair
Hot Water
Ice Maker
Internet Access
Iron and Board
Minimum Age Limit
Pack n play
Satellite or Cable
Self Check-In
Single Level Home
Smoke Detector
Streaming TV Viewing Services
Washing Machine
Wireless Internet
Bed Linens Provided
Dining Table
Family Friendly
24-hour Front Desk
Convenience Store
Fitness Center
Gift Shop
Hot Tub
Outdoor Pool



Frequently Asked Questions

If you would like to request an early check-in, a late checkout, or a trip extension, please reach out to our reservations team! While not every request can be honored, we will do our absolute best to make it work!
We work hard to make sure your stay is issue-free! If issues arise, please let us know as soon as you can. Your welcome letter will share multiple ways that you can get in touch with us and we will work quickly to fix what comes up. Please note that regular maintenance items may take up to 24 hours to resolve. 
Typically, maid service is only scheduled for after your departure. For stays of 30+ days, we may require one or more cleaning visits to the home. If you would like to add a cleaning stop during your stay, just reach out and let us know! Prices vary on the size of the home. 

Please be aware that during peak or holiday seasons, 4p check-in may not be guaranteed. Our team will reach out if we need to slightly delay your check-in.

The primary renter must be 25+ years of age and proof may be required at any time.

Please make sure the information we have (phone number, email address) for the primary renter is accurate and up to date at all times. We work hard to share all applicable information for the home and in the event of an emergency, we need to make sure we can get ahold of you! 

ADDITIONAL FEES - Additional fees will be added to the reservation by adding any of the following to your reservation: pets, pool heat, grill rental, crib rental, early check-in, late checkout, additional guests, etc. These fees must be paid in full before the trip begins. Some Resort Communities will charge additional amenities fees and these may or may not be included in your reservation, and they may or may not be optional. By signing this agreement, non-optional fees are due to the resort and they may pursue legal action if those fees are not paid. 

Smoking and/or vaping of any kind is strictly prohibited. Florida law prohibits smoking/vaping on balconies of shared housing (condos/apartments) or shared entryways with other units. Fines starting at $500 will be issued for ANY evidence of smoking or vaping is found in the unit after your departure.

Pets are allowed in designated homes ONLY and are required to be included in the occupancy disclosed with your booking. Additional fees, security deposits, and a health screening are required of any pet. Unauthorized pets will result in immediate removal and up to a $500 fine.

Your home will be furnished with bed linens, blankets, bath towels, washcloths, and pool towels, if applicable. It will also have ONE of each of the following: body soap, shampoo, conditioner, dish soap, dishwasher tab, clothes washer tab, 1 garbage bag per garbage can, toilet paper, and paper towels. Since occupancy and stay lengths vary, please be prepared to purchase any additional supplies needed for your stay.

FINES/DAMAGES - Any damages to the home or its contents are the financial responsibility of the tenant. Fines will be assessed for but are not limited to the following: tampering of any kind with pool equipment, unauthorized early check-ins or late check-outs, unauthorized pets, smoking of any kind in the home, additional cleanings, etc. If it is determined that a maintenance call-out is a false report or due to an issue caused by the Tenant or any of their guests, the tenant may be charged a trip fee (on top of any applicable repair costs). Costs incurred to clear drain lines, sewer lines, and garbage disposals of blockages caused by the Tenant will be charged to the Tenant.

The owner or owner's agents may enter the premises due to an emergency, necessary/agreed-upon repairs/alterations/improvements/services, or showing to prospective purchasers, renters, or contractors. If you report a maintenance issue, expect that we will send teams to fix them. 
Do not move or remove any furnishings from the premises or property. Fines will be incurred for theft or damages. 
The tenant is responsible for the collection and removal of all trash during the stay. Specific trash instructions will be shared in your welcome letter. 
No barbeque grills of any kind are permitted in front yards, garages, inside the unit, or on balconies. Grills used in the rear of the home must be outside of the pool cage (if installed), a minimum of 10 feet from the home's structure, and must not be used under an awning, lanai, or overhang. No open flames (candles, turkey fryers, fire pits, tiki torches, etc) are permitted inside or outside of the home. Do not dismantle or tamper with smoke detectors, carbon monoxide detectors, pool alarms or fire extinguishers as they are there for your protection. 

iTrip nor the Owner of the premises assume any liability for (i) loss, damage, illness, or injury to persons or their personal property that occurs during their stay on the premises; (ii) any inconveniences, damage, loss, or injury arising from any temporary defects or stoppage in supply of water, gas, cable service, internet access, electricity or plumbing or (iii) any inconveniences, damage, loss or injury arising from or due to weather conditions, natural disasters, acts of God, or other reasons beyond their control.

Please report any maintenance needs and we will respond as quickly as possible. Refunds will not be made for maintenance issues including, but not limited to, utility outages, HOA-controlled amenities, heating and air conditioning, appliances, televisions, and internet/WIFI.

Parking is limited to the designated area(s) and guests assume all risks. Neither the Owner, Owners Association, nor iTrip is responsible for any vehicle damage/theft. No boats, jet skis, campers, trailers, or RVs, are allowed. Please check your welcome letter for specific HOA rules regarding parking. 

Tenant acknowledges that if the premises reserved include a pool and/or spa, no lifeguard is on duty. The pool, spa, and patio/deck can be dangerous areas, the deck/patio can be slippery when wet, and injury may occur. Diving, horseplay, or running is prohibited. No child or adult non-swimmer is permitted to use the pool without adult supervision by a strong swimmer. NO GLASS is allowed in the pool area. 

The pool alarm and pool fence are required by Florida law and MUST NOT be tampered with or disabled. Tenant must immediately report any problems with pool, spa, or safety fencing. Tenant and guests accept and assume all risks involved in using the pool, hot tub, and patio/deck and agree that neither the Owner, owners’ association nor iTrip accepts any responsibility whatsoever in the case(s) of accident or illness resulting from use of these amenities.

The maximum occupancy is based on the property limitations in the rental reservation. No parties or events are allowed. Tenants will be removed, fined, and will forfeit all monies for: Exceeding maximum occupancy, any illegal activity, damage to the premises or to neighboring properties; and any acts interfering with neighbors’ right to quiet of their premises.
Quiet Time: 10:00PM – 7:00AM

There may be stairs to enter the premises (see pictures and inquire if any concerns).

Tenant and any guest of Tenant shall obey all FLORIDA state laws, as well as LOCAL laws and HOA rules while they are on the premises. Failure to abide by the laws of Florida may result in removal and forfeiture of rental fees and security/damage deposits.

HOAs and Resorts
Many of our units reside in communities controlled by an HOA (Home Owner's Association), and we must abide by their rules. These rules may include (but are not limited to): registering all vehicles and drivers staying at the unit, vehicle restrictions and limits, registering all guests of the unit, specific trash protocol, pet breed restrictions, quiet times, additional amenity fees, gated entry, and more. Our team will be in touch if your unit falls under an HOA that has additional requirements for entry and specific HOA and Resort rules and requirements will be shared in your welcome letter. 

Some Resort Communities require additional fees to be paid to the resort and these fees may or may not be included in your reservation totals. Regardless of if these fees are included in your reservation or not, you acknowledge that you are responsible for paying them, and agree to do so. 

Accidents happen! Please report any damages as soon as possible so we can work to have them resolved. Ultimately, as the guest, you are responsible financially for any damages that occur to the property during your reservation. 



Great condo near Disney
4/5 stars
Great location, beautiful surrounding atmosphere. Lovely and great first impression of the condo upon walk in. Everything about the condo was exceptional. It was clean, stylish, and roomy. The rooms were well equipped and comfortable. I was very pleased with my stay. I hope to be back for a longer visit in the future.
- Taishae

Thank you for your review Taishae we have shared with our team and look forward to your next stay with us. Thank you.

- Manager Response
Perfect for a Family of Four
4/5 stars
This is a great place. We had only one minor hiccup in the whole process. When we arrived at the condo on our check-in date, it was not cleaned yet. Dishes still in dishwasher, wet towels in bathroom, beds not washed, etc We called the cleaning service number on our information packet and even though it was 7:30 in the evening, they had a team of 4 cleaners there within 30 minutes to clean the place. We were able to go to the near-by Walmart for groceries and supplies while they were cleaning. The problem was remedied very quickly and efficiently. The pool, market, grill, and recreation area was fantastic. The beds were firm, but we are used to a soft mattress, so just something we had to get used to. The condo is really a perfect layout for a family of four. We would definitely go back to Windsor Hills on our next trip to Florida!!
- Diana

Thank you for your review Diana. An unfortunate incident happened with the housekeeper that caused her to have to be hospitalized. There was an obvious communication breakdown on our end and we apologize for it. Thank you for your comments and your stay with us and we hope you stay with us again, your next experience will be perfect.

- Manager Response
Great place, very clean!
4/5 stars
Loads of space, very clean and has been quite so far. Fantastic spot to get to Disney. Only down side in the bed in the main bedroom, it’s extremely noisy, to the point we have thought about putting the mattress on the floor! But not enough room, would have been perfect otherwise.
- Angela

Thank you for your review Angela, we will check the mattress. Thank you

- Manager Response
iTrip Review
5/5 stars
- Jose

Thank you for your review Jose, we look forward to your next stay with us. Thank you.

- Manager Response
Fantastic checkin and family condo
5/5 stars
The check in process was so easy, as soon as we got here we were able to check in and we checked in about an hour early. Everything has been superb and Windsor Hills is amazing. Will definitely stay here again
- Alissa

Thank you for your review Alissa, we have shared with our team and look forward to your next stay with us. Thank you.

- Manager Response

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Toll Free (888) 847-0086