7741 Windsor Hills

5 BR
5 Baths
Sleeps 10

Privacy & Convenience await you in this Windsor Hills Resort 5 bed 5 bath pool home - its only 2 Miles from Disney!

This awesome home sleeps up to 10 people comfortably with two downstairs Master Bedrooms, one king and one queen. All bedrooms have flat-panel TVs.

The bed and bath layout consists of:


King Master and Master Bathroom

Queen Master and Master Bathroom

Twin Bedroom

Shared Full Bath


Queen Bedroom

Twin Bedroom

2 Full Bathrooms with shower/tub combos

The Windsor Hills community is one of the top locations for families looking to stay off-property on their Disney Vacation. The resort boasts some INCREDIBLE amenities, including:

• Clubhouse

• 140,000 Gallon Swimming Pool & Water Park

• 10 Person Hot Tub

• Recreation Park with Tennis/Pickleball Court, Putting Green, Basketball and Sand Volleyball courts (equipment may be available at the clubhouse)

• Movie Theater

• Fitness Center

• Marketplace and Grill

• Cyber Cafe

• Ping Pong Tables

•DVD Rentals


And more!


• During the month of September 2024, the resort's main pool will be closed for resurfacing

Sleeping Arrangements

Downstairs Master Suite #1 King
Downstairs Master Suite #2 Queen
Downstairs Twin Bedroom Twin (2)
Upstairs Queen Bedroom Queen
Upstairs Twin Bedroom Twin (2)

Bathroom Configuration

King Master Bathroom: Toilet, Shower
Queen Master Bathroom: Toilet, Combo Tub Shower
Downstairs Shared Bathroom: Toilet, Combo Tub Shower
Upstairs Shared Bathroom: Toilet, Combo Tub Shower
Additional Upstairs Full Bathroom: Toilet, 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
Fire Extinguisher
Fitness Room
Game Room
Hair Dryer
Hot Water
Ice Maker
Internet Access
Iron and Board
Minimum Age Limit
Ping Pong Table
Pool Table
Private Pool
Satellite or Cable
Self Check-In
Smoke Detector
Washing Machine
Wireless Internet
Bed Linens Provided
Dining Table
Enhanced Cleaning
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. 



Awesome stay
5/5 stars
Me and my family stayed at this home for 3 nights and every night was everything and more! The home accommodated everyone and we didn’t have not one complaint. I will stay at this location again.
- Tanisha

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

- Manager Response
Fabulous stay
5/5 stars
We have just returned from a wonderful stay at Windsor Hills. This is our second stay in this location. We love it. It is the perfect location to explore the area. The house was extremely comfortable with everything we needed. As a group of 8, we had loads of space to have time to ourselves and together as a group. On this trip we did not hire a car, this worked out perfectly as Uber’s were very reliable and reasonably priced. I would like to mention Itrip in this review. This was my first time using this website. I had to contact them a few times during this trip with some questions, they were outstanding with their help and very fast responses each time I needed to contact them. I would definitely book my next trip with them again.
- Anne

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

- Manager Response
All in all a great house and trip
4/5 stars
The house was very nice to stay in. Its slighlty dated in its decor. The pool area stones could use a little bit of tlc. They were very uneven and had grass growing between some of them. The cleaners did skip some dusting, but it wasn’t anything we couldn’t live with. The house was very well stocked with towels and everyday kitchen amenities. We had a few minor issues when we arrived (such as a light bulb out, lamp broken, remote control in one room not working) and someone arrived promptly to correct them. The kitchen stools should be replaced as they are very wobbly and had rungs about to pop out. The house was very nice and open concept and allowed for plenty of space for our party. All in all we would stay here again.
- Amy

Thank you for your review Amy. The pool deck is constructed with pavers which sometimes allows grass to begin to grow between them in spots so we will get it addressed. We will also check the bar stools. Thank you.

- Manager Response
Windsor Hills 7741
4/5 stars
Overall, a good experience. The layout of the house fit our needs well. Enjoyed full sun on the pool. A couple of recommendations: Not enough beach towels, or dishwashing and laundry pods, garbage bags. I would recommend when guests purchase these types of items that the leftovers of these types of products be left in the house for the next guests. Having a crib and highchair included as part of the package would be beneficial. We went out and purchased our own due to the high cost of renting those items. In addition, some maintenance on the pool decking would be beneficial. Had many weeds coming up through the cracks in the pool decking area. Also a rip in the lanai screen allowed squirrels to enter the pool area.
- David

Hi David thank you for your review and comments. The home does have a washer and dryer to launder linens during stays. Vacation homes are self catering however we do provide a starter pack of amenities that you noted. Should there be any of those items left by previous guests they are kept in the home for next guests. We do offer a service for baby items who installs them prior to a guest stay and removes them at check out where they are returned to their shop for cleaning and inspection. We will investigate the pool deck and screen and will address appropriately. Thank you.

- Manager Response
Great house great location
5/5 stars
House is like it is pictured. Plenty of room for everyone. Furniture is in very good condition. Conveniently located to many of the attractions down in Florida. Would definitely rent this house again.
- Laura

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

- Manager Response
Great house super clean
5/5 stars
Walked in the house. Smelled clean. House was great. Bedrooms were as explained and bathrooms were clean. Great place foe kids
- Michael

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

- Manager Response
1/5 stars
Horrible arrival experience. Got to the gate at 11:00pm with two toddlers and our name is not on the list to get in. Called the agent we were dealing with and the company and no reply, just voicemails. Horrible experience to be googling hotels in the area your first night of vacation at 11pm with two kids asleep. Finally someone called us back and added us to the system so we could get in. Not the greatest way to start our vacation.
- Janis

Hi Janis. It is unfortunate that you didn't tell the whole story, so here is the rest of the story. You created your booking on November 18, 2021 and we clearly state in our booking correspondence that you need to provide us with a list of occupants names so that we can enter everyone into the security system at the resort otherwise you will not be allowed entry. Upon receiving your call late in the evening of your arrival we found that you sent the names of your party to us at 10pm on the day of your arrival. We do not monitor emails 24/7 (however we do have a 24 hour emergency phone number where you can always reach us). You had plenty of time to provide us with the names long before your arrival to the resort. We feel your review is quite unfair.

- Manager Response
5/5 stars
What better to say other than you put smiles on my six children. Everything was great
- Yosef

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

- Manager Response
Dance moms
5/5 stars
We were group of moms attending UDA dance Nationals at Espn. House is very convenient to everything. House was very clean and freshly cleaned carpet. A few comments would be some additional bedding/blankets available in each room. Winters are chilly and no others blankets available if all the rooms are used. Could use a few more supplies in kitchen for cooking, mixing bowls etc. Twin beds need better padding, mattresses are like a rock. Main TV very, very confusing with 4 remotes on coffee table on arrival. Overall a very good stay!
- Lori

Thank you for your review and comments Lori, we have shared with our team. We will review the blanket count and kitchen items. We provide TV operation instructions, perhaps you missed them. Thank you and we look forward to your next stay with us.

- Manager Response
Terrible Customer Service
1/5 stars
I will never ever do business with this company. We checked-in Friday and I sent a request for pool service cause cleaning valve is not working and pool is filthy, it's Sunday and the pool is in the same condition. I was told the manager was gonna get notified but apparently that individual don't care. PLEASE avoid booking with this company. They don't reply to messages.
- Llamas

Thank you for your comments Juan. We checked into this and found that we had a communication breakdown between the reservations team and the person responsible for pool service. We acknowledge the issue and have corrected it and apologize to you for the miss. Thank you.

- Manager Response
Family Thanksgiving
5/5 stars
This home was perfect for our family of 10. Having a heated private pool was enjoyed as well as the huge pool and water slides at the beautiful clubhouse area. We would definitely rent again whenever we can. Location was great for our two days at Disney!!
- Nancy

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

- Manager Response
5/5 stars
Great place very quick to respond and very helpful.
- Dianna

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

- Manager Response
Fee Fo Review
5/5 stars
Excellent service from iTrip, even when we had to reschedule due to a family emergency. The accommodation was just as described and the process was very easy and straightforward.
- Lisa

Thank you for your review and recognition of our team. We look forward to your next stay with us, thank you.

- Manager Response
7741 Teascone - December 2019
5/5 stars
Our family of 5 just returned from a 5 night stay at 7741 Teascone Blvd. The house was perfect - exactly as described. There was plenty of room for us to get together in the kitchen/living area and also plenty of space for each person to have their own room. The staff at iTrip was also very responsive and helpful.
- Lisa

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

- Manager Response
Wonderful stay
5/5 stars
I enjoyed my stay here on teascone Blvd..the staff were exceptional and friendly.i was in close proximity to everything I needed..the house is wonderful! There one maintenace issue but when I called it was handled expeditiously! Thanks I will be back soon. Ywonns
- Ywonna

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

- Manager Response
Wonderful house and location !!!
5/5 stars
Upon arrival we were beyond happy with our choice to stay here. The pictures do not do this house justice! It’s roomy and comfortable and the pool is a great addition. Our host had items we needed the first night without having to go shopping which was very helpful. Another great thing about the house is the location, we are minutes away from the Disney parks which is a huge plus! Could be more happy.
- Jillian

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

- Manager Response
Fee Fo Review
5/5 stars
Great house Great location Great price
- Brandon
Lovely house
5/5 stars
My stay was great. The House was very spacious and my family love it. We will be using them on our next vacation.
- Rolina

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

- Manager Response
My stay at Windsor hills resort Kissimmee.
5/5 stars
The first in pression was good until we started to explore our apartment. no icemaker in the refrigerator. No light on the pool deck . Children's bedroom closet door hanging off . Master bedroom shower door hanging off . Cosmetic mirror hanging down wont stay up when in uses .. AC temperature not cooling enough ..
- Leroy J

Thank you for your review however we are quite surprised by your comments. We did not hear from your during your stay nor did we find issues noted. Thank you

- Manager Response
Amazing rental property
5/5 stars
We recently stayed at 7741 Windsor Hills home and we found it to not only be one of the cleanest properties I've stayed at but very functional for a large family. There was 7 people in total and never once did the space feel small. This property is decorated beautifully. I would recommend this property, which I already have, to anyone with a large family needing a great space to relax at in between going to the theme parks!!
- Victoria

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