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Windsor Hills Pool View Condo - Spectacular Pool Views

Bedrooms 3
Property type condo
Minimum Stay 2 - 7 nights

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Minimum Stay
2 - 7 nights

About the property

Windsor Hills Pool Condo: 3 Bedrooms + sleeper / sofa, 2 Baths, (Sleeps 6-8)

Windsor Hills Resort Orlando is perfectly located only minutes away from the Walt Disney World resort and has quickly become one of the most popular resorts in Orlando and also is a favorite among families wishing to stay in a villa or vacation home.

Windsor Hills Pool View Condo, located poolside, offers the most spectacular pool views at the Windsor Hills resort in Kissimmee, Florida.

There are eight condo buildings in Windsor Hills.

This condo is located in building #8 poolside and is closest to the clubhouse.

Windsor Hills Pool View Condo features a brand new kitchen with all new stainless steel appliances as well as granite counter tops.

The condo has all upgraded furniture throughout.

Windsor Hills Pool View Condo has two king size master bedrooms as well as a third bedroom with two twins. All of which feature world class, pillow top mattresses to give you the most comfortable night's sleep available at the Windsor Hills Resort.

Each bedroom at the condo features High Definition television as well as a DVD player.

The condo offers your family a queen size sleeper sofa in the living room to allow for up to 8 guests.

Wake up early in the morning to see the hot air balloons rising in the distance or enjoy the Windsor Hills lake views from the windows as well as from the screened in balcony.

Windsor Hills welcomes guests from all over the world and over 800 of those families have called the condo their home away from home.

Over 140 past guests have written reviews of the stay at the condo. Your family are most welcome to read through these truly wonderful reviews.

The Windsor Hills Resort is truly a safe place for your family to call their home during your Walt Disney World vacation.

Windsor Hills is gated and offers 24 hour security.

Windsor Hills and Windsor Hills Pool View Condo are the perfect choice for your dream Disney area vacation.

Important: This VRBO ad only allows for a two payment plan as far as when payments are due on the condo rental. This condo actually uses a 3 payment plan. Unfortunately there is no way to implement a 3 payment plan with this ad. Please be advised that there can be up to three payment due dates for this rental. First payment due date at time of rental. Second payment comes due 90 days prior to check-in while the final payment is due 60 days prior to check-in.

Security deposit: The information posted on this VRBO ad is NOT CORRECT.

The security deposit is not due 60 days in advance of stay as is mentioned here but instead comes due 30 days prior to check-in for deposits made through Paypal or check. Deposits left by credit card are due 7 days prior to check in.

It is regrettable that this ad does not allow for differences in payment schedules and / deposits. Please feel free to view the condo's direct website PoolViewCondo for more information or email owner anytime at all.

More Details

Member since: 2005
Speaks: english, Brazilian guests - please email me in english
Response time:
Within an hour
Response rate:
Calendar last updated:
January 22, 2017

About Richie

Back in the summer of 2004 I met with the builders of Windsor Hills and said to them 'The only property I want is the condo that your going to build by the pool.' I was told...'sorry we are not building that condo yet.' To which I said 'No soon as you decide to build it let me know as that will be my home away from home.' That was the very beginning of Windsor Hills Pool View Condo. Since then I have had the pleasure of welcoming over 600 families to my pool side home.

Richie purchased this condo in 2005

Why Richie chose Central/Disney/Orlando Area

Windsor Hills Pool View Condo offer guests the most beautiful pool views and even lake views and is also closest to the clubhouse at the Windsor Hills resort.

Windsor Hills Pool View Condo is located close to the Walt Disney World resort.

What makes this condo unique

Guests staying at condo only need to grab a pool towel and walk downstairs when they are ready to lay pool side under a tropical palm tree.

Guestbook comments from the owner

We very much enjoyed our stay at Mr. Dagostino's "Pool View" condo at Windsor Hills. It was exactly as he described in the web site with no negative surprises. The location was perfect with very convenient access to all the Disney attractions. The condo was clean and well maintained. Mr. Dagostino was very honest, straightforward and a pleasure to work with. We would definitely rent from him again should our travels take us to the Orlando area in the future. You will definitely enjoy your stay.
Sep 2005
  • 1 of 83


Exceptional! 5/5 -
(72 traveler reviews)

Windsor Hills Pool View Condo - Spectacular Pool Views
average rating of 4.9583335 based on 155 reviews

Wonderful Christmas 🎄

  • 5 of 5

We just spent Christmas week. Best way to spend Christmas. The condo was perfect, clean & best view. It had everything we needed. Richie answered all questions quickly and was very accommodating.

Thank you Richie....Happy New Year!

  • Submitted: Jan 1, 2017
  • Stayed: Dec 2016
  • Source: VRBO, from HomeAway
Owner's Response: Michelle, Hurray! I am so happy to hear that your family loved your Christmas week stay at my condo. I hope it really was a truly wonderful week for your family. What a perfect place to celebrate Christmas. My only regret is that the condo no longer has the Christmas tree that I used to keep there. I would have loved to have shared our tree with your family. I really do hope that someday if your family decides to vacation again in the Orlando area you'll consider calling my condo your home away from home once again. Thanks also for taking time out to share your memories with my future guests. I really can not begin to express how grateful I am and how much it means to all of them. I wish you and your family a wonderful New Year. Richie
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Last minute booking

  • 5 of 5

I was born and raised in Flordia, moved to GA for 20 years and we have returned to live on the west coast. I have used VRBO for years to find vacation rentals on the beach, but little did I know there were more options than the cramped hotel rooms near Disney, or the resorts which are ridiculously priced. I found Richie's place on a whim. I checked VRBO and had no idea there were rentals that close to Disney for such reasonable rates. For what we would have spent on a hotel room, we rented his 3bdm/2bth Condo with more than enough amenities at the resort for all ages. We will absolutely rent from Richie again and perhaps next time will enjoy the complex as many other families did during our stay. Richie was so easy to work with and we will be returning soon.


Holly Johnsey

  • Submitted: Dec 20, 2016
  • Stayed: Dec 2016
  • Source: VRBO, from HomeAway
Owner's Response: Tony and Holly, I can not even begin to tell you how absolutely thrilled I am to know that your family enjoyed your stay at my condo and also the Windsor Hills Resort as much as you did! I know that there are so many other homes that you could have chosen to call your home and am truly grateful that you chose mine to be your own. Especially knowing that you could have stayed right on Disney property. That makes your review even that much more special. Thank you do very much for taking the time to share your awesome review with my future guests. My guests tell me all the time that it was simply due to the wonderful reviews from my past guests like your family that allowed them to feel comfortable enough to book their stay online with me. I wish you and your family a wonderful holiday season and look forward to hearing from you again. Richie
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  • 5 of 5

The condo was perfect. The beds were very comfortable and the condo was very clean. The owner was very helpful and replied back quickly to answer any questions. Would use the condo again.

  • Submitted: Nov 27, 2016
  • Stayed: Nov 2016
  • Source: HomeAway
Owner's Response: Wendy, Perfect! Wow. Thank you! Your review has really made my day so much brighter! It has always been my desire for my guests to really feel at home at my condo. I am so glad to know that your family really did feel at home there. I am already looking forward to the day when I see an email in my inbox saying that your family wishes to call my home your own once again. Thank you so much for taking the time to share your memories with my future guests. I know how much it means to them. I also know how much it means to me. Thank you. Richie
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Another great stay

  • 5 of 5

We feel blessed having found this condo some years ago and have just enjoyed another week in this well-equipped, perfectly-located home away from home. Richie makes your stay even more accommodating by providing details ahead of time regarding condo rules and use. I was pleasantly surprised to receive an email a week before our arrival, reminding me of my personalized door entry code - the same one I had used during my previous visit. Just another example of superior record-keeping combined with a personal touch.

You'll find "starter" paper goods in the condo, but be aware that extra paper towels, toilet paper, etc. will most likely be needed and should be picked up either at the on-site store or off-site. This and other details are included in the comprehensive guidelines provided by Richie ahead of time. We felt good about leaving extras behind for the next guest, such as pods for the Keurig, etc.

Another perfect stay for us, but our not our last. Thanks, Richie, for sharing your wonderful home with so many others.

  • Submitted: Nov 18, 2016
  • Stayed: Nov 2016
  • Source: VRBO, from HomeAway
Owner's Response: Jim, I am so incredibly glad to know that your family really enjoyed their stay once again at the condo. That really is all I ever wish for my guests. Thank you so very much for all of your kind words regarding me and my home. I so greatly appreciate it. I must tell you that to hear that my home has been a blessing to your family is truly the best complement that anyone could ever give. The condo really is my family’s home away from home, as you know, and has really been a blessing to us as well. I am just so glad to have had the chance to share it with your family. I really do look forward to seeing an email in my inbox someday in the future telling me that your family would like to call my home your own once again. I wish you and your family well. Richie
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Excellent family condo and location

  • 5 of 5

Richie offers a great location and excellent amenities at Windsor Hills, only a very short, simple drive to Disney. The condo is well appointed and comfortable and very clean. The clubhouse and pool are very close by and convenient. We swam everyday in the large pool with the kids and loved it. Mornings were great to kickoff with coffee on the balcony overseeing the beautiful pool area. Parking is close by, just outside the condo, with a convenient elevator to the third floor. It is a gated community and security staff we're always pleasant. Restaurants are only a few minutes drive away, and we ventured out to some of the malls and outlets for shopping. Overall, we had an amazing stay and Richie, the owner, was always available to answer questions or offer advice prior to or during our stay. We would recommend his condo to anyone.

  • Submitted: Nov 6, 2016
  • Stayed: Oct 2016
  • Source: VRBO, from HomeAway
Owner's Response: Wow! Kelli you have no idea how thrilled I am to see that your family truly loved their stay at my condo. Your review has made my day! Thank you so much for sharing your wonderful memories with my future guests. There is nothing in the world more helpful to other guests than to read how happy families like yours were during your stay. I really do hope that someday, if you ever decide to vacation again in the Orlando area, you'll consider calling my home your own again. It was truly my pleasure sharing my home with your family. Again ... thank you so much! Richie
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A wonderful place and very accommodating!!

  • 5 of 5

We arrived a bit late in the evening. We had a question for the condo manager so the resort let us use their phone and we were able to reach the manager right away. The resort stayed open a while after closing to ensure we could use their phone again if need be.

Our stay was during Hurricane Matthew so the owners contacted us to make sure everything was alright and were very flexible if we needed an extra days stay.

Of course the rooms were very clean and it had everything we could ask for and more.

We loved the pool and the lifeguard was great watching the kids on the slide.

We had no problems parking close to the condo daily.

Disney and Universal were just a short drive away.

Everything we needed to know was sent to us in advance.

Best of all.... the beds were really comfortable for a very much needed good nights sleep.

Thanks so much!

  • Submitted: Oct 11, 2016
  • Stayed: Oct 2016
  • Source: VRBO, from HomeAway
Owner's Response: Laura, I am so glad that your family really enjoyed your stay at my condo as well as the resort too! Nothing in the world makes me happier to hear. You have no idea how much it means to me that you mentioned that you had a really comfortable sleep! When I purchased those mattresses for the condo the owner of the store thought I was CRAZY for buying world class pillow tops ... he said to me "No one buys those for a rental!" So then I told him .. my condo is my home and I want nothing more than for my guests to truly feel at home at my home. I found that so insulting what he said. So hearing that you really felt at home makes me know that it was all worth while! I"m also really glad that everyone at the resort was so helpful to you. That is something that really makes Windsor Hills so special. I must say that they are really helpful to me as well when I need them. I really do hope that someday your family will choose to call my home your own once again. Your family are most welcome. It was my pleasure sharing my home with your family. Richie
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World Class Golf

Hot air balooning and so much more only minutes away!


Rates & Availability

Kissimmee Condo Rental Rates

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly Event
Feb 1 2017 - Feb 4 2017
2 night minimum stay
May 13 2017 - May 29 2017
6 night minimum stay
Jun 24 2017 - Jun 27 2017
2 night minimum stay
Jul 9 2017 - Aug 4 2017
7 night minimum stay
Aug 5 2017 - Sep 2 2017
6 night minimum stay
My Standard Rate
5 night minimum stay

Additional information about rental rates

clean $75 + Tax
Refundable damage deposit $500
Tax Rate 13.5%

Payment Schedule: Initial payment is $100.00 per week. 2nd payment due 90 days prior to check-in. 3rd payment due 60 days prior to check-in. Do to space limitations on this ad I can only show 2 payments due dates but there are actually three. Refer to the Payment Schedule page on condo's website for more info:

Owner's Cancellation Policy

  • 100% refund if canceled at least 60 days before arrival date.
Enter dates for accurate pricing
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Available arrival
Available stay (no arrival)


Kissimmee Condo Accommodation and Amenities

Property Type:
  • condo
  • floor 3
  • Guests provide their own meals
  • Housekeeper Optional
Floor Area:
  • 1412 sq. ft.
Location Type:
  • Beach ...
  • Lake View
  • Lakefront
  • Resort
  • Village
  • Water View
  • Waterfront
  • Waterfront
  • Adventure
  • Budget
  • Family
  • Historic
  • Romantic
  • Sports & Activities
  • Tourist Attractions
  • Air Conditioning
  • Alarm Clock
  • Basic Soaps
  • Broadband Access
  • Ceiling Fans
  • Clothes Dryer
  • Elevator ...
  • Fitness Room / Equipment ...
  • Free Long Distance ...
  • Hair Dryer
  • Heating
  • Internet ...
  • Iron & Board
  • Linens Provided ...
  • Living Room ...
  • Local Maps
  • Parking ...
  • Parking On Street
  • Parking for RV/Boat/Trailer ...
  • Sofa Bed
  • Telephone ...
  • Toilet Paper
  • Towels Provided ...
  • Washing Machine ...
  • Wireless Internet
  • Blender
  • Coffee Maker
  • Cooking Utensils ...
  • Dishes & Utensils ...
  • Dishwasher
  • Freezer
  • Ice Maker
  • Kitchen ...
  • Kitchenette
  • Microwave
  • Oven
  • Pantry Items ...
  • Refrigerator
  • Stove ...
  • Stove
  • Toaster
  • Child's Highchair
  • Dining ...
  • Dining Room
  • seating for 6 people
  • 2 Bathrooms
  • Master bathroom - toilet , combination tub/shower , Granite counter tops and yes a hair dryer too
    Second bathroom - toilet , combination tub/shower , Granite countertops and yes a hair dryer too
  • Both bathrooms feature granite counter tops ..... and before you ask....yes they both have hair dryers
  • 3 Bedrooms, Sleeps 8
  • Master bedroom - 1 king , High end - World class pillow top mattress
    Master suite #2 - 1 king , high end - World class pillow top mattress
    Bedroom 3 - 2 twin/ single , Two twin beds
    Convertible bed(s) - 1 sleep sofa /futon , Queen size sleeper sofa in the living room
  • King size beds in both master bed rooms; both world class pillow top mattresses. - Two twins, a queen size sleeper sofa and a pack and play for the very little ones
  • Books ...
  • CD Player
  • DVD Player ...
  • Game Room ...
  • Ping Pong Table
  • Pool Table ...
  • Satellite / Cable ...
  • Stereo ...
  • Television ...
  • Toys ...
  • Video Game Console ...
  • Video Games ...
  • Balcony ...
  • Beach Towels
  • Bicycles
  • Deck / Patio ...
  • Gated Community
  • Golf ...
  • Kayak / Canoe
  • Lanai / Gazebo
  • Lawn / Garden ...
  • Outdoor Grill ...
  • Sand Box
  • Screen Porch / Veranda
  • Tennis ...
  • Tennis Court
  • Walkway to Water
  • Events Allowed
  • Long-term Renters Welcome
  • Low Allergen Environment
  • Minimum Age Limit for Renters ...
  • children welcome
  • non smoking only
  • pets not allowed ...
  • suitable for elderly or infirm
  • wheelchair accessible
Pool / Spa:
  • Communal Pool ...
  • Heated Pool
  • Hot Tub ...
  • Outdoor Hot Tub
  • Outdoor Pool
  • Shared Hot Tub
Onsite Services:
  • Car Available
  • Massage
  • Staff
  • botanical garden
  • churches
  • cinemas
  • festivals
  • health/beauty spa
  • library
  • live theater
  • marina
  • museums
  • playground
  • pond
  • recreation center
  • restaurants
  • synagogues
  • theme parks
  • water parks
  • zoo
Leisure Activities:
  • bird watching
  • boating
  • horseback riding
  • luaus
  • miniature golf
  • outlet shopping
  • paddle boating
  • photography
  • scenic drives
  • shopping
  • sight seeing
  • walking
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • basketball court
  • cycling
  • fishing
  • freshwater fishing
  • golf
  • golf privileges optional
  • hiking
  • hot air ballooning
  • hunting
  • jet skiing
  • kayaking
  • mountain biking
  • pier fishing
  • racquetball
  • sailing
  • snorkeling
  • snorkeling/diving
  • sound/bay fishing
  • swimming
  • tennis
  • water skiing
  • water tubing
  • wind-surfing
The condo has it's own website. Google Windsor Hills Pool View Condo to view the condo's website. Free Wireless Internet Free Long Distance Calling to 40 countries Free Calls to USA and Canada and more! HDTV big screen in living room High Definition TV in the 2nd and 3rd bedroom as well. TV's of at least 32' in all rooms! DVD/ CD Players in all rooms iPod docking station Playstion 3 King Size master bedrooms - World Class Pillow Top Mattreses

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