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Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Windsor Hills Resort - Pool View Condo - Spectacular Pool Views

Bedrooms 3
Space 1,412 sq ft
Property type condo
Minimum Stay 2 - 6 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.

The living room features a 50" smart tv plus PlayStation 4.

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.

Note: Please be advised that your reservation will be both booked and confirmed directly from the owner after your initial payment has been placed. After booking you will receive a rental agreement directly from the owner. Attached to this VRBO ad is a document that explains further.

More Details

Member since: 2005
Premier Partner

This VRBO partner has demonstrated and is committed to fast response times, the best rates, and a great guest experience.

Speaks: english, Brazilian guests - please email me in english
Response time:
Within an hour
Response rate:
Calendar last updated:
August 19, 2018

About Richie

Back in the summer of 2004 I met with the builders of Windsor Hills Resort 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 900 families to my pool side home.

Richie purchased this condo in 2005

Why Richie chose Kissimmee

Windsor Hills Resort - 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
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Kissimmee Condo Accommodation and Amenities

Property Type:
  • condo
  • floor 3
Building Type:
  • building
  • Guests provide their own meals
  • Housekeeper Optional
Floor Area:
  • 1412 sq ft
House Rules:
  • Check-in: 4:00 PM
  • /
  • Check-out: 10:00 AM
  • Max. occupancy: 8
  • Max. adults: 8
  • Min. age of primary renter: 25
  • Children welcome
  • Parties/events not allowed ...
  • Pets not allowed
  • Non smoking only
  • "Rental agreement" mentioned by Homeaway is NOT the actual agreement between owner and guest. That agreement will be emailed to guest after booking.
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
  • 1 bicycles
  • Long-term Renters Welcome
  • Low Allergen Environment
  • 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 Big screen tv in the master bedroom 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 4 King Size master bedrooms - World Class Pillow Top Mattreses


Exceptional! 5/5 -
(104 traveler reviews)

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Windsor Hills Resort - Pool View Condo - Spectacular Pool Views
average rating of 4.951923 based on 187 reviews

Sister Trip to Disney!

  • 5 of 5

My sister and I enjoyed our nine day stay at this property. The Windsor Hills Pool View condo was very clean, well equipped, and had a great view of pool. After a long day at Disney it was nice to come back to the VERY comfortable beds! Perhaps the best thing about this condo was the owner, Richie. He was so very nice to work with. We would not hesitate to recommend this condo to anyone planning a trip to this part of Florida. If we get to return next year, Richie's condo will be our first choice!

  • Submitted: Mar 6, 2018
  • Stayed: December 2017
  • Source: VRBO, from HomeAway
Owner's Response: Charlotte, words can not express how much brighter my day is right now after having read the wonderful review that you left for my future guests. It was such a pleasure having you and your sister as my guests. Thank you so much for mentioning the pillow top mattresses! The day I purchased all of the mattresses for the condo the manager of the Hudson’s furniture store told me I was crazy for spending so much money “on a rental.” I can’t begin to tell you how insulting that was to me. I told him ... it’s not a rental but rather a true home for my guests. Thank you so much for taking the time to review my condo. I know all of my future guests truly appreciate it ... as do I Can’t wait till the day that you choose to call my home your own once again. Richie
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Great location for relaxing Disney vacation

  • 5 of 5

Our second stay in this unit. Perfect for families with room for kids, mom/dad and grandparents. Lots of room, clean, modern condo. Great view of pool, Pool is big, clean and has lots of chairs for sunbathing along with games for the kids. 24hour guarded gate with easy access. 10 mins from WDW Animal Kingdom Park. Owner is great to work with and very accommodating.

Our third trip to this unit is being planned.

  • Submitted: Aug 15, 2018
  • Stayed: July 2018
  • Source: VRBO, from HomeAway
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It was exactly expected if not better! We felt at home the moment we arrived.

  • 5 of 5

The condo was clean and well kept. We loved the little surprises like the beautifully set dining room table, basket of toys for the little ones to play with during our stay, and having beach towels to use. We would recommend this suite to anyone and everyone! Love love loved it!

  • Submitted: Jul 22, 2018
  • Stayed: July 2018
  • Source: HomeAway
Owner's Response: Emily, I really don't even know how to properly express how happy I am to know that your family loved the condo as much as you did. Your review has truly brightened my day. There are a million reasons why I am so delighted but one of them is simply because each of the toys that you described were hand chosen by my kids during virtually all of our visits to our homes. Countless times, while shopping at Target for the condo, I'd find a new princess doll in my shopping cart, or Pluto .... just another stuffed Disney character that my kids chose for children like yours to enjoy during your stay. It brought me great joy to share our home with your family. I really do hope that someday if you ever decide to vacation again in Orlando you'll consider calling my home your own once again. Richie
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Excellent place to stay

  • 5 of 5

Pool View Condo was everything depicted in the description. It was clean and comfortable. It was very convenient to all of the Disney parks. Richie’s directions were perfect. He has been a pleasure to work with. I highly recommend this rental.

  • Submitted: Jul 2, 2018
  • Stayed: June 2018
  • Source: VRBO, from HomeAway
Owner's Response: Lauren, thank you so much for caring enough about me and my home to leave such a wonderful review. Your kind words have truly made my morning so much brighter. As if the sun just shined right through my windows. Thank you for sharing your memories with all of my awesome future guests. I know how much it means to them to read such wonderful memories. Thank you. Thank you. Richie
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  • 5 of 5

beautiful,clean , definitely would stay here again

  • Submitted: Jun 26, 2018
  • Stayed: June 2018
  • Source: VRBO, from HomeAway
Owner's Response: Tracy, I am so glad that your family chose to call my condo your home away from home. It was truly my pleasure having your family as my guests. Thank you so very much for caring enough about me and my home to leave such a wonderful review. I am so incredibly appreciative. I really do hope that someday your family will decide to call my condo your home once again. I wish you and your family well. Richie
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Beautiful condo

  • 5 of 5

Beautifully furnished and decorated condo. Spacious and very clean. Richie was wonderful to work with and answered all questions promptly. Excellent value and so much better than staying g in a hotel. Location is very convenient, as it's just a short walk (2 mins) to pool and clubhouse.

  • Submitted: Jun 23, 2018
  • Stayed: May 2018
  • Source: VRBO, from HomeAway
Owner's Response: Kim, thank you so much for your kind words regarding me and my condo. I really do appreciate it. I am so thrilled to know that your family really enjoyed your stay. I really am. I really hope that your family truly felt at home too. I hope that someday if your family decides to vacation again in Orlando that you'll consider calling my home your own once again. Thank you again for going out of your way to share your wonderful memories with my future guests. Richie
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World Class Golf

Hot air balooning and so much more only minutes away!


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

clean $75 + Tax
Refundable damage deposit $500

Owner's Cancellation Policy

  • 100% refund if canceled at least 60 days before arrival date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.