1. Home
  2. USA
  3. Florida
  4. Orlando Disney
  5. Kissimmee
  6. Houses and villas in Windsor Hills

Our best houses and villas in Windsor Hills

Check out our best houses and villas in Windsor Hills.

  • Villa in Windsor Hills, Florida: Windsor Hills Retreat
    • 6 bedroom villa
    • Sleeps 12

    Windsor Hills villa to rent

    Spacious luxury property situated at the top of the exclusive gated community of Windsor Hills in Kissimmee. Private south facing pool and spa. 2 miles from Disney and Universal is 15 mins drive away.

    From £786 per week
    (47)
  • House in Windsor Hills, Florida
    • 6 bedroom house
    • Sleeps 12

    Holiday home with private pool in Windsor Hills, Florida

    This is not only a rental property, our home is furnished and decorated to the highest standard and offers you the amenities of a 5-star resort combined with the space and style of a family home.

    From £938 per week
     
  • Villa in Windsor Hills, Florida
    • 6 bedroom villa
    • Sleeps 12

    Villa to rent in Windsor Hills, Florida

    Luxury 6 bedroom 4 bathroom pool villa with games room. Just 2 miles from Walt Disney world Orlando Florida. Set within the world renowned gated community of Windsor Hills resort

    From £1,336 per week
     
  • House in Windsor Hills, Florida
    • 3 bedroom house
    • Sleeps 6

    Windsor Hills holiday home rental with private pool

    Lovely family townhome with greater privacy than most, on Windsor Hills Resort. Smoke-free and pet-free home. We owned our vacation home since 2004 and visit here ourselves for a month each year.

    From £645 per week
    (1)

Reviews of our holiday lettings in Windsor Hills

We have 48 reviews of our holiday lettings in Windsor Hills.

3 bedroom Windsor Hills holiday home rental with private pool
July 2019

Fantastic communication from owner booking and leading up to the stay. Lovely town house owners have thought of everything that you could need to make your holiday enjoyable and stress free. We would totally recommend and would defiantly stay here again if we have another holiday in Orlando.

Read more
Renter: Victoria
Victoria Family from Crawley, United Kingdom
6 bedroom Windsor Hills villa to rent
December 2018

Just back from another enjoyable stay at Windsor Hills Retreat. The villa was the same as last time, beautifully presented and with the lovely heated (payable extra) pool just makes the perfect base for exploring Orlando & further a field. We love the christmas decorations up too as feels like home from home then. Dealing with Natasha is always a pleasure. We are just looking at times we can go back and enjoy it yet again. Highly recommend!

Read more
Renter: Kay
Kay Family from Llanfechain, United Kingdom
6 bedroom Windsor Hills villa to rent
August 2017

Modern, clean villa and exactly as described in a great location for Animal Kingdom park and Disney. Very well stocked, the appliances were the best we've ever had. Natasha was a pleasure also.

Read more
Renter: Philip
Philip Family from Elstree, Herts, United Kingdom
6 bedroom Windsor Hills villa to rent
February 2017

Over the moon with the villa! Was shocked at the size of the property , its massive ! Comfortable beds, lovely pool and seating area. great facilities. Very clean.Excellent location. Would highly recommend.

Read more
Renter: Catherine
Catherine Large group from West Berkshire , United Kingdom
6 bedroom Windsor Hills villa to rent
December 2016

Beautiful villa with lots to do. The pool & spa were gorgeous. Bedrooms were huge & lots of space for clothes etc. Games room was great. Was a huge villa for the 4 of us but loved it, if your in a large family to fill the villa then it would be perfect also. You are literally within 2 miles of all Disney parks. Yes roads were busy as it was Christmas but no different than in the uk! Thank you for letting us enjoy this beautiful house.

Read more
Renter: Kay
Kay Family from Llanfechain, United Kingdom
6 bedroom Windsor Hills villa to rent
June 2016

Stayed June/July 2016 with 8 adults and 4 children. The Villa was well laid out, very clean and had everything you could need for a self-catering holiday. The pool was a good sixe and had acovered area if you prefer staying out of the sun, the games room has a great pool table. The villa is within 5 minutes of various restaurants and supermarkets. Disney's main entrance is only 5 mins away and we also went out to Universal (25 mins), Seaworld (20 mins), Outlet shopping (20 mins) Clearwater and Busch Gardens (about 1.5 hrs) which is well worth the drive by the way. We would recommend this Villa for your next Florida Holiday

Read more
Renter: Christopher
Christopher Family from Motherwell, United Kingdom