Villas in Windsor Hills

Book a villa in Windsor Hills for a relaxing holiday: we have 7 villas in Windsor Hills for you to rent

  • Save £100's booking your holiday letting
    Clickstay is a low cost holiday home rental website offering direct bookings with owners. We don't charge service fees, making it unlikely for you to find a cheaper holiday property elsewhere.
  • Price comparison made easy
    Our owners provide links to their listings on Airbnb, Booking.com and Vrbo - making it easy for you to compare prices. You should always find the lowest price on Clickstay.
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    Have direct contact with our owners by using our messaging system. We don't filter out messages between you and the owner.
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Lowest price pledge

Owners have the lowest prices on Clickstay

Clickstay logo
5%*
Airbnb logo
14 - 18
Booking dot com logo
15 - 25%
Vrbo logo
15%
*5% paid by the owner.

Our best villas in Windsor Hills

Check out our best villas in Windsor Hills.
  • Villa in Windsor Hills, Florida: Windsor Hills Retreat

    Windsor Hills villa to rent

    (64)
    6 bedroom villa • Sleeps 12

    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.

    Lowest price pledge
    From £1,822 per week
  • Villa in Windsor Hills, Florida

    Windsor Hills holiday villa rental with private pool

    5 bedroom villa • Sleeps 10

    Windsor Hills Resort- Minutes to Clubhouse

    Lowest price pledge
    From £1,271 per week
  • Villa in Windsor Hills, Florida

    Villa to rent in Windsor Hills, Florida

    6 bedroom villa • Sleeps 12

    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 £1,483 per week
  • Villa in Windsor Hills, Florida

    Villa with private pool in Windsor Hills, Florida

    5 bedroom villa • Sleeps 12

    FIVE STAR Florida villa with Pool, Spa and Lanai. King Master bedroom suites, walk in closets and en-suite bathrooms. Queen bedroom. Star Wars and Lion King themed bedrooms. Superhero Games Room.

    From £1,779 per week
  • Villa in Windsor Hills, Florida

    Holiday villa in Windsor Hills, Florida, with private pool

    6 bedroom villa • Sleeps 12

    A sun-kissed south-facing pool. Immerse yourself with the perfect blend of relaxation and entertainment as you create unforgettable memories at this home in Windsor Hills Resort

    Lowest price pledge
    From £1,267 per week
  • Villa in Windsor Hills, Florida

    Villa with private pool in Windsor Hills, Florida

    5 bedroom villa • Sleeps 10

    Escape to serenity in our luxurious 5 bed 5 bath home offering stunning sunsets, privacy with no rear neighbors and an enchanting overlook of the beautiful surroundings at Windsor Hills Resort

    Lowest price pledge
    From £1,334 per week
  • Villa in Windsor Hills, Florida

    Villa rental in Windsor Hills, Florida, with private pool

    6 bedroom villa • Sleeps 12

    FIVE STAR Florida villa with Pool, Spa and Lanai. King Master bedroom suites, walk in closets and en-suite bathrooms. Queen bedroom. Frozen, Star Wars and Harry Potter bedrooms. Superhero Games Room.

    From £1,957 per week

Prices and Availability for villas in Windsor Hills

Cheapest monthJanuary 2025 average weekly price £2,05286% of villas are available
High seasonDecember 2024 average weekly price £2,69886% of villas are available

All data is for the next 12 months and all the prices are the average weekly cost (Saturday - Saturday).

Price information for villas in Windsor Hills (2024 - 2025)

£0£3,070£2,303£1,535£768FebruaryMarchAprilMayJuneJulyAugustSeptemberOctoberNovemberDecemberJanuary
Average weekly price

Average weekly prices for villas in Windsor Hills

The prices graph for villas in Windsor Hills shows you the average weekly price for one of our villas over the next twelve months. December and March are the most expensive months to rent a villa in Windsor Hills where the average price is £2,698 in December and £2,606 in March. The cheapest month to rent a villa is in January where the average weekly price is £1,955 (18/01 - 25/01). The average price of a villa in Windsor Hills varies considerably between regions, distance from the nearest beach and the size of the villa. See the graph for average weekly prices for our top destinations in Windsor Hills below.

Availability for villas in Windsor Hills (2024 - 2025)

0%100%75%50%25%FebruaryMarchAprilMayJuneJulyAugustSeptemberOctoberNovemberDecemberJanuary
Average available villas

Weekly availability for villas in Windsor Hills

The graph above shows the availability of our villa holiday rentals in Windsor Hills over the next twelve months. February (17/02 - 24/02) is the busiest time to rent a villa in Windsor Hills where none of our villas are available to book. The quietest time to visit Windsor Hills at the moment is in September (14/09 - 21/09) where 100% of our villas have availability.