List your home
Apply filters
£ to

Holiday homes 29

Reset search

Show results on map

Filter your search

Price per night

Price per night

£ to per night

Bedrooms

Location

  • United States Clear
  • Florida Clear
  • Central Florida Clear
  • Kissimmee Clear
  • Windsor Hills Resort Clear

Location

  • All locations

more +

less -

Filters applied: Wi-Fi available (29)

To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more
29 Results   |  

from £65 / night

£450 - £725 / week

View

10 Photos

Kissimmee / Windsor Hills Resort

Townhouse / 3 Bedrooms / sleeps 8

4 Nights min stay

Add to shortlist

from £65 / night

£450 - £725 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
10 minutes to Disney Gated community giving great security Five star resort with many features close to the house Luxurious family home.  …see more

from £158 / night

£1100 - £1700 / week

View

Very Good 4.5/5 

23 Photos

Kissimmee / Windsor Hills Resort

Villa / 6 Bedrooms / sleeps 14

Very Good 4.5/5 

1 night min stay

Add to shortlist

from £158 / night

£1100 - £1700 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
6 bedroom 4 bathroom Villa, South facing pool & spa located in the Windsor Hills Resort just 1.5 miles (2.5 km) from the gates of Walt Disney World. The resort offers a variety of recreation and activities for all ages and there are an abundance of golf courses nearby. Rental Period and Occupancy: Check-in time is 4 p.m. Check out time is 10 a.m.  …see more

from £128 / night

£895 - £1550 / week

View

Excellent 5/5 

24 Photos

Kissimmee / Windsor Hills Resort

Villa / 6 Bedrooms / sleeps 14

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £128 / night

£895 - £1550 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
New 2010 Luxury 5 Star, 6 Bed 4 bath. 2 Miles from Disney. Free calls, Local, national & international, WiFi. South facing Private heated Pool & Spa. Gas BBQ (Grill). Tvs in all rms. Games Rm with 42" Lcd & Xbox 360, air hockey, pool tab, Foosball & electronic darts. Free Club house with Pool/Jacuzzi , Free tennis courts, Putting green, Basket ball & BBQ area, water slides  …see more

Featured properties

from £180 / night

£1260 - £1855 / week

View

Excellent 5/5 

21 Photos

Kissimmee / Windsor Hills Resort

Villa / 6 Bedrooms / sleeps 12

Excellent 5/5 

1 night min stay

Add to shortlist

from £180 / night

£1260 - £1855 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Luxury 6 bedroom private villa with private pool, games room in the world renowned gated community of Windsor Hills Resort just 2 miles from the gated of Walt Disney World in Kissimmee, Orllando Florida  …see more

from £116 / night

£812 - £1085 / week

View

Excellent 5/5 

16 Photos

Kissimmee / Windsor Hills Resort

Villa / 5 Bedrooms / sleeps 10

Excellent 5/5 

5 Nights min stay

Add to shortlist

from £116 / night

£812 - £1085 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Santa Caterina is located in the beautiful Windsor Hills Resort where you can enjoy all the comforts and amenities of home with all the attractions and the social interactions of a First Class Resort. ALL PRICES QUOTED INCLUDE 13% FLORIDA TAX Refundable security deposit £200 Check in 4pm Check out 11am  …see more

from £180 / night

£1260 - £1855 / week

View

Excellent 5/5 

18 Photos

Kissimmee / Windsor Hills Resort

Villa / 6 Bedrooms / sleeps 12

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £180 / night

£1260 - £1855 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
Luxury pool villa home with 6 bedroom, 4 bathroom, games room in a world renowned gated community of Windsor Hills resort. Located just 2 miles from the front gates of Walt Disneyland Orlando, Florida.  …see more

from £189 / night

£1323 - £1876 / week

View

 

24 Photos

Kissimmee / Windsor Hills Resort

Villa / 6 Bedrooms / sleeps 12

 

5 Nights min stay

Add to shortlist

from £189 / night

£1323 - £1876 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
This villa is situated in the prestigous Windsor Hills resort. Only 1.5 miles from Walt Disney World and all the major Orlando attractions. Great, Yeah!  …see more

from £182 / night

£1274 - £1624 / week

View

24 Photos

Kissimmee / Windsor Hills Resort

Villa / 6 Bedrooms / sleeps 12

5 Nights min stay

Add to shortlist

from £182 / night

£1274 - £1624 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
This villa is situated in the prestigous Windsor Hills resort. Only 1.5 miles from Walt Disney World and all the major Orlando attractions. Great, Yeah!  …see more

from £210 / night

£1470 - £1624 / week

View

24 Photos

Kissimmee / Windsor Hills Resort

Villa / 6 Bedrooms / sleeps 12

5 Nights min stay

Add to shortlist

from £210 / night

£1470 - £1624 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
This villa is situated in the exclusive resort of Windsor Hills. Only 1.5 miles from Walt Disney World and all the major Orlando attractions. Great, Yeah!  …see more

from £186 / night

£1302 - £1708 / week

View

24 Photos

Kissimmee / Windsor Hills Resort

Villa / 5 Bedrooms / sleeps 10

5 Nights min stay

Add to shortlist

from £186 / night

£1302 - £1708 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
This villa is situated in the exclusive resort of Windsor Hills. Only 1.5 miles from Walt Disney World and all the major Orlando attractions. Great, Yeah!  …see more

from £110 / night

£764 - £1271 / week

View

24 Photos

Kissimmee / Windsor Hills Resort

Villa / 5 Bedrooms / sleeps 12

5 Nights min stay

Add to shortlist

from £110 / night

£764 - £1271 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
** 2014 discounts available , up to 30% off ** 5 min from Disney! Windsor Hills 5* Gated Resort. Luxury villa. Private South Facing Pool with Spa. Games Room. Free Wi-fi. Resort amenities: Large heated pool, water slide, movie theatre, children's play area. Cable TV. X-box. Close to Restaurants and Outlet Shops. Daily shuttle buses.  …see more

from £70 / night

£484 - £646 / week

View

Very Good 4/5 

20 Photos

Kissimmee / Windsor Hills Resort

Townhouse / 3 Bedrooms / sleeps 8

Very Good 4/5 

7 Nights min stay

Add to shortlist

from £70 / night

£484 - £646 / week

View

Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Luxury 3 bedroom, 3 bathroom home, with splash pool. Located on a holiday resort complex with fabulous facilities, including huge swimming pool with fun slide. Only 2 miles from Disney.  …see more

from £109 / night

£760 - £1000 / week

View

Excellent 5/5 

19 Photos

Kissimmee / Windsor Hills Resort

Villa / 5 Bedrooms / sleeps 14

Excellent 5/5 

5 Nights min stay

Add to shortlist

from £109 / night

£760 - £1000 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 64 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Stunning 5 bed, 5 bath house with pool & jacuzzi, games room and den in the Windsor Hills gated community, less than 5 minutes from Disney. Our holiday home has over 2,700 square feet of space including 3 king bedrooms and a kids bedroom with 2 sets of bunk beds. Windsor Hills is the most highly rated community in the Orlando area and is less than 2 miles from Disney.  …see more

from £64 / night

£448 / week

View

18 Photos

Kissimmee / Windsor Hills Resort

Condo / 3 Bedrooms / sleeps 8

3 Nights min stay

Add to shortlist

from £64 / night

£448 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 89 km
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
 …see more

from £200 / night

£1400 - £1500 / week

View

23 Photos

Kissimmee / Windsor Hills Resort

Villa / 6 Bedrooms / sleeps 14

4 Nights min stay

Add to shortlist

from £200 / night

£1400 - £1500 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
The Windsor Hills Resort clubhouse features a huge lagoon-style pool with water slide and hot tub, children's playground, state-of-the-art fitness center, sand volleyball, basketball and tennis courts, 40-seat movie theatre, video arcade and billiards. Windsor Hills is located in Kissimmee just 2 miles (3km) from the gates of Walt Disney World.  …see more

from £104 / night

£723 - £746 / week

View

Excellent 5/5 

17 Photos

Kissimmee / Windsor Hills Resort

Bungalow / 4 Bedrooms / sleeps 8

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £104 / night

£723 - £746 / week

View

Key info:

  • Nearest beach 110 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Location. Location. Location! We are close to all amenities within the resort ( volleyball, tennis and basketball courts; putting green, large pool, water slide and jacuzzi ; video games and movie theatre) and we are close to all Disney theme and water parks! The resort is just minutes from great places to eat, play, and shop! Enjoy villa living at hotel prices.  …see more

from £81 / night

£565 - £1310 / week

View

Very Good 4/5 

20 Photos

Kissimmee / Windsor Hills Resort

Villa / 4 Bedrooms / sleeps 8

Very Good 4/5 

3 Nights min stay

Add to shortlist

from £81 / night

£565 - £1310 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
A 4 bedroom luxury Villa, with pool,spa and games room at the prestigious Windsor Hills community, within 2 Miles of Walt Disney World. Windsor Hills has a five star clubhouse with Lagoon Pool, hot tub, slides, Cinema, Gym, Games Room, Shop & “Castle” play area.  …see more

from £184 / night

£1288 - £1701 / week

View

14 Photos

Kissimmee / Windsor Hills Resort

House / 6 Bedrooms / sleeps 12

5 Nights min stay

Add to shortlist

from £184 / night

£1288 - £1701 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 97 km
  • Swimming pool
  • Ask owner if suitable for children
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
REF: TOP VILLAS - Windsor Hills Resort 16 All of our villas here at Top Villas are professionally managed by an onsite property team to ensure you have a perfect stay, Call us today 24/7 for an instant quote, availability, special deals or if you have any questions, regarding our amazing villa in Windsor Hills Resort, Orlando. This spacious Villa is located less than 2 miles away from Disney, approximately 20 minutes to Universal Studios theme parks and Sea World and only an hour away from from a number of beaches; all of these features makes it the perfect place for a family vacation. Key Features 6 Bedrooms (sleeps 12) - 2 themed bedrooms 4 Bathrooms - 2 en-suites Private Swimming Pool and Spa Games Room (garage conversion) Hair Dryer Wi-Fi Local attractions, i.e. Disney, Universal Studios and Sea World Bedrooms Bedroom 1 - King Bed with en-suite Bedroom 2 - King Bed with en-suite Bedroom 3 - King Bed Bedroom 4 - Queen Bed Bedroom 5 - Twin Bedroom with Mickey Mouse theme Bedroom 6 - Twin Bedroom with Disney Princess theme General Sitting Area Dining Area, with seating for 6 people Fully Equipped Kitchen Open Living Room Games Room Exterior Swimming Pool Spa Pool Deck Sun Loungers Alfresco Dining Area Entertainment Games Room Cable TV Wi-Fi Resort facilities By staying in this stunning Windsor Hills Resort villa, you will get free access to the following facilities: Huge lagoon style water park complex with a double Olympic sized heated pool Impressive clubhouse with games room including billiards, table tennis and arcade games State of the art fitness centre with cardio machines and weights Free use of the in house HD movie theatre that sits 48 persons Flood lit tennis court Basket Ball court Sand volleyball court Golf putting green A castle themes children's play area Picnic and BBQ area Grocery and Sundries shop 24-hour gated and guarded entrance Shuttle bus service to shops and parks (small charge) DVD rental service and ATM Business Meeting rooms  …see more

from £163 / night

£1138 - £1603 / week

View

28 Photos

Kissimmee / Windsor Hills Resort

Villa / 5 Bedrooms / sleeps 12

3 Nights min stay

Add to shortlist

from £163 / night

£1138 - £1603 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
 …see more

from £52 / night

£362 - £904 / week

View

23 Photos

Kissimmee / Windsor Hills Resort

Condo / 3 Bedrooms / sleeps 6

3 Nights min stay

Add to shortlist

from £52 / night

£362 - £904 / week

View

Key info:

  • Nearest beach 143 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
 …see more

from £129 / night

£903 - £1355 / week

View

34 Photos

Kissimmee / Windsor Hills Resort

Villa / 5 Bedrooms / sleeps 12

5 Nights min stay

Add to shortlist

from £129 / night

£903 - £1355 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
 …see more

from £130 / night

£904 - £1355 / week

View

Excellent 5/5 

22 Photos

Kissimmee / Windsor Hills Resort

House / 6 Bedrooms / sleeps 12

Excellent 5/5 

1 night min stay

Add to shortlist

from £130 / night

£904 - £1355 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
 …see more

from £130 / night

£904 - £1355 / week

View

Excellent 5/5 

24 Photos

Kissimmee / Windsor Hills Resort

House / 6 Bedrooms / sleeps 12

Excellent 5/5 

1 night min stay

Add to shortlist

from £130 / night

£904 - £1355 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
 …see more

from £129 / night

£903 - £1259 / week

View

35 Photos

Kissimmee / Windsor Hills Resort

Villa / 6 Bedrooms / sleeps 12

7 Nights min stay

Add to shortlist

from £129 / night

£903 - £1259 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
 …see more

from £113 / night

£791 - £1017 / week

View

12 Photos

Kissimmee / Windsor Hills Resort

House / 5 Bedrooms / sleeps 10

5 Nights min stay

Add to shortlist

from £113 / night

£791 - £1017 / week

View

Key info:

  • Nearest beach 129 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
 …see more

from £78 / night

£546 - £610 / week

View

15 Photos

Kissimmee / Windsor Hills Resort

Townhouse / 3 Bedrooms / sleeps 7

3 Nights min stay

Add to shortlist

from £78 / night

£546 - £610 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
  • Private garden
 …see more

from £60 / night

£419 - £580 / week

View

Excellent 5/5 

25 Photos

Kissimmee / Windsor Hills Resort

Condo / 3 Bedrooms / sleeps 8

Excellent 5/5 

1 night min stay

Add to shortlist

from £60 / night

£419 - £580 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
 …see more

from £90 / night

£628 - £899 / week

View

9 Photos

Kissimmee / Windsor Hills Resort

Condo / 3 Bedrooms / sleeps 6

1 night min stay

Add to shortlist

from £90 / night

£628 - £899 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
 …see more

from £77 / night

£538 - £764 / week

View

12 Photos

Kissimmee / Windsor Hills Resort

Condo / 3 Bedrooms / sleeps 6

1 night min stay

Add to shortlist

from £77 / night

£538 - £764 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
 …see more

Don’t let an old browser slow down your holiday

Your browser is out of date and might not work well with our website. Download the latest version to speed up your hunt for the perfect holiday home.

Just click on the icons to get to the download page