30 Best Vacation Rentals in Windsor Hills Resort - Holiday Lettings - Cabins

Close

Windsor Hills Resort

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this vacation rental you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

30 Vacation rentals

(13) Very Good 

24

Villa rental in Kissimmee with golf nearby

Kissimmee / Windsor Hills Resort

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 80 mi
  • Swimming pool
A Brand new 2010, '5' Star Luxurious 6 bed, 4 bath fully air conditioned executive Villa in Archfeld Blvd, Windsor Hills Resort, with Free local, National & international call to over 40 destinations & free wireless internet. You also have your own pr  …see more

from $173 / night

$1169 - $1842 / week

Book View

from $173 / night

(7) Excellent 

28

Vacation villa in Kissimmee

Kissimmee / Windsor Hills Resort

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This fabulous 5 Bed/5 Bath Executive Villa with Games Room can easily accommodate 10 guests in absolute comfort. Fully air conditioned and with the added luxury of ceiling fans in all rooms the property offers total privacy and space to relax and enjoy your holiday of a  …see more

from $148 / night

$1032 - $1378 / week

Book View

from $148 / night

(5) Excellent 

55

Vacation villa with golf nearby in Kissimmee

Kissimmee / Windsor Hills Resort

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly
Our Villa in Windsor Hills is a BEAUTIFUL custom designed home. Windsor Hills is a secure gated community that has all the amenities of a 5 star hotel or resort, but with the comfort, convenience, and privacy of staying in a high end home. Facilities Air Conditioning F  …see more

from $225 / night

$1575 / week

Book View

from $225 / night

(5) Very Good 

74

Villa rental in Kissimmee with swimming pool, golf nearby

Kissimmee / Windsor Hills Resort

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
Our 4 bedroom / 4 bathroom, newly built vacation home has a beautiful corner lot in the prestigious Windsor Hills Resort and has over 1800 sq ft of living space. Sleeping up to 8 people comfortably, our home boasts 1 king bedroom with ensuite, 1 queen bedroom with ensu  …see more

from $135 / night

$945 / week

Inquire View

from $135 / night

(4) Excellent 

23

Vacation villa in Kissimmee

Kissimmee / Windsor Hills Resort

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Book your vacation now at our beautiful home (South Facing Pool) with pool & spa located in the Windsor Hills Resort and choose a better way to spend quality time together on vacation. Brand new in 2010 and re-furnished and decorated in 2012 our 6 bedroom 4 bath 2,  …see more

from $200 / night

$1400 / week

Book View

from $200 / night

24

Vacation villa in Kissimmee

Kissimmee / Windsor Hills Resort

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Spread out and enjoy your very own sunny six bedroom, four bathroom villa in Windsor Hills Resort. Best of all, it is only two miles to Walt Disney World!NO REAR NEIGHBOURS! To ensure your privacy, we chose a premium location that overlooks a natural area, not a  …see more

from $270 / night

$1801 - $2600 / week

Book View

from $270 / night

(3) Excellent 

61

Kissimmee Vacation villa rental

Kissimmee / Windsor Hills Resort

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 64 mi
  • Swimming pool
There are very few rental homes offering this level of accommodation (space, games room, 5 en suite bedrooms, pool, standard of furniture and decor...) and it also has one further unique advantage: due to it's location our house pool deck is not overlooked by neigh  …see more

from $147 / night

$877 - $1715 / week

Book View

from $147 / night

(2) Very Good 

35

Vacation townhouse rental

Kissimmee / Windsor Hills Resort

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
Our spacious 3 bedroom townhouse is well equipped with everything necessary to meet all of your holiday needs. Each bedroom has its own en-suite shower facilities, with the master bedroom having a super king sized bed, the twin room having two single beds and the 3rd b  …see more

from $108 / night

$750 - $1001 / week

Book View

from $108 / night

42

Condo rental in Kissimmee

Kissimmee / Windsor Hills Resort

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
3 Bedroom 2 Bathroom Condo Sleeps 6 Welcome to Minion Cove, our 3 bedroom 2 bathroom condo located in the beautiful 5 star gated community of Windsor Hills located less than 2 miles from the main gates of Walt Disney World. Windsor Hills is one of the newest and greates  …see more

from $110 / night

$770 - $1191 / week

Book View

from $110 / night

(2) Very Good 

14

Kissimmee Vacation villa rental

Kissimmee / Windsor Hills Resort

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
our beautiful villa at 7764 Teascone Bvld. Windsor Hills Reserve will provide you the best of time on your vacation. You are welcome here to be at your ease. Additional features for the house:- • Games room – Pool, Air hockey, Basketball and Play Station 2. • Bab  …see more

from $220 / night

$1500 - $1550 / week

Book View

from $220 / night

(6) Excellent 

18

Vacation bungalow with swimming pool, golf nearby in Kissimmee

Kissimmee / Windsor Hills Resort

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 110 mi
  • Swimming pool
  • Child friendly
The villa accommodates 8 people, and is equipped with everything needed to make your stay enjoyable. There are four bedrooms complete with full baths: two king master suites, a queen and a bedroom with twin beds. The chair in the nook makes into a single twin. Each ba  …see more

from $165 / night

$1156 / week

Inquire View

from $165 / night

(15) Excellent 

21

Vacation villa with golf nearby in Kissimmee

Kissimmee / Windsor Hills Resort

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
(1) High quality new furniture imported for England(2) Two twin rooms with themed bed-linen for the children if required (SpongeBob SquarePants, Mickey mouse or neutral). Play Station PS II in each bedroom with a selection of games.(3) Fully fitted granite kitch  …see more

from $191 / night

$1334 - $2134 / week

Book View

from $191 / night

(1) Very Good 

20

Kissimmee Vacation villa rental

Kissimmee / Windsor Hills Resort

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 100 mi
  • Swimming pool
Harmony Haven is a vacation home that has 4 bedrooms, 4 bathrooms, games room, fully screened in swimming pool, spa, and lanai. This fully air-conditioned vacation home is located less than 5 miles from Disney in Windsor Hills, a resort-style community. With its impre  …see more

from $95 / night

$840 / week

Book View

from $95 / night

(12) Excellent 

18

Vacation villa with golf nearby in Kissimmee

Kissimmee / Windsor Hills Resort

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
(1) High quality new furniture imported for England(2) Two twin rooms with themed bed-linen for the children if required (SpongeBob SquarePants, Tinkerbell, Cars. Play Station PS II in each bedroom with a selection of games.(3) Fully fitted granite kitchen with  …see more

from $191 / night

$1334 - $2134 / week

Book View

from $191 / night

20

Villa rental in Kissimmee with golf nearby

Kissimmee / Windsor Hills Resort

6 12 4 nights min

  • 6 bedrooms
  • Sleeps 12
  • 4 nights min
  • Nearest beach 116 mi
  • Swimming pool
  • Child friendly
2 miles to Disney - Luxury 6 bed, 4 bath - South facing private Palm Tree lined pool & spa with covered patio area. No expense spared, large LCD flat screen TVs in every room, premium & HD cable channels, Sony BluRay/DVD players, Nintendo Wii, Xbox 360, iHome alarm  …see more

from $225 / night

$1575 / week

Book View

from $225 / night

(1) Excellent 

51

Vacation townhouse in Kissimmee

Kissimmee / Windsor Hills Resort

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Welcome to our See The Mouse Townhouse situated just two miles south of the Walt Disney World resort.The Townhouse is luxuriously furnished and consists of three bedrooms all with en-suite bath/shower rooms on two levels. There is a plunge/spa pool (can be heate  …see more

from $96 / night

$634 - $1142 / week

Book View

from $96 / night

18

Kissimmee / Windsor Hills Resort

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $150 / night

$1051 - $1251 / week

Book View

from $150 / night

(1)  

14

Kissimmee / Windsor Hills Resort

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 143 mi
  • Swimming pool
  • Child friendly

 …see more

from $90 / night

$631 - $1191 / week

Book View

from $90 / night

(3) Very Good 

23

Kissimmee / Windsor Hills Resort

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 113 mi
  • Swimming pool
  • Child friendly

 …see more

from $120 / night

$770 / week

Book View

from $120 / night

(3) Excellent 

12

Kissimmee / Windsor Hills Resort

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 129 mi
  • Swimming pool
  • Child friendly

 …see more

from $145 / night

$1226 / week

Book View

from $145 / night

53

Kissimmee / Windsor Hills Resort

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 118 mi
  • Swimming pool
  • Child friendly

 …see more

from $100 / night

$950 / week

Book View

from $100 / night

(5) Excellent 

28

Kissimmee / Windsor Hills Resort

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $85 / night

$590 - $760 / week

Book View

from $85 / night

33

Kissimmee / Windsor Hills Resort

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $180 / night

$1400 - $2339 / week

Book View

from $180 / night

9

Kissimmee / Windsor Hills Resort

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Swimming pool
  • Air conditioning

 …see more

from $135 / night

$1067 / week

Book View

from $135 / night

25

Kissimmee / Windsor Hills Resort

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 105 mi
  • Swimming pool
  • Child friendly

 …see more

from $195 / night

$1365 / week

Book View

from $195 / night

23

Kissimmee / Windsor Hills Resort

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning

 …see more

from $85 / night

$596 / week

Book View

from $85 / night

18

Kissimmee / Windsor Hills Resort

3 8 5 nights min

  • 3 bedrooms
  • Sleeps 8
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 89 mi
  • Swimming pool

 …see more

from $100 / night

$693 / week

Book View

from $100 / night

15

Kissimmee / Windsor Hills Resort

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $90 / night

$631 / week

Book View

from $90 / night

15

Kissimmee / Windsor Hills Resort

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Swimming pool
  • Air conditioning
  • Private garden

 …see more

from $125 / night

$845 / week

Book View

from $125 / night

(1) Excellent 

16

Kissimmee / Windsor Hills Resort

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $120 / night

$834 / week

Book View

from $120 / night