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

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27 Vacation rentals

(11) Excellent 

28

Vacation villa in Windsor Hills Resort

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 $169 / night

$1183 - $1560 / week

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from $169 / night

(3) Excellent 

20

Villa rental in Kissimmee with golf nearby

Kissimmee / Windsor Hills Resort

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • 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 $220 / night

$1540 / week

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from $220 / 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 $119 / night

$833 / week

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Responds fast!
avg. 1 hour 45 minutes

from $119 / night

(9) Excellent 

55

Vacation villa with golf nearby in Windsor Hills Resort

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 $240 / night

$1680 / week

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from $240 / night

(13) Very Good 

24

Villa rental in Windsor Hills Resort 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 private heated Pool …see more

from $169 / night

$1092 - $1885 / week

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Responds fast!
avg. 2 hours 17 minutes

from $169 / night

(2) Very Good 

20

Windsor Hills Resort 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 $120 / night

$840 / week

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from $120 / night

(4) Excellent 

61

Windsor Hills Resort 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 neighbouri …see more

from $150 / night

$897 - $1755 / week

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from $150 / night

15

Vacation townhouse rental

Kissimmee / Windsor Hills Resort

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Windsor Hills is an exclusive resort situated in the very heart of Kissimmee, Orlando. Its fantastic location is just one of its great features. It is only two miles from Disney World and very close to Orlandos other main attractions, such as Universal Studios and the s …see more

from $105 / night

$735 / week

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from $105 / night

(5) Very Good 

14

Windsor Hills Resort Vacation villa rental

Kissimmee / Windsor Hills Resort

6 13 1 night min

  • 6 bedrooms
  • Sleeps 13
  • 1 night min
  • 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. • Baby/Infa …see more

from $230 / night

$1600 / week

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from $230 / night

(13) 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 imported furniture from 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 large fri …see more

from $234 / night

$1638 - $2503 / week

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from $234 / night

(4) 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 $115 / night

$800 / week

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from $115 / 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

$1800 - $2600 / week

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Responds fast!
avg. 3 hours 58 minutes

from $270 / night

(5) Very Good 

74

Villa rental in Windsor Hills Resort 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

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from $135 / night

(11) Excellent 

20

Vacation bungalow with swimming pool, golf nearby in Windsor Hills Resort

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 and four full baths: two king master suites, a queen and a bedroom with twin beds. The chair in the nook makes into a single twin if necessary. …see more

from $165 / night

$1155 / week

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from $165 / night

(15) Excellent 

21

Vacation villa with golf nearby in Windsor Hills Resort

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 $234 / night

$1638 - $2503 / week

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from $234 / night

(7) Excellent 

28

Vacation condo with shared pool in Windsor Hills Resort

Kissimmee / Windsor Hills Resort

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Dreaming of a Disney Vacation? Why stay in a cramped, overpriced hotel room when you can rent a beautiful 3 bedroom condo in a luxury resort just 2 miles from the entrance to Walt Disney World! Lots of room, a full kitchen, and all the modern amenities you'd expect from …see more

from $85 / night

$575 - $729 / week

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Responds fast!
avg. 2 hours 47 minutes

from $85 / night

(3) Excellent 

12

Windsor Hills Resort Vacation home rental

Kissimmee / Windsor Hills Resort

5 10 1 night min

  • 5 bedrooms
  • Sleeps 10
  • 1 night min
  • Nearest beach 129 mi
  • Swimming pool
  • Child friendly
You will not believe the stunning look of this home until you view the photos. Live like royalty for the duration of your vacation, just completed Magnolia View, offers the very best in luxury with each of the 5 bedrooms having their own bathroom. Magnolia View is in T …see more

from $154 / night

$1078 / week

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from $154 / night

11

Vacation villa with golf nearby in Windsor Hills Resort

Kissimmee / Windsor Hills Resort

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 105 mi
  • Swimming pool
  • Child friendly
“Pooh's Palace” is a fully-equipped 5-bedroom, 5-bathroom luxury vacation villa. The home is located in the newest section of Windsor Hills Resort. Pooh's Palace is situated on a hill – no one overlooks our yard or pool. The eastern facing lanai, pool and spa get ful …see more

from $185 / night

$1159 - $2942 / week

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from $185 / night

23

Vacation condo in Windsor Hills Resort

Kissimmee / Windsor Hills Resort

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
This Disney Magical Family Getaway condo is located in the 5 star resort Windsor Hills. With its impressive entrance and manned gatehouse, you will feel on vacation immediately. Located 5 minutes from Walt Disney World, Windsor Hills resort is the closest vacation home …see more

from $50 / night

$595 / week

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Responds fast!
avg. 3 hours 37 minutes

from $50 / night

(5) Excellent 

23

Vacation townhouse in Windsor Hills Resort

Kissimmee / Windsor Hills Resort

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 113 mi
  • Swimming pool
  • Child friendly
Our Town home is located just minutes from the Disney Parks -the Magic Kingdom, Epcot, Animal Kingdom and MGM Studios as well as Downtown Disney and Disney Wide World of Sports. It is also close to Sea World, Universal Studios and Island of Adventure. The town ho …see more

from $110 / night

$770 / week

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Responds fast!
avg. 1 hour 39 minutes

from $110 / night

33

Vacation villa rental

Kissimmee / Windsor Hills Resort

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
GRAND OPENING for this beautiful south facing villa at Windsor Hills Resort. The house is professionally designed and renovated with star hotel quality. Brand new high standard bedding linens to ensure you the most comfortable night sleep. * 2 Master bedroom sui …see more

from $215 / night

$1399 - $2299 / week

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from $215 / night

(3)  

14

Vacation condo with shared pool, golf nearby in Windsor Hills Resort

Kissimmee / Windsor Hills Resort

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 143 mi
  • Swimming pool
  • Child friendly
The location of Sunlake resorts is one mile from the Disney world entrance gate in Kissimmee Florida. It is very spacious kitchen and living room with flat TV. you may relax with your family, enjoy golf near by, have family trip to Disney world. It is very convenient f …see more

from $90 / night

$630 - $1190 / week

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Responds fast!
avg. 3 hours 32 minutes

from $90 / night

15

Vacation townhouse with swimming pool, golf nearby in Kissimmee

Kissimmee / Windsor Hills Resort

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Swimming pool
  • Air conditioning
  • Private garden
1416 sq. ft, 3 Bedroom and 3 bathroom townhouse, with private patio, splash pool and private driveway. Located in beautiful Kissimmee, Windsor Hills is the closest gated community resort to Disney World, which is less than 2 miles away and easily accessible to I …see more

from $125 / night

$845 / week

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from $125 / night

(2) Excellent 

16

Vacation townhouse in Windsor Hills Resort

Kissimmee / Windsor Hills Resort

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Perfect for a family vacation at Disney. Newly renovated contemporary and spacious townhouse in a spectacular gated resort community with all amenities. Location, Location, Location: less than 2 miles from Disney theme parks, in Orlando. Parking , Wi-Fi, washer/dryer. …see more

from $99 / night

$750 / week

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Responds fast!
avg. 3 hours 21 minutes

from $99 / night

18

Windsor Hills Resort Vacation condo rental

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
Windsor Hills Resort is only a 25 minute drive from the Orlando International Airport, and is situated central to all if Orlando's famous attractions. The resorts amenities include gated community, water park with Olympic Size Swimming Pool, fountains, waterslides, spa, …see more

from $99 / night

$693 / week

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from $99 / night

15

Vacation condo in Kissimmee

Kissimmee / Windsor Hills Resort

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
WINDSOR HOLIDAY LUXURY Here's holiday luxury you'll feel right at home with. Windsor Hills is a superb 24 hour secure gated resort community located 2..5 miles from Walt Disney world. Our 2 bedroomed, 2 bathroomed executive CONDO, THE GREAT ESCAPE IS A HA …see more

from $90 / night

$630 / week

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from $90 / night

53

Vacation townhouse with swimming pool in Windsor Hills Resort

Kissimmee / Windsor Hills Resort

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 118 mi
  • Swimming pool
  • Child friendly
Welcome to our beautiful 2-Story Mickey Town Home which has 3 Bedroom/3 En-suite bathroom in the prestigious gated resort of Windsor Hills which is the closest gated community to Walt Disney World, just 2 Miles to the Gates! Our home has a full equipped kitchen, with d …see more

from $99 / night

$693 / week

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from $99 / night