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

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Windsor Hills Resort

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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

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from $167 / night

$1165 - $1536 / week

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Responds fast!
avg. 3 hours 25 minutes

from $167 / night

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(8) 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

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from $240 / night

$1680 / week

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from $240 / night

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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

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from $109 / night

$763 / week

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Responds fast!
avg. 1 hour 26 minutes

from $109 / night

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(3) 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

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from $148 / night

$884 - $1729 / week

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from $148 / night

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“Luxury in the sun”

Reviewed 28 Oct 2011

Home from home - if home had all these mod cons and a heated pool outside the lounge and a games room in the garage. Great location for Disney assuming you have a car. Plenty of local restaurants and … More

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(3) Very Good 

14

Windsor Hills Resort 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. • Baby/Infa …see more

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from $200 / night

$1400 / week

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from $200 / night

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(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

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from $135 / night

$945 / week

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from $135 / night

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“Home from home... Fantastic!!”

Reviewed 1 Oct 2015

My husband & i stayed here with our teenage daughter & her friend, what a great holiday we all had! The villa was perfect... Centrally located on the 192, really comfortable & stylish with every conve… More

“Lovely villa”

Reviewed 9 Aug 2016

Very good if you are visiting Disney parks they are very close by. The villa was in a very nice neighbourhood also it was well maintained. Also the security gates made us feel very secure. Slight… More

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(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

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from $167 / night

$1076 - $1856 / week

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from $167 / night

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“Excellent Villa highly recommend it, great location.”

Reviewed 13 Oct 2012

Property was excellent, close to Disney and places to eat. The weather was nice and the complex where the villa was situated was well looked after, nice and clean and staff was pleasant.… More

“Had a wonderful holiday with all the family”

Reviewed 15 Aug 2012

Stayed at a very nice villa in a good location a couple of miles from the Disney Parks The surrounding area was always very clean & tidy & well looked after. Could not have asked for anything more, … More

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(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

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from $120 / night

$840 / week

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from $120 / night

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“Lovely villa in a super location”

Reviewed 5 Sep 2013

We all thoroughly enjoyed our stay at Harmony Haven with its good standard, spacious accommodation and super swimming pool. We travelled with our children and grandchildren and we all enjoyed the … More

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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

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from $105 / night

$735 / week

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from $105 / night

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(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

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from $115 / night

$800 / week

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from $115 / night

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“FANTASTIC!”

Reviewed 30 Mar 2016

I would highly recommend this 3 bedroom townhouse with heated pool. It was everything and more when we arrived. The outdoor pool was perfect for the kids and the park in the back yard was great to hav… More

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(3) Excellent 

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

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from $200 / night

$1400 / week

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from $200 / night

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(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

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from $231 / night

$1613 - $2464 / week

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from $231 / night

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“Fantastic villa, great location!”

Reviewed 8 Nov 2014

Dunestone is a very smart, spacious and well-positioned villa in a great gated community. So close to Disney and only mins from the I-4 allowing easy access to all of Orlando's attractions. The owner… More

“Lovely Villa”

Reviewed 21 Jan 2014

Another great stay in villa Dunestone, We stayed here over christmas and it was everything we could of asked for. Great location and a lovely villa resort. Would highly recommend. We will be back… More

“Home for home !”

Reviewed 18 Jul 2013

Excellent property. Large spacious house with lovely comfortable beds, great games room and pool. We really enjoyed our stay in Dunestone a flawless villa with all that we needed at hand, close to loc… More

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(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

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from $231 / night

$1613 - $2464 / week

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from $231 / night

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“A fantastic place to stay, would highly recommend!”

Reviewed 6 Dec 2014

This is a perfect villa for a family holiday to Orlando! The complex is pristine and very safe. The villa itself had everything you could wish for and more. The owners had thought of everything to mak… More

“This house was exactly what my family needed to complete the most amazing trip to Disney World!”

Reviewed 6 Dec 2014

This condo was beautiful and was exactly what we needed to ensure a good night's sleep for all my children (and the adults too). The only thing you would need to know in advance is, you have to buy mo… More

“Excellent”

Reviewed 6 Dec 2014

Tthe house was nice and clean and located in a quiet and peaceful area close to Diseny. Can be recommended… More

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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

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from $270 / night

$1800 - $2600 / week

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Responds fast!
avg. 3 hours 47 minutes

from $270 / night

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(7) 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

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from $165 / night

$1155 / week

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from $165 / night

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(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

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from $124 / night

$862 / week

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from $124 / night

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(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

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from $85 / night

$575 - $799 / week

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Responds fast!
avg. 2 hours 55 minutes

from $85 / night

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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

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from $90 / night

$630 / week

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from $90 / night

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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

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from $50 / night

$595 / week

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Responds fast!
avg. 3 hours 37 minutes

from $50 / night

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(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

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from $90 / night

$630 - $1190 / week

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Responds fast!
avg. 2 hours 38 minutes

from $90 / night

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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

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from $172 / night

$1083 - $2753 / week

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from $172 / night

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(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

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from $99 / night

$750 / week

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Responds fast!
avg. 3 hours 21 minutes

from $99 / night

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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

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from $125 / night

$845 / week

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from $125 / night

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(4) 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

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from $110 / night

$771 / week

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Responds fast!
avg. 1 hour 20 minutes

from $110 / night

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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

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from $99 / night

$693 / week

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Responds fast!
avg. 3 hours 56 minutes

from $99 / night

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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

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from $215 / night

$1400 - $2299 / week

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from $215 / night

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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

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from $99 / night

$693 / week

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from $99 / night

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