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Windsor Hills Vacation Rentals & Homes - 40 Rentals Available

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40 Vacation rentals

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(3)

1 / 25

Davenport Villa - 4.3 miles away

  • 4
  • 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“We were very happy with the property, I only wish the pool area was keep a little cleaner, I think most of all the pool cover flooded up. The house was very nice. I hope we left the house nice. Thank you. Pamela”
- Review left on 06/19/2016

$125.00

Very Good (3 reviews)

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from $125.00 / night

(61)

1 / 51

Kissimmee Villa - 0.1 miles away

  • 5
  • 10
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Great big house Excellent location for parks Very reasonable Owner gave great directions for when you show up Also pool really came in handy”
- Review left on 06/28/2018

$144.00

Excellent (61 reviews)

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from $144.00 / night

(5)

1 / 41

Orlando Villa - 4.2 miles away

  • 7
  • 18
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“We loved it here. It was a nice to be able to use the club house. Lots of stores by for shopping. We would go there again...”
- Review left on 09/06/2016

$184.00

Very Good (5 reviews)

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from $184.00 / night

(43)

1 / 30

Four Corners Villa - 1.6 miles away

  • 7
  • 25
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 40 mi
  • Swimming pool

Responds fast! Avg. 1 hour 9 minutes

“We had an excellent stay in the villa and all my family and friends had a great stay. Everything was working correctly. . It is minutes from Disney parks and shopping stores. The Villa is closed and is safe. All communications with the owner were...”
- Review left on 02/21/2018

$249.00

Very Good (43 reviews)

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from $249.00 / night

(11)

1 / 29

Four Corners Villa - 0.1 miles away

  • 3
  • 8
  • min stay varies
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
“Was a very nice vacation will do it again next year possibly the same place dont have any complaints”
- Review left on 08/22/2017

$79.00

Very Good (11 reviews)

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from $79.00 / night

(12)

1 / 32

Orlando Villa - 7.3 miles away

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 46 minutes

“This is the place to stay if you're in the Orlando area. Andy was more than helpful the house is amazing and the Game room was a huge bonus for the kids..Will be my place of choice for years to come...”
- Review left on 07/05/2018

$132.00

Excellent (12 reviews)

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from $132.00 / night

(37)

1 / 45

Orlando Townhouse - 19.1 miles away

  • 4
  • 9
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 4 minutes

“Our stay was great, vacation home rentals was the right choice for where to stay while visiting the theme parks...”
- Review left on 10/28/2017

$100.00

Excellent (37 reviews)

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from $100.00 / night

(23)

1 / 28

Kissimmee Townhouse - 0.1 miles away

  • 3
  • 8
  • min stay varies
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
“The location is perfect for a Disney vacation. You can't get much closer to DisneyWorld without staying onsite. I prefer to stay offsite whenever we visit, because it's nice to be able to "escape" from all the Disney magic every now and then. The...”
- Review left on 10/27/2017

$85.00

Excellent (23 reviews)

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from $85.00 / night

(2)

1 / 22

ChampionsGate Townhouse - 5.1 miles away

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 1 minutes

“House was decorated well, very clean, and spacious. Was nice having these accommodations versus a hotel. Highly recommended...”
- Review left on 10/31/2017

$147.00

Very Good (2 reviews)

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from $147.00 / night

1 / 33

Orlando Townhouse - 12.5 miles away

  • 4
  • 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 52 minutes

$107.00

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from $107.00 / night

(10)

1 / 33

Kissimmee House - 0.1 miles away

  • 6
  • 15
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 47 minutes

“We've stayed in a lot of vacation homes in this area over the last 20 years and I have to say that this was one of the best equipped that we've ever stayed in. The house has been recently renovated and everything was very nice and clean. The pool is...”
- Review left on 03/11/2017

$190.00

Excellent (10 reviews)

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from $190.00 / night

(53)

1 / 27

Kissimmee Townhouse - 0.1 miles away

  • 3
  • 8
  • min stay varies
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
“The accommodations were excellent, all the amenities required for a comfortable stay, the place was very clean, the HVAC worked fine no issues. I recommend staying here to anyone. Than you for everything Manny and Carmen we will be back soon...”
- Review left on 01/23/2017

$85.00

Very Good (53 reviews)

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from $85.00 / night

(12)

Certificate of Excellence

1 / 55

Orlando Villa - 6.6 miles away

  • 7
  • 16
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Certificate of Excellence

“We really enjoyed the week we spent at the house. It has all we needed: a room that was big enough for each family. It was easy to get to malls, parks, etc. The kids had a lot of fun in the game room, and, of course, the pool. Parents enjoyed the...”
- Review left on 12/12/2016

$172.00

Excellent (12 reviews)

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from $172.00 / night

(6)

1 / 27

Kissimmee House - 0.1 miles away

  • 3
  • 8
  • min stay varies
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly

$85.00

Average (6 reviews)

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from $85.00 / night

1 / 67

Orlando House - 12.5 miles away

  • 8
  • 16
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 1 minutes

$302.00

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from $302.00 / night

1 / 45

Orlando House - 12.5 miles away

  • 7
  • 14
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 1 minutes

$336.00

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from $336.00 / night

(6)

1 / 29

Four Corners House - 0.1 miles away

  • 3
  • 8
  • min stay varies
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly

$85.00

Excellent (6 reviews)

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from $85.00 / night

(13)

1 / 27

Davenport House - 5.2 miles away

  • 5
  • 12
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“We took our three kids and their three grandparents to Disney in December. I was so nervous this home was too good to be true, but it turned out even better than I expected. The pool and hot tub were wonderful, we had everything we needed in the...”
- Review left on 03/13/2017

$130.00

Excellent (13 reviews)

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from $130.00 / night

1 / 84

Orlando House - 12.5 miles away

  • 8
  • 16
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 1 minutes

$302.00

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from $302.00 / night

(16)

1 / 73

Orlando Villa - 19.1 miles away

  • 4
  • 9
  • min stay varies
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 4 minutes

“From our first look, we loved it. Our only regret is that we spent so much time at Disney/Universal/local attractions that we didn't spend enough time at the resort. Everything was clean and comfortable. Our kids loved the pool. We were pleased...”
- Review left on 06/18/2018

$110.00

Excellent (16 reviews)

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from $110.00 / night

1 / 19

Orlando House - 12.5 miles away

  • 3
  • 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 54 minutes

$153.00

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from $153.00 / night

(85)

1 / 101

Davenport Villa - 5.6 miles away

  • 4
  • 10
  • 3 nights min
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 4 minutes

“We stayed here for 16 nights in October 2018 as a family of 5 and had a fantastic time. The villa is very spacious and was like a home from home. The pool and spa are great with a nice seating area for outdoor dining and the area is quiet so no...”
- Review left on 10/28/2018

$120.00

Excellent (85 reviews)

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from $120.00 / night

(62)

1 / 47

Davenport Villa - 5.1 miles away

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“The location was perfect and made ease of getting to where we needed to go and all the convenience items were close by. The house was well laid out and provided plenty of space for the 5 of us. We would definitely recommend this place to anyone...”
- Review left on 11/22/2017

$114.00

Excellent (62 reviews)

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from $114.00 / night

(23)

1 / 20

Orlando House - 6.8 miles away

  • 4
  • 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 58 minutes

“We had so much fun in this house that we did not want to leave, everything u need that u can forget at Last minute is here. Our car broke down at last minute so I had to take my brothers so in all this I forgot my baby's stroller and playpin, Janet...”
- Review left on 08/18/2017

$125.00

Excellent (23 reviews)

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from $125.00 / night

1 / 45

Davenport House - 11.2 miles away

  • 6
  • 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 1 minutes

$290.00

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from $290.00 / night

1 / 9

Kissimmee Villa - 11.8 miles away

  • 6
  • 14
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$287.00

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from $287.00 / night

(5)

1 / 24

Davenport Villa - 5.8 miles away

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“My family of four took our first Disney vacation and rented this beautiful home. The decor was beautiful and it was spotless. Everything you can need on your trip is available to you in this home. They even had stuff for the beach. My kids loved...”
- Review left on 03/16/2017

$120.00

Excellent (5 reviews)

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from $120.00 / night

1 / 36

Orlando House - 12.5 miles away

  • 5
  • 10
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 1 minutes

$172.00

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from $172.00 / night

1 / 19

Orlando House - 12.5 miles away

  • 4
  • 10
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 52 minutes

$167.00

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from $167.00 / night

1 / 28

Orlando House - 12.5 miles away

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 1 minutes

$147.00

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from $147.00 / night

(2)

1 / 41

Orlando Townhouse - 12.5 miles away

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 1 minutes

$147.00

Very Good (2 reviews)

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from $147.00 / night

(18)

1 / 27

Four Corners Villa - 1 miles away

  • 4
  • 8
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 38 minutes

“The house was extremely clean, very comfortable and perfect for our family. It was ready when we got to Florida and it had everything we needed while we were on vacation. I received my deposit back as soon as I got home and the owner was very nice...”
- Review left on 02/17/2017

$161.00

Excellent (18 reviews)

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from $161.00 / night

1 / 45

Orlando Townhouse - 12.5 miles away

  • 4
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 1 minutes

$147.00

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from $147.00 / night

(5)

1 / 21

Davenport Villa - 4.3 miles away

  • 5
  • 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 18 minutes

“A great 5 bedroom villa on a well presented and gated community. Large TV in living room and TV's in all bedrooms. Great games room and south facing pool to keep everyone happy. Owners and Jenny from management company are brilliant. Excellent base...”
- Review left on 07/12/2015

$162.00

Very Good (5 reviews)

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from $162.00 / night

1 / 21

Davenport Cottage - 7.9 miles away

  • 1
  • 2
  • min stay varies
  • Child friendly
  • Air conditioning

$43.00

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from $43.00 / night

(4)

1 / 29

Kissimmee Villa - 11.9 miles away

  • 6
  • 14
  • 2 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Responds fast! Avg. 46 minutes

“We had a wonderful time at this home. The house is spotless and the bedrooms are all very comfortable. The pool is lovely and we also took advantage of having access to the huge clubhouse pool . The commute to Disney was easy and quick. The owner...”
- Review left on 05/16/2016

$196.00

Very Good (4 reviews)

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from $196.00 / night

(9)

1 / 24

Davenport Villa - 5 miles away

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“The house was nice and clean ,the kitchen had everything we need ,the baby staff was so helpful with my little daughter .my kids enjoyed the pool it was interesting.i forget our passports in the house and I called the office and they send them to us...”
- Review left on 02/11/2016

$148.00

Excellent (9 reviews)

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from $148.00 / night

1 / 31

Orlando House - 12.5 miles away

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 1 minutes

$138.00

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from $138.00 / night

1 / 24

Orlando House - 12.5 miles away

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 1 minutes

$178.00

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from $178.00 / night

1 / 20

Orlando House - 12.5 miles away

  • 5
  • 10
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 1 minutes

$121.00

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from $121.00 / night