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Windermere Vacation Rentals & Beach Rentals - 3676 Rentals Available

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3,676 Vacation rentals

1 / 25

Windermere House

  • 4
  • 10
  • min stay varies
  • Swimming pool
  • Ask about children

$1,000.00

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from $1,000.00 / night

1 / 18

Windermere House

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

$107.00

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from $107.00 / night

1 / 55

Windermere House

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

$238.00

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from $238.00 / night

Your search has been expanded 15.2 miles to include more rentals

(53)

1 / 27

Kissimmee Townhouse - 12.4 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

$86.00

Very Good (53 reviews)

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from $86.00 / night

1 / 45

Orlando House - 5.4 miles away

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

Responds fast! Avg. 51 minutes

$336.00

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from $336.00 / night

(1)

1 / 43

Orlando House - 5.4 miles away

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

Responds fast! Avg. 51 minutes

$155.00

Excellent (1 reviews)

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from $155.00 / night

1 / 38

Kissimmee Townhouse - 13.1 miles away

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 51 minutes

$147.00

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from $147.00 / night

(2)

1 / 32

Orlando House - 5.4 miles away

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 51 minutes

$167.00

Excellent (2 reviews)

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from $167.00 / night

(43)

1 / 57

Kissimmee House - 12.1 miles away

  • 6
  • 12
  • 4 nights min
  • Nearest beach 113 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 19 minutes

$218.00

Excellent (43 reviews)

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from $218.00 / night

1 / 49

Orlando House - 5.4 miles away

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

Responds fast! Avg. 51 minutes

$267.00

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from $267.00 / night

(10)

1 / 32

Four Corners Villa - 13 miles away

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

Responds fast! Avg. 57 minutes

“We stayed here for 5 nights the last week of March for our spring break. We enjoyed 3 days at Disney, the location was pretty convenient and relatively close to the main street to Disney. My sister and the kids utilized the clubhouse pool and...”
- Review left on 04/09/2017

$99.00

Excellent (10 reviews)

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from $99.00 / night

(3)

1 / 47

Orlando House - 5.4 miles away

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

Responds fast! Avg. 51 minutes

“The house is very nice and comfortable. Quite and nice neighborhood. Close to Disney parks. The only detail is the fact that is described as a 4 bathroom and has just 3 for guess to use, one on the master and 2 outside the bedrooms...”
- Review left on 12/25/2016

$302.00

Very Good (3 reviews)

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from $302.00 / night

(1)

1 / 56

Orlando House - 5.4 miles away

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

Responds fast! Avg. 51 minutes

$302.00

Excellent (1 reviews)

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from $302.00 / night

(20)

1 / 17

Four Corners Villa - 12.3 miles away

  • 4
  • 8
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Responds fast! Avg. 3 hours 32 minutes

“The house was fantastic. The kitchen was well equipped with everything you would need to cook with. The pool was very nice. The community was quiet which was nice to sit out by the pool and read. All the beds were comfortable. Plenty of towels...”
- Review left on 07/14/2016

$144.00

Excellent (20 reviews)

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from $144.00 / night

(2)

1 / 25

Kissimmee House - 12.7 miles away

  • 6
  • 12
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“The house was beautiful. It was clean when we arrived and in very good condition. Everyone enjoyed the playroom. The house is very spacious. I would love to visit this house again when I come back to the area. Would love to see a larger television...”
- Review left on 12/04/2013

$183.00

Very Good (2 reviews)

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from $183.00 / night

(76)

1 / 27

Davenport Villa - 15.2 miles away

  • 3
  • 7
  • 4 nights min
  • Ask about children
  • Air conditioning
“The summer bay resort through Exploria is amazing. The one bedroom condos are beautiful and I would recommend them to anyone. So thankful they were able to accommodate us and move us into the resort and we're so thankful...”
- Review left on 03/20/2017

$137.00

Very Good (76 reviews)

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from $137.00 / night

(6)

1 / 37

Kissimmee House - 11 miles away

  • 3
  • 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 0 minutes

“I was here from 1/29-2/26 and the stay was awesome. The house was everything that was advertised and the pictures were right on. The house was very clean and equipped with all the thing a person needs to enjoy a month in sunny Orlando. We didn't...”
- Review left on 02/27/2017

$132.00

Excellent (6 reviews)

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from $132.00 / night

1 / 12

Kissimmee Cottage - 14.5 miles away

  • 1
  • 2
  • min stay varies
  • Ask about children
  • Air conditioning

$78.00

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from $78.00 / night

(2)

1 / 15

Kissimmee Condo - 13.3 miles away

  • 3
  • 6
  • 3 nights min
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 6 minutes

“This place met our expectations. Clean, fully equipped, safe, close to the pool, theater room,gym and max of 10 minutes to the disney parks. Stores are like 5 minutes away. I am glad we choose this particular condo. The owners get back to you within...”
- Review left on 06/03/2017

$98.00

Excellent (2 reviews)

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from $98.00 / night

(1)

1 / 47

Kissimmee Apartment - 12.6 miles away

  • 2
  • 6
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 15 minutes

$114.00

Excellent (1 reviews)

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from $114.00 / night

(15)

1 / 30

Four Corners Townhouse - 12.9 miles away

  • 4
  • 10
  • min stay varies
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 1 hour 22 minutes

“I had a wonderful, week long vacation in this beautiful condo! I was with a small group, but this condo will sleep 10 in beds! Very fresh and new with lovely d?cor including 2 beautiful rooms with king beds (very comfortable), and 2 cute Disney...”
- Review left on 01/13/2016

$183.00

Excellent (15 reviews)

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from $183.00 / night

1 / 36

Orlando House - 5.4 miles away

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

Responds fast! Avg. 51 minutes

$147.00

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from $147.00 / night

1 / 21

Orlando House - 5.4 miles away

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 51 minutes

$233.00

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from $233.00 / night

(1)

1 / 55

Orlando House - 5.4 miles away

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

Responds fast! Avg. 51 minutes

$267.00

Very Good (1 reviews)

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from $267.00 / night

1 / 17

Orlando Townhouse - 5.4 miles away

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

Responds fast! Avg. 51 minutes

$141.00

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from $141.00 / night

1 / 44

Orlando House - 5.4 miles away

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

Responds fast! Avg. 51 minutes

$267.00

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from $267.00 / night

1 / 20

Orlando House - 5.4 miles away

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

Responds fast! Avg. 51 minutes

$147.00

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from $147.00 / night

1 / 17

Orlando Condo - 5.4 miles away

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 51 minutes

$136.00

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from $136.00 / night

1 / 56

Orlando House - 5.4 miles away

  • 9
  • 18
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 51 minutes

$353.00

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from $353.00 / night

1 / 38

Orlando Townhouse - 5.4 miles away

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 51 minutes

$159.00

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from $159.00 / night

1 / 54

Orlando House - 5.4 miles away

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

Responds fast! Avg. 51 minutes

$302.00

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from $302.00 / night

1 / 51

Orlando House - 5.4 miles away

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

Responds fast! Avg. 51 minutes

$353.00

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from $353.00 / night

(8)

1 / 35

Kissimmee Townhouse - 11.4 miles away

  • 3
  • 7
  • min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
“This was a nice, spacious townhouse style condo. We were happy and comfortable. It was as advertised. Would stay there again...”
- Review left on 06/25/2016

$69.00

Very Good (8 reviews)

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from $69.00 / night

1 / 59

Orlando House - 5.4 miles away

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

Responds fast! Avg. 51 minutes

$296.00

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from $296.00 / night

1 / 42

Kissimmee Apartment - 12.6 miles away

  • 1
  • 4
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 15 minutes

$102.00

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from $102.00 / night

(8)

1 / 23

Kissimmee Apartment - 11.5 miles away

  • 3
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 46 minutes

“This is an excellent place to stay and enjoy Orlando. It is very close to all of the attractions and access to all major highways. The condo is clean, safe and furnished completely. This was our 2nd time renting from the owner nd have always been...”
- Review left on 01/03/2017

$70.00

Very Good (8 reviews)

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from $70.00 / night

1 / 31

Kissimmee Villa - 14.5 miles away

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

Responds fast! Avg. 5 minutes

$184.00

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from $184.00 / night

(9)

1 / 29

Kissimmee House - 14.2 miles away

  • 4
  • 14
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 5 minutes

$172.00

Very Good (9 reviews)

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from $172.00 / night

1 / 18

Reunion House - 15 miles away

  • 8
  • 18
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,009.00

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from $1,009.00 / night

1 / 18

Four Corners House - 12.6 miles away

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

$165.00

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from $165.00 / night