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Windermere Vacation Rentals & Beach Rentals - 3544 Rentals Available

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3,544 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

Your search has been expanded 18.2 miles to include more rentals

1 / 36

Orlando House - 5.4 miles away

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

Responds fast! Avg. 1 hour 17 minutes

$172.00

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from $172.00 / night

(85)

1 / 101

Davenport Villa - 18.2 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

$129.00

Excellent (85 reviews)

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from $129.00 / night

1 / 28

Davenport House - 15.7 miles away

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

Responds fast! Avg. 3 hours 46 minutes

$107.00

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from $107.00 / night

(13)

1 / 17

Davenport Villa - 14.7 miles away

  • 8
  • 18
  • min stay varies
  • Nearest beach 110 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 1 hour 50 minutes

“We had a group of 11 golfers and had no problem finding plenty of space fro all in this wondeful house. Everything was in great condition and there is no complaint at all with this home. Communication with the owners was better than any other of...”
- Review left on 03/06/2017

$217.00

Excellent (13 reviews)

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from $217.00 / night

(4)

1 / 12

Davenport Villa - 17.6 miles away

  • 4
  • 10
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Our experience renting this home was great Al took great care of us from the first day. The house was very clean along with the pool and the house is huge pictures do not do a justice. We look forward to renting again in the future. Once again thank...”
- Review left on 03/28/2016

$229.00

Excellent (4 reviews)

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from $229.00 / night

1 / 49

Orlando House - 5.4 miles away

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

Responds fast! Avg. 1 hour 17 minutes

$267.00

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from $267.00 / night

(11)

1 / 27

Davenport Villa - 16 miles away

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

Responds fast! Avg. 2 hours 56 minutes

“We arrived at the home at 2am. There was a light on for us and easy access. The place was exactly as the photos showed. It was very clean. We comfortable seating in living room and breakfast nook. Pool was right out the back door very private. The...”
- Review left on 09/26/2016

$104.00

Excellent (11 reviews)

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from $104.00 / night

1 / 16

Orlando Townhouse - 5.4 miles away

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

Responds fast! Avg. 1 hour 22 minutes

$138.00

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from $138.00 / night

1 / 18

Orlando Townhouse - 5.4 miles away

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

Responds fast! Avg. 1 hour 17 minutes

$104.00

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from $104.00 / night

(3)

1 / 30

Orlando House - 5.4 miles away

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

Responds fast! Avg. 1 hour 17 minutes

“Walking into this home was amazing everything was great, I will be contacting this group again in the near future. I would recommend this to all my friends and family. Our plan was to go to Legoland and Universal Studios the kids had so much fun at...”
- Review left on 12/30/2016

$201.00

Very Good (3 reviews)

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from $201.00 / night

(3)

1 / 33

Orlando House - 5.4 miles away

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

Responds fast! Avg. 1 hour 17 minutes

“What a great experience! The house was fully loaded with great amenities. The community and clubhouse were fantastic and very upscale. We will be definitely coming back...”
- Review left on 12/12/2016

$167.00

Excellent (3 reviews)

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from $167.00 / night

1 / 30

Orlando House - 5.4 miles away

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

Responds fast! Avg. 1 hour 17 minutes

$138.00

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from $138.00 / night

1 / 26

Orlando House - 5.4 miles away

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

Responds fast! Avg. 1 hour 22 minutes

$250.00

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from $250.00 / night

(3)

1 / 43

Kissimmee Villa - 14.1 miles away

  • 7
  • 18
  • min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
“This is a big house! Three families would have no problems here and plently of space not to be under each others feet. Close to Disney and main route to all the normal popular attractions. House was clean and tidy, kitchen had everything should you...”
- Review left on 04/20/2015

$188.00

Excellent (3 reviews)

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from $188.00 / night

1 / 52

Orlando House - 5.4 miles away

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

Responds fast! Avg. 1 hour 54 minutes

$267.00

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from $267.00 / night

(7)

1 / 30

Four Corners House - 12.5 miles away

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

Responds fast! Avg. 1 hour 49 minutes

“The house was ideally located, within close proximity of the theme parks.We loved the home layout and the large pool which catered very well for the family members which totalled 8. We were able to meet the owners, whom we found to be extremely...”
- Review left on 10/15/2016

$199.00

Excellent (7 reviews)

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from $199.00 / night

1 / 17

Orlando House - 5.4 miles away

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

Responds fast! Avg. 1 hour 54 minutes

$149.00

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from $149.00 / night

1 / 19

Orlando House - 5.4 miles away

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

Responds fast! Avg. 1 hour 54 minutes

$187.00

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from $187.00 / night

1 / 66

Orlando House - 5.4 miles away

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

Responds fast! Avg. 1 hour 17 minutes

$267.00

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from $267.00 / night

1 / 51

Orlando House - 5.4 miles away

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

Responds fast! Avg. 1 hour 17 minutes

$353.00

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from $353.00 / night

1 / 46

Orlando Townhouse - 5.4 miles away

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

Responds fast! Avg. 1 hour 22 minutes

$147.00

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from $147.00 / night

(2)

1 / 51

Kissimmee Villa - 13.8 miles away

  • 4
  • 10
  • min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning

$75.00

Average (2 reviews)

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from $75.00 / night

(1)

1 / 36

Orlando Townhouse - 5.4 miles away

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

Responds fast! Avg. 1 hour 22 minutes

$136.00

Average (1 reviews)

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from $136.00 / night

1 / 38

Orlando House - 5.4 miles away

  • 5
  • 11
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 54 minutes

$262.00

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from $262.00 / night

(3)

1 / 37

Kissimmee Townhouse - 13.7 miles away

  • 3
  • 7
  • 1 night min
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 16 minutes

$102.00

Very Good (3 reviews)

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from $102.00 / night

1 / 57

Orlando House - 5.4 miles away

  • 10
  • 20
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 17 minutes

$336.00

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from $336.00 / night

1 / 31

Orlando Townhouse - 5.4 miles away

  • 4
  • 8
  • min stay varies
  • Child friendly

Responds fast! Avg. 1 hour 17 minutes

$132.00

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from $132.00 / night

(13)

1 / 7

Kissimmee House - 12.6 miles away

  • 3
  • 6
  • 3 nights min
  • Nearest beach 65 mi
  • Swimming pool
  • Child friendly
“Our stay in Kissimmee was like home away from home. We thoroughly enjoyed the lovely big heated pool. Location was perfect. We recommend this villa highly. Stewart Zemp was a pleasure to rent from...”
- Review left on 03/13/2017

$161.00

Very Good (13 reviews)

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from $161.00 / night

1 / 18

Orlando House - 5.4 miles away

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

Responds fast! Avg. 1 hour 17 minutes

$216.00

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from $216.00 / night

1 / 23

Orlando Condo - 5.4 miles away

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

Responds fast! Avg. 1 hour 22 minutes

$138.00

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from $138.00 / night

1 / 51

Orlando House - 5.4 miles away

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

Responds fast! Avg. 1 hour 17 minutes

$290.00

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from $290.00 / night

1 / 22

Orlando House - 5.4 miles away

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

Responds fast! Avg. 1 hour 18 minutes

$181.00

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from $181.00 / night

1 / 15

Orlando House - 5.4 miles away

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

Responds fast! Avg. 1 hour 22 minutes

$155.00

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from $155.00 / night

1 / 61

Orlando House - 5.4 miles away

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

Responds fast! Avg. 1 hour 17 minutes

$302.00

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from $302.00 / night

1 / 65

Orlando House - 5.4 miles away

  • 14
  • 28
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 17 minutes

$599.00

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from $599.00 / night

1 / 43

Orlando Townhouse - 5.4 miles away

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

Responds fast! Avg. 1 hour 17 minutes

$153.00

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from $153.00 / night

1 / 48

Orlando House - 5.4 miles away

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

Responds fast! Avg. 1 hour 22 minutes

$267.00

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from $267.00 / night

(1)

1 / 26

Kissimmee Villa - 14.3 miles away

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

Responds fast! Avg. 5 minutes

$132.00

Excellent (1 reviews)

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from $132.00 / night