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Winter Park Vacation Rentals & Beach Rentals - 645 Rentals Available

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645 Vacation rentals

1 / 18

Winter Park House

  • 8
  • 20
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$266.00

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from $266.00 / night

Your search has been expanded 19.3 miles to include more rentals

1 / 39

Orlando Townhouse - 11.8 miles away

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

Responds fast! Avg. 46 minutes

$147.00

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from $147.00 / night

1 / 27

Orlando House - 11.8 miles away

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

Responds fast! Avg. 46 minutes

$153.00

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from $153.00 / night

(1)

1 / 30

Orlando House - 11.9 miles away

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

Responds fast! Avg. 47 minutes

$216.00

Very Good (1 reviews)

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from $216.00 / night

1 / 47

Kissimmee Apartment - 19 miles away

  • 2
  • 6
  • min stay varies
  • Child friendly
  • Air conditioning

$139.00

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from $139.00 / night

1 / 20

Orlando House - 11.8 miles away

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

Responds fast! Avg. 29 minutes

$130.00

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from $130.00 / night

1 / 51

Orlando House - 11.8 miles away

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

Responds fast! Avg. 29 minutes

$267.00

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from $267.00 / night

1 / 51

Orlando House - 11.8 miles away

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

Responds fast! Avg. 29 minutes

$353.00

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from $353.00 / night

1 / 37

Orlando Townhouse - 11.8 miles away

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

Responds fast! Avg. 29 minutes

$181.00

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from $181.00 / night

1 / 37

Orlando Condo - 11.8 miles away

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 29 minutes

$113.00

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from $113.00 / night

1 / 48

Orlando House - 11.8 miles away

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

Responds fast! Avg. 29 minutes

$267.00

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from $267.00 / night

(5)

1 / 15

Orlando Townhouse - 11.8 miles away

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

Responds fast! Avg. 29 minutes

“Our trip to Orlando was in march so you defentitly need the pool heated, The house was amazing ! Super big and nicely decorated. I would totally recommend renting one of these vacation homes...”
- Review left on 03/17/2017

$138.00

Very Good (5 reviews)

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from $138.00 / night

(1)

1 / 27

Orlando Townhouse - 11.8 miles away

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

Responds fast! Avg. 29 minutes

$130.00

Excellent (1 reviews)

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from $130.00 / night

1 / 32

Orlando House - 11.8 miles away

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

Responds fast! Avg. 29 minutes

$184.00

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from $184.00 / night

1 / 31

Orlando House - 11.8 miles away

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

Responds fast! Avg. 29 minutes

$129.00

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from $129.00 / night

(1)

1 / 24

Orlando House - 11.8 miles away

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

Responds fast! Avg. 29 minutes

$178.00

Excellent (1 reviews)

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from $178.00 / night

1 / 27

Orlando House - 11.8 miles away

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

Responds fast! Avg. 29 minutes

$187.00

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from $187.00 / night

1 / 29

Orlando House - 11.8 miles away

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

Responds fast! Avg. 29 minutes

$204.00

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from $204.00 / night

1 / 31

Orlando Townhouse - 11.8 miles away

  • 4
  • 8
  • min stay varies
  • Child friendly

Responds fast! Avg. 28 minutes

$132.00

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from $132.00 / night

1 / 21

Orlando House - 11.8 miles away

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

Responds fast! Avg. 28 minutes

$187.00

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from $187.00 / night

1 / 30

Orlando Townhouse - 11.8 miles away

  • 4
  • 8
  • min stay varies
  • Child friendly

Responds fast! Avg. 28 minutes

$129.00

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from $129.00 / night

1 / 30

Orlando House - 11.8 miles away

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

Responds fast! Avg. 28 minutes

$124.00

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from $124.00 / night

1 / 29

Orlando House - 11.8 miles away

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

Responds fast! Avg. 28 minutes

$216.00

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from $216.00 / night

1 / 48

Orlando House - 11.8 miles away

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

Responds fast! Avg. 28 minutes

$302.00

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from $302.00 / night

(1)

1 / 53

Orlando House - 11.8 miles away

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

Responds fast! Avg. 28 minutes

$302.00

Average (1 reviews)

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from $302.00 / night

1 / 22

Orlando House - 11.8 miles away

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

Responds fast! Avg. 28 minutes

$164.00

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from $164.00 / night

1 / 32

Orlando House - 11.8 miles away

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

Responds fast! Avg. 28 minutes

$181.00

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from $181.00 / night

1 / 21

Orlando House - 11.8 miles away

  • 5
  • 10
  • min stay varies
  • Child friendly

Responds fast! Avg. 28 minutes

$161.00

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from $161.00 / night

(2)

1 / 61

Orlando House - 11.8 miles away

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

Responds fast! Avg. 28 minutes

$302.00

Very Good (2 reviews)

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from $302.00 / night

(9)

1 / 12

Kissimmee House - 19.2 miles away

  • 2
  • 6
  • 1 night min
  • Nearest beach 95 mi
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 29 minutes

“I stayed for 5months at this house and it was great. Had everything needed to cook, fenced in backyard for my dog, neighbors were great and I was only 10 minutes from give kids the world where I volunteered. Lots of places to eat and close to all...”
- Review left on 04/11/2016

$98.00

Excellent (9 reviews)

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from $98.00 / night

1 / 48

Kissimmee Townhouse - 19.3 miles away

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

$191.00

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from $191.00 / night

1 / 54

Orlando House - 11.8 miles away

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

Responds fast! Avg. 28 minutes

$353.00

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from $353.00 / night

(1)

1 / 9

Orlando Condo - 15.1 miles away

  • 1
  • 6
  • 2 nights min
  • Ask about children
  • Air conditioning

$75.00

Excellent (1 reviews)

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from $75.00 / night

1 / 28

Orlando House - 11.8 miles away

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

Responds fast! Avg. 28 minutes

$281.00

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from $281.00 / night

1 / 53

Orlando House - 11.8 miles away

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

Responds fast! Avg. 28 minutes

$302.00

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from $302.00 / night

1 / 50

Orlando House - 11.8 miles away

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

Responds fast! Avg. 28 minutes

$227.00

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from $227.00 / night

1 / 62

Orlando House - 11.8 miles away

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

Responds fast! Avg. 28 minutes

$599.00

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from $599.00 / night

1 / 47

Orlando House - 11.8 miles away

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

Responds fast! Avg. 28 minutes

$267.00

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from $267.00 / night

(1)

1 / 36

Orlando Townhouse - 11.8 miles away

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

Responds fast! Avg. 28 minutes

$129.00

Average (1 reviews)

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from $129.00 / night

1 / 46

Orlando Condo - 11.9 miles away

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

Responds fast! Avg. 28 minutes

$147.00

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from $147.00 / night