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Winter Park Vacation Rentals & Beach Rentals - 697 Rentals Available

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697 Vacation rentals

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(2)

1 / 41

Orlando Townhouse - 11.8 miles away

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

Responds fast! Avg. 2 hours 22 minutes

$147.00

Very Good (2 reviews)

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from $147.00 / night

1 / 42

Orlando House - 11.8 miles away

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

Responds fast! Avg. 2 hours 22 minutes

$267.00

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from $267.00 / night

(21)

Certificate of Excellence

1 / 78

Orlando Villa - 5.2 miles away

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

Responds fast! Avg. 1 hour 59 minutes

Certificate of Excellence

“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

$114.00

Excellent (21 reviews)

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from $114.00 / night

1 / 20

Orlando House - 11.8 miles away

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

Responds fast! Avg. 2 hours 22 minutes

$130.00

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from $130.00 / night

1 / 19

Orlando House - 11.8 miles away

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

Responds fast! Avg. 2 hours 22 minutes

$159.00

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from $159.00 / night

(38)

Certificate of Excellence

1 / 54

Orlando Townhouse - 5.2 miles away

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

Responds fast! Avg. 1 hour 59 minutes

Certificate of Excellence

“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

$114.00

Excellent (38 reviews)

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from $114.00 / night

1 / 45

Orlando House - 11.8 miles away

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

Responds fast! Avg. 2 hours 22 minutes

$313.00

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from $313.00 / night

1 / 135

Orlando Apartment - 13 miles away

  • 3
  • 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 41 minutes

$157.00

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from $157.00 / night

(2)

1 / 43

Orlando House - 11.8 miles away

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

Responds fast! Avg. 2 hours 22 minutes

$155.00

Very Good (2 reviews)

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from $155.00 / night

1 / 24

Orlando House - 11.8 miles away

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

Responds fast! Avg. 2 hours 22 minutes

$178.00

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from $178.00 / night

1 / 19

Orlando House - 11.8 miles away

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

Responds fast! Avg. 2 hours 22 minutes

$176.00

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from $176.00 / night

(1)

1 / 36

Orlando House - 11.8 miles away

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

Responds fast! Avg. 2 hours 21 minutes

$176.00

Excellent (1 reviews)

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from $176.00 / night

1 / 56

Orlando House - 11.9 miles away

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

Responds fast! Avg. 2 hours 22 minutes

$336.00

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from $336.00 / night

1 / 84

Orlando House - 11.8 miles away

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

Responds fast! Avg. 2 hours 22 minutes

$302.00

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from $302.00 / night

1 / 45

Orlando House - 11.8 miles away

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

Responds fast! Avg. 2 hours 22 minutes

$336.00

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from $336.00 / night

1 / 45

Orlando Townhouse - 11.8 miles away

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

Responds fast! Avg. 2 hours 22 minutes

$147.00

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from $147.00 / night

(1)

1 / 54

Orlando House - 11.8 miles away

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

Responds fast! Avg. 2 hours 22 minutes

$450.00

Excellent (1 reviews)

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from $450.00 / night

1 / 67

Orlando House - 11.8 miles away

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

Responds fast! Avg. 2 hours 22 minutes

$302.00

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from $302.00 / night

1 / 28

Orlando House - 11.8 miles away

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

Responds fast! Avg. 2 hours 22 minutes

$147.00

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from $147.00 / night

1 / 25

Orlando House - 11.8 miles away

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

Responds fast! Avg. 2 hours 22 minutes

$155.00

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from $155.00 / night

1 / 39

Orlando House - 11.8 miles away

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

Responds fast! Avg. 2 hours 22 minutes

$227.00

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from $227.00 / night

1 / 25

Orlando House - 11.9 miles away

  • 5
  • 10
  • min stay varies
  • Child friendly

Responds fast! Avg. 2 hours 22 minutes

$126.00

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from $126.00 / night

1 / 46

Orlando Townhouse - 11.8 miles away

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

Responds fast! Avg. 2 hours 21 minutes

$159.00

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from $159.00 / night

1 / 31

Orlando House - 11.8 miles away

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

Responds fast! Avg. 2 hours 22 minutes

$155.00

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from $155.00 / night

1 / 63

Orlando House - 11.8 miles away

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

Responds fast! Avg. 2 hours 22 minutes

$302.00

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from $302.00 / night

(3)

1 / 31

Orlando House - 11.8 miles away

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

Responds fast! Avg. 2 hours 22 minutes

$184.00

Very Good (3 reviews)

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from $184.00 / night

(1)

1 / 97

Orlando Apartment - 12.9 miles away

  • 2
  • 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 41 minutes

$139.00

Very Good (1 reviews)

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from $139.00 / night

(7)

1 / 24

Orlando Townhouse - 11.8 miles away

  • 3
  • 7
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 22 minutes

“The location was perfect. Only took us about 15-20 minutes to get to Disney. The kids loved the pirate room with all the dress up accessories and pirate themed toys. The house had everything we needed and the beds were all very cozy. Would highly...”
- Review left on 05/08/2018

$172.00

Excellent (7 reviews)

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from $172.00 / night

1 / 57

Orlando House - 11.8 miles away

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

Responds fast! Avg. 2 hours 22 minutes

$267.00

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from $267.00 / night

(1)

1 / 44

Orlando House - 11.8 miles away

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

Responds fast! Avg. 2 hours 22 minutes

$302.00

Excellent (1 reviews)

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from $302.00 / night

1 / 20

Orlando House - 11.8 miles away

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

Responds fast! Avg. 2 hours 22 minutes

$92.00

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from $92.00 / night

(1)

1 / 22

Orlando House - 11.9 miles away

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

Responds fast! Avg. 2 hours 22 minutes

$189.00

Excellent (1 reviews)

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from $189.00 / night

1 / 40

Orlando Townhouse - 11.8 miles away

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

Responds fast! Avg. 2 hours 22 minutes

$147.00

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from $147.00 / night

1 / 24

Orlando Townhouse - 11.8 miles away

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

Responds fast! Avg. 2 hours 22 minutes

$147.00

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from $147.00 / night

(2)

1 / 24

Orlando Townhouse - 11.8 miles away

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

Responds fast! Avg. 2 hours 22 minutes

“convenient to Disney which was the purpose of our trip. Older home but clean and well taken care of. No TV in the downstairs bedroom. Would rent again...”
- Review left on 03/04/2017

$104.00

Very Good (2 reviews)

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from $104.00 / night

1 / 39

Orlando Townhouse - 11.8 miles away

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

Responds fast! Avg. 2 hours 22 minutes

$147.00

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from $147.00 / night

(5)

1 / 50

Orlando House - 11.8 miles away

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

Responds fast! Avg. 2 hours 22 minutes

$233.00

Excellent (5 reviews)

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from $233.00 / night

1 / 38

Orlando Townhouse - 11.8 miles away

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

Responds fast! Avg. 2 hours 20 minutes

$147.00

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from $147.00 / night

1 / 51

Orlando House - 11.8 miles away

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

Responds fast! Avg. 2 hours 22 minutes

$227.00

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from $227.00 / night

1 / 34

Orlando House - 11.9 miles away

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

Responds fast! Avg. 2 hours 21 minutes

$262.00

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from $262.00 / night