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Winter Park Vacation Rentals & Beach Rentals - 386 Rentals Available

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386 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 19.6 miles to include more rentals

(31)

1 / 31

Orlando Townhouse - 11.8 miles away

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

Responds fast! Avg. 1 hour 30 minutes

“Excellent place to spend your vacation in. I am glad we stayed!There was one little issue with the heater not on but I called and they came right out and fixed it. We had a great time and enjoyed the home a lot! I hope to use again in the future...”
- Review left on 11/26/2017

$130.00

Very Good (31 reviews)

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from $130.00 / night

(5)

1 / 50

Kissimmee House - 19.3 miles away

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

Responds fast! Avg. 1 hour 34 minutes

$233.00

Excellent (5 reviews)

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from $233.00 / night

1 / 54

Orlando House - 11.8 miles away

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

Responds fast! Avg. 1 hour 34 minutes

$302.00

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from $302.00 / night

1 / 47

Orlando House - 11.8 miles away

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

$267.00

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from $267.00 / night

1 / 19

Orlando House - 11.8 miles away

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

Responds fast! Avg. 2 hours 12 minutes

$187.00

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from $187.00 / night

1 / 24

Orlando House - 11.8 miles away

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

Responds fast! Avg. 1 hour 39 minutes

$130.00

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from $130.00 / night

1 / 48

Orlando House - 11.8 miles away

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

Responds fast! Avg. 2 hours 0 minutes

$302.00

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from $302.00 / night

1 / 46

Orlando Condo - 11.9 miles away

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

Responds fast! Avg. 2 hours 0 minutes

$147.00

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from $147.00 / night

1 / 33

Orlando Townhouse - 11.8 miles away

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

$147.00

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from $147.00 / night

1 / 35

Orlando House - 11.8 miles away

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

Responds fast! Avg. 2 hours 23 minutes

$290.00

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from $290.00 / night

(1)

1 / 30

Orlando House - 11.8 miles away

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

Responds fast! Avg. 2 hours 8 minutes

“Me and my family enjoyed ourself at this facility. Nice, clean and quiet area. We Will be booking again in the future...”
- Review left on 09/19/2017

$132.00

Excellent (1 reviews)

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from $132.00 / night

1 / 26

Orlando Townhouse - 11.8 miles away

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

Responds fast! Avg. 1 hour 16 minutes

$129.00

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from $129.00 / night

1 / 51

Orlando House - 11.8 miles away

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

Responds fast! Avg. 1 hour 30 minutes

$267.00

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from $267.00 / night

(3)

1 / 42

Orlando House - 11.8 miles away

  • 8
  • 16
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

Responds fast! Avg. 1 hour 29 minutes

“I have enjoyed staying at your facility with my family. It was very clean and special things in the home.spacious with no negative thoughts. Thank you for renting your villa to us...”
- Review left on 12/08/2016

$292.00

Excellent (3 reviews)

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from $292.00 / night

1 / 47

Orlando House - 11.8 miles away

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

Responds fast! Avg. 1 hour 40 minutes

$147.00

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from $147.00 / night

1 / 19

Orlando House - 11.8 miles away

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

Responds fast! Avg. 3 hours 2 minutes

$187.00

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from $187.00 / night

(1)

1 / 23

Orlando House - 11.8 miles away

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

Responds fast! Avg. 3 hours 2 minutes

$204.00

Excellent (1 reviews)

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from $204.00 / night

(5)

1 / 63

Orlando Condo - 12.9 miles away

  • 3
  • 8
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 44 minutes

“Excellent apartment close to all parks and shopping centres also a short drive from airport a major plus after a full days travel.have stayed in vista cay a few times and always found it to be in immaculate condition and as I said previously the...”
- Review left on 07/18/2016

$217.00

Very Good (5 reviews)

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from $217.00 / night

1 / 54

Orlando House - 11.8 miles away

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

Responds fast! Avg. 2 hours 48 minutes

$267.00

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from $267.00 / night

1 / 21

Orlando House - 11.8 miles away

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

Responds fast! Avg. 3 hours 18 minutes

$187.00

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from $187.00 / night

(1)

1 / 42

Orlando House - 11.8 miles away

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

Responds fast! Avg. 3 hours 39 minutes

$267.00

Very Good (1 reviews)

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from $267.00 / night

1 / 19

Orlando House - 11.8 miles away

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

Responds fast! Avg. 3 hours 39 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. 3 hours 11 minutes

$159.00

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from $159.00 / night

(2)

1 / 24

Orlando Townhouse - 11.8 miles away

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

Responds fast! Avg. 3 hours 11 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 / 21

Orlando Condo - 11.8 miles away

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

Responds fast! Avg. 3 hours 11 minutes

$104.00

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from $104.00 / night

1 / 31

Orlando House - 11.8 miles away

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

Responds fast! Avg. 3 hours 11 minutes

$129.00

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from $129.00 / night

1 / 55

Orlando House - 11.8 miles away

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

Responds fast! Avg. 3 hours 11 minutes

$302.00

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from $302.00 / night

1 / 63

Orlando House - 11.8 miles away

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

Responds fast! Avg. 3 hours 11 minutes

$302.00

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from $302.00 / night

1 / 17

Orlando House - 11.8 miles away

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

Responds fast! Avg. 3 hours 11 minutes

$153.00

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from $153.00 / night

1 / 56

Kissimmee House - 19.4 miles away

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

Responds fast! Avg. 3 hours 11 minutes

$336.00

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from $336.00 / night

1 / 43

Orlando House - 11.8 miles away

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

Responds fast! Avg. 3 hours 11 minutes

$353.00

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from $353.00 / night

(27)

1 / 64

Kissimmee Villa - 19.3 miles away

  • 4
  • 8
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“My wife and I had an enjoyable, relaxing 8 week stay at the villa this past winter and were impressed with the cleanliness while the neighborhood itself is quiet and serene. We were close to a local park with basketball and tennis courts along with...”
- Review left on 03/28/2016

$138.00

Excellent (27 reviews)

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from $138.00 / night

(7)

1 / 36

Orlando House - 11.8 miles away

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

Responds fast! Avg. 3 hours 11 minutes

“We were hoping for the best and that's what we got!!!!! Very nice area everyone at the club house was so nice. The property was wonderful, clean, well furnished, and did I mention Clean!!!! All thumbs up from our group. Joe Lorentz Ovation...”
- Review left on 01/17/2017

$230.00

Very Good (7 reviews)

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from $230.00 / night

1 / 65

Orlando House - 11.8 miles away

  • 6
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 11 minutes

$267.00

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from $267.00 / night

1 / 48

Orlando House - 11.8 miles away

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

Responds fast! Avg. 3 hours 11 minutes

$267.00

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from $267.00 / night

1 / 42

Orlando Townhouse - 11.8 miles away

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

Responds fast! Avg. 3 hours 11 minutes

$147.00

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from $147.00 / night

1 / 44

Orlando House - 11.8 miles away

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

Responds fast! Avg. 3 hours 11 minutes

$302.00

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from $302.00 / night

1 / 31

Orlando House - 11.8 miles away

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

Responds fast! Avg. 3 hours 11 minutes

$167.00

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from $167.00 / night

(7)

1 / 47

Kissimmee House - 19.6 miles away

  • 3
  • 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“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 (7 reviews)

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from $132.00 / night