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Winter Park Vacation Rentals & Beach Rentals - 183 Rentals Available

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183 Vacation rentals

1 / 18

Winter Park House

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

$278.00

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from $278.00 / night

Your search has been expanded 19.7 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 / 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)

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

1 / 21

Orlando Condo - 11.8 miles away

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

$104.00

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from $104.00 / 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 30 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 / 17

Orlando House - 11.8 miles away

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

Responds fast! Avg. 3 hours 28 minutes

$153.00

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from $153.00 / 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. 3 hours 33 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

$104.00

Excellent (9 reviews)

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from $104.00 / night

1 / 25

Orlando Townhouse - 11.8 miles away

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

Responds fast! Avg. 2 hours 44 minutes

$104.00

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from $104.00 / night

(2)

1 / 28

Orlando House - 11.8 miles away

  • 6
  • 12
  • min stay varies
  • Child friendly

Responds fast! Avg. 2 hours 52 minutes

“Great atmosphere awesome home very clean plenty of space. Really enjoyed ourselves, very impressed hope home is available next time we need one...”
- Review left on 11/13/2017

$155.00

Very Good (2 reviews)

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from $155.00 / night

1 / 15

Orlando House - 11.8 miles away

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

Responds fast! Avg. 2 hours 55 minutes

$199.00

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from $199.00 / night

(1)

1 / 24

Orlando House - 11.8 miles away

  • 6
  • 12
  • min stay varies
  • Child friendly

Responds fast! Avg. 1 hour 33 minutes

$178.00

Excellent (1 reviews)

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from $178.00 / night

(1)

1 / 22

Orlando House - 11.8 miles away

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

Responds fast! Avg. 1 hour 33 minutes

$195.00

Average (1 reviews)

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from $195.00 / night

1 / 30

Orlando House - 11.8 miles away

  • 6
  • 12
  • min stay varies
  • Child friendly

Responds fast! Avg. 1 hour 43 minutes

$178.00

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from $178.00 / night

(4)

1 / 43

Orlando House - 11.9 miles away

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

Responds fast! Avg. 1 hour 43 minutes

$159.00

Excellent (4 reviews)

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from $159.00 / night

1 / 45

Orlando House - 11.8 miles away

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

Responds fast! Avg. 1 hour 43 minutes

$189.00

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from $189.00 / night

(1)

1 / 22

Orlando House - 11.8 miles away

  • 6
  • 12
  • min stay varies
  • Child friendly

Responds fast! Avg. 1 hour 43 minutes

$195.00

Excellent (1 reviews)

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from $195.00 / night

1 / 28

Orlando House - 11.8 miles away

  • 6
  • 12
  • min stay varies
  • Child friendly

Responds fast! Avg. 1 hour 43 minutes

$265.00

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from $265.00 / night

1 / 56

Kissimmee House - 19.4 miles away

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

Responds fast! Avg. 1 hour 43 minutes

$336.00

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from $336.00 / night

1 / 34

Orlando House - 11.8 miles away

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

Responds fast! Avg. 1 hour 43 minutes

$184.00

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from $184.00 / night

(11)

1 / 24

Orlando Townhouse - 11.8 miles away

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

Responds fast! Avg. 1 hour 43 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 (11 reviews)

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from $172.00 / night

1 / 36

Orlando House - 11.8 miles away

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

Responds fast! Avg. 1 hour 43 minutes

$181.00

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from $181.00 / night

1 / 31

Orlando Townhouse - 11.8 miles away

  • 4
  • 8
  • min stay varies
  • Child friendly

Responds fast! Avg. 1 hour 43 minutes

$138.00

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from $138.00 / night

1 / 19

Orlando House - 11.8 miles away

  • 4
  • 8
  • min stay varies
  • Child friendly
  • Air conditioning
  • Private garden

Responds fast! Avg. 1 hour 43 minutes

$132.00

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from $132.00 / night

1 / 21

Orlando House - 11.8 miles away

  • 5
  • 10
  • min stay varies
  • Child friendly

Responds fast! Avg. 1 hour 43 minutes

$161.00

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from $161.00 / night

1 / 21

Orlando House - 11.8 miles away

  • 5
  • 10
  • min stay varies
  • Child friendly

Responds fast! Avg. 1 hour 43 minutes

$155.00

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from $155.00 / night

1 / 39

Kissimmee Townhouse - 19.7 miles away

  • 4
  • 10
  • min stay varies
  • Nearest beach 99 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 41 minutes

$114.00

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from $114.00 / night

(22)

1 / 28

Kissimmee Apartment - 19.7 miles away

  • 4
  • 10
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 97 mi
  • Swimming pool

Responds fast! Avg. 41 minutes

“We really enjoyed our stay at this beautiful rental. The property was well kept, clean and we didn't had any issues the time we spent there. I really liked that the property didn't have carpet. 2 master bedrooms for the adults and 2 smaller rooms...”
- Review left on 01/05/2017

$114.00

Very Good (22 reviews)

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from $114.00 / night

(5)

1 / 63

Orlando Condo - 12.9 miles away

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

$263.00

Very Good (5 reviews)

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from $263.00 / night

1 / 29

Orlando Townhouse - 11.8 miles away

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

Responds fast! Avg. 1 hour 43 minutes

$113.00

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from $113.00 / night

1 / 24

Orlando Condo - 11.8 miles away

  • 2
  • 4
  • min stay varies
  • Child friendly

Responds fast! Avg. 1 hour 43 minutes

$85.00

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from $85.00 / night

(4)

1 / 36

Orlando House - 11.8 miles away

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

Responds fast! Avg. 1 hour 43 minutes

“This was an amazing experience for my family! The house was beautiful! Everything was perfect. Management was on point and if I could give 10 stars I would...”
- Review left on 01/29/2018

$184.00

Excellent (4 reviews)

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from $184.00 / night

1 / 33

Orlando House - 11.8 miles away

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

Responds fast! Avg. 1 hour 45 minutes

$167.00

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from $167.00 / night

1 / 32

Orlando House - 11.8 miles away

  • 5
  • 10
  • min stay varies
  • Child friendly

Responds fast! Avg. 1 hour 45 minutes

$238.00

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from $238.00 / night

1 / 31

Orlando House - 11.8 miles away

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

Responds fast! Avg. 1 hour 45 minutes

$176.00

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from $176.00 / night

1 / 29

Orlando House - 11.8 miles away

  • 8
  • 19
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 45 minutes

$292.00

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from $292.00 / night

(4)

1 / 40

Orlando House - 11.8 miles away

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

Responds fast! Avg. 1 hour 45 minutes

“We had a wonderful trip! Home looked just as the pictures described. Game room was amazing pool was refreshing after a long day at the park. Will definitely like to stay again...”
- Review left on 06/18/2018

$201.00

Very Good (4 reviews)

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from $201.00 / night

(1)

1 / 45

Orlando House - 11.8 miles away

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

Responds fast! Avg. 1 hour 45 minutes

$207.00

Excellent (1 reviews)

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from $207.00 / night