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Winter Park 2-bedroom Apartments, Condos & More - 76 Rentals Available.

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76 Vacation rentals

Filters applied: 2+ Bedrooms

1 / 24

Winter Park Townhouse

  • 4
  • 12
  • Min stay varies
  • Ski
  • Child friendly
  • Air conditioning

$450

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from $450 / night

(3)

1 / 22

Winter Park Condo

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Ski
  • Child friendly

$115

Excellent (3 reviews)

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from $115 / night

(3)

1 / 23

Winter Park House

  • 5
  • 19
  • Min stay varies
  • Ask about children
  • Pet friendly
“We planned a long weekend getaway with our 4 offspring, their spouse & 1 grandkid. The home is perfect with 4 rooms for sleeping and a comfy living area with fireplace adjacent to the kitchen. The beds were comfortable, the deck was great for morning...”
- Review left on 09/27/2016

$250

Very Good (3 reviews)

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from $250 / night

(1)

1 / 13

Winter Park Townhouse

  • 4
  • 12
  • Min stay varies
  • Ask about children
“Our family stayed In the Swenson's home while skiing. We found the ski rental at "Epic" very easy and we were all pleased with their equipment. We also used the bus to and from the ski resort. With a family our size this was a great convenience. The...”
- Review left on 02/17/2010

$330

Excellent (1 reviews)

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from $330 / night

(7)

1 / 32

Winter Park House

  • 3
  • 10
  • Min stay varies
  • Child friendly

$195

Excellent (7 reviews)

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from $195 / night

(4)

1 / 27

Winter Park House

  • 3
  • 9
  • Min stay varies
  • Child friendly

$200

Excellent (4 reviews)

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from $200 / night

1 / 24

Winter Park House

  • 2
  • 5
  • Min stay varies
  • Swimming pool
  • Child friendly

from $155 / night

(23)

1 / 25

Winter Park House

  • 3
  • 10
  • Min stay varies
  • Child friendly

$203

Very Good (23 reviews)

Inquire

from $203 / night

(3)

1 / 25

Winter Park House

  • 3
  • 10
  • Min stay varies
  • Child friendly

$193

Very Good (3 reviews)

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from $193 / night

(2)

1 / 33

Winter Park House

  • 4
  • 14
  • Min stay varies
  • Child friendly

$378

Very Good (2 reviews)

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from $378 / night

(22)

1 / 28

Winter Park House

  • 2
  • 8
  • Min stay varies
  • Child friendly
  • Pet friendly

$168

Very Good (22 reviews)

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from $168 / night

(15)

1 / 26

Winter Park House

  • 2
  • 8
  • Min stay varies
  • Child friendly

$168

Very Good (15 reviews)

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from $168 / night

(12)

1 / 30

Winter Park House

  • 2
  • 6
  • Min stay varies
  • Child friendly

$168

Very Good (12 reviews)

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from $168 / night

(1)

1 / 33

Winter Park House

  • 3
  • 11
  • Min stay varies
  • Child friendly

$189

Excellent (1 reviews)

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from $189 / night

(9)

1 / 24

Winter Park House

  • 3
  • 10
  • Min stay varies
  • Child friendly

$253

Excellent (9 reviews)

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from $253 / night

(1)

1 / 26

Winter Park House

  • 4
  • 10
  • Min stay varies
  • Child friendly

$327

Excellent (1 reviews)

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from $327 / night

(19)

1 / 27

Winter Park House

  • 2
  • 8
  • Min stay varies
  • Swimming pool
  • Child friendly

$155

Excellent (19 reviews)

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from $155 / night

(2)

1 / 34

Winter Park House

  • 4
  • 16
  • Min stay varies
  • Child friendly

$458

Excellent (2 reviews)

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from $458 / night

1 / 28

Winter Park House

  • 3
  • 11
  • Min stay varies
  • Child friendly

from $193 / night

(1)

1 / 23

Winter Park House

  • 2
  • 8
  • Min stay varies
  • Child friendly

$168

Excellent (1 reviews)

Inquire

from $168 / night

1 / 31

Winter Park House

  • 5
  • 16
  • Min stay varies
  • Child friendly

from $443 / night

1 / 24

Winter Park House

  • 3
  • 11
  • Min stay varies
  • Child friendly

from $203 / night

1 / 26

Winter Park House

  • 3
  • 8
  • Min stay varies
  • Child friendly

from $195 / night

(5)

1 / 26

Winter Park House

  • 4
  • 12
  • Min stay varies
  • Child friendly

$273

Very Good (5 reviews)

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from $273 / night

(34)

1 / 33

Winter Park House

  • 4
  • 10
  • Min stay varies
  • Child friendly

$273

Very Good (34 reviews)

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from $273 / night

(1)

1 / 24

Winter Park House

  • 2
  • 6
  • Min stay varies
  • Child friendly

$168

Very Good (1 reviews)

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from $168 / night

(6)

1 / 32

Winter Park House

  • 3
  • 8
  • Min stay varies
  • Child friendly

$195

Very Good (6 reviews)

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from $195 / night

(19)

1 / 25

Winter Park House

  • 2
  • 9
  • Min stay varies
  • Swimming pool
  • Child friendly

$155

Excellent (19 reviews)

Inquire

from $155 / night

(2)

1 / 26

Winter Park House

  • 4
  • 10
  • Min stay varies
  • Child friendly

$271

Excellent (2 reviews)

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from $271 / night

1 / 36

Winter Park House

  • 4
  • 15
  • Min stay varies
  • Child friendly

from $419 / night

(7)

1 / 24

Winter Park House

  • 3
  • 9
  • Min stay varies
  • Child friendly

$203

Very Good (7 reviews)

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from $203 / night

(6)

1 / 30

Winter Park House

  • 3
  • 10
  • Min stay varies
  • Child friendly

$253

Very Good (6 reviews)

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from $253 / night

(1)

1 / 31

Winter Park House

  • 2
  • 7
  • Min stay varies
  • Swimming pool
  • Child friendly

$159

Excellent (1 reviews)

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from $159 / night

(10)

1 / 27

Winter Park House

  • 3
  • 10
  • Min stay varies
  • Child friendly
  • Pet friendly

$235

Excellent (10 reviews)

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from $235 / night

(2)

1 / 33

Winter Park House

  • 7
  • 30
  • Min stay varies
  • Child friendly

$669

Excellent (2 reviews)

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from $669 / night

(21)

1 / 33

Winter Park House

  • 4
  • 12
  • Min stay varies
  • Child friendly

$350

Very Good (21 reviews)

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from $350 / night

(6)

1 / 32

Winter Park House

  • 2
  • 8
  • Min stay varies
  • Child friendly

$168

Very Good (6 reviews)

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from $168 / night

(1)

1 / 30

Winter Park House

  • 5
  • 19
  • Min stay varies
  • Child friendly

$491

Excellent (1 reviews)

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from $491 / night

(16)

1 / 29

Winter Park House

  • 2
  • 7
  • Min stay varies
  • Child friendly

$168

Very Good (16 reviews)

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from $168 / night

(16)

1 / 29

Winter Park House

  • 2
  • 8
  • Min stay varies
  • Child friendly

$168

Excellent (16 reviews)

Inquire

from $168 / night