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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

Book

from $450 / night

(3)

1 / 22

Winter Park Condo

  • 2
  • 6
  • 2 nights min
  • Swimming pool
  • Ski
  • Child friendly

$295

Excellent (3 reviews)

Book

from $295 / night

(3)

1 / 23

Winter Park House

  • 5
  • 19
  • Min stay varies
  • Ask about children
  • Pet friendly

$250

Very Good (3 reviews)

Inquire

from $250 / night

(1)

1 / 13

Winter Park Townhouse

  • 4
  • 12
  • Min stay varies
  • Ask about children

$330

Excellent (1 reviews)

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from $330 / night

(5)

1 / 31

Winter Park House

  • 4
  • 12
  • Min stay varies
  • Child friendly

$273

Very Good (5 reviews)

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from $273 / night

1 / 28

Winter Park House

  • 3
  • 11
  • Min stay varies
  • Child friendly

from $193 / night

(34)

1 / 33

Winter Park House

  • 4
  • 10
  • Min stay varies
  • Child friendly

$273

Very Good (34 reviews)

Inquire

from $273 / night

1 / 31

Winter Park House

  • 5
  • 16
  • Min stay varies
  • Child friendly

from $443 / night

(16)

1 / 29

Winter Park House

  • 3
  • 8
  • Min stay varies
  • Child friendly

$213

Very Good (16 reviews)

Inquire

from $213 / night

(2)

1 / 26

Winter Park House

  • 2
  • 6
  • Min stay varies
  • Child friendly

$167

Very Good (2 reviews)

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from $167 / night

(3)

1 / 25

Winter Park House

  • 3
  • 10
  • Min stay varies
  • Child friendly

$193

Very Good (3 reviews)

Inquire

from $193 / night

1 / 26

Winter Park House

  • 3
  • 8
  • Min stay varies
  • Child friendly

from $195 / night

(16)

1 / 29

Winter Park House

  • 2
  • 8
  • Min stay varies
  • Child friendly

$167

Excellent (16 reviews)

Inquire

from $167 / night

(1)

1 / 25

Winter Park House

  • 4
  • 12
  • Min stay varies
  • Child friendly

$358

Excellent (1 reviews)

Inquire

from $358 / night

1 / 36

Winter Park House

  • 4
  • 15
  • Min stay varies
  • Child friendly

from $420 / night

(2)

1 / 33

Winter Park House

  • 4
  • 14
  • Min stay varies
  • Child friendly

$378

Very Good (2 reviews)

Inquire

from $378 / night

(21)

1 / 33

Winter Park House

  • 4
  • 12
  • Min stay varies
  • Child friendly

$350

Very Good (21 reviews)

Inquire

from $350 / night

(18)

1 / 32

Winter Park House

  • 5
  • 16
  • Min stay varies
  • Child friendly

$450

Very Good (18 reviews)

Inquire

from $450 / night

1 / 27

Winter Park House

  • 3
  • 9
  • Min stay varies
  • Child friendly

from $213 / night

(19)

1 / 25

Winter Park House

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

$155

Excellent (19 reviews)

Inquire

from $155 / night

(1)

1 / 33

Winter Park House

  • 3
  • 11
  • Min stay varies
  • Child friendly

$189

Excellent (1 reviews)

Inquire

from $189 / night

(10)

1 / 27

Winter Park House

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

$235

Excellent (10 reviews)

Inquire

from $235 / night

(9)

1 / 30

Winter Park House

  • 4
  • 10
  • Min stay varies
  • Child friendly

$358

Very Good (9 reviews)

Inquire

from $358 / night

(2)

1 / 33

Winter Park House

  • 7
  • 30
  • Min stay varies
  • Child friendly

$668

Excellent (2 reviews)

Inquire

from $668 / night

1 / 27

Winter Park House

  • 5
  • 12
  • Min stay varies
  • Child friendly

from $327 / night

1 / 24

Winter Park House

  • 3
  • 12
  • Min stay varies
  • Child friendly

from $204 / night

(23)

1 / 25

Winter Park House

  • 3
  • 11
  • Min stay varies
  • Child friendly

$204

Very Good (23 reviews)

Inquire

from $204 / night

(1)

1 / 23

Winter Park House

  • 2
  • 8
  • Min stay varies
  • Child friendly

$167

Excellent (1 reviews)

Inquire

from $167 / night

(1)

1 / 26

Winter Park House

  • 2
  • 6
  • Min stay varies
  • Child friendly

$167

Excellent (1 reviews)

Inquire

from $167 / night

(27)

1 / 29

Winter Park House

  • 2
  • 6
  • Min stay varies
  • Child friendly

$167

Very Good (27 reviews)

Inquire

from $167 / night

(1)

1 / 30

Winter Park House

  • 3
  • 11
  • Min stay varies
  • Child friendly
  • Pet friendly

$235

Excellent (1 reviews)

Inquire

from $235 / night

(7)

1 / 24

Winter Park House

  • 3
  • 9
  • Min stay varies
  • Child friendly

$204

Very Good (7 reviews)

Inquire

from $204 / night

(4)

1 / 24

Winter Park House

  • 2
  • 6
  • Min stay varies
  • Child friendly

$167

Very Good (4 reviews)

Inquire

from $167 / night

(12)

1 / 24

Winter Park House

  • 3
  • 10
  • Min stay varies
  • Child friendly

$189

Very Good (12 reviews)

Inquire

from $189 / night

(1)

1 / 31

Winter Park House

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

$159

Excellent (1 reviews)

Inquire

from $159 / night

(9)

1 / 24

Winter Park House

  • 3
  • 10
  • Min stay varies
  • Child friendly

$253

Excellent (9 reviews)

Inquire

from $253 / night

(24)

1 / 25

Winter Park House

  • 3
  • 8
  • Min stay varies
  • Swimming pool
  • Child friendly

$189

Excellent (24 reviews)

Inquire

from $189 / night

(2)

1 / 26

Winter Park House

  • 4
  • 10
  • Min stay varies
  • Child friendly

$271

Excellent (2 reviews)

Inquire

from $271 / night

(11)

1 / 30

Winter Park House

  • 4
  • 15
  • Min stay varies
  • Child friendly

$358

Very Good (11 reviews)

Inquire

from $358 / night

(6)

1 / 32

Winter Park House

  • 2
  • 8
  • Min stay varies
  • Child friendly

$167

Very Good (6 reviews)

Inquire

from $167 / night