Search 105,200+ Vacation Rentals

Winter Park Apartments & Condos with Swimming Pool - 40 Rentals Available.

Payment Protection
To book this vacation rental you need to pay through the Vacation Home Rentals website. We can’t protect your payment if you don’t pay through us. Learn more

3 Vacation rentals

Filters applied: Swimming pool

(24)

1 / 24

Winter Park House

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

$188

Excellent (24 reviews)

Inquire

from $188 / night

(2)

1 / 24

Winter Park House

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

$152

Excellent (2 reviews)

Inquire

from $152 / night

(3)

1 / 25

Winter Park House

  • 1
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly

$118

Very Good (3 reviews)

Inquire

from $118 / night

Your search has been expanded 37.4 miles to include more rentals

(4)

1 / 25

Keystone House - 36.8 miles away

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children

$215

Very Good (4 reviews)

Inquire

from $215 / night

(6)

1 / 26

Keystone House - 36.8 miles away

  • 1
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children

$160

Very Good (6 reviews)

Inquire

from $160 / night

(1)

1 / 32

Keystone House - 36.8 miles away

  • 3
  • 7
  • Min stay varies
  • Swimming pool
  • Ask about children

$325

Excellent (1 reviews)

Inquire

from $325 / night

(5)

1 / 28

Keystone House - 36.9 miles away

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children

$214

Excellent (5 reviews)

Inquire

from $214 / night

(8)

1 / 32

Keystone House - 37.1 miles away

  • 3
  • 8
  • Min stay varies
  • Swimming pool
  • Ask about children

$437

Very Good (8 reviews)

Inquire

from $437 / night

(3)

1 / 12

Keystone House - 37.1 miles away

  • 1
  • 4
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$164

Average (3 reviews)

Inquire

from $164 / night

1 / 23

Keystone House - 37.2 miles away

  • 1
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children

from $250 / night

(3)

1 / 12

Keystone Apartment - 37.2 miles away

  • 1
  • 4
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$164

Average (3 reviews)

Inquire

from $164 / night

1 / 26

Keystone House - 37.2 miles away

  • 3
  • 8
  • Min stay varies
  • Swimming pool
  • Ask about children

from $440 / night

(4)

1 / 21

Keystone House - 37.2 miles away

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children

$315

Excellent (4 reviews)

Inquire

from $315 / night

1 / 26

Keystone Apartment - 37.2 miles away

  • 2
  • 8
  • Min stay varies
  • Swimming pool
  • Ask about children

from $139 / night

(12)

1 / 23

Keystone Studio - 37.2 miles away

  • -1
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children

$194

Average (12 reviews)

Inquire

from $194 / night

1 / 31

Keystone House - 37.2 miles away

  • 3
  • 8
  • Min stay varies
  • Swimming pool
  • Ask about children

from $440 / night

(9)

1 / 33

Keystone House - 37.2 miles away

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children

$313

Excellent (9 reviews)

Inquire

from $313 / night

1 / 30

Keystone Apartment - 37.2 miles away

  • 3
  • 8
  • Min stay varies
  • Swimming pool
  • Ask about children

from $541 / night

1 / 21

Keystone Apartment - 37.2 miles away

  • 1
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children

from $100 / night

(2)

1 / 25

Keystone House - 37.2 miles away

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children

$315

Very Good (2 reviews)

Inquire

from $315 / night

(2)

1 / 22

Keystone Condo - 37.3 miles away

  • 1
  • 4
  • Min stay varies
  • Swimming pool
  • Ski
  • Child friendly

$99

Excellent (2 reviews)

Inquire

from $99 / night

1 / 26

Keystone Condo - 37.3 miles away

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

from $128 / night

1 / 15

Keystone House - 37.3 miles away

  • 2
  • 9
  • Min stay varies
  • Swimming pool
  • Ask about children

from $285 / night

1 / 25

Keystone Apartment - 37.3 miles away

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children

from $129 / night

(1)

1 / 25

Keystone Apartment - 37.3 miles away

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children

$129

Excellent (1 reviews)

Inquire

from $129 / night

1 / 30

Keystone Apartment - 37.3 miles away

  • 3
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children

from $437 / night

1 / 27

Keystone House - 37.3 miles away

  • 1
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children

from $109 / night

(6)

1 / 25

Keystone House - 37.3 miles away

  • 1
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children

$224

Very Good (6 reviews)

Inquire

from $224 / night

(7)

1 / 33

Keystone House - 37.3 miles away

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children

$313

Very Good (7 reviews)

Inquire

from $313 / night

1 / 21

Keystone House - 37.3 miles away

  • 1
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children

from $225 / night

1 / 22

Keystone Apartment - 37.3 miles away

  • 1
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children

from $100 / night

(5)

1 / 24

Keystone House - 37.3 miles away

  • 3
  • 8
  • Min stay varies
  • Swimming pool
  • Ask about children

$325

Very Good (5 reviews)

Inquire

from $325 / night

(10)

1 / 39

Keystone House - 37.3 miles away

  • 3
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children

$437

Very Good (10 reviews)

Inquire

from $437 / night

(1)

1 / 26

Keystone Apartment - 37.4 miles away

  • 1
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children

$100

Very Good (1 reviews)

Inquire

from $100 / night

1 / 27

Keystone House - 37.4 miles away

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children

from $175 / night

1 / 24

Keystone House - 37.4 miles away

  • 1
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children

from $175 / night

1 / 31

Keystone House - 37.4 miles away

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children

from $210 / night

1 / 27

Keystone House - 37.4 miles away

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children

from $315 / night

1 / 34

Keystone House - 37.4 miles away

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children

from $315 / night

1 / 22

Keystone House - 37.4 miles away

  • 1
  • 5
  • Min stay varies
  • Swimming pool
  • Ask about children

from $225 / night