50 Best Winter Park Apartments on Holiday Lettings - Condos

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95 Vacation rentals

(82) Excellent 

22

Grand County / Winter Park

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly

from $89 / night

$549 - $776 / week

Book View

from $89 / night

(6) Excellent 

19

Grand County / Winter Park

3 12 2 nights min

  • 3 bedrooms
  • Sleeps 12
  • 2 nights min
  • Ski
  • Child friendly

from $196 / night

$1200 - $2600 / week

Book View

from $196 / night

33

Grand County / Winter Park

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+

from $100 / night

$693 - $1225 / week

Book View

from $100 / night

(3) Excellent 

43

Grand County / Winter Park

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach/lakeside relaxation
  • Ski
  • Child friendly

from $151 / night

$976 - $3500 / week

Book View

from $151 / night

(7) Excellent 

30

Grand County / Winter Park

2 8 Min stay varies

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

from $129 / night

$1944 / week

Book View

from $129 / night

18

Grand County / Winter Park

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly

from $151 / night

$1051 / week

Book View

from $151 / night

(1) Excellent 

27

Grand County / Winter Park

4 14 Min stay varies

  • 4 bedrooms
  • Sleeps 14
  • Min stay varies
  • Child friendly
  • Pet friendly

from $360 / night

$2877 - $6840 / week

Book View

from $360 / night

(3) Very Good 

20

Grand County / Winter Park

2 7 Min stay varies

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

from $125 / night

$875 / week

Book View

from $125 / night

26

Grand County / Winter Park

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Suitable for children age 5+

from $100 / night

$693 - $1604 / week

Book View

from $100 / night

(4) Excellent 

31

Grand County / Winter Park

2 10 Min stay varies

  • 2 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly

from $120 / night

$1784 / week

Book View

from $120 / night

24

Grand County / Winter Park

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ski
  • Child friendly

from $165 / night

$1155 / week

Book View

from $165 / night

14

Grand County / Winter Park

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly

from $80 / night

$554 / week

Inquire View

from $80 / night

24

Grand County / Winter Park

6 24 Min stay varies

  • 6 bedrooms
  • Sleeps 24
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Pet friendly

from $420 / night

$2671 - $8645 / week

Book View

from $420 / night

(1) Excellent 

26

Grand County / Winter Park

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly

from $265 / night

$1856 - $6644 / week

Book View

from $265 / night

(1) Excellent 

23

Grand County / Winter Park

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ski
  • Child friendly

from $149 / night

$1043 / week

Book View

from $149 / night

(8) Excellent 

27

Grand County / Winter Park

2 8 Min stay varies

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

from $129 / night

$1944 / week

Book View

from $129 / night

(5) Excellent 

22

Grand County / Winter Park

1 6 Min stay varies

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

from $100 / night

$1144 / week

Book View

from $100 / night

(3) Very Good 

17

Grand County / Winter Park

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly

from $100 / night

$600 - $1380 / week

Book View

from $100 / night

25

Grand County / Winter Park

2 8 Min stay varies

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

from $176 / night

$1225 - $3493 / week

Book View

from $176 / night

(2) Excellent 

18

Grand County / Winter Park

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly

from $131 / night

$900 / week

Book View

from $131 / night

26

Grand County / Winter Park

6 20 Min stay varies

  • 6 bedrooms
  • Sleeps 20
  • Min stay varies
  • Child friendly
  • Pet friendly

from $416 / night

$2591 - $10088 / week

Book View

from $416 / night

(3) Very Good 

17

Grand County / Winter Park

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Swimming pool
  • Child friendly

from $211 / night

$1380 / week

Book View

from $211 / night

(1) Excellent 

30

Grand County / Winter Park

3 11 Min stay varies

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

from $236 / night

$1646 / week

Inquire View

from $236 / night

(3) Very Good 

25

Grand County / Winter Park

1 6 Min stay varies

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

from $119 / night

$827 / week

Inquire View

from $119 / night

26

Grand County / Winter Park

3 11 Min stay varies

  • 3 bedrooms
  • Sleeps 11
  • Min stay varies
  • Child friendly

from $276 / night

$1932 / week

Inquire View

from $276 / night

34

Grand County / Winter Park

5 19 Min stay varies

  • 5 bedrooms
  • Sleeps 19
  • Min stay varies
  • Child friendly

from $605 / night

$4235 / week

Inquire View

from $605 / night

(2) Excellent 

24

Grand County / Winter Park

2 8 Min stay varies

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

from $153 / night

$1071 / week

Inquire View

from $153 / night

24

Grand County / Winter Park

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly

from $116 / night

$805 - $2765 / week

Book View

from $116 / night

(1) Excellent 

18

Grand County / Winter Park

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly

from $140 / night

$974 / week

Inquire View

from $140 / night

22

Grand County / Winter Park

1 6 Min stay varies

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

from $100 / night

$1144 / week

Book View

from $100 / night

(1) Excellent 

24

Grand County / Winter Park

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly

from $175 / night

$1044 - $3144 / week

Book View

from $175 / night

(3) Excellent 

27

Grand County / Winter Park

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from $129 / night

$1944 / week

Book View

from $129 / night

(5) Very Good 

31

Grand County / Winter Park

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly

from $273 / night

$1911 / week

Inquire View

from $273 / night

(3) Excellent 

38

Grand County / Winter Park

7 18 Min stay varies

  • 7 bedrooms
  • Sleeps 18
  • Min stay varies
  • Ski
  • Child friendly

from $1051 / night

$6551 / week

Book View

from $1051 / night

(4) Excellent 

26

Grand County / Winter Park

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly

from $213 / night

$1491 / week

Inquire View

from $213 / night

23

Grand County / Winter Park

4 10 2 nights min

  • 4 bedrooms
  • Sleeps 10
  • 2 nights min
  • Child friendly

from $437 / night

$2551 / week

Book View

from $437 / night

(1) Excellent 

30

Grand County / Winter Park

5 19 Min stay varies

  • 5 bedrooms
  • Sleeps 19
  • Min stay varies
  • Child friendly

from $492 / night

$3438 / week

Inquire View

from $492 / night

(24) Excellent 

24

Grand County / Winter Park

3 8 Min stay varies

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

from $189 / night

$1323 / week

Inquire View

from $189 / night

(16) Very Good 

30

Grand County / Winter Park

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly

from $213 / night

$1491 / week

Inquire View

from $213 / night

(1) Very Good 

21

Grand County / Winter Park

4 14 Min stay varies

  • 4 bedrooms
  • Sleeps 14
  • Min stay varies
  • Child friendly
  • Pet friendly

from $360 / night

$2156 - $6840 / week

Book View

from $360 / night

1