50 Best Winter Park Apartments on Holiday Lettings - Condos

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Winter Park

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85 Vacation rentals

Travelers going to Winter Park are booking February dates now. Secure your vacation rental today and have the perfect trip.

(5) Very Good 

24

Grand County / Winter Park

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Ask about pets

 …see more

from $137 / night

$960 - $2604 / week

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from $137 / night

18

Grand County / Winter Park

2 6 Min stay varies

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

 …see more

from $150 / night

$1050 / week

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from $150 / night

26

Grand County / Winter Park

4 12 Min stay varies

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

 …see more

from $265 / night

$1855 - $5943 / week

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from $265 / 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+

 …see more

from $100 / night

$694 - $1226 / week

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from $100 / night

24

Grand County / Winter Park

2 6 Min stay varies

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

 …see more

from $135 / night

$811 - $1951 / week

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from $135 / night

24

Grand County / Winter Park

3 8 Min stay varies

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

 …see more

from $149 / night

$894 - $2994 / week

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from $149 / night

24

Grand County / Winter Park

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children

 …see more

from $204 / night

$1422 - $4894 / week

Inquire View

from $204 / night

22

Grand County / Winter Park

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+

 …see more

from $100 / night

$714 - $2794 / week

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from $100 / night

31

Grand County / Winter Park

2 10 Min stay varies

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

 …see more

from $120 / night

$873 - $4333 / week

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from $120 / night

(1) Excellent 

20

Grand County / Winter Park

2 7 Min stay varies

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

 …see more

from $130 / night

$910 / week

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from $130 / night

27

Grand County / Winter Park

2 8 Min stay varies

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

 …see more

from $129 / night

$944 - $4544 / week

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from $129 / night

(9) Very Good 

7

Grand County / Winter Park

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Child friendly
  • Pet friendly

 …see more

from $111 / night

$650 / week

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from $111 / night

(2) Excellent 

22

Grand County / Winter Park

2 6 2 nights min

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

 …see more

from $129 / night

$865 - $1025 / week

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from $129 / night

(1) Very Good 

34

Grand County / Winter Park

2 8 Min stay varies

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

 …see more

from $335 / night

$2338 - $3802 / week

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from $335 / night

(2) Good 

24

Grand County / Winter Park

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Ask about children
  • Pet friendly

 …see more

from $282 / night

$1974 - $6083 / week

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from $282 / night

(2) Excellent 

30

Grand County / Winter Park

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+

 …see more

from $129 / night

$944 - $4544 / week

Book View

from $129 / night

(2) Very Good 

17

Grand County / Winter Park

2 6 Min stay varies

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

 …see more

from $111 / night

$660 - $1120 / week

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from $111 / night

28

Grand County / Winter Park

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Ask about pets

 …see more

from $291 / night

$2038 - $10500 / week

Inquire View

from $291 / night

(2) Excellent 

43

Grand County / Winter Park

3 9 Min stay varies

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

 …see more

from $150 / night

$976 - $3500 / week

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from $150 / night

(3) Excellent 

13

Grand County / Winter Park

1 4 Min stay varies

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

 …see more

from $80 / night

$475 - $1301 / week

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from $80 / night

25

Grand County / Winter Park

1 4 Min stay varies

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

 …see more

from $125 / night

$875 - $1912 / week

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from $125 / night

(2) Good 

23

Grand County / Winter Park

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Ask about children

 …see more

from $179 / night

$1253 - $5565 / week

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from $179 / 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+

 …see more

from $100 / night

$694 - $1674 / week

Book View

from $100 / night

28

Grand County / Winter Park

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Ask about children

 …see more

from $379 / night

$2654 - $5593 / week

Inquire View

from $379 / night

(1) Excellent 

4

Grand County / Winter Park

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly

 …see more

from $91 / night

$530 - $1081 / week

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from $91 / night

27

Grand County / Winter Park

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Pet friendly

 …see more

from $129 / night

$944 - $4544 / week

Book View

from $129 / night

(1) Excellent 

18

Grand County / Winter Park

2 6 Min stay varies

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

 …see more

from $130 / night

$900 - $1051 / week

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from $130 / night

(2)  

22

Grand County / Winter Park

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Ask about pets

 …see more

from $118 / night

$820 - $2045 / week

Inquire View

from $118 / night

(6) Very Good 

20

Grand County / Winter Park

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children

 …see more

from $329 / night

$2297 - $5902 / week

Inquire View

from $329 / 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

 …see more

from $310 / night

$2164 - $8645 / week

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from $310 / night

(4) Excellent 

34

Grand County / Winter Park

5 11 Min stay varies

  • 5 bedrooms
  • Sleeps 11
  • Min stay varies
  • Ask about children

 …see more

from $604 / night

$4221 - $11901 / week

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from $604 / night

(4) Very Good 

36

Grand County / Winter Park

3 8 Min stay varies

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

 …see more

from $175 / night

$1226 - $2765 / week

Inquire View

from $175 / night

(1) Excellent 

20

Grand County / Winter Park

4 14 Min stay varies

  • 4 bedrooms
  • Sleeps 14
  • Min stay varies
  • Ski
  • Child friendly
  • Private garden

 …see more

from $495 / night

$3250 - $8451 / week

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from $495 / night

(3) Very Good 

27

Grand County / Winter Park

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children

 …see more

from $329 / night

$2297 - $5384 / week

Inquire View

from $329 / night

22

Grand County / Winter Park

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Pet friendly

 …see more

from $100 / night

$714 - $2794 / week

Book View

from $100 / night

26

Grand County / Winter Park

6 20 Min stay varies

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

 …see more

from $310 / night

$2164 - $10087 / week

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from $310 / night

32

Grand County / Winter Park

3 8 Min stay varies

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

 …see more

from $200 / night

$1544 - $7694 / week

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from $200 / night

25

Grand County / Winter Park

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Pet friendly

 …see more

from $129 / night

$944 - $4544 / week

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from $129 / night

34

Grand County / Winter Park

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children

 …see more

from $291 / night

$2038 - $6994 / week

Inquire View

from $291 / night

(1) Excellent 

23

Grand County / Winter Park

2 6 Min stay varies

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

 …see more

from $149 / night

$1043 / week

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from $149 / night