50 Best Winter Park Apartments on Holiday Lettings - Condos

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Winter Park

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545 Vacation rentals

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

(6) Excellent 

18

Grand County / Winter Park

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly

 …see more

from $172 / night

$1200 - $4862 / week

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from $172 / 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 $311 / night

$2174 - $4438 / week

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from $311 / night

(3) Very Good 

17

Grand County / Winter Park

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Ask about children

 …see more

from $212 / night

$1391 / week

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from $212 / 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 $147 / night

$1024 / week

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from $147 / night

7

Grand County / Winter Park

2 10 2 nights min

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

 …see more

from $152 / night

$1739 / week

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from $152 / night

(3) Excellent 

10

Grand County / Winter Park

2 6 Min stay varies

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

 …see more

from $101 / night

$706 - $2279 / week

Inquire View

from $101 / night

30

Grand County / Winter Park

2 10 Min stay varies

  • 2 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+

 …see more

from $170 / night

$1183 - $4333 / week

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from $170 / night

19

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 $196 / night

$1369 - $3641 / week

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from $196 / 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 $200 / night

$1393 - $4543 / week

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from $200 / night

24

Grand County / Winter Park

2 8 Min stay varies

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

 …see more

from $139 / night

$967 - $3987 / week

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from $139 / night

15

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 $308 / night

$2152 - $6802 / week

Inquire View

from $308 / night

(1) Excellent 

28

Grand County / Winter Park

2 8 Min stay varies

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

 …see more

from $200 / night

$1393 - $4543 / week

Book View

from $200 / 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

$693 - $2234 / week

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from $100 / night

(9) Very Good 

7

Grand County / Winter Park

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Child friendly
  • Pet friendly

 …see more

from $111 / night

$656 - $1008 / week

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from $111 / night

(9) Very Good 

18

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 $147 / night

$1024 - $4213 / week

Inquire View

from $147 / night

(2) Very Good 

24

Grand County / Winter Park

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ask about children
  • Ask about pets

 …see more

from $147 / night

$1024 - $4354 / week

Inquire View

from $147 / night

(21) Very Good 

43

Grand County / Winter Park

4 12 Min stay varies

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

 …see more

from $448 / night

$3133 - $13625 / week

Inquire View

from $448 / night

(15) Very Good 

31

Grand County / Winter Park

3 8 Min stay varies

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

 …see more

from $249 / night

$1743 - $5080 / week

Inquire View

from $249 / 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

 …see more

from $262 / night

$1250 - $6894 / week

Book View

from $262 / 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

$478 - $1311 / week

Book View

from $80 / 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

$666 - $1391 / week

Book View

from $111 / night

(18) Excellent 

25

Grand County / Winter Park

2 9 Min stay varies

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

 …see more

from $190 / night

$1327 - $4763 / week

Inquire View

from $190 / 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 $130 / night

$904 - $2794 / week

Book View

from $130 / night

(23) Very Good 

33

Grand County / Winter Park

3 11 Min stay varies

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

 …see more

from $371 / night

$2597 - $9921 / week

Inquire View

from $371 / night

(4) Very Good 

10

Grand County / Winter Park

2 6 Min stay varies

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

 …see more

from $111 / night

$777 - $2787 / week

Inquire View

from $111 / night

(2) Very Good 

22

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 $183 / night

$1278 - $3267 / week

Inquire View

from $183 / night

(34) Very Good 

34

Grand County / Winter Park

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly

 …see more

from $317 / night

$2216 - $6597 / week

Inquire View

from $317 / night

(16) Excellent 

53

Grand County / Winter Park

2 8 Min stay varies

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

 …see more

from $193 / night

$1348 - $5842 / week

Inquire View

from $193 / night

(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 $139 / night

$967 - $2625 / week

Inquire View

from $139 / night

(52) Very Good 

25

Grand County / Winter Park

1 4 Min stay varies

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

 …see more

from $163 / night

$1136 - $3980 / week

Inquire View

from $163 / 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 $152 / night

$983 - $3528 / week

Book View

from $152 / night

(19) Excellent 

28

Grand County / Winter Park

2 8 Min stay varies

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

 …see more

from $190 / night

$1327 - $5638 / week

Inquire View

from $190 / night

(3) Very Good 

26

Grand County / Winter Park

1 4 Min stay varies

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

 …see more

from $155 / night

$1080 - $3564 / week

Inquire View

from $155 / night

(7) Excellent 

31

Grand County / Winter Park

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly

 …see more

from $301 / night

$2103 - $10019 / week

Inquire View

from $301 / night

(2) Very Good 

9

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 $96 / night

$671 - $2145 / week

Inquire View

from $96 / night

(1) Excellent 

25

Grand County / Winter Park

2 8 Min stay varies

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

 …see more

from $190 / night

$1327 - $4763 / week

Inquire View

from $190 / night

(15) Very Good 

26

Grand County / Winter Park

2 8 Min stay varies

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

 …see more

from $193 / night

$1348 - $5842 / week

Inquire View

from $193 / night

11

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 $227 / night

$1588 - $6802 / week

Inquire View

from $227 / night

(10) Excellent 

32

Grand County / Winter Park

3 10 Min stay varies

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

 …see more

from $259 / night

$1807 - $5398 / week

Inquire View

from $259 / night

(6) Very Good 

11

Grand County / Winter Park

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

 …see more

from $101 / night

$706 - $2279 / week

Inquire View

from $101 / night

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