50 Best Winter Park Apartments on Holiday Lettings - Condos

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Winter Park

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322 Vacation rentals

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

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 $99 / night

$693 - $1225 / week

Book View

from $99 / night

(6) Excellent 

19

Grand County / Winter Park

3 12 2 nights min

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

 …see more

from $195 / night

$1200 - $2600 / week

Book View

from $195 / night

(1) Very Good 

22

Grand County / Winter Park

Studio 6 2 nights min

  • Studio
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

 …see more

from $130 / night

$910 / week

Inquire View

from $130 / night

(81) Excellent 

22

Grand County / Winter Park

2 6 3 nights min

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

 …see more

from $89 / night

$549 - $800 / week

Book View

from $89 / night

(3) Excellent 

10

Grand County / Winter Park

Studio 6 2 nights min

  • Studio
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

 …see more

from $100 / night

$700 / week

Inquire View

from $100 / night

(1) Very Good 

34

Grand County / Winter Park

Studio 8 Min stay varies

  • Studio
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children

 …see more

from $268 / night

$1876 / week

Inquire View

from $268 / night

(4) Very Good 

10

Grand County / Winter Park

Studio 6 2 nights min

  • Studio
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

 …see more

from $110 / night

$770 / week

Inquire View

from $110 / night

(6) Excellent 

18

Grand County / Winter Park

Studio 10 Min stay varies

  • Studio
  • Sleeps 10
  • Min stay varies
  • Child friendly

 …see more

from $170 / night

$1190 / week

Inquire View

from $170 / night

24

Grand County / Winter Park

Studio 8 Min stay varies

  • Studio
  • Sleeps 8
  • Min stay varies
  • Ask about children

 …see more

from $264 / night

$1848 / week

Inquire View

from $264 / night

(3) Good 

9

Grand County / Winter Park

Studio 4 2 nights min

  • Studio
  • Sleeps 4
  • 2 nights min
  • Ask about children
  • Ask about pets

 …see more

from $95 / night

$665 / week

Inquire View

from $95 / night

(4) Very Good 

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 $79 / night

$474 - $1300 / week

Book View

from $79 / night

21

Grand County / Winter Park

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Ask about children
  • Ask about pets

 …see more

from $145 / night

$1015 - $2219 / week

Inquire View

from $145 / night

15

Grand County / Winter Park

Studio 8 Min stay varies

  • Studio
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Ask about pets

 …see more

from $225 / night

$1575 / week

Inquire View

from $225 / night

29

Grand County / Winter Park

Studio 4 Min stay varies

  • Studio
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children

 …see more

from $128 / night

$896 / week

Inquire View

from $128 / night

27

Grand County / Winter Park

Studio 5 2 nights min

  • Studio
  • Sleeps 5
  • 2 nights min
  • Ask about children
  • Ask about pets

 …see more

from $100 / night

$700 / week

Inquire View

from $100 / night

24

Grand County / Winter Park

Studio 13 Min stay varies

  • Studio
  • Sleeps 13
  • Min stay varies
  • Ask about children
  • Ask about pets

 …see more

from $350 / night

$2450 / week

Inquire View

from $350 / night

24

Grand County / Winter Park

Studio 6 2 nights min

  • Studio
  • Sleeps 6
  • 2 nights min
  • Ask about children
  • Ask about pets

 …see more

from $135 / night

$945 / week

Inquire View

from $135 / night

(1) Very Good 

23

Grand County / Winter Park

Studio 4 Min stay varies

  • Studio
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children

 …see more

from $128 / night

$896 / week

Inquire View

from $128 / night

22

Grand County / Winter Park

1 6 Min stay varies

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

 …see more

from $99 / night

$1143 / week

Book View

from $99 / night

(3) 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

Book View

from $129 / night

(2) Good 

23

Grand County / Winter Park

Studio 4 Min stay varies

  • Studio
  • Sleeps 4
  • Min stay varies
  • Ask about children

 …see more

from $189 / night

$1323 / week

Inquire View

from $189 / night

22

Grand County / Winter Park

Studio 8 2 nights min

  • Studio
  • Sleeps 8
  • 2 nights min
  • Ask about children
  • Ask about pets

 …see more

from $145 / night

$1015 / week

Inquire View

from $145 / night

21

Grand County / Winter Park

Studio 6 2 nights min

  • Studio
  • Sleeps 6
  • 2 nights min
  • Ask about children
  • Ask about pets

 …see more

from $130 / night

$910 / week

Inquire View

from $130 / night

(7) Excellent 

30

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

$1943 / week

Book View

from $129 / night

(2) Good 

13

Grand County / Winter Park

Studio 8 2 nights min

  • Studio
  • Sleeps 8
  • 2 nights min
  • Ask about children
  • Ask about pets

 …see more

from $155 / night

$1085 / week

Inquire View

from $155 / night

(1) Excellent 

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

Book View

from $265 / night

20

Grand County / Winter Park

Studio 6 2 nights min

  • Studio
  • Sleeps 6
  • 2 nights min
  • Ask about children
  • Ask about pets

 …see more

from $145 / night

$1015 / week

Inquire View

from $145 / night

21

Grand County / Winter Park

Studio 6 2 nights min

  • Studio
  • Sleeps 6
  • 2 nights min
  • Ask about children
  • Ask about pets

 …see more

from $115 / night

$805 / week

Inquire View

from $115 / night

(1) Very Good 

20

Grand County / Winter Park

Studio 7 2 nights min

  • Studio
  • Sleeps 7
  • 2 nights min
  • Ask about children
  • Ask about pets

 …see more

from $130 / night

$910 / week

Inquire View

from $130 / night

(2) Very Good 

26

Grand County / Winter Park

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Ask about children

 …see more

from $102 / night

$714 / week

Inquire View

from $102 / night

(1) Excellent 

24

Grand County / Winter Park

3 8 Min stay varies

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

 …see more

from $174 / night

$1044 - $3144 / week

Book View

from $174 / night

(3) Very Good 

27

Grand County / Winter Park

Studio 6 Min stay varies

  • Studio
  • Sleeps 6
  • Min stay varies
  • Ask about children

 …see more

from $240 / night

$1680 / week

Inquire View

from $240 / 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

$975 - $3500 / week

Book View

from $150 / night

(2) Good 

26

Grand County / Winter Park

Studio 4 Min stay varies

  • Studio
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children

 …see more

from $141 / night

$987 / week

Inquire View

from $141 / 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 $100 / night

$600 - $1380 / week

Book View

from $100 / night

(4) Very Good 

19

Grand County / Winter Park

Studio 4 2 nights min

  • Studio
  • Sleeps 4
  • 2 nights min
  • Ask about children
  • Ask about pets

 …see more

from $100 / night

$700 / week

Inquire View

from $100 / 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

Book View

from $149 / night

(6) Excellent 

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

$1943 / week

Book View

from $129 / night

(24) Excellent 

24

Grand County / Winter Park

Studio 8 Min stay varies

  • Studio
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly

 …see more

from $189 / night

$1323 / week

Inquire View

from $189 / night

31

Grand County / Winter Park

Studio 6 2 nights min

  • Studio
  • Sleeps 6
  • 2 nights min
  • Ask about children
  • Ask about pets

 …see more

from $137 / night

$959 / week

Inquire View

from $137 / night

1