10 Best Vacation Rentals in Winter Park - Holiday Lettings - Cabins

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14 Vacation rentals

18

Central Florida / Winter Park

8 17 Min stay varies

  • 8 bedrooms
  • Sleeps 17
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $351 / night

$2450 - $4200 / week

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from $351 / night

(2) Excellent 

27

Central Florida / Winter Park

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Private garden

 …see more

from $80 / night

$511 - $650 / week

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from $80 / night

18

Central Florida / Winter Park

8 18 Min stay varies

  • 8 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $351 / night

$2450 - $4200 / week

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from $351 / night

13

Central Florida / Winter Park

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from $143 / night

$1001 / week

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from $143 / night

37

Central Florida / Winter Park

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 60 mi
  • Child friendly
  • Air conditioning

 …see more

from $76 / night

$500 - $650 / week

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from $76 / night

35

Central Florida / Winter Park

4 8 Min stay varies

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

 …see more

from $595 / night

$3996 - $6300 / week

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from $595 / night

18

Central Florida / Winter Park

8 18 Min stay varies

  • 8 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $351 / night

$2450 - $4200 / week

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from $351 / night

35

Central Florida / Winter Park

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 81 mi
  • Child friendly

 …see more

from $276 / night

$1800 / week

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from $276 / night

40

Central Florida / Winter Park

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly

 …see more

from $99 / night

$600 / week

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from $99 / night

14

Central Florida / Winter Park

1 4 30 nights min

  • 1 bedroom
  • Sleeps 4
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

 …see more

from $114 / night

$798 / week

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from $114 / night

27

Central Florida / Winter Park

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly

 …see more

from $75 / night

$496 - $645 / week

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from $75 / night

22

Central Florida / Winter Park

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Air conditioning

 …see more

from $76 / night

$500 - $650 / week

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from $76 / night

20

Central Florida / Winter Park

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Private garden

 …see more

from $80 / night

$511 - $1070 / week

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from $80 / night

28

Central Florida / Winter Park

1 4 Min stay varies

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

 …see more

from $99 / night

$693 / week

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from $99 / night