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

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17 Vacation rentals

(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

from $80 / night

$510 - $625 / week

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from $80 / 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

from $75 / night

$499 - $625 / week

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from $75 / night

27

Central Florida / Winter Park

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly

from $75 / night

$499 / week

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from $75 / night

28

Central Florida / Winter Park

1 4 Min stay varies

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

from $99 / night

$693 / week

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from $99 / night

(1) Excellent 

20

Central Florida / Winter Park

1 2 3 nights min

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

from $80 / night

$510 - $625 / week

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from $80 / night

22

Central Florida / Winter Park

1 2 Min stay varies

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

from $75 / night

$499 - $625 / week

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from $75 / 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

from $350 / night

$2450 / week

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from $350 / 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

from $114 / night

$798 / week

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from $114 / night

35

Central Florida / Winter Park

4 8 Min stay varies

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

from $595 / night

$3995 - $6300 / week

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from $595 / night

24

Central Florida / Winter Park

1 3 1 night min

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

from $45 / night

$385 / week

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from $45 / 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

from $350 / night

$2450 / week

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from $350 / night

(1) Excellent 

13

Central Florida / Winter Park

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 88 mi
  • Child friendly
  • Air conditioning

from $143 / night

$1000 / week

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from $143 / night

18

Central Florida / Winter Park

8 17 Min stay varies

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

from $350 / night

$2450 / week

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from $350 / 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

from $99 / night

$599 / week

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from $99 / 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

from $350 / night

$2450 / week

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from $350 / night

9

Central Florida / Winter Park

1 2 3 nights min

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

from $85 / night

$550 / week

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from $85 / night

17

Central Florida / Winter Park

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly

from $290 / night

$2030 / week

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from $290 / night

1