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Family Friendly Holidays in Winter Park - Holiday Lettings

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405 family friendly properties

Winter Park holiday apartment rental

Winter Park apartment

4 bedrooms • 3 bathrooms • sleeps 12

from £142 / night

£989 / week

1 / 27

Holiday condo with shared pool in Winter Park

Winter Park condo

2 bedrooms • 2 bathrooms • sleeps 4

1 review

from £148 / night

£1,033 / week

1 / 18

Winter Park holiday home rental

Winter Park house

5 bedrooms • 5 bathrooms • sleeps 12

from £268 / night

£1,875 / week

1 / 29

Winter Park ski apartment to rent.

Winter Park apartment

2 bedrooms • 2 bathrooms • sleeps 7

1 review

from £105 / night

£733 / week

1 / 25

Winter Park ski apartment to rent.

Winter Park apartment

1 bedroom • 1 bathroom • sleeps 4

from £72 / night

£501 / week

1 / 26

Winter Park holiday home rental

Winter Park house

4 bedrooms • 3 bathrooms • sleeps 12

1 review

from £220 / night

£1,534 / week

1 / 26

Holiday apartment in Winter Park

Winter Park apartment

3 bedrooms • 2 bathrooms • sleeps 10

from £98 / night

£682 / week

1 / 24

Winter Park ski townhouse to rent.

Winter Park townhouse

3 bedrooms • 3 bathrooms • sleeps 8

from £183 / night

£1,275 / week

1 / 21

Holiday villa with shared pool in Winter Park

Winter Park villa

• 1 bathroom • sleeps 4

4 reviews

from £41 / night

£243 / week

1 / 14

Holiday log cabin letting

Winter Park log cabin

4 bedrooms • 4 bathrooms • sleeps 10

from £412 / night

£2,400 / week

1 / 23

Winter Park holiday home rental

Winter Park house

3 bedrooms • 3 bathrooms • sleeps 8

from £177 / night

£1,235 / week

1 / 29

Holiday home in Winter Park

Winter Park house

3 bedrooms • 3 bathrooms • sleeps 8

from £130 / night

£909 / week

1 / 35

Winter Park holiday condo rental

Winter Park condo

2 bedrooms • 2 bathrooms • sleeps 10

from £130 / night

£812 / week

1 / 0

Holiday home in Winter Park

Winter Park house

3 bedrooms • 4 bathrooms • sleeps 8

from £242 / night

£1,690 / week

1 / 28

Holiday log cabin in Winter Park

Winter Park log cabin

4 bedrooms • 4 bathrooms • sleeps 10

from £264 / night

£1,847 / week

1 / 25

Holiday log cabin in Winter Park

Winter Park log cabin

2 bedrooms • 2 bathrooms • sleeps 8

from £117 / night

£819 / week

1 / 24

Ski villa to rent in Winter Park

Winter Park villa

9 bedrooms • 6 bathrooms • sleeps 36

1 review

from £1,459 / night

£10,208 / week

1 / 26

Winter Park ski home to rent.

Winter Park house

9 bedrooms • 9 bathrooms • sleeps 28

2 reviews

from £876 / night

£6,131 - £10,877 / week

1 / 29

Home rental in Winter Park with shared pool

Winter Park house

3 bedrooms • 4 bathrooms • sleeps 8

from £202 / night

£1,415 / week

1 / 16

Ski studio to rent in Winter Park

Winter Park studio

Studio • 1 bathroom • sleeps 3

3 reviews

from £165 / night

£1,153 / week

1 / 19

Ski condo to rent in Winter Park

Winter Park condo

2 bedrooms • 2 bathrooms • sleeps 10

from £144 / night

£1,009 / week

1 / 10

Home rental in Winter Park

Winter Park house

5 bedrooms • 4 bathrooms • sleeps 14

from £647 / night

£4,526 / week

1 / 14

Winter Park holiday home rental

Winter Park house

1 bedroom • 1 bathroom • sleeps 4

from £129 / night

£903 / week

1 / 18

Holiday apartment rental

Winter Park apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £151 / night

£1,057 / week

1 / 24

Townhouse rental in Winter Park

Winter Park townhouse

3 bedrooms • 4 bathrooms • sleeps 10

from £177 / night

£1,233 / week

1 / 29

Townhouse letting in Winter Park

Winter Park townhouse

3 bedrooms • 3 bathrooms • sleeps 10

from £164 / night

£1,142 / week

1 / 35

Condo rental in Winter Park

Winter Park condo

1 bedroom • 1 bathroom • sleeps 4

from £78 / night

£540 / week

1 / 36

Winter Park holiday apartment let

Winter Park apartment

2 bedrooms • 2 bathrooms • sleeps 8

from £93 / night

£648 / week

1 / 34

Holiday condo in Winter Park

Winter Park condo

3 bedrooms • 2 bathrooms • sleeps 8

from £439 / night

£3,073 / week

1 / 24

Winter Park holiday condo rental

Winter Park condo

2 bedrooms • 2 bathrooms • sleeps 8

from £126 / night

£881 / week

1 / 24

Holiday home with shared pool in Winter Park

Winter Park house

3 bedrooms • 3 bathrooms • sleeps 9

1 review

from £168 / night

£1,176 / week

1 / 33

Ski home to rent in Winter Park

Winter Park house

7 bedrooms • 7 bathrooms • sleeps 18

5 reviews

from £567 / night

£5,299 / week

1 / 38

Holiday studio rental

Winter Park studio

Studio • 1 bathroom • sleeps 6

from £65 / night

£449 / week

1 / 31

Winter Park ski apartment to rent.

Winter Park apartment

1 bedroom • 1 bathroom • sleeps 4

from £168 / night

£1,171 / week

1 / 24

Holiday condo in Winter Park

Winter Park condo

1 bedroom • 1 bathroom • sleeps 6

from £135 / night

£943 / week

1 / 10

Holiday home in Winter Park

Winter Park house

4 bedrooms • 4 bathrooms • sleeps 10

from £189 / night

£1,319 / week

1 / 27

Winter Park holiday townhouse rental

Winter Park townhouse

3 bedrooms • 3 bathrooms • sleeps 7

1 review

from £148 / night

£1,034 / week

1 / 29

Holiday condo in Winter Park

Winter Park condo

2 bedrooms • 2 bathrooms • sleeps 8

from £96 / night

£671 / week

1 / 19

Holiday condo in Winter Park

Winter Park condo

2 bedrooms • 3 bathrooms • sleeps 9

from £99 / night

£688 / week

1 / 26

Winter Park holiday condo rental

Winter Park condo

2 bedrooms • 3 bathrooms • sleeps 8

from £102 / night

£711 / week

1 / 28

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