Houses in Winter Park and Villas – Holiday Lettings - Holiday Rentals Winter Park

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3,411 Holiday homes

27

Holiday home in Winter Park

Central Florida / Winter Park

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Nearest beach 100 km
  • Child friendly
  • Air conditioning

from £67 / night

£445 / week

Book View

Responds fast!
avg. 2 hours 19 minutes

from £67 / night

(2) Excellent 

27

Holiday home letting

Central Florida / Winter Park

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Nearest beach 100 km
  • Suitable for children age 5+
  • Air conditioning

from £72 / night

£455 / week

Book View

Responds fast!
avg. 2 hours 19 minutes

from £72 / night

37

Holiday home with golf nearby in Winter Park

Central Florida / Winter Park

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Nearest beach 60 km
  • Child friendly
  • Air conditioning

from £67 / night

£445 / week

Book View

Responds fast!
avg. 2 hours 19 minutes

from £67 / night

35

Holiday home rental

Central Florida / Winter Park

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 81 km
  • Child friendly

from £401 / night

£2,184 / week

Book View

from £401 / night

(2) Excellent 

13

Holiday home in Winter Park

Central Florida / Winter Park

2 5 7 nights min

  • 2 bedrooms
  • sleeps 5
  • 7 nights min
  • Nearest beach 88 km
  • Child friendly
  • Air conditioning

from £128 / night

£891 / week

Book View

Responds fast!
avg. 1 hour 19 minutes

from £128 / night

(3) Very Good 

22

Winter Park holiday home rental

Central Florida / Winter Park

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Nearest beach 100 km
  • Child friendly
  • Air conditioning

from £72 / night

£473 / week

Book View

Responds fast!
avg. 2 hours 19 minutes

from £72 / night

10

Townhouse rental in Winter Park

Central Florida / Winter Park

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Child friendly

from £116 / night

£811 / week

Book View

from £116 / night

11

Holiday home letting

Central Florida / Winter Park

3 5 1 night min

  • 3 bedrooms
  • sleeps 5
  • 1 night min
  • Nearest beach 30 km
  • Child friendly
  • Air conditioning

from £94 / night

£535 / week

Book View

from £94 / night

(2) Average 

20

Winter Park holiday home rental

Central Florida / Winter Park

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Nearest beach 100 km
  • Child friendly
  • Air conditioning

from £72 / night

£455 / week

Book View

Responds fast!
avg. 2 hours 19 minutes

from £72 / night

29

Holiday studio in Winter Park

Central Florida / Winter Park

Studio 4 2 nights min

  • Studio
  • sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly

from £78 / night

£513 / week

Book View

from £78 / night

35

Winter Park holiday villa rental

Central Florida / Winter Park

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Child friendly
  • Air conditioning
  • Private garden

from £531 / night

£3,563 - £5,271 / week

Book View

from £531 / night

14

Winter Park holiday home rental

Central Florida / Winter Park

1 5 1 night min

  • 1 bedroom
  • sleeps 5
  • 1 night min
  • Nearest beach 80 km
  • Child friendly
  • Air conditioning

from £80 / night

£517 / week

Book View

from £80 / night

Great rentals within 20 miles that match your search

Distance approx 19.56 miles from Winter Park Show on Map

18

Holiday home in Kissimmee

Central Florida / Kissimmee

4 12 3 nights min

  • 4 bedrooms
  • sleeps 12
  • 3 nights min
  • Child friendly

from £81 / night

£561 / week

Book View

Responds fast!
avg. 1 hour 54 minutes

from £81 / night

Distance approx 12.97 miles from Winter Park Show on Map

27

Orlando holiday condo rental

Orlando / Vista Cay

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Swimming pool

from £214 / night

£1,497 / week

Book View

Responds fast!
avg. 1 hour 15 minutes

from £214 / night

Distance approx 12.89 miles from Winter Park Show on Map

(37) Excellent 

Certificate of Excellence

12

Holiday villa in Orlando

Central Florida / Orlando

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Certificate of Excellence

from £151 / night

£936 - £1,444 / week

Book View

Responds fast!
avg. 1 hour 59 minutes

from £151 / night

Distance approx 19.84 miles from Winter Park Show on Map

(4) Excellent 

24

Holiday apartment with shared pool in Orlando

Central Florida / Orlando

2 8 2 nights min

  • 2 bedrooms
  • sleeps 8
  • 2 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £223 / night

£1,560 / week

Book View

from £223 / night

Distance approx 4.91 miles from Winter Park Show on Map

(1) Excellent 

22

Holiday home in Orlando

Central Florida / Orlando

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £139 / night

£936 - £1,061 / week

Book View

Responds fast!
avg. 1 hour 25 minutes

from £139 / night

Distance approx 19.84 miles from Winter Park Show on Map

22

Holiday apartment with shared pool in Celebration

Florida / Celebration

3 10 3 nights min

  • 3 bedrooms
  • sleeps 10
  • 3 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £286 / night

£1,996 / week

Book View

from £286 / night

Distance approx 19.39 miles from Winter Park Show on Map

22

Holiday home in Buena Ventura Lakes

Florida / Buena Ventura Lakes

3 7 5 nights min

  • 3 bedrooms
  • sleeps 7
  • 5 nights min
  • Nearest beach 80 km
  • Child friendly
  • Air conditioning

from £79 / night

£549 / week

Book View

from £79 / night

Distance approx 19.84 miles from Winter Park Show on Map

18

Holiday apartment with shared pool in Celebration

Florida / Celebration

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £161 / night

£1,123 / week

Book View

from £161 / night

Distance approx 18.68 miles from Winter Park Show on Map

27

Holiday condo in Celebration

Florida / Celebration

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £64 / night

£443 / week

Book View

Responds fast!
avg. 10 minutes

from £64 / night

Distance approx 16.11 miles from Winter Park Show on Map

11

Holiday hotel apartment rental

Central Florida / Orlando

2 8 3 nights min

  • 2 bedrooms
  • sleeps 8
  • 3 nights min
  • Nearest beach 64 km
  • Swimming pool
  • Child friendly

from £192 / night

£1,292 / week

Book View

from £192 / night

Distance approx 18.06 miles from Winter Park Show on Map

54

Holiday condo in Orlando

Central Florida / Orlando

1 6 5 nights min

  • 1 bedroom
  • sleeps 6
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £106 / night

£669 - £967 / week

Book View

from £106 / night

Distance approx 19.84 miles from Winter Park Show on Map

24

Holiday apartment with shared pool in Celebration

Florida / Celebration

2 8 2 nights min

  • 2 bedrooms
  • sleeps 8
  • 2 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £223 / night

£1,560 / week

Book View

from £223 / night

Distance approx 19.84 miles from Winter Park Show on Map

24

Holiday apartment rental

Florida / Celebration

4 12 2 nights min

  • 4 bedrooms
  • sleeps 12
  • 2 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £361 / night

£2,525 / week

Book View

from £361 / night

Distance approx 19.03 miles from Winter Park Show on Map

27

Holiday townhouse with swimming pool in Kissimmee

Central Florida / Kissimmee

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £142 / night

£992 / week

Book View

from £142 / night

Distance approx 19.84 miles from Winter Park Show on Map

20

Holiday apartment with shared pool in Celebration

Florida / Celebration

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £161 / night

£1,123 / week

Book View

from £161 / night

Distance approx 4.25 miles from Winter Park Show on Map

81

Villa letting in Orlando with shared pool

Central Florida / Orlando

8 18 5 nights min

  • 8 bedrooms
  • sleeps 18
  • 5 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £446 / night

£3,119 / week

Book View

from £446 / night

Distance approx 9.5 miles from Winter Park Show on Map

35

Holiday home rental

Florida / Ventura

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Child friendly
  • Air conditioning
  • Private garden

from £169 / night

£1,158 / week

Book View

from £169 / night

Distance approx 9.75 miles from Winter Park Show on Map

34

Orlando holiday apartment accommodation

Central Florida / Orlando

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £90 / night

£624 / week

Book View

Responds fast!
avg. 1 hour 51 minutes

from £90 / night

Distance approx 19.84 miles from Winter Park Show on Map

24

Holiday apartment in Celebration

Florida / Celebration

2 8 2 nights min

  • 2 bedrooms
  • sleeps 8
  • 2 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £223 / night

£1,560 / week

Book View

from £223 / night

Distance approx 19.84 miles from Winter Park Show on Map

18

Holiday apartment rental

Florida / Celebration

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £161 / night

£1,123 / week

Book View

from £161 / night

Distance approx 19.04 miles from Winter Park Show on Map

20

Holiday home with swimming pool in Celebration

Florida / Celebration

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Car not necessary

from £231 / night

£1,616 / week

Book View

Responds fast!
avg. 2 hours 46 minutes

from £231 / night

Distance approx 16.87 miles from Winter Park Show on Map

9

Holiday apartment in Orlando

Central Florida / Orlando

1 8 7 nights min

  • 1 bedroom
  • sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning

from £166 / night

£1,158 / week

Book View

from £166 / night

Distance approx 19.84 miles from Winter Park Show on Map

21

Holiday apartment with shared pool in Celebration

Florida / Celebration

3 10 3 nights min

  • 3 bedrooms
  • sleeps 10
  • 3 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £286 / night

£1,996 / week

Book View

from £286 / night

Distance approx 19.84 miles from Winter Park Show on Map

24

Holiday apartment with shared pool in Celebration

Florida / Celebration

2 8 2 nights min

  • 2 bedrooms
  • sleeps 8
  • 2 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £223 / night

£1,559 / week

Book View

from £223 / night

Distance approx 19.84 miles from Winter Park Show on Map

18

Holiday apartment with shared pool in Celebration

Florida / Celebration

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £161 / night

£1,123 / week

Book View

from £161 / night

Distance approx 19.84 miles from Winter Park Show on Map

21

Holiday apartment with shared pool in Celebration

Florida / Celebration

3 10 3 nights min

  • 3 bedrooms
  • sleeps 10
  • 3 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £286 / night

£1,996 / week

Book View

from £286 / night

Distance approx 12.93 miles from Winter Park Show on Map

20

Holiday townhouse in Kissimmee

Central Florida / Kissimmee

3 8 1 night min

  • 3 bedrooms
  • sleeps 8
  • 1 night min
  • Child friendly
  • Air conditioning

from £133 / night

£930 / week

Book View

from £133 / night

Distance approx 19.15 miles from Winter Park Show on Map

12

Home rental in Kissimmee with swimming pool

Central Florida / Kissimmee

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Car not necessary

from £137 / night

£955 - £2,127 / week

Book View

Responds fast!
avg. 2 hours 46 minutes

from £137 / night

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