Cottages in Windermere and Log cabins - Holiday Lettings - Holiday Rentals Windermere

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21,519 Holiday homes

25

Windermere holiday home let

Central Florida / Windermere

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Ask owner if suitable for children

from £775 / night

£5,420 / week

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from £775 / night

7

Holiday home letting

Central Florida / Windermere

5 8 2 nights min

  • 5 bedrooms
  • sleeps 8
  • 2 nights min
  • Nearest beach 115 km
  • Swimming pool
  • Child friendly

from £223 / night

£1,335 / week

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Responds fast!
avg. 2 hours 2 minutes

from £223 / night

31

Holiday townhouse with shared pool in Windermere

Central Florida / Windermere

4 8 5 nights min

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

from £100 / night

£695 / week

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from £100 / night

49

Windermere holiday guest house rental

Central Florida / Windermere

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min

from £89 / night

£665 - £851 / week

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from £89 / night

31

Holiday townhouse with shared pool in Windermere

Central Florida / Windermere

4 8 5 nights min

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

from £100 / night

£695 / week

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Responds fast!
avg. 2 hours 20 minutes

from £100 / night

8

Holiday home in Windermere

Central Florida / Windermere

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly

from £145 / night

£1,010 - £2,312 / week

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from £145 / night

18

Holiday home in Windermere

Central Florida / Windermere

4 8 5 nights min

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

from £83 / night

£580 / week

Enquire View

from £83 / night

16

Windermere holiday condo rental

Central Florida / Windermere

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £78 / night

£540 / week

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from £78 / night

14

Holiday home in Windermere

Central Florida / Windermere

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child friendly

from £174 / night

£1,217 - £2,119 / week

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from £174 / night

13

Holiday home with shared pool in Windermere

Central Florida / Windermere

3 6 2 nights min

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

from £312 / night

£2,668 / week

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from £312 / night

21

Holiday condo with shared pool in Windermere

Central Florida / Windermere

3 8 6 nights min

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

from £201 / night

£1,407 / week

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from £201 / night

16

Windermere holiday condo rental

Central Florida / Windermere

1 6 2 nights min

  • 1 bedroom
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £85 / night

£592 / week

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from £85 / night

15

Holiday condo in Windermere

Central Florida / Windermere

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £71 / night

£492 / week

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from £71 / night

7

Holiday townhouse rental

Central Florida / Windermere

4 8 5 nights min

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

from £150 / night

£1,046 / week

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Responds fast!
avg. 1 hour 13 minutes

from £150 / night

16

Holiday condo with shared pool in Windermere

Central Florida / Windermere

2 6 2 nights min

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

from £106 / night

£739 / week

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from £106 / night

13

Holiday condo with shared pool in Windermere

Central Florida / Windermere

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £92 / night

£640 / week

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from £92 / night

15

Holiday condo in Windermere

Central Florida / Windermere

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £129 / night

£900 / week

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from £129 / night

10

Holiday home in Windermere

Central Florida / Windermere

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
  • Car not necessary

from £126 / night

£653 - £1,143 / week

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from £126 / night

Great rentals within 20 miles that match your search

Distance approx 14.16 miles from Windermere

(5) Excellent 

16

Villa rental in Kissimmee

Kissimmee / Indian Ridge

3 6 7 nights min

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

from £109 / night

£745 - £882 / week

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from £109 / night

Distance approx 17.12 miles from Windermere

(7) Very Good 

61

Holiday condo in Davenport

Davenport / Terrace Ridge

3 7 5 nights min

  • 3 bedrooms
  • sleeps 7
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £75 / night

£487 - £709 / week

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Responds fast!
avg. 3 hours 0 minutes

from £75 / night

Distance approx 15.95 miles from Windermere

(4) Very Good 

13

Villa rental in Kissimmee with shared pool, golf nearby

Kissimmee / Orange Lake Resort

2 8 1 night min

  • 2 bedrooms
  • sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £152 / night

£1,063 / week

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from £152 / night

Distance approx 12.58 miles from Windermere

21

Holiday home with swimming pool in Four Corners

Central Florida / Four Corners

5 12 7 nights min

  • 5 bedrooms
  • sleeps 12
  • 7 nights min
  • Swimming pool
  • Car not necessary

from £187 / night

£1,304 / week

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Responds fast!
avg. 3 hours 50 minutes

from £187 / night

Distance approx 13.03 miles from Windermere

54

Four Corners holiday home rental

Central Florida / Four Corners

8 20 min stay varies

  • 8 bedrooms
  • sleeps 20
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £168 / night

£1,151 - £2,390 / week

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Responds fast!
avg. 3 hours 8 minutes

from £168 / night

Distance approx 11.96 miles from Windermere

5

Kissimmee holiday villa rental

Central Florida / Kissimmee

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £254 / night

£1,774 / week

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from £254 / night

Distance approx 15 miles from Windermere

24

Villa rental in Davenport

Central Florida / Davenport

6 12 5 nights min

  • 6 bedrooms
  • sleeps 12
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £173 / night

£1,211 / week

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from £173 / night

Distance approx 7.59 miles from Windermere Show on Map

(18) Very Good 

20

Orlando holiday hotel apartment rental

Central Florida / Orlando

2 6 2 nights min

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

from £221 / night

£1,544 / week

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from £221 / night

Distance approx 17.84 miles from Windermere

(1) Excellent 

41

ChampionsGate holiday home rental

Central Florida / ChampionsGate

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Nearest beach 130 km
  • Swimming pool
  • Child friendly

from £133 / night

£930 / week

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from £133 / night

Distance approx 18.91 miles from Windermere

(18) Excellent 

Certificate of Excellence

39

Holiday villa rental

Central Florida / Kissimmee

4 10 4 nights min

  • 4 bedrooms
  • sleeps 10
  • 4 nights min
  • Nearest beach 56 km
  • Swimming pool
  • Child friendly

Certificate of Excellence

from £142 / night

£1,152 / week

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Responds fast!
avg. 1 hour 41 minutes

from £142 / night

Distance approx 15.86 miles from Windermere

50

Holiday townhouse in Kissimmee

Central Florida / Kissimmee

5 14 3 nights min

  • 5 bedrooms
  • sleeps 14
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £150 / night

£1,049 / week

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from £150 / night

Distance approx 7.68 miles from Windermere Show on Map

27

Orlando holiday villa rental

Central Florida / Orlando

2 6 7 nights min

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

from £220 / night

£1,556 / week

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from £220 / night

Distance approx 11.49 miles from Windermere

24

Holiday apartment with shared pool in Four Corners

Central Florida / Four Corners

4 8 min stay varies

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

from £98 / night

£682 - £1,048 / week

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Responds fast!
avg. 9 minutes

from £98 / night

Distance approx 8.44 miles from Windermere

34

Holiday apartment rental

Central Florida / Orlando

3 8 2 nights min

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

from £124 / night

£868 / week

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from £124 / night

Distance approx 12.8 miles from Windermere

31

Home rental in Four Corners

Central Florida / Four Corners

6 12 4 nights min

  • 6 bedrooms
  • sleeps 12
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £240 / night

£1,676 / week

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from £240 / night

Distance approx 14.45 miles from Windermere

38

Holiday home with swimming pool in Kissimmee

Central Florida / Kissimmee

7 16 min stay varies

  • 7 bedrooms
  • sleeps 16
  • min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £396 / night

£2,771 / week

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from £396 / night

Distance approx 12.54 miles from Windermere

16

Kissimmee holiday home rental

Central Florida / Kissimmee

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £109 / night

£758 / week

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from £109 / night

Distance approx 11.78 miles from Windermere

26

Holiday home with swimming pool in Four Corners

Central Florida / Four Corners

3 6 5 nights min

  • 3 bedrooms
  • sleeps 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

from £149 / night

£1,043 / week

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Responds fast!
avg. 3 hours 50 minutes

from £149 / night

Distance approx 12.54 miles from Windermere

28

Kissimmee holiday home rental

Central Florida / Kissimmee

4 12 min stay varies

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

from £109 / night

£758 / week

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from £109 / night

Distance approx 12.67 miles from Windermere

34

Four Corners holiday home rental

Central Florida / Four Corners

5 12 7 nights min

  • 5 bedrooms
  • sleeps 12
  • 7 nights min
  • Swimming pool
  • Car not necessary

from £192 / night

£1,339 / week

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Responds fast!
avg. 3 hours 56 minutes

from £192 / night

Distance approx 12.86 miles from Windermere

59

Four Corners holiday home rental

Central Florida / Four Corners

6 14 7 nights min

  • 6 bedrooms
  • sleeps 14
  • 7 nights min
  • Swimming pool
  • Car not necessary
  • Air conditioning

from £394 / night

£2,752 / week

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from £394 / night

Distance approx 14.23 miles from Windermere

75

Four Corners holiday home rental

Central Florida / Four Corners

9 20 7 nights min

  • 9 bedrooms
  • sleeps 20
  • 7 nights min
  • Swimming pool
  • Car not necessary

from £621 / night

£4,345 / week

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from £621 / night

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