Apartments in Winter Haven and Houses - Holiday Lettings - Holiday Rentals Winter Haven

Close

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

7,961 Holiday homes

24

Villa rental in Winter Haven

Central Florida / Winter Haven

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child friendly
  • Air conditioning

from £93 / night

£652 / week

Book View

Responds fast!
avg. 3 hours 19 minutes

from £93 / night

31

Villa rental in Winter Haven

Central Florida / Winter Haven

2 7 min stay varies

  • 2 bedrooms
  • sleeps 7
  • min stay varies
  • Child friendly
  • Air conditioning

from £107 / night

£745 / week

Book View

Responds fast!
avg. 3 hours 19 minutes

from £107 / night

(3) Very Good 

22

Holiday villa in Winter Haven

Central Florida / Winter Haven

3 6 4 nights min

  • 3 bedrooms
  • sleeps 6
  • 4 nights min
  • Nearest beach 126 km
  • Swimming pool
  • Child friendly

from £110 / night

£765 - £1,080 / week

Book View

Responds fast!
avg. 3 hours 4 minutes

from £110 / night

(3) Excellent 

20

Holiday home in Winter Haven

Central Florida / Winter Haven

3 10 3 nights min

  • 3 bedrooms
  • sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £201 / night

£1,401 / week

Book View

from £201 / night

(6) Excellent 

28

Holiday home in Winter Haven

Central Florida / Winter Haven

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden

from £71 / night

£443 / week

Book View

from £71 / night

29

Villa letting in Winter Haven

Central Florida / Winter Haven

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child friendly
  • Air conditioning

from £93 / night

£652 / week

Book View

Responds fast!
avg. 3 hours 19 minutes

from £93 / night

(2) Average 

12

Holiday home in Winter Haven

Central Florida / Winter Haven

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Child friendly
  • Air conditioning
  • Ask about pets

from £58 / night

£355 / week

Book View

Responds fast!
avg. 2 hours 59 minutes

from £58 / night

28

Villa rental in Winter Haven

Central Florida / Winter Haven

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child friendly
  • Air conditioning

from £93 / night

£652 / week

Book View

Responds fast!
avg. 3 hours 19 minutes

from £93 / night

10

Holiday home in Winter Haven

Central Florida / Winter Haven

2 5 90 nights min

  • 2 bedrooms
  • sleeps 5
  • 90 nights min
  • Air conditioning
  • Pet friendly
  • Private garden

from £55 / night

£384 / week

Book View

Responds fast!
avg. 1 hour 35 minutes

from £55 / night

34

Villa rental in Winter Haven

Central Florida / Winter Haven

2 6 min stay varies

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

from £107 / night

£745 / week

Book View

Responds fast!
avg. 3 hours 19 minutes

from £107 / night

33

Villa rental in Winter Haven

Central Florida / Winter Haven

2 7 min stay varies

  • 2 bedrooms
  • sleeps 7
  • min stay varies
  • Child friendly
  • Air conditioning

from £107 / night

£745 / week

Book View

Responds fast!
avg. 3 hours 19 minutes

from £107 / night

Great rentals within 20 miles that match your search

Distance approx 16.68 miles from Winter Haven

(9) Very Good 

16

Orlando holiday villa rental

Central Florida / Orlando

4 8 5 nights min

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

from £155 / night

£802 - £859 / week

Book View

from £155 / night

Distance approx 14.21 miles from Winter Haven

(31) Very Good 

36

Holiday villa with swimming pool in Davenport

Davenport / Tivoli Manor

4 8 min stay varies

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

from £70 / night

£460 - £565 / week

Book View

Responds fast!
avg. 3 hours 8 minutes

from £70 / night

Distance approx 12.28 miles from Winter Haven

(5) Excellent 

46

Davenport holiday home rental

Central Florida / Davenport

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £128 / night

£890 / week

Book View

Responds fast!
avg. 51 minutes

from £128 / night

Distance approx 17.31 miles from Winter Haven

22

Davenport holiday villa rental

Davenport / Windwood Bay

4 8 5 nights min

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

from £109 / night

£760 / week

Book View

from £109 / night

Distance approx 18.24 miles from Winter Haven

(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

Book View

Responds fast!
avg. 3 hours 0 minutes

from £75 / night

Distance approx 19.27 miles from Winter Haven

12

Holiday villa with indoor pool, golf nearby in Davenport

Central Florida / Davenport

4 10 5 nights min

  • 4 bedrooms
  • sleeps 10
  • 5 nights min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly

from £115 / night

£802 / week

Book View

from £115 / night

Distance approx 18.9 miles from Winter Haven

23

Holiday villa with golf nearby in Davenport

Davenport / Sandy Ridge

4 8 5 nights min

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

from £86 / night

£602 / week

Book View

from £86 / night

Distance approx 16.79 miles from Winter Haven

56

Davenport holiday home rental

Central Florida / Davenport

6 14 min stay varies

  • 6 bedrooms
  • sleeps 14
  • min stay varies
  • Child friendly

from £207 / night

£1,177 - £1,842 / week

Book View

from £207 / night

Distance approx 17.22 miles from Winter Haven

(11) Very Good 

Certificate of Excellence

46

Holiday villa with golf nearby in Orlando

Central Florida / Orlando

8 18 4 nights min

  • 8 bedrooms
  • sleeps 18
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

Certificate of Excellence

from £347 / night

£2,357 - £2,979 / week

Book View

Responds fast!
avg. 12 minutes

from £347 / night

Distance approx 12.5 miles from Winter Haven

11

Holiday apartment in Davenport

Central Florida / Davenport

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Suitable for children age 5+

from £108 / night

£754 / week

Book View

from £108 / night

Distance approx 19.2 miles from Winter Haven

(35) Excellent 

Certificate of Excellence

34

Holiday villa rental

Central Florida / Davenport

4 8 5 nights min

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

Certificate of Excellence

from £85 / night

£534 / week

Book View

Responds fast!
avg. 2 hours 48 minutes

from £85 / night

Distance approx 9.88 miles from Winter Haven Show on Map

20

Holiday home with golf nearby in Orlando

Central Florida / Orlando

7 16 min stay varies

  • 7 bedrooms
  • sleeps 16
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £160 / night

£801 - £2,223 / week

Book View

Responds fast!
avg. 2 hours 29 minutes

from £160 / night

Distance approx 12.03 miles from Winter Haven

19

Davenport holiday villa accommodation

Central Florida / Davenport

6 12 5 nights min

  • 6 bedrooms
  • sleeps 12
  • 5 nights min
  • Child friendly

from £165 / night

£1,152 / week

Book View

Responds fast!
avg. 51 minutes

from £165 / night

Distance approx 16.89 miles from Winter Haven

(4) Excellent 

16

Davenport holiday villa rental

Central Florida / Davenport

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £133 / night

£930 / week

Book View

Responds fast!
avg. 2 hours 10 minutes

from £133 / night

Distance approx 14.22 miles from Winter Haven

(6) Excellent 

35

Home rental in Davenport

Central Florida / Davenport

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly

from £125 / night

£801 / week

Book View

Responds fast!
avg. 2 hours 7 minutes

from £125 / night

Distance approx 16.43 miles from Winter Haven

9

Holiday home in ChampionsGate

Central Florida / ChampionsGate

4 10 min stay varies

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

from £107 / night

£747 / week

Book View

from £107 / night

Distance approx 18.53 miles from Winter Haven

42

Holiday home in Four Corners

Central Florida / Four Corners

4 8 7 nights min

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

from £134 / night

£934 / week

Book View

Responds fast!
avg. 2 hours 54 minutes

from £134 / night

Distance approx 17.28 miles from Winter Haven

(5) Very Good 

21

Holiday villa with golf nearby in Davenport

Davenport / Champions Gate

9 22 min stay varies

  • 9 bedrooms
  • sleeps 22
  • min stay varies
  • Swimming pool
  • Air conditioning
  • Private garden

from £287 / night

£2,005 / week

Book View

Responds fast!
avg. 1 hour 23 minutes

from £287 / night

Distance approx 17.89 miles from Winter Haven

49

Davenport holiday villa rental

Central Florida / Davenport

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

from £98 / night

£667 / week

Book View

from £98 / night

Distance approx 19.27 miles from Winter Haven

30

Holiday villa with golf nearby in Davenport

Central Florida / Davenport

7 16 min stay varies

  • 7 bedrooms
  • sleeps 16
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £151 / night

£1,052 / week

Book View

Responds fast!
avg. 1 hour 57 minutes

from £151 / night

Distance approx 17.24 miles from Winter Haven

(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

Book View

from £133 / night

Distance approx 18.71 miles from Winter Haven

30

Home rental in Reunion with swimming pool

Central Florida / Reunion

5 13 min stay varies

  • 5 bedrooms
  • sleeps 13
  • min stay varies
  • Swimming pool
  • Ask owner if suitable for children

from £257 / night

£1,799 / week

Book View

Responds fast!
avg. 19 minutes

from £257 / night

Distance approx 18.85 miles from Winter Haven

22

Holiday home in Davenport

Central Florida / Davenport

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Ask owner if suitable for children

from £107 / night

£747 / week

Book View

from £107 / night

Distance approx 17.24 miles from Winter Haven

15

Holiday home in Davenport

Central Florida / Davenport

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Suitable for children age 5+

from £176 / night

£1,227 / week

Book View

from £176 / night

Distance approx 19.72 miles from Winter Haven

24

Holiday villa with swimming pool in Four Corners

Central Florida / Four Corners

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £116 / night

£810 / week

Book View

Responds fast!
avg. 9 minutes

from £116 / night

Distance approx 17.24 miles from Winter Haven

15

Davenport holiday home rental

Central Florida / Davenport

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Suitable for children age 5+

from £176 / night

£1,227 / week

Book View

from £176 / night

Distance approx 17.42 miles from Winter Haven

23

ChampionsGate holiday townhouse rental

Central Florida / ChampionsGate

5 13 min stay varies

  • 5 bedrooms
  • sleeps 13
  • min stay varies
  • Swimming pool
  • Car not necessary

from £141 / night

£984 - £2,422 / week

Book View

from £141 / night

Distance approx 19.47 miles from Winter Haven

22

Holiday villa with swimming pool in Four Corners

Central Florida / Four Corners

5 10 5 nights min

  • 5 bedrooms
  • sleeps 10
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

from £224 / night

£1,569 / week

Book View

from £224 / night

Distance approx 16.88 miles from Winter Haven

5

Holiday villa with swimming pool in Loughman

Central Florida / Loughman

6 14 min stay varies

  • 6 bedrooms
  • sleeps 14
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

from £861 / night

£5,795 / week

Book View

from £861 / night

Also consider