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Holiday Lettings
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> Apartments and houses in Winter Haven

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

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5 Holiday homes

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Home rental in Winter Haven

Winter Haven house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

from £134 / night

£938 / week

1 / 0

Holiday home in Winter Haven

Winter Haven house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 11

from £247 / night

£1,377 - £4,228 / week

1 / 51

Holiday apartment in Winter Haven

Winter Haven apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £104 / night

£660 - £1,914 / week

1 / 51

Home rental in Winter Haven

Winter Haven house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from £173 / night

£1,048 - £2,968 / week

1 / 51

Home accommodation in Winter Haven

Winter Haven house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from £150 / night

£1,048 - £1,933 / week

1 / 51

Great rentals within 20 miles that match your search

Home rental in Davenport

Davenport house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

from £156 / night

£1,015 / week

1 / 28

Holiday home with golf nearby in Davenport

Davenport house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from £156 / night

£1,093 / week

1 / 17

Holiday home with swimming pool, golf nearby in Orlando

Orlando house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 16

from £153 / night

£1,067 - £1,811 / week

1 / 42

Davenport holiday apartment rental

Davenport apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8
7 reviews

from £102 / night

£712 / week

1 / 30

Holiday villa in Davenport

Davenport villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8
20 reviews

from £153 / night

£1,067 / week

1 / 48

Holiday townhouse in Davenport

Davenport townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7
1 review

from £111 / night

£776 / week

1 / 16

Townhouse accommodation in Reunion with golf nearby

Reunion townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6
3 reviews

from £130 / night

£815 - £903 / week

1 / 31

Davenport holiday villa rental

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10
18 reviews

from £137 / night

£878 / week

1 / 21

Villa accommodation in Orlando with golf nearby

Orlando villa

  • 14 bedrooms
  • 16 bathrooms
  • sleeps 30

from £3,233 / night

£22,628 / week

1 / 153

Orlando holiday villa rental

Orlando villa

  • 10 bedrooms
  • 11 bathrooms
  • sleeps 24
1 review

from £2,014 / night

£14,094 / week

1 / 61

Holiday villa with golf nearby in Davenport

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8
2 reviews

from £92 / night

£640 / week

1 / 52

Holiday villa in Davenport

Davenport villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14
11 reviews

from £370 / night

£2,586 / week

1 / 61

Holiday villa with golf nearby in Haines City

Haines City villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6
6 reviews

from £97 / night

£646 / week

1 / 27

Holiday home rental

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8
29 reviews

from £109 / night

£762 / week

1 / 45

Holiday home with swimming pool in Davenport

Davenport house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from £127 / night

£886 / week

1 / 60

Reunion holiday home rental

Reunion house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10
8 reviews

from £416 / night

£2,619 / week

1 / 54

Holiday condo with shared pool, golf nearby in Reunion

Reunion condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6
6 reviews

from £153 / night

£1,042 / week

1 / 40

Villa rental in Davenport with golf nearby

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £111 / night

£776 / week

1 / 20

ChampionsGate holiday villa rental

ChampionsGate villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 18

from £324 / night

£2,263 / week

1 / 68

Davenport holiday villa rental

Davenport villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 20

from £323 / night

£2,257 / week

1 / 63

Villa rental in Davenport with swimming pool, golf nearby

Davenport villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 20
1 review

from £266 / night

£1,862 / week

1 / 70

Holiday villa in Davenport

Davenport villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12
23 reviews

from £155 / night

£1,080 / week

1 / 53

Holiday home rental

Davenport house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 15
38 reviews

from £277 / night

£1,933 - £2,160 / week

1 / 63

Villa rental in Haines City with golf nearby

Haines City villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7
8 reviews

from £120 / night

£841 / week

1 / 16

Holiday home in Davenport

Davenport house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from £139 / night

£970 / week

1 / 24

Holiday villa with swimming pool, golf nearby in Davenport

Davenport villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 20
1 review

from £271 / night

£1,895 / week

1 / 66

Villa rental in Davenport with swimming pool, golf nearby

Davenport villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 20

from £271 / night

£1,895 / week

1 / 59

Villa rental in Poinciana

Poinciana villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6
6 reviews

from £89 / night

£591 / week

1 / 42

Davenport holiday home rental

Davenport house

  • 12 bedrooms
  • 5 bathrooms
  • sleeps 24
2 reviews

from £527 / night

£3,685 / week

1 / 100

Holiday home with shared pool in Davenport

Davenport house

  • 12 bedrooms
  • 6 bathrooms
  • sleeps 24
2 reviews

from £527 / night

£3,685 / week

1 / 100

Holiday villa with golf nearby in Davenport

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £126 / night

£882 / week

1 / 23

Holiday home with golf nearby in Davenport

Davenport house

  • 20 bedrooms
  • 11 bathrooms
  • sleeps 50
2 reviews

from £1,820 / night

£9,181 - £34,265 / week

1 / 139

Holiday villa with golf nearby in Davenport

Davenport villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10
4 reviews

from £172 / night

£1,203 / week

1 / 24

Holiday villa with swimming pool, golf nearby in Orlando

Orlando villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12
3 reviews

from £273 / night

£1,908 / week

1 / 24

Villa rental in Davenport

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8
12 reviews

from £162 / night

£1,132 / week

1 / 20

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Winter Haven holidays

Whether you're in Winter Haven because of the kids (hello, Legoland!) or flying solo, there is something for everyone in this city! Why not visit Holiday Lettings for the perfect Winter Haven holiday rental that you can relax in when you're done exploring?

About Winter Haven

The earliest people known to what is now Winter Haven were the Timucua and the Calusa. In the 1860s, the first settlers came to Winter Haven and it wasn't named Winter Haven until 1885 by P.D. Eycleshimer.

Winter Haven has a myriad of interconnected lakes. Started in 1915 and completed by the early 1920s, be sure to check out the Chain of Lakes!

Winter Haven has a long history which you can find out about at the Museum of Winter Haven.

The second largest city in Polk County, Winter Haven is home to a variety of cultural experiences. Located between Tampa and Orlando, there is plenty to do in this fabulous city!

Whether you want to discover your inner water baby by chequing out the watersports Winter Haven has to offer, or you'd rather just relax and enjoy the eclectic food scene, Winter Haven is for everybody!

What to do

Why not start your day off by exploring Downtown Winter Haven? Full of great shops and restaurants, you will really get a feel of Winter Haven here!

When you're done exploring, head on over to The Chain of Lakes so you can take part in a spot of fishing. Too boring? Then there are many watersports you can enjoy, such as jet skiing, water tubing, and boating.

Make sure to check out the fountain in Central Park, which changes its colours during holidays!

Winter Haven holds many events throughout the year. Enjoy local musicians at Pickin in the Park held the first Friday of the month.

check out the local produce at the Farmer's Market, which is held every Thursday 8 am - 5 pm.

Last but not least, be sure to check out Legoland which is the second-largest Legoland in the world. The kids will be sure to enjoy it!

Top Winter Haven travel tips

Winter Haven enjoys a mild climate throughout most of the year, so you can mostly get away with a light sweater. Be aware of the occasional shower during the summer months, though!

You'll be able to get to Winter Haven quite easily from Orlando. Orlando International Airport is only 45 minutes away. You can also access Winter Haven via Tampa International Airport. However, this is slightly further away.

You can easily get around Winter Haven by bus using the two bus services on offer: Winter Haven Area Transit and Citrus connection.

Winter Haven is the perfect holiday spot as there are so many things to do! Whether you're an art lover or a watersports enthusiast, Winter Haven doesn't turn anybody away. Find the perfect Winter Haven holiday rental Holiday Lettings!

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