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Make a holiday villa in Winter Haven your home away from home

About as central as it's possible to get in Florida, Winter Haven holiday villas and apartments put you bang in the middle of the Sunshine State. As an absolute mecca for waterskiing enthusiasts, the area is riddled with over 50 lakes, interconnected by man-made canals; it's a positive nirvana for water sports. Holiday accommodation in Winter Haven are all fully air-conditioned, with all the modern appliances to keep your stay free of hassle. Nearly all Winter Haven rentals have access to a pool and welcome children, though only a few are accessible via wheelchair.

Things to do

-Theme parks: Opening just a couple of years ago on the site that was formerly Cypress Gardens, one of the world's first theme parks, Legoland Florida is a great family attraction. Legoland's 145 acres of park host over 50 Lego-themed rides, shows and attractions, as well as the preserved botanical garden area built by the former resident.

-Lakes: Winter Haven calls itself 'The Chain of Lakes City', and it's easy to see why. By far the most prominent features surrounding your Winter Haven holiday accommodation are the lakes and interconnecting waterways; teeming with wildlife, this is one of the world's premier bass fishing destinations, too.

-Watersports: With so many lakes, watersports are Winter Haven's raison d'etre. Cypress Gardens was instrumental in the invention of the sport of waterskiing, so the facilities for getting wet, and the variety of ways of doing so, are myriad. Rentals at Winter Haven are never far from the opportunity.

-Nightlife: There are far more bars and restaurants than needed to cater to a town of 26,000, which tells you all you need to know about Winter Haven's popularity as a holiday resort. From fast food to fine dining, laid-back pubs to energetic dance halls, there's something for everyone.

-Beaches: There's not much in the way of sandy beaches in this lake-strewn area, but either coast is only an hour away by car. From the amazing beaches at Tampa Bay in the west, to the equally pristine sand and surf of the Atlantic Space Coast, you're spoiled for choice.

Weather in Winter Haven

You could expect Florida's subtropical climate to be the hottest here, which is about as far from the sea as you can get in Florida. Fortunately, the extensive wetlands have a similar moderating influence, so temperatures in the summer rarely get intolerable. Typical highs don't exceed the mid-30°C mark, and this is further tempered by the summer thunderstorms which tend to cool things down a little. Winters are on a par with the British summer, so temperatures top 20°C and rainfall is infrequent at best.

Travel to Winter Haven

As close as Winter Haven is to Orlando and Tampa, it would be silly to fly into anywhere else, at only 48 and 59 miles away respectively. Public transport tends to be a bit of a joke in the US, and the automobile reigns supreme, so flying and driving a hire car is really the most effective, and cheapest, option. There is an Amtrak station in Winter Haven, however, which gives you the chance to experience an authentic American train trip, but they're somewhat unreliable when it comes to timetables. Nearby Lakeland has the only Greyhound station.

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Viewed 13 times in the last 48 hours
  • 4 BR House
  • 3 BA
  • 1833 sq ft
Excellent! 4.6/5
(28 reviews)
avg/night
28
Viewed 21 times in the last 48 hours
  • 3 BR House
  • 2 BA
  • 1200 sq ft
Excellent! 4.7/5
(18 reviews)
avg/night
Premier Partner
18
Viewed 14 times in the last 48 hours
  • 4 BR House
  • 3 BA
  • 1600 sq ft
Wonderful! 4.9/5
(36 reviews)
avg/night
Premier Partner
36
Viewed 10 times in the last 48 hours
  • 3 BR Condo
  • 2 BA
  • 1218 sq ft
Exceptional! 5/5
(24 reviews)
avg/night
24
Viewed 6 times in the last 48 hours
  • 4 BR Villa
  • 3 BA
  • 2500 sq ft
avg/night
1
Viewed 10 times in the last 48 hours
  • 3 BR House
  • 2 BA
Excellent! 4.4/5
(7 reviews)
avg/night
7
Viewed 39 times in the last 48 hours
  • 4 BR Villa
  • 3 BA
  • 1956 sq ft
Excellent! 4.7/5
(44 reviews)
avg/night
44
  • 3 BR Villa
  • 2 BA
  • 1142 sq ft
Excellent! 4.7/5
(21 reviews)
avg/night
Premier Partner
21
Viewed 12 times in the last 48 hours
  • 3 BR House
  • 2 BA
  • 1650 sq ft
Wonderful! 4.8/5
(32 reviews)
avg/night
32
Viewed 17 times in the last 48 hours
  • 4 BR House
  • 3 BA
  • 1650 sq ft
Wonderful! 4.9/5
(62 reviews)
avg/night
Premier Partner
62
Viewed 5 times in the last 48 hours
  • 4 BR Villa
  • 3 BA
Excellent! 4.7/5
(15 reviews)
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Premier Partner
15
  • 4 BR House
  • 3 BA
  • 1946 sq ft
Excellent! 4.7/5
(14 reviews)
avg/night
Premier Partner
14
Viewed 9 times in the last 48 hours
  • 5 BR Villa
  • 4 BA
  • Separate Toilet
  • 2773 sq ft
Wonderful! 4.9/5
(14 reviews)
avg/night
Premier Partner
14
Viewed 30 times in the last 48 hours
  • 3 BR Villa
  • 2 BA
Excellent! 4.7/5
(61 reviews)
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Premier Partner
61
Viewed 34 times in the last 48 hours
  • 3 BR House
  • 2 BA
  • 1130 sq ft
Excellent! 4.7/5
(24 reviews)
avg/night
24
Viewed 34 times in the last 48 hours
  • 3 BR House
  • 2 BA
  • 1750 sq ft
Excellent! 4.6/5
(19 reviews)
avg/night
19
  • 3 BR Villa
  • 2 BA
  • 1594 sq ft
Excellent! 4.7/5
(38 reviews)
avg/night
38
  • 4 BR Villa
  • 3 BA
  • 1928 sq ft
Wonderful! 4.9/5
(15 reviews)
avg/night
Premier Partner
15
Viewed 13 times in the last 48 hours
  • 3 BR Villa
  • 2 BA
avg/night
2
  • 4 BR Villa
  • 3 BA
  • 1600 sq ft
Exceptional! 5/5
(26 reviews)
avg/night
Premier Partner
26
  • 2 BR Condo
  • 2 BA
  • 1123 sq ft
Wonderful! 4.9/5
(7 reviews)
avg/night
Premier Partner
7
Viewed 5 times in the last 48 hours
  • 4 BR Villa
  • 3 BA
  • 1956 sq ft
Exceptional! 5/5
(12 reviews)
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Premier Partner
12
  • 2 BR Villa
  • 2 BA
  • 785 sq ft
Excellent! 4.6/5
(45 reviews)
avg/night
Premier Partner
45
  • 3 BR Townhome
  • 2 BA
  • Separate Toilet
  • 1370 sq ft
Wonderful! 4.9/5
(35 reviews)
avg/night
35
  • 4 BR Villa
  • 3 BA
avg/night
4
  • 3 BR Villa
  • 2 BA
Wonderful! 4.8/5
(17 reviews)
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Premier Partner
17
  • 4 BR Villa
  • 3 BA
  • 1650 sq ft
Exceptional! 5/5
(4 reviews)
avg/night
Premier Partner
4
Viewed 9 times in the last 48 hours
  • 3 BR House
  • 2 BA
  • 1500 sq ft
Excellent! 4.6/5
(5 reviews)
avg/night
Premier Partner
5
  • 3 BR Villa
  • 2 BA
Exceptional! 5/5
(4 reviews)
avg/night
4
Viewed 9 times in the last 48 hours
  • 5 BR House
  • 4 BA
avg/night
1
  • 4 BR Villa
  • 3 BA
Excellent! 4.4/5
(10 reviews)
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10
Viewed 35 times in the last 48 hours
  • 3 BR House
  • 2 BA
Excellent! 4.6/5
(14 reviews)
avg/night
Premier Partner
14
Viewed 28 times in the last 48 hours
  • 4 BR Villa
  • 3 BA
Very Good! 4.2/5
(5 reviews)
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5
  • 3 BR House
  • 2 BA
Wonderful! 4.9/5
(7 reviews)
avg/night
7
  • 3 BR House
  • 2 BA
  • 1130 sq ft
Wonderful! 4.8/5
(16 reviews)
avg/night
Premier Partner
16
  • 3 BR Villa
  • 2 BA
Exceptional! 5/5
(6 reviews)
avg/night
6
Viewed 6 times in the last 48 hours
  • 4 BR House
  • 3 BA
  • 2200 sq ft
Wonderful! 4.9/5
(9 reviews)
avg/night
Premier Partner
9
  • 3 BR Villa
  • 2 BA
avg/night
2
  • 3 BR Townhome
  • 2 BA
  • 1300 sq ft
Wonderful! 4.9/5
(22 reviews)
avg/night
Premier Partner
22
Viewed 11 times in the last 48 hours
  • 4 BR Villa
  • 3 BA
avg/night
2
  • 4 BR House
  • 3 BA
avg/night
2
Viewed 23 times in the last 48 hours
  • 3 BR Condo
  • 2 BA
  • 1300 sq ft
Wonderful! 4.8/5
(44 reviews)
avg/night
44
  • 4 BR Villa
  • 2 BA
  • 1894 sq ft
Excellent! 4.5/5
(28 reviews)
avg/night
Premier Partner
28
Viewed 22 times in the last 48 hours
  • 3 BR House
  • 2 BA
  • 1130 sq ft
avg/night
1
Viewed 32 times in the last 48 hours
  • 5 BR House
  • 4 BA
avg/night
3
Viewed 12 times in the last 48 hours
  • 4 BR House
  • 2 BA
Excellent! 4.5/5
(8 reviews)
avg/night
8
Viewed 6 times in the last 48 hours
  • 4 BR Villa
  • 3 BA
  • 1550 sq ft
Wonderful! 4.9/5
(103 reviews)
avg/night
Premier Partner
103
Viewed 28 times in the last 48 hours
  • 3 BR Villa
  • 2 BA
avg/night
1
  • 3 BR Villa
  • 2 BA
  • 1278 sq ft
Excellent! 4.7/5
(33 reviews)
avg/night
33
Viewed 9 times in the last 48 hours
  • 6 BR House
  • 5 BA
  • Separate Toilet
  • 3475 sq ft
Wonderful! 4.9/5
(11 reviews)
avg/night
Premier Partner
11

Winter Haven Holiday Homes & Villas (300+)

Recent Reviews

Excellent property, just what it says on the tin

5 of 5
We stayed as a family of 10 for a week. The house was exactly as described, large enough for our family with everything we needed to get together and have more fun after a hard day at the parks! Highly recommended.
  • Review Submitted: Aug 20, 2018
  • Date of Stay: Jul 2018

Amazing Villa

5 of 5
This was our first visit to this villa and it exceeded our expectations. The views over the golf course were fantastic the villa was clean and well presented and had everything you would need. Having the pool was a bonus for the grandchildren. The owner made the booking process very easy and would highly recommend staying here to family and friends
  • Review Submitted: May 28, 2018
  • Date of Stay: May 2018