HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
Verified Review icon check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag pet-dog svg-multiunit Default Owner Icon heart-filled

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.

Wonderful! 4.9/5
(8 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 6
House #915394vb
8
Viewed 25 times in the last 48 hours
Excellent! 4.4/5
(36 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 6
House #292488vb
36
Viewed 56 times in the last 48 hours
Wonderful! 4.8/5
(31 reviews)
avg/night
  • 5 BR
  • 5 BA
  • Sleeps 18
House #452437vb
31
Viewed 67 times in the last 48 hours
Excellent! 4.5/5
(10 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Separate Toilet
  • Sleeps 4
Townhome #688860vb
10
Viewed 37 times in the last 48 hours
Excellent! 4.3/5
(18 reviews)
avg/night
  • 4 BR
  • 4 BA
  • Sleeps 12
House #239029vb
18
Viewed 56 times in the last 48 hours
Very Good! 4.2/5
(10 reviews)
avg/night
  • 4 BR
  • 2 BA
  • Sleeps 8
House #784388vb
10
Viewed 15 times in the last 48 hours
Wonderful! 4.8/5
(13 reviews)
avg/night
  • 4 BR
  • 3 BA
  • Sleeps 8
House #980140vb
13
Viewed 32 times in the last 48 hours
Exceptional! 5/5
(5 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 8
House #7020516
5
Viewed 12 times in the last 48 hours
Exceptional! 5/5
(7 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 8
House #3598724
7
Viewed 28 times in the last 48 hours
  • 3 BR
  • 2 BA
  • Sleeps 8
House #4010682
avg/night
  • 3 BR
  • 4 BA
  • Sleeps 6
House #4178419
2
Viewed 16 times in the last 48 hours
Exceptional! 5/5
(9 reviews)
avg/night
  • 3 BR
  • 3 BA
  • Sleeps 10
House #833008vb
9
Viewed 12 times in the last 48 hours
  • 2 BR
  • 1 BA
  • Sleeps 4
Recreational Vehicle #956770vb
3
Viewed 11 times in the last 48 hours
Exceptional! 5/5
(6 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 2
Cottage #614884vb
6
Viewed 37 times in the last 48 hours
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 3
Cabin #868244vb
3
Viewed 25 times in the last 48 hours
Exceptional! 5/5
(6 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 7
House #513036vb
6
Viewed 13 times in the last 48 hours
Wonderful! 4.9/5
(8 reviews)
avg/night
  • 1 BR
  • 1 BA
  • Sleeps 4
Cabin #843594vb
8
Viewed 24 times in the last 48 hours
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 6
House #441073vb
3
Viewed 8 times in the last 48 hours
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 8
House #494849vb
1
Viewed 10 times in the last 48 hours
avg/night
  • 4 BR
  • 3 BA
  • Separate Toilet
  • Sleeps 8
House #1103645vb
Viewed 10 times in the last 48 hours
  • 3 BR
  • 1 BA
  • Sleeps 6
Bed And Breakfast #4620723
Viewed 8 times in the last 48 hours
  • 4 BR
  • 3 BA
  • Sleeps 14
House #1070956vb
Viewed 10 times in the last 48 hours
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 4
House #4383110
Viewed 6 times in the last 48 hours
Wonderful! 4.9/5
(15 reviews)
avg/night
  • 5 BR
  • 5 BA
  • Sleeps 12
House #25712vb
15
Viewed 573 times in the last 48 hours
Wonderful! 4.8/5
(28 reviews)
avg/night
  • 9 BR
  • 5 BA
  • Sleeps 28
House #4172017
28
Viewed 503 times in the last 48 hours
Exceptional! 5/5
(9 reviews)
avg/night
  • 5 BR
  • 5 BA
  • Sleeps 11
House #6919153
9
Viewed 126 times in the last 48 hours
Excellent! 4.7/5
(19 reviews)
avg/night
  • 5 BR
  • 4 BA
  • Sleeps 12
Villa #8127090
19
Viewed 171 times in the last 48 hours
Wonderful! 4.9/5
(43 reviews)
avg/night
  • 4 BR
  • 3 BA
  • Sleeps 8
Villa #1186901
43
Viewed 59 times in the last 48 hours
Excellent! 4.6/5
(16 reviews)
avg/night
  • 2 BR
  • 2 BA
  • Sleeps 6
Condo #1636389
16
Viewed 33 times in the last 48 hours
Wonderful! 4.8/5
(34 reviews)
avg/night
  • 5 BR
  • 4 BA
  • Separate Toilet
  • Sleeps 12
Villa #1034900
34
Viewed 72 times in the last 48 hours
Excellent! 4.7/5
(14 reviews)
avg/night
  • 4 BR
  • 3 BA
  • Separate Toilet
  • Sleeps 8
Villa #1882748
14
Viewed 79 times in the last 48 hours
Exceptional! 5/5
(20 reviews)
avg/night
  • 5 BR
  • 4 BA
  • Separate Toilet
  • Sleeps 10
Villa #4257329
20
Viewed 113 times in the last 48 hours
Wonderful! 4.9/5
(7 reviews)
avg/night
  • 5 BR
  • 4 BA
  • Sleeps 10
House #411948vb
7
Viewed 71 times in the last 48 hours
Wonderful! 4.9/5
(124 reviews)
avg/night
  • 5 BR
  • 5 BA
  • Sleeps 12
Villa #93899
124
Viewed 53 times in the last 48 hours
Wonderful! 4.9/5
(15 reviews)
avg/night
  • 4 BR
  • 2 BA
  • Sleeps 8
Villa #3850892
15
Viewed 49 times in the last 48 hours
Exceptional! 5/5
(8 reviews)
avg/night
  • 4 BR
  • 3 BA
  • Sleeps 8
Villa #1873690
8
Viewed 110 times in the last 48 hours
Wonderful! 4.8/5
(33 reviews)
avg/night
  • 4 BR
  • 3 BA
  • Sleeps 8
Villa #69391
33
Viewed 57 times in the last 48 hours
Excellent! 4.3/5
(12 reviews)
avg/night
  • 4 BR
  • 3 BA
  • Sleeps 8
Villa #6772792
12
Viewed 47 times in the last 48 hours
Wonderful! 4.8/5
(24 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 8
Villa #8110519
24
Viewed 37 times in the last 48 hours
Wonderful! 4.8/5
(29 reviews)
avg/night
  • 4 BR
  • 3 BA
  • Sleeps 8
Villa #3665439
29
Viewed 53 times in the last 48 hours
  • 4 BR
  • 3 BA
  • Sleeps 9
#8118888
3
Viewed 34 times in the last 48 hours
  • 3 BR
  • 3 BA
  • Sleeps 6
House #912066vb
1
Exceptional! 5/5
(22 reviews)
avg/night
  • 5 BR
  • 3 BA
  • Sleeps 12
House #3467516
22
Viewed 43 times in the last 48 hours
Excellent! 4.7/5
(34 reviews)
avg/night
  • 6 BR
  • 4 BA
  • Separate Toilets
  • Sleeps 14
Villa #3561059
34
Viewed 47 times in the last 48 hours
Wonderful! 4.9/5
(59 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 8
Condo #905352
59
Viewed 27 times in the last 48 hours
Excellent! 4.7/5
(15 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 8
Condo #74574
15
Viewed 45 times in the last 48 hours
Wonderful! 4.9/5
(41 reviews)
avg/night
  • 6 BR
  • 4 BA
  • Separate Toilet
  • Sleeps 12
House #586096vb
41
Viewed 77 times in the last 48 hours
Excellent! 4.6/5
(16 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 7
Villa #466058vb
16
Viewed 17 times in the last 48 hours
Excellent! 4.5/5
(26 reviews)
avg/night
  • 4 BR
  • 3 BA
  • Sleeps 8
House #603330vb
26
Viewed 116 times in the last 48 hours
Exceptional! 5/5
(20 reviews)
avg/night
  • 3 BR
  • 2 BA
  • Sleeps 6
House #4023493
20
Viewed 28 times in the last 48 hours

Winter Haven Holiday Homes & Villas (300+)

 

Recent Reviews

Fantastic.

5 of 5
We arrived on 31st May 2017 for 2 weeks, everything was as described on the website there was more than enough room for our family of 8 it was a very spacious villa. The villa is very well kept and clean. Management were great, we called Anthony on the first day as the internet and TV were down he talked us through what to do and was very helpful. We loved the location of the villa being only a 10 minute drive to Disney, 25 minutes to universal and other attraction and only an hour and 20 to Clear water the most beautiful beach. We loved spending time at the pool and found the neighbourhood very quiet and peaceful. We felt very safe in the villa, being in a gated community and fitted with an alarm. Overall we had a fantastic time in your lovely home and would like to thank you Stephen & Julia for having us, we look forward to visiting again.
  • Review Submitted: Jun 19, 2017
  • Date of Stay: May 2017

Lovely villa ideally located for Parks.

4 of 5
Nice spacious villa, ideal base.
  • Review Submitted: Jun 11, 2017
  • Date of Stay: May 2017