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 Family icon

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.

Cancel Clear Filters Apply Filters
More Filters

Price Per Night

£ £

Bedrooms

Bathrooms

Payment Options

Property Type

Popular Searches

Facilities

Location Type

Local Area

Property Details

Clear Filters
Use filters to narrow your search results!
Viewed 138 times in the last 48 hours
Exceptional! 5/5
(12 reviews)
avg/night
House #3955447
12
Viewed 8 times in the last 48 hours
Excellent! 4.4/5
(45 reviews)
avg/night
House #292488vb
45
Viewed 71 times in the last 48 hours
Wonderful! 4.8/5
(10 reviews)
avg/night
Cabin #843594vb
10
Viewed 34 times in the last 48 hours
avg/night
Recreational Vehicle #956770vb
3
Viewed 40 times in the last 48 hours
Wonderful! 4.9/5
(9 reviews)
avg/night
House #915394vb
9
Viewed 142 times in the last 48 hours
Wonderful! 4.8/5
(36 reviews)
avg/night
House #452437vb
36
Viewed 15 times in the last 48 hours
Excellent! 4.6/5
(5 reviews)
avg/night
House #4178419
5
Viewed 14 times in the last 48 hours
Exceptional! 5/5
(8 reviews)
avg/night
House #7020516
8
Viewed 78 times in the last 48 hours
Excellent! 4.3/5
(21 reviews)
avg/night
House #239029vb
21
Viewed 12 times in the last 48 hours
avg/night
House #4757420
1
Viewed 28 times in the last 48 hours
Exceptional! 5/5
(7 reviews)
avg/night
Cottage #614884vb
7
Viewed 18 times in the last 48 hours
Exceptional! 5/5
(12 reviews)
avg/night
House #833008vb
12
Viewed 33 times in the last 48 hours
avg/night
Condo #280128vb
Viewed 34 times in the last 48 hours
Exceptional! 5/5
(5 reviews)
avg/night
House #440866vb
5
Viewed 48 times in the last 48 hours
avg/night
House #494849vb
2
Viewed 6 times in the last 48 hours
avg/night
Bed And Breakfast #4620723
Viewed 11 times in the last 48 hours
avg/night
House #1211261vb
Viewed 23 times in the last 48 hours
avg/night
House #1103645vb
Viewed 30 times in the last 48 hours
avg/night
House #4010682
Viewed 198 times in the last 48 hours
Exceptional! 5/5
(6 reviews)
avg/night
House #1053035vb
6
Viewed 227 times in the last 48 hours
avg/night
Villa #4707135
1
Viewed 519 times in the last 48 hours
avg/night
Villa #1185551vb
Viewed 74 times in the last 48 hours
avg/night
Villa #1009312vb
2
Viewed 90 times in the last 48 hours
Excellent! 4.7/5
(52 reviews)
avg/night
Villa #205369
52
Viewed 109 times in the last 48 hours
Wonderful! 4.8/5
(29 reviews)
avg/night
Villa #817624vb
29
Viewed 85 times in the last 48 hours
avg/night
Villa #1130613vb
2
Viewed 86 times in the last 48 hours
avg/night
Villa #4615953
Viewed 122 times in the last 48 hours
Wonderful! 4.8/5
(6 reviews)
avg/night
House #761005vb
6
Viewed 149 times in the last 48 hours
Premier Partner
avg/night
House #4721873
3
Viewed 50 times in the last 48 hours
Premier Partner
avg/night
House #1144442vb
4
Viewed 35 times in the last 48 hours
Wonderful! 4.9/5
(9 reviews)
avg/night
Villa #1853593
9
Viewed 52 times in the last 48 hours
Premier Partner
Wonderful! 4.9/5
(29 reviews)
avg/night
Villa #1405658
29
Viewed 145 times in the last 48 hours
Exceptional! 5/5
(28 reviews)
avg/night
House #235657vb
28
Viewed 59 times in the last 48 hours
Premier Partner
Exceptional! 5/5
(33 reviews)
avg/night
House #4023493
33
Viewed 128 times in the last 48 hours
Wonderful! 4.8/5
(5 reviews)
avg/night
House #1151232vb
5
Viewed 25 times in the last 48 hours
avg/night
Villa #1105257vb
Viewed 24 times in the last 48 hours
Wonderful! 4.9/5
(19 reviews)
avg/night
Villa #3565546
19
Viewed 72 times in the last 48 hours
Wonderful! 4.9/5
(10 reviews)
avg/night
Villa #460880vb
10
Viewed 22 times in the last 48 hours
Wonderful! 4.9/5
(24 reviews)
avg/night
Villa #8162356
24
Viewed 87 times in the last 48 hours
Premier Partner
Wonderful! 4.8/5
(38 reviews)
avg/night
Bungalow #496744vb
38
Viewed 39 times in the last 48 hours
avg/night
Villa #4270951
3
Viewed 83 times in the last 48 hours
Excellent! 4.7/5
(6 reviews)
avg/night
Villa #514884vb
6
Viewed 10 times in the last 48 hours
avg/night
House #4192923
2
Viewed 56 times in the last 48 hours
Premier Partner
Excellent! 4.7/5
(25 reviews)
avg/night
Villa #709251vb
25
Viewed 59 times in the last 48 hours
Excellent! 4.7/5
(52 reviews)
avg/night
Villa #9719vb
52
Viewed 14 times in the last 48 hours
avg/night
House #927341vb
1
Viewed 41 times in the last 48 hours
Premier Partner
avg/night
Condo #4738318
1
Viewed 62 times in the last 48 hours
Exceptional! 5/5
(8 reviews)
avg/night
Villa #4666919
8
Viewed 72 times in the last 48 hours
avg/night
Villa #4317998
3
Viewed 43 times in the last 48 hours
Wonderful! 4.8/5
(29 reviews)
avg/night
Bungalow #624462vb
29

Winter Haven Holiday Homes & Villas (300+)

 

Recent Reviews

Daughter Graduation

5 of 5
Beautiful home! Thank you so much for sharing your beautiful home with me and my family. We enjoy our stay and accommodations. The only problem — yes there was one problem— no fault of our hosts - our stay was too short !!!! Look forward to returning. Again THANK YOU!!
  • Review Submitted: Dec 16, 2017
  • Date of Stay: Dec 2017

Clean, relaxing and comfortable,

4 of 5
Very enjoyable, ideal size for a whole family or as in our case just the two of us. Not too far from the parks, plenty of places nearby to eat or shop. Would recommend very highly
  • Review Submitted: Nov 09, 2017
  • Date of Stay: Oct 2017