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 39 times in the last 48 hours
  • 5 BR House
  • 5 BA
  • 6000 sq ft
Wonderful! 4.8/5
(37 reviews)
avg/night
Premier Partner
37
Viewed 49 times in the last 48 hours
  • 3 BR House
  • 2 BA
Excellent! 4.4/5
(46 reviews)
avg/night
Premier Partner
46
Viewed 14 times in the last 48 hours
  • 2 BR House
  • 1 BA
  • 1100 sq ft
Exceptional! 5/5
(5 reviews)
avg/night
5
Viewed 6 times in the last 48 hours
  • 6 BR House
  • 3 BA
  • 3500 sq ft
Exceptional! 5/5
(16 reviews)
avg/night
16
Viewed 17 times in the last 48 hours
  • 3 BR House
  • 4 BA
  • 3800 sq ft
Excellent! 4.7/5
(6 reviews)
avg/night
Premier Partner
6
Viewed 13 times in the last 48 hours
  • 3 BR House
  • 3 BA
  • 2700 sq ft
Excellent! 4.7/5
(15 reviews)
avg/night
15
Viewed 11 times in the last 48 hours
  • 3 BR House
  • 2 BA
Exceptional! 5/5
(9 reviews)
avg/night
9
Viewed 25 times in the last 48 hours
  • 3 BR House
  • 2 BA
Wonderful! 4.9/5
(11 reviews)
avg/night
Premier Partner
11
Viewed 27 times in the last 48 hours
  • 2 BR House
  • 2 BA
  • 1800 sq ft
avg/night
2
Viewed 19 times in the last 48 hours
  • 3 BR House
  • 2 BA
  • 2500 sq ft
avg/night
1
Viewed 8 times in the last 48 hours
  • 1 BR Cottage
  • 1 BA
  • 600 sq ft
Exceptional! 5/5
(7 reviews)
avg/night
7
Viewed 19 times in the last 48 hours
  • 4 BR House
  • 3 BA
  • 3200 sq ft
avg/night
Viewed 61 times in the last 48 hours
  • 4 BR House
  • 4 BA
  • 2800 sq ft
Excellent! 4.3/5
(23 reviews)
avg/night
23
Viewed 7 times in the last 48 hours
  • 3 BR House
  • 2 BA
  • 2400 sq ft
avg/night
1
Viewed 28 times in the last 48 hours
  • 3 BR House
  • 2 BA
  • 1617 sq ft
avg/night
1
  • 3 BR Mobile Home
  • 2 BA
  • 1500 sq ft
avg/night
2
Viewed 13 times in the last 48 hours
  • 4 BR House
  • 3 BA
  • Separate Toilet
avg/night
Viewed 86 times in the last 48 hours
  • 2 BR Condo
  • 2 BA
  • 1 sq ft
avg/night
Viewed 80 times in the last 48 hours
  • 4 BR House
  • 2 BA
Exceptional! 5/5
(17 reviews)
avg/night
17
Viewed 113 times in the last 48 hours
  • 3 BR Villa
  • 2 BA
Excellent! 4.7/5
(10 reviews)
avg/night
10
Viewed 54 times in the last 48 hours
  • 3 BR Villa
  • 2 BA
  • 1142 sq ft
Excellent! 4.7/5
(18 reviews)
avg/night
Premier Partner
18
Viewed 43 times in the last 48 hours
  • 3 BR Villa
  • 2 BA
Wonderful! 4.9/5
(15 reviews)
avg/night
15
Viewed 18 times in the last 48 hours
  • 8 BR House
  • 5 BA
Wonderful! 4.8/5
(6 reviews)
avg/night
6
Viewed 126 times in the last 48 hours
  • 4 BR House
  • 4 BA
  • 2300 sq ft
Exceptional! 5/5
(31 reviews)
avg/night
Premier Partner
31
Viewed 74 times in the last 48 hours
  • 4 BR Villa
  • 3 BA
avg/night
Viewed 100 times in the last 48 hours
  • 5 BR House
  • 4 BA
  • 2800 sq ft
avg/night
Premier Partner
2
Viewed 6 times in the last 48 hours
  • 4 BR Villa
  • 3 BA
Wonderful! 4.9/5
(15 reviews)
avg/night
Premier Partner
15
Viewed 69 times in the last 48 hours
  • 6 BR House
  • 5 BA
  • Separate Toilet
Wonderful! 4.8/5
(5 reviews)
avg/night
Premier Partner
5
Viewed 70 times in the last 48 hours
  • 5 BR Villa
  • 5 BA
avg/night
1
Viewed 61 times in the last 48 hours
  • 5 BR Villa
  • 4 BA
  • Separate Toilet
  • 2680 sq ft
avg/night
Premier Partner
1
Viewed 27 times in the last 48 hours
  • 4 BR House
  • 2 BA
avg/night
4
Viewed 69 times in the last 48 hours
  • 5 BR Villa
  • 4 BA
avg/night
4
Viewed 20 times in the last 48 hours
  • 3 BR Villa
  • 2 BA
avg/night
1
Viewed 62 times in the last 48 hours
  • 3 BR Villa
  • 2 BA
Excellent! 4.7/5
(53 reviews)
avg/night
53
Viewed 65 times in the last 48 hours
  • 2 BR Condo
  • 2 BA
  • 1123 sq ft
avg/night
Premier Partner
3
Viewed 17 times in the last 48 hours
  • 4 BR Villa
  • 3 BA
Excellent! 4.7/5
(21 reviews)
avg/night
Premier Partner
21
Viewed 65 times in the last 48 hours
  • 5 BR Villa
  • 4 BA
  • 2800 sq ft
Exceptional! 5/5
(25 reviews)
avg/night
25
Viewed 53 times in the last 48 hours
  • 6 BR House
  • 5 BA
  • 3475 sq ft
Exceptional! 5/5
(5 reviews)
avg/night
5
Viewed 50 times in the last 48 hours
  • 4 BR House
  • 3 BA
  • 1600 sq ft
Exceptional! 5/5
(31 reviews)
avg/night
31
Viewed 67 times in the last 48 hours
  • 6 BR Villa
  • 4 BA
avg/night
4
Viewed 26 times in the last 48 hours
  • 4 BR Villa
  • 3 BA
  • 1928 sq ft
Wonderful! 4.8/5
(11 reviews)
avg/night
11
Viewed 26 times in the last 48 hours
  • 6 BR Villa
  • 5 BA
  • Separate Toilet
  • 3475 sq ft
Excellent! 4.3/5
(9 reviews)
avg/night
Premier Partner
9
Viewed 54 times in the last 48 hours
  • 5 BR Villa
  • 4 BA
  • 3000 sq ft
avg/night
Premier Partner
1
Viewed 146 times in the last 48 hours
  • 4 BR House
  • 2 BA
  • 1412 sq ft
Excellent! 4.4/5
(10 reviews)
avg/night
Premier Partner
10
Viewed 19 times in the last 48 hours
  • 5 BR Villa
  • 4 BA
  • Separate Toilet
  • 2500 sq ft
Wonderful! 4.8/5
(26 reviews)
avg/night
26
Viewed 57 times in the last 48 hours
  • 3 BR House
  • 2 BA
  • 1750 sq ft
Excellent! 4.6/5
(14 reviews)
avg/night
14
Viewed 193 times in the last 48 hours
  • 5 BR House
  • 4 BA
  • Separate Toilet
  • 3039 sq ft
Excellent! 4.6/5
(11 reviews)
avg/night
11
Viewed 27 times in the last 48 hours
  • 3 BR House
  • 2 BA
  • 1200 sq ft
Wonderful! 4.9/5
(15 reviews)
avg/night
15
Viewed 63 times in the last 48 hours
  • 5 BR House
  • 4 BA
  • Separate Toilet
  • 4226 sq ft
Excellent! 4.7/5
(12 reviews)
avg/night
Premier Partner
12
Viewed 37 times in the last 48 hours
  • 3 BR House
  • 2 BA
Wonderful! 4.8/5
(6 reviews)
avg/night
6

Winter Haven Holiday Homes & Villas (300+)

 

Recent Reviews

This house has it all-Can't wait to rent it again!

5 of 5
We have rented in the Watersong Community for 8 years and this is by far the nicest house we have ever stayed in. The house is fully equipped - there is nothing that we needed but did not have. Everything was very clean upon arrival. The owner, Wendy, was very responsive and easy to work with. She made you feel like an extended member of her family. The management company she uses was also very responsive. We had to call them due to an issue with the kitchen faucet and gas grill and they were there the same day and fixed what we needed quickly. We have already rented this house for 2019. We have stayed in many homes that you can tell are being rented just to collect the money but not this one this home you really feel like you are at home.
  • Review Submitted: Apr 04, 2018
  • Date of Stay: Mar 2018

The home was spacious, well equipped, comfortable, and a wonderful place to stay for our family.

5 of 5
The home was spacious, well equipped, comfortable, and a wonderful place to stay for our family. Alonzo was a great host, super accessible and eager to please. Our only complaint was we had to eventually return home! I'd recommend the house and Alonzo without reservation.
  • Review Submitted: Mar 26, 2018
  • Date of Stay: Mar 2018