We use cookies to provide you with the best browsing experience. The data collected by cookies is used to optimise the website for our users and deliver an appropriate service and relevant information to you. By using our site we assume you’re aware and agree to use the cookies for this purpose.

Winter Haven Vacation Rentals

Winterhaven Travel Guide

Set between Tampa and Orlando, Winterhaven is home to the largest LEGOLAND in the world, as well as stunning canal linked lakes, forest trails, and lush botanical gardens. Visitors can find so many places to discover, explore, and enjoy during their time here.

Things to Do in Winterhaven

Bok Tower Gardens are a tranquil area of luscious tropical gardens and bird sanctuary, known for their majestic singing tower. The bells of the tower are rung several times a day and the area is just wonderful to walk around.There are 50 lakes here, either within or just outside the city limits, where you can fish, take a boat ride, go paddle boarding or fly boarding, or join a guided cruise through the canals. A trip to LEGOLAND is a must if you're with little ones, and different events take place here all year round.

Best Time to Visit Winterhaven

January to April are the best months to plan a trip to Winterhaven.

Price and Availability Index in Winter Haven

Most expensive
Most availability
, , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0

The most expensive month to stay in a vacation rental in Winter Haven is in January, while the cheapest month is in September. The most popular time to book a vacation rental in Winter Haven is in the high season in March. Winter Haven has its low season in November, when less people are visiting and the vacation home occupancy rate drops.

The cheapest day to stay at a vacation rental in Winter Haven tends to be Wednesday, while the most expensive day tends to be Sunday. Vacation homes in Winter Haven tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.

The weather in Winter Haven

86º 50º
0.2
84º 39º
0.66
86º 34º
1.29
87º 46º
1.01
89º 40º
0.58
96º 51º
0.46
97º 55º
1.52
95º 69º
11.25
97º 73º
6.68
96º 73º
4.51
94º 70º
9.28
91º 47º
3.36
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Rainy days
Powered by:

This climate histogram shows you the weather patterns in Winter Haven. The hottest month in Winter Haven is June, when temperatures peak at 97 ˚F. The coolest month is January, when temperatures drop to 34 ˚F. The wettest month in Winter Haven is June with 11.25 inches of rain, while the driest month is November with 0.2 inches of rain.

Vacation Rentals in Winter Haven

Browse accommodations from all the best providers including Airbnb, Homeaway, VRBO and more at AllTheRooms.com. AllTheRooms has 321 vacation rentals, hotels and other great places to stay during your time in Winter Haven, with everything from cheap hostels and homestays to luxury Airbnbs and hotels. A trip to Winter Haven can be affordable - our lowest price accommodation is available at $17 per night. A typical accommodation in Winter Haven costs on average $124 per night.

Those looking to get some work done during their trip to Winter Haven can pick from 92 places to stay that provide WiFi. 14 of our accommodations in include a breakfast in the price. You can keep up with your workout regime by staying at one of 4 accommodations that provide gym facilities. Driving to Winter Haven? Then choose one of the 90 places to stay that comes with a parking spot included. 31 hotels and vacation rentals have a pool or jacuzzi.

If you're traveling with a furry friend, then be sure to choose one of the 28 pet-friendly accommodations available.

We combine a wide variety of Winter Haven accommodations including vacation rentals, homestays, hostels and other unique places to stay into one easy search. We show results from more than 6 providers, including 65 places to stay from Airbnb, 12 accommodations from Homeaway and 11 places to stay from VRBO.

144 accommodations in Winter Haven have been reviewed: 56% are rated excellent or good. 73 places to stay in are instantly bookable.

Destinations near Winter Haven

Our providers