Winter Haven Vacation Rentals

Our Favorite Vacation Rentals in Winter Haven

holiday home for max. 12 persons in Haines City, Florida

TUIVillasFrom $1245
View Deal
Estate Home Close To All

Booking.comFrom $500
View Deal
Vacation home 3 Bedroom Next to LEGOLAND
Excellent
HolidayLettingsFrom $176
View Deal
holiday home for max. 8 persons in Davenport, Florida
Okay
TUIVillasFrom $619
View Deal
Haines City Pool Homes

Booking.comFrom $126
View Deal
Lakeview Tiny Home by Legoland/Disney w/ boats!

HolidayLettingsFrom $114
View Deal
4 Bed-Waterfront-Resort near Disney

HolidayLettingsFrom $396
View Deal
Orlando 3Bed 2BATH HOME, NEAR LEGOLAND AND OTHER ATTRACTIONS

HolidayLettingsFrom $201
View Deal

Winter Haven Vacation Rentals with a Pool

Mid-Cent Mod Condo W.Havn/Fireplace
Excellent
AirbnbFrom $199
View Deal
DazaniA Dream Haven near Legoland
Good
AirbnbFrom $218
View Deal
Tranquility ...our parks,on lake.
Excellent
AirbnbFrom $106
View Deal
The Treehouse at Camellia Grove - Winter Haven
Excellent
AirbnbFrom $132
View Deal

Winter Haven Vacation Rentals with Wi-Fi

Horse Farm on a Beautiful Lake
Excellent
AirbnbFrom $140
View Deal
VACATION HOME MINUTES FROM LEGOLAND!!

AirbnbFrom $1080
View Deal
Ariana Place - Tree House Like Lakefront Views
Excellent
AirbnbFrom $104
View Deal
GOLF RESORT HOME
Excellent
AirbnbFrom $95
View Deal

Winter Haven Pet-Friendly Vacation Rentals

Save Big this Summer-4 Bdrm Pool Home

HolidayLettingsFrom $396
View Deal
Summer Special Save big on Resort Home

HolidayLettingsFrom $396
View Deal
Limited Time Discounts on 4 Bdrm Balmoral Resort

HolidayLettingsFrom $396
View Deal
Pool Home at Resort near Disney

HolidayLettingsFrom $317
View Deal

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 in Winter Haven

Most expensive

Most availability

The most expensive month to stay in a vacation rental in Winter Haven is in April, 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 September, 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

SEE FULL WEATHER FORECAST:

95º 62º

7.58

94º 71º

5.19

96º 71º

13.13

95º 71º

6.15

96º 75º

5.77

94º 55º

0.64

90º 41º

1.14

86º 41º

6.91

81º 27º

1.86

88º 50º

1.01

86º 42º

0.58

90º 56º

4.42

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Jan

Feb

Mar

Apr

Rainy days

SEE FULL WEATHER FORECAST:

This climate histogram shows you the weather patterns in Winter Haven. The hottest month in Winter Haven is June, when temperatures peak at 96 ˚F. The coolest month is January, when temperatures drop to 27 ˚F. The wettest month in Winter Haven is July with 13.13 inches of rain, while the driest month is March with 0.58 inches of rain.

What Expert Travelers Think

— I travel to Boston regularly and I like to use AllTheRooms as it’s tricky to find good accommodation at a good price. The platform is easy to use and provides a complete set of features that saves me time and money on every trip
Clwyd ProbertWhitehat
Visit Whitehat
— I love All the Rooms because instead of having to check one place for home rentals, another for hotel, another for bed and breakfasts, and yet another for a room rental in a private residence, I can finally see EVERYTHING at one site; saving me considerable time
Jeff CampbellMiddle Class Dad
Middle Class Dad
— I use and I recommend AllTheRooms because it is a complete platform. It helps to save a lot of time, it gives all the main information about price, location, and features. In a few steps, I can easily find the best place to stay according to my criteria.
My AnasaMy Anasa
Visit My Anasa

Vacation Rentals in Winter Haven

At AllTheRooms.com we have vacation rentals from all of the best providers - Airbnb, VRBO, Agoda and more. AllTheRooms has 396 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 vacation in Winter Haven can be budget-friendly - the lowest price rental is available at $20 per night. On average, an accommodation in Winter Haven will cost you $123 per night.

If you need internet access during your stay in Winter Haven, then you can choose from over 106 places to stay that provide WiFi internet. 15 places to stay include a morning meal. You can maintain your workout routine by staying at one of 5 accommodations that provide gym facilities. Driving to Winter Haven? Then choose one of the 107 places to stay that comes with a parking spot included. 40 accommodations come with a pool or jacuzzi

Those traveling with a cat, dog or some other animal can stay in one of 30 accommodations that are designated as pet-friendly.

In Winter Haven AllTheRooms currently aggregates hotels, vacation rentals, hostels from more than 6 providers, including 88 places to stay from Airbnb, 7 accommodations from VRBO and 7 places to stay from Agoda.

189 of our accommodations in Winter Haven have been reviewed and rated. 69% are rated great. 83 places to stay in are instantly bookable.