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Winter Haven Vacation Rentals

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Our Favorite Vacation Rentals in Winter Haven

  • Vacation home 3 Bedroom Next to LEGOLAND
    Vacation home 3 Bedroom Next to LEGOLAND
    Excellent3br Home/Apartment
    HolidayLettingsFrom $176
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  • holiday home for max. 6 persons in Kissimmee, Florida
    holiday home for max. 6 persons in Kissimmee, Florida
     Country House
    TUIVillasFrom $630
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  • Legoland/Disney Lakeview TINY HOUSE Boats included
    Legoland/Disney Lakeview TINY HOUSE Boats included
     1br Boat
    HolidayLettingsFrom $121
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  • holiday home for max. 12 persons in Haines City, Florida
    holiday home for max. 12 persons in Haines City, Florida
     Country House
    TUIVillasFrom $1227
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  • Lakefront Home with beach and soooo much more!
    Lakefront Home with beach and soooo much more!
     3br Home/Apartment
    HolidayLettingsFrom $358
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  • holiday home for max. 8 persons in Davenport, Florida
    holiday home for max. 8 persons in Davenport, Florida
    OkayCountry House
    TUIVillasFrom $574
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  • Summer SALE-Balmoral Resort 4 Bedroom Pool Home
    Summer SALE-Balmoral Resort 4 Bedroom Pool Home
     4br Home/Apartment
    HolidayLettingsFrom $424
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  • holiday home for max. 8 persons in Kissimmee, Florida
    holiday home for max. 8 persons in Kissimmee, Florida
     Country House
    TUIVillasFrom $685
    View Deal
See all 402 deals in Winter Haven

Winter Haven Vacation Rentals with a Pool

  • MID CENTURY MODERN TOWNHOUSE W/2 FIREPLACES
    MID CENTURY MODERN TOWNHOUSE W/2 FIREPLACES
     2br Home/Apartment
    AirbnbFrom $178
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  • The Treehouse at Camellia Grove - Winter Haven
    The Treehouse at Camellia Grove - Winter Haven
    Excellent1br Home/Apartment
    AirbnbFrom $133
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  • Horse Farm on a Beautiful Lake
    Horse Farm on a Beautiful Lake
    Excellent2br Home/Apartment
    AirbnbFrom $141
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  • Florida Getaway near Legoland& Orlando Attractions
    Florida Getaway near Legoland& Orlando Attractions
    Excellent3br Other
    AirbnbFrom $157
    View Deal
See all deals in Winter Haven with a pool

Winter Haven Vacation Rentals with Wi-Fi

  • The Old Haven - An Enduring Piece of Nostalgia
    The Old Haven - An Enduring Piece of Nostalgia
    Excellent4br Other
    AirbnbFrom $164
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  • #138 Cozy beautiful home- 0.5 miles from downtown!
    #138 Cozy beautiful home- 0.5 miles from downtown!
    Excellent3br Home/Apartment
    AirbnbFrom $153
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  • The Blue Ranch
    The Blue Ranch
    Excellent3br Home/Apartment
    AirbnbFrom $107
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  • The Flamingo
    The Flamingo
    Excellent3br Home/Apartment
    AirbnbFrom $119
    View Deal
See all deals in Winter Haven with WiFis

Winter Haven Pet-Friendly Vacation Rentals

  • Summer Savings-4 Bedroom Pool Home
    Summer Savings-4 Bedroom Pool Home
     4br Home/Apartment
    HolidayLettingsFrom $424
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  • SUMMER Special-Balmoral Resort Home
    SUMMER Special-Balmoral Resort Home
     4br Home/Apartment
    HolidayLettingsFrom $424
    View Deal
  • Pool Home at Resort near Disney
    Pool Home at Resort near Disney
     3br Home/Apartment
    HolidayLettingsFrom $354
    View Deal
  • Your Summer Pool Home
    Your Summer Pool Home
     3br Home/Apartment
    HolidayLettingsFrom $354
    View Deal
See all deals in Winter Haven that allow pets

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
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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

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
95º 62º
7.58
94º 71º
5.19
Jul
Aug
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Dec
Jan
Feb
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Rainy days
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

Vacation Rentals in Winter Haven

Browse rentals from all your favorite providers including Airbnb, Agoda, Priceline and more at AllTheRooms.com. AllTheRooms has 395 vacation rentals, hotels and other great places to stay while you enjoy Winter Haven, with everything from inexpensive hostels and homestays to luxury Airbnbs and hotels. For those trying to keep costs down, the lowest priced place to stay in Winter Haven comes in at $20 a night. The average price of an accommodation is $113 per night.

Those looking to get some work finished during their trip to Winter Haven can pick from 129 places to stay that have WiFi. We have 17 accommodations that come with breakfast included. You can keep up with your workout regime by staying at one of 5 accommodations that provide gym facilities. If you are driving to Winter Haven, you'll want to pick from 124 places to stay that provide parking. 49 vacation rentals have a a pool or jacuzzi

Those traveling with a dog, cat or some other animal can stay in any of 33 accommodations that are designated as pet-friendly.

We combine a wide variety of Winter Haven accommodations including vacation rentals, home stays, hostels and other unique places to stay into one easy search. We show results from more than 3 providers, including 112 places to stay from Airbnb, 7 accommodations from Agoda and 6 places to stay from Priceline.

204 of our accommodations in Winter Haven have been reviewed and rated. 68% are rated great. You can instantly book any of 98 places to stay right now.

Destinations near Winter Haven