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Winter Haven Vacation Rentals

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  2. United States of America
  3. Florida
  4. Winter Haven

Our Favorite Vacation Rentals in Winter Haven

  • Lake Front Hideaway in Auburndale Florida just 2mi off of I-4
     Country House
    Booking.com
    From
    $227
  • Lake Lucerne Villa
     4br Home/Apartment
    HolidayLettings
    From
    $216
  • Davenport Villa SDGCCPB7 Platinum
     Country House
    Booking.com
    From
    $1,120
  • Disney 45 minutes away! LegoLand 10 minutes away!!!
     3br Home/Apartment
    HolidayLettings
    From
    $131
  • Estate Home Close To All
     Country House
    Booking.com
    From
    $500
  • Vacation home 3 Bedroom Next to LEGOLAND
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $176
  • Pixie Dust Villa (B) Four-bedroom Villa
     Country House
    Booking.com
    From
    $168
  • Legoland/Disney Lakeview TINY HOUSE Boats included
     Boat
    HolidayLettings
    From
    $114
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Check prices for these upcoming dates

Winter Haven Vacation Rentals with a Pool

  • 1963 Mid Century Modern Home Near Tampa / Orlando
    Good3br Home/Apartment
    Airbnb
    From
    $339
  • The Treehouse at Camellia Grove - Winter Haven
    ExcellentHome/Apartment
    Airbnb
    From
    $133
  • Horse Farm on a Beautiful Lake
    Excellent2br Home/Apartment
    Airbnb
    From
    $141
  • Private Poolside Villa
    ExcellentHome/Apartment
    Airbnb
    From
    $68
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Winter Haven Vacation Rentals with Wi-Fi

  • Historic 1910 Home close to LEGOLAND & Disney
    Excellent2br Home/Apartment
    Airbnb
    From
    $119
  • 138 Cozy home- .5 mi to dwntwn, 3.9 mi to Legoland
    Excellent3br Home/Apartment
    Airbnb
    From
    $153
  • The Blue Ranch
    Good3br Home/Apartment
    Airbnb
    From
    $107
  • The Flamingo
    Excellent3br Home/Apartment
    Airbnb
    From
    $119
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Winter Haven Pet-Friendly Vacation Rentals

  • Lakefront Home with beach and soooo much more!
     3br Home/Apartment
    HolidayLettings
    From
    $358
  • All En-Suite Pool Home
     4br Home/Apartment
    HolidayLettings
    From
    $425
  • Vacation Resort with FREE Activities
     4br Home/Apartment
    HolidayLettings
    From
    $425
  • 4 Bed-Waterfront-Resort near Disney
     4br Home/Apartment
    HolidayLettings
    From
    $425
Show all

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.

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Price and Availability in Winter Haven

Most expensive
Most availability
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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 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.
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The Weather in Winter Haven

Rainy days
96 º75
6
94 º55
1
90 º41
1
86 º41
7
81 º27
2
88 º50
1
86 º42
1
90 º56
4
95 º62
8
94 º71
5
96 º71
13
95 º71
6
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Rainy days

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

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What Expert Travelers Think

  • — I love AllTheRooms because it is not only local homes for renting, and not only hotels, but everything combined. When I am about to book a place to stay, I usually spend a couple of hours looking through both hotel sites and local home sites, comparing the prices and places.

    Alli Sims
    Alli SimsAlli Sims
    Visit Alli Sims

  • — I love AllTheRooms because it enables me to compare a range of providers in just one search. I'd normally spend time checking prices across a range of platforms by visiting different websites one-by-one, so this helps me to save time on my accommodation searches while planning my upcoming trips

    Kacie Morgan
    Kacie MorganThe Rare Welsh Bit
    The Rare Welsh Bit

  • — When I plan a trip, I no longer waste time visiting multiple websites in search of the best accommodations. Now, I just go to AllTheRooms and immediately find everything from luxury villas to pet-friendly rentals! All in one place

    Whitney Wear
    Whitney WearTravel Better Guide
    Travel Better Guide

Vacation Rentals in Winter Haven

At AllTheRooms.com we have accommodations from all of the best providers - Airbnb, Agoda, Priceline and others. We have 463 vacation rentals, hotels and other accommodation types in Winter Haven ranging from inexpensive options to extravagant places to stay. A vacation in Winter Haven can be budget-friendly - the lowest price accommodation is available at $17 a night. The average price of an accommodation is around $109 per night.

If you want internet access during your stay in Winter Haven, then you can choose from over 156 places to stay that provide WiFi internet. We have 24 accommodations that include a breakfast included. Fitness fanatics can get a workout in during their stay by choosing from 8 accommodations that have gym facilities. If you are driving to Winter Haven, you'll want to pick from 152 places to stay that provide parking. 58 accommodations come with a pool or jacuzzi

AllTheRooms has 35 pet-friendly places to stay in Winter Haven, so if you're traveling with your cat or dog you won't have any trouble.

In Winter Haven AllTheRooms currently aggregates hotels, vacation rentals, hostels from more than 3 providers, including 135 places to stay from Airbnb, 6 accommodations from Agoda and 6 places to stay from Priceline.

232 of our accommodations in Winter Haven have been reviewed and rated. 62% are rated great. 124 places to stay in are instantly bookable.

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