Winter Haven Vacation Rentals

Our Favorite Vacation Rentals in Winter Haven

  • 625 Avenue M SE
     Country House
    Booking.com
    From
    $120
  • NEW! Charming Lake Eloise Home w/Boat Ramp Access!
     Home/Apartment
    HolidayLettings
    From
    $180
  • *3/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1724
     Country House
    Booking.com
    From
    $75
  • NEW! Lake Hamilton Home w/ Pool, 27 Mi to Disney!
     5br Home/Apartment
    HolidayLettings
    From
    $272
  • Lake Front Hideaway in Auburndale Florida just 2mi off of I-4
     Country House
    Booking.com
    From
    $252
  • Beautiful Vacation Home, Private Room Close to Disney!!
     Home/Apartment
    HolidayLettings
    From
    $43
  • Southern Dunes - 1420 Park By Fairytale VR
     4-star Country House
    Booking.com
    From
    $182
  • WARM RETREAT! GREAT LOCATION! 15 MIN TO DISNEY!
     Home/Apartment
    HolidayLettings
    From
    $104

Check prices for these upcoming dates

Winter Haven Vacation Rentals with a Pool

  • FANTASTIC MID CENTURY MODERN CONDO W/2 FIREPLACES
    Excellent2br Home/Apartment
    Airbnb
    From
    $149
  • FEATURED Mid Century Modern Home Tampa / Orlando
    Good3br Home/Apartment
    Airbnb
    From
    $325
  • The Treehouse at Camellia Grove - Winter Haven
    ExcellentHome/Apartment
    Airbnb
    From
    $133
  • Horse Farm on a Beautiful Lake
    Excellent2br Home/Apartment
    Airbnb
    From
    $141

Winter Haven Vacation Rentals with Wi-Fi

  • Historic 1910 Home close to LEGOLAND & Disney
    Excellent2br Home/Apartment
    Airbnb
    From
    $120
  • Sweet Cottage- 5 mi to Legoland & 0.5 mi to dwntwn
    Excellent2br Home/Apartment
    Airbnb
    From
    $153
  • The Blue Ranch
    Good3br Home/Apartment
    Airbnb
    From
    $107
  • The Flamingo
    Excellent3br Home/Apartment
    Airbnb
    From
    $119

Winter Haven Pet-Friendly Vacation Rentals

  • Family Golf Resort 'Villa Bonita' Southern Dunes
    Good3br Country House
    HolidayLettings
    From
    $166
  • Modern Cottage at Lake Cannon
    Good3br Home/Apartment
    Airbnb
    From
    $96
  • Peaceful Casita on Tropical Food Forest
     Home/Apartment
    Airbnb
    From
    $85
  • Beautiful Vacation Cottage Close to Everything #4
     Home/Apartment
    Airbnb
    From
    $170

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
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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.

The Weather in Winter Haven

Rainy days
90° 41°
1
86° 41°
7
81° 27°
2
88° 50°
1
86° 42°
1
90° 56°
4
95° 62°
8
94° 71°
5
96° 71°
13
95° 71°
6
96° 75°
6
94° 55°
1
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
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.

What Expert Travelers Think

  • — I love that AllTheRooms has everything in one place when I need to find accommodations that fit my family. Plus it provides all the details I need to help me make the best choice. I often recommend AllTheRooms to friends and family visiting NYC and they agree that it’s a great. Such a time saver!

    Monica
    MonicaNYCTechMommy
  • — My favorite thing about AllTheRooms is that it combines both rentals and hotels available so you can see an entire view of what is available in a certain area. I was able to see listings on AllTheRooms that I never even saw on other travel sites!

    Daniella Flores
    Daniella FloresILIKETODABBLE
  • — Like the buttons on the calendar which say today, tomorrow - that will make it easy for booking on the road. Website looks great - clean and easy to understand.

    Samantha Wragg
    Samantha WraggCoco Travels

Vacation Rentals in Winter Haven

Browse places to stay from all your favorite providers including Airbnb, Agoda, Priceline and many more at AllTheRooms.com. AllTheRooms has 520 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. For those trying to save money, the cheapest place to stay in Winter Haven comes in at $17 a night. On average, a place to stay in Winter Haven will cost you $101 per night.

If you need to stay connected during your vacation, then you can choose from over 175 accommodations in Winter Haven that have WiFi. We have 25 accommodations that include a breakfast included. Choose from 9 places to stay that provide gym facilities, so you won't miss a single workout. If you are driving to Winter Haven, you'll want to pick from 167 places to stay that provide parking. 64 places to stay have a a pool or jacuzzi

AllTheRooms has 36 pet-friendly places to stay in Winter Haven, so if you're traveling with your pet you won't have any problems.

AllTheRooms compares vacation rentals, hotels and other bespoke accommodation types from loads of providers in Winter Haven, including 165 places to stay from Airbnb, 7 accommodations from Agoda and 6 places to stay from Priceline

235 accommodations in Winter Haven have been reviewed; 55% are rated excellent or good. 145 places to stay in are instantly bookable.

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