Winter Haven Vacation Rentals

Our Favorite Vacation Rentals in Winter Haven

  • Haines City Pool Homes
     Country House
    Booking.com
    From
    $126
  • Pool Home in a Luxury Resort
     4br Home/Apartment
    HolidayLettings
    From
    $390
  • Beautiful Vacation Home, Private Room Close to Disney!!
     Home/Apartment
    HolidayLettings
    From
    $43
  • Calabay Parc at Tower Lake Getaway
    Good6br Country House
    Flipkey
    From
    $536
  • Sweet Cottage- 5 mi to Legoland & 0.5 mi to dwntwn
    Excellent2br Home/Apartment
    Airbnb
    From
    $154
  • The Paradise Hide Away
    ExcellentHome/Apartment
    Airbnb
    From
    $97
  • LOFT HAVEN in WINTER HAVEN minutes to LEGOLAND
     Home/Apartment
    Airbnb
    From
    $170
  • Lego my Bungalow
    ExcellentHome/Apartment
    Airbnb
    From
    $55

Check prices for these upcoming dates

Winter Haven Vacation Rentals with a Pool

  • Winter Haven Pool Cabana- 3 doors from Legoland.
    ExcellentHome/Apartment
    Airbnb
    From
    $198
  • 全新!阳光温馨联排度假别墅,离奥兰多迪士尼10分钟车程,游泳池健身房会所,温暖舒适
     3br Home/Apartment
    Airbnb
    From
    $209
  • Estate Home in the center of it all.
     4br Home/Apartment
    Airbnb
    From
    $678
  • House for rent in Orlando area with basketball ct
    Excellent6br Home/Apartment
    Airbnb
    From
    $1,966

Winter Haven Vacation Rentals with Wi-Fi

  • Walton House - New 2BR/2BA Cottage on Lake Alfred!
    Excellent2br Home/Apartment
    Airbnb
    From
    $253
  • Zetta's Hide-a-Way
    ExcellentHome/Apartment
    Airbnb
    From
    $82
  • Disney relaxing Tree House
    ExcellentHome/Apartment
    Airbnb
    From
    $101
  • Bartow's Hidden Gem
    NiceHome/Apartment
    Airbnb
    From
    $77

Winter Haven Pet-Friendly Vacation Rentals

  • RV/CAMPER PARKING w/ Indoor Bathroom & Laundry!!
     Home/Apartment
    Airbnb
    From
    $32
  • Clothing Optional campsite in Central Florida #1
    ExcellentHome/Apartment
    Airbnb
    From
    $11
  • Calabay Parc at Tower Lake Getaway
    Good6br Home/Apartment
    Airbnb
    From
    $345
  • Clothing Optional Campsite in Central Florida #2
    ExcellentHome/Apartment
    Airbnb
    From
    $17

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
83° 40°
3
90° 49°
2
88° 44°
1
91° 55°
2
98° 68°
1
100° 73°
10
99° 73°
12
97° 75°
8
98° 69°
4
95° 70°
5
90° 49°
3
86° 41°
3
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Rainy days

This climate histogram shows you the weather patterns in Winter Haven. The warmest months in Winter Haven are July and June, when temperatures reach 100 ˚F. The coolest month is December, when temperatures drop to 40 ˚F. The wettest month in Winter Haven is June with 11.89 inches of rain, while the driest month is October with 1.43 inches of rain.

What Expert Travelers Think

  • — 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 Campbell
    Jeff CampbellMiddle Class Dad
  • — 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
  • — As a mom of 5 kids who enjoy traveling, I love AllTheRooms! It is quick and easy to find the best deal on lodging that fits our family, in the area we'd like. AllTheRooms really does save you time, money, and hassle.

    Becky
    BeckyKid World Citizen

Vacation Rentals in Winter Haven

Browse accommodations from all your favorite providers including Airbnb, Priceline, Agoda and others at AllTheRooms.com. AllTheRooms has 435 rentals, hotels and other great places to stay during your time in Winter Haven, with everything from inexpensive hostels and homestays to luxury Airbnbs and hotels. A trip to Winter Haven can be budget-friendly - the lowest price rental is available at $15 a night. On average, an accommodation in Winter Haven will cost you $96 per night.

If you need internet access during your stay in Winter Haven, then you can choose from over 157 places to stay that provide WiFi internet. 17 places to stay include a breakfast. Fitness addicts can get a workout in during their stay by choosing from 11 accommodations that have gyms. If you're planning on arriving in Winter Haven by car, be sure to choose from 161 accommodations that provide parking. We have 64 accommodations that have a pool or jacuzzi.

Those traveling with a dog, cat or some other animal can stay in one of 35 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 149 places to stay from Airbnb, 18 accommodations from Priceline and 7 places to stay from Agoda.

228 accommodations in Winter Haven have been reviewed; 59% are rated excellent or good. 121 places to stay in are instantly bookable.

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