Choose from 339 vacation rentals located in Winter Haven, Florida. Top filters in Winter Haven include Air conditioner, Kitchen or Kitchenette, and Internet / Wifi. Prices range from $39 to $1,275 per night. Our most popular vacation rental types near Winter Haven are Apartment and Hotel.

Top vacation rentals in Winter Haven

Outdoor pool
4.6 / 5.0
Outstanding(131 Ratings)
Looking for Relaxation?Near Legoland and Disney
House
 in Lake Alfred
6 guests · 4 bedrooms · 2 baths
Garden · Pool · Kitchen or Kitchenette

Enjoy the best of Winter Haven in our House, Looking for Relaxation?Near Legoland and Disney . A stunning property with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Fridge, microwave, oven, stovetop
4.8 / 5.0
Outstanding(102 Ratings)
Huge Luxury Lake House on the Chain of Lakes - near Legoland!
House
 in Winter Haven
15 guests · 5 bedrooms · 5 baths
Ski in / Ski out · Garden · Pool

Looking to create some memories in Winter Haven? Look no further than our House, Huge Luxury Lake House on the Chain of Lakes - near Legoland!. Enjoy top-rated amenities including Air conditioner, Dishwasher and Fireplace, and more.

$$$$
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Property building, On site
3.3 / 5.0
Average(522 Ratings)
Howard Johnson by Wyndham Winter Haven FL
Motel
 in Winter Haven
1 king bed
Pool · Pets allowed · Kitchen or Kitchenette

Looking to create some memories in Winter Haven? Look no further than our Motel, Howard Johnson by Wyndham Winter Haven FL. Enjoy top-rated amenities including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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Bedroom
3.7 / 5.0
Good(281 Ratings)
Rodeway Inn & Suites
Hotel
 in Haines City
2star
2 queen beds
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Discover the beauty of Winter Haven with a stay at Rodeway Inn & Suites, a top rated Hotel with amenities such as Air conditioner, Internet / Wifi and Kitchen or Kitchenette, and more.

$$$$
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Search by amenity

Explore vacation rentals with the most popular amenities in Winter Haven

Vacation rentals with air conditioning in Winter Haven

Property view
2.3 / 5.0
Fair (97 Ratings)
Travel Inn Winter Haven
Hotel
 in Winter Haven
2star
1 king bed
Pool · Pets allowed · Kitchen or Kitchenette

Discover the beauty of Winter Haven with a stay at Travel Inn Winter Haven, a top rated Hotel with amenities such as Air conditioner, Internet / Wifi and Pets allowed, and more.

$$$$
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Facade/entrance
3.1 / 5.0
Average(216 Ratings)
Lake Roy Beach Inn - Winter Haven
Hotel
 in Winter Haven
2star
2 queen beds
Garden · Pool · Kitchen or Kitchenette

This attractive Hotel in Winter Haven, $71 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Property view
3.6 / 5.0
Good(158 Ratings)
Lake Ida Beach Resort
Campground/ RV Resort
 in Winter Haven
Garden · Pool · Kitchen or Kitchenette

Soak up the beauty of Winter Haven in our Campground/ RV Resort, Lake Ida Beach Resort. With a range of amenities such as Air conditioner, Internet / Wifi and Laundry, you'll feel right at home.

$$$$
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Day, Swimming pool, Swimming pool
4.2 / 5.0
Excellent(1,580 Ratings)
LEGOLAND® Florida Resort
Resort
 in Winter Haven
1 bunk bed, 1 king bed, 1 single bed
Pool · Kitchen or Kitchenette · Air conditioner

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Winter Haven, at $63 per night for your next great vacation.

$$$$
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Winter Haven

Winter Haven travel guide

Let us help you plan your perfect Winter Haven vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Winter Haven, and more.

Frequently asked questions

What is the price range for rentals in Winter Haven?

Vacation rentals in Winter Haven have a price range between $39-$1,275. The average price for rentals in Winter Haven is $150 per night.

What are the most popular vacation rental amenities in Winter Haven?

  • Air conditioner
  • Kitchen or Kitchenette
  • Internet / Wifi

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