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Winter Haven Vacation Rentals

Find 264 available offers from 6 partners
Winter Haven
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Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
House
Apartment
Resort
Distance to center
Max. 1 km
Max. 2 km
Max. 5 km
Rating
Outstanding: 4.5+
Very Good: 4+
Good: 3.5+

Discover beautiful vacation rentals in Winter Haven, Florida

Located in Central Florida, Winter Haven is home to 50 lakes, making it an ideal destination for waterskiing and fishing enthusiasts. So if you are visiting for some fun on the lake, there is a broad range of vacation homes to choose from in Winter Haven. Depending on your budget, you can get a luxury condo, villa or an apartment that offers the ultimate comfort and convenience. There are vacation houses that feature spectacular lakeside views while providing welcoming neighborhood charm.

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Save up to 82%

Best Vacation Home Deals in Winter Haven

House Winter Haven
Apr 22 - Apr 29
-52%
$366
$175 per night
House ∙ 8 guests ∙ 3 bedrooms
House in Winter Haven with Electric Fireplace + Lake Views
4.3
"Very good" (10 ratings)
Winter Haven, Polk County, Florida, United States
Details
Evolve
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House Winter Haven
May 1 - May 8
-82%
$392
$73 per night
House ∙ 7 guests ∙ 2 bedrooms
Family Friendly House in Winter Haven with Grill
5.0
"Excellent" (7 ratings)
Winter Haven, Polk County, Florida, United States
Details
Evolve
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Motel Winter Haven
Jun 24 - Jul 1
-19%
$123
$100 per night
Motel ∙ 4 guests ∙ 1 bedroom
Motel in Winter Haven with Yard
Winter Haven, Polk County, Florida, United States
Free cancellation
Details
Expedia
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Find a rental that fits your preferences among the 264 fantastic options from more than 6 partner websites in Winter Haven. The website HomeToGo instantaneously compares all of these rentals so you can save up to 82%!

Book Vacation Rental Offers with the Highest User Rating

Top-Rated Rentals and Accommodations in Winter Haven

House Winter Haven
Jun 24 - Jul 1
$140 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Winter Haven with Grill
4.8
"Excellent" (61 ratings)
Winter Haven, Polk County, Florida, United States
Details
Vrbo
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House Winter Haven
Aug 5 - Aug 12
$339 per night
House ∙ 12 guests ∙ 4 bedrooms
House in Winter Haven with Pool
5.0
"Excellent" (22 ratings)
Winter Haven, Polk County, Florida, United States
Details
Vrbo
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House Winter Haven
May 1 - May 8
-82%
$392
$73 per night
House ∙ 7 guests ∙ 2 bedrooms
Family Friendly House in Winter Haven with Grill
5.0
"Excellent" (7 ratings)
Winter Haven, Polk County, Florida, United States
Details
Evolve
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Recommended Vacation Rentals in Winter Haven

Find your perfect vacation rental in Winter Haven: from $58 per night

House Winter Haven
May 20 - May 27
$305 per night
House ∙ 12 guests ∙ 4 bedrooms
House in Winter Haven with Large Pool
5.0
"Excellent" (33 ratings)
Winter Haven, Polk County, Florida, United States
Details
Vrbo
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Cottage Winter Haven
Feb 10 - Feb 17
$90 per night
Cottage ∙ 3 guests ∙ 2 bedrooms
Cottage in Winter Haven
4.7
"Outstanding" (39 ratings)
Winter Haven, Polk County, Florida, United States
Details
Vrbo
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House Winter Haven
Sep 23 - Sep 30
$140 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Winter Haven with Grill
4.8
"Excellent" (61 ratings)
Winter Haven, Polk County, Florida, United States
Details
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Motel Winter Haven
Jan 1 - Jan 8
-18%
$145
$119 per night
Motel ∙ 4 guests ∙ 1 bedroom
Motel in Winter Haven with Pool
3.7
"Good" (653 ratings)
Winter Haven, Polk County, Florida, United States
Details
Get a Room
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House Winter Haven
Sep 16 - Sep 23
$179 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Winter Haven with Outdoor Pool
4.0
"Very good" (1 rating)
Winter Haven, Polk County, Florida, United States
Details
Vrbo
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House Winter Haven
Sep 23 - Sep 30
$337 per night
House ∙ 12 guests ∙ 4 bedrooms
House in Winter Haven with Pool
5.0
"Excellent" (22 ratings)
Winter Haven, Polk County, Florida, United States
Details
Vrbo
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Boat Winter Haven
Jun 3 - Jun 10
$86 per night
Boat ∙ 3 guests ∙ 1 bedroom
Beautiful Boat in Winter Haven
4.7
"Outstanding" (30 ratings)
Winter Haven, Polk County, Florida, United States
Details
Vrbo
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Apartment Winter Haven
Sep 23 - Sep 30
-43%
$104
$86 per night
Apartment ∙ 3 guests ∙ 1 bedroom
Rental Apartment in Winter Haven with Grill & Yard
5.0
"Excellent" (34 ratings)
Winter Haven, Polk County, Florida, United States
Details
Vrbo
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House Winter Haven
May 6 - May 13
$114 per night
House ∙ 6 guests ∙ 2 bedrooms
House in Winter Haven
4.0
"Very good" (1 rating)
Winter Haven, Polk County, Florida, United States
Details
Vrbo
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Find Fantastic yet Inexpensive Offers

Budget-friendly Vacation Rentals in Winter Haven

Apartment Winter Haven
May 6 - May 13
$58 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Charming Apartment in Winter Haven with Yard
5.0
"Excellent" (3 ratings)
Winter Haven, Polk County, Florida, United States
Details
Vrbo
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House Winter Haven
May 6 - May 13
$115 per night
House ∙ 6 guests ∙ 2 bedrooms
House in Winter Haven
4.0
"Very good" (1 rating)
Winter Haven, Polk County, Florida, United States
Details
Vrbo
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House Winter Haven
May 20 - May 27
$126 per night
House ∙ 5 guests ∙ 2 bedrooms
House in Winter Haven with Yard + Lake Views
4.8
"Excellent" (5 ratings)
Winter Haven, Polk County, Florida, United States
Details
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Vacation rentals with Wi-Fi

Stay connected while traveling and book a Winter Haven accommodation with high-speed internet.

House Internet Winter Haven
Apr 28 - May 5
$107 per night
House ∙ 9 guests ∙ 3 bedrooms
Entire House in Winter Haven with Yard
4.8
"Excellent" (72 ratings)
Winter Haven, Polk County, Florida, United States
Internet
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House Internet Winter Haven
Jun 10 - Jun 17
-32%
$265
$180 per night
House ∙ 6 guests ∙ 2 bedrooms
House in Winter Haven with Pool, Grill & Yard
5.0
"Excellent" (13 ratings)
Winter Haven, Polk County, Florida, United States
Internet
Details
Vrbo
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House Internet Winter Haven
Jul 29 - Aug 5
$119 per night
House ∙ 8 guests ∙ 3 bedrooms
House in Winter Haven with Yard & Grill
5.0
"Excellent" (55 ratings)
Winter Haven, Polk County, Florida, United States
Internet
Details
Vrbo
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Apartments and vacation rentals with a kitchen

Cook up a feast on your next vacation and book a Winter Haven rental with full kitchen.

House Kitchen Winter Haven
Jan 27 - Feb 3
$125 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Winter Haven
Winter Haven, Polk County, Florida, United States
Kitchen
Details
Vrbo
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House Kitchen Winter Haven
May 20 - May 27
$306 per night
House ∙ 12 guests ∙ 4 bedrooms
House in Winter Haven with Large Pool
5.0
"Excellent" (33 ratings)
Winter Haven, Polk County, Florida, United States
Kitchen
Details
Vrbo
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House Kitchen Winter Haven
May 13 - May 20
-70%
$331
$100 per night
House ∙ 6 guests ∙ 3 bedrooms
Beautiful Vacation Home in Winter Haven with Electric Fireplace
Winter Haven, Polk County, Florida, United States
Kitchen
Details
Vrbo
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Vacation rentals and apartments with air conditioning

Keep cool during your trip to Winter Haven and book a vacation rental with air conditioning.

House Air conditioning Winter Haven
May 6 - May 13
$140 per night
House ∙ 7 guests ∙ 3 bedrooms
Beautiful House in Winter Haven with Grill
4.8
"Excellent" (64 ratings)
Winter Haven, Polk County, Florida, United States
Air conditioning
Details
Vrbo
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Apartment Air conditioning Winter Haven
Jul 8 - Jul 15
-32%
$119
$81 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Wonderful Apartment in Winter Haven with Yard & Grill
4.9
"Excellent" (31 ratings)
Winter Haven, Polk County, Florida, United States
Air conditioning
Details
Vrbo
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Cottage Air conditioning Winter Haven
Feb 10 - Feb 17
$91 per night
Cottage ∙ 3 guests ∙ 2 bedrooms
Cottage in Winter Haven
4.7
"Outstanding" (39 ratings)
Winter Haven, Polk County, Florida, United States
Air conditioning
Details
Vrbo
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Popular Rental Amenities in Winter Haven

  • Internet (225)
  • TV (199)
  • Air conditioning (196)
  • Microwave (169)
  • No smoking (162)
  • No pets (157)
  • Pool (132)
  • Kitchen (118)
  • Washer (93)
  • Wheelchair access (69)
  • Yard (63)
  • Dishwasher (55)

Select a filter to find an accommodation meeting your criteria among the 264 properties in Winter Haven. Many vacation rentals in Winter Haven offer "Internet" or "TV," which makes it a great vacation spot if you need internet access during your vacation or you never miss an episode of your favorite show. You could even look for accommodations if you want a rental with a balcony or a patio (21 rentals include "Fenced" in Winter Haven) or if you want a rental with a jacuzzi (2 rentals in Winter Haven include "Hot tub").

The Weather in Winter Haven

max.
Min.
72°
52°
8 days 8
max.
Min.
75°
55°
7 days 7
max.
Min.
79°
59°
6 days 6
max.
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84°
64°
8 days 8
max.
Min.
90°
68°
8 days 8
max.
Min.
91°
73°
17 days 17
max.
Min.
91°
75°
19 days 19
max.
Min.
91°
75°
17 days 17
max.
Min.
90°
73°
14 days 14
max.
Min.
86°
68°
7 days 7
max.
Min.
79°
59°
6 days 6
max.
Min.
77°
59°
7 days 7
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Check out the climate diagram for Winter Haven. The highest average temperatures are in the month of June. Conversely, January is the coolest month in Winter Haven, with temperatures going under 52° The rainiest month is July while the driest month is March.

7-Day Weather Forecast in Winter Haven

Wed, 22 Mar
84°
57°

0%

9 h

11 mi/h

Thu, 23 Mar
86°
60°

0%

10 h

10 mi/h

Fri, 24 Mar
91°
60°

0%

10 h

9 mi/h

Sat, 25 Mar
91°
62°

0%

10 h

14 mi/h

Sun, 26 Mar
93°
68°

10%

8 h

5 mi/h

Mon, 27 Mar
91°
66°

0%

10 h

8 mi/h

Tue, 28 Mar
87°
68°

10%

4 h

10 mi/h

Accommodations for your vacation in Winter Haven

Many of the listings (60.5%) in Winter Haven are house rental. They are the most typical accommodations in this destination. Interestingly, type of accommodation in particular, this type of property in particular is $301 per night, with an average area of 167 m². Moreover, most house rental in this destination can welcome 8 guests, which makes it a perfect destination for large groups. If you would prefer to book another accommodation type, you could check apartment rental, which are the other most frequent property type in Winter Haven. These properties cost $117 a night on average and have an average size of 34 m².
Where to find the best food in Winter Haven?

Where to find delicious local food

If you are into seafood, Harry's Old Place offers local favorites such as sweet and spicy shrimp, fried gator bites, and baked oysters. For those who love steak, Manny's Original Chophouse is a family-friendly spot for roasted prime ribs, country fried steak and boneless chops. Carrabba's Italian Grill is a popular joint for guests who want to try Italian cuisines, such as Chicken Bryan, Pollo Sorrento, and Pollo Rosa Maria.

What are the best nightlife spots in Winter Haven?

Get out for some fun

Make the most of your stay by trying out some of the locals clubs and sports bars. Somewhere Sports Bar & Grill is popular for karaoke music and boasts an extensive drink list of wine, beer and more. If you want to have fun with friends, Jessie's Lounge is the go-to spot for live music and dance nights. Or, you could try Apple Lounge if you want a cool place to eat, hang out, play pool and listen to music.

Where are the unique attractions in Winter Haven?

Things to Do

Enjoy a spot of beauty with serene gardens by visiting Bok Tower Gardens which boasts a 205-foot Singing Tower Carillon with a bell that plays every day. Sherman's Antique features a 5,000 sq. ft. of treasures for guests to see. If you love musicals or stage readings, Theater Winter Haven offers shows and main stage productions to make your visit enjoyable.

Information about vacation rentals in Winter Haven

🏡 Vacation rentals 264 properties
💳 Possible discounts up to 62%
🌙 Nightly prices starting at $58
⭐ Popular amenities Internet, TV and Air conditioning
🐾 Pet friendly accommodations 30 properties
🏊 Vacation rentals with pools 146 properties

Frequently Asked Questions

What is the nightly price for a vacation rental in Winter Haven?

The price of a night's stay in Winter Haven starts at $58. If you are looking for a house rental, the nightly price is $301 on average. A apartment rental Winter Haven will cost on average $117 per night.

How many vacation rentals are available for booking in Winter Haven?

Currently there are 264 vacation homes to choose from for your upcoming trip.

What amenities are most popular for vacation homes in Winter Haven?

If you're looking to book a vacation rental in Winter Haven, others search for accommodation with these amenities: TV, Internet and Air conditioning.

How many vacation homes with pools are in Winter Haven?

Winter Haven has 146 Hotel room and Motel room options on offer to rent.

Are pets allowed in vacation rentals in Winter Haven?

In case if you are traveling with a dog in Winter Haven - 11% of rentals are pet-friendly.

What's the best time of year to travel to Winter Haven?

June and July are usually the warmest months in Winter Haven with temperatures around 91 °F. The coldest months in Winter Haven are January and February, with 52 °F on average.

We list offers from thousands of providers, including:

Booking.com Vacation Rentals in Winter Haven TripAdvisor Vacation Rentals in Winter Haven Vrbo Vacation Rentals in Winter Haven VacationRentals.com Vacation Rentals in Winter Haven HouseTrip Vacation Rentals in Winter Haven FlipKey Vacation Rentals in Winter Haven Homestay.com Vacation Rentals in Winter Haven Only-apartments Vacation Rentals in Winter Haven Interhome Vacation Rentals in Winter Haven Novasol Vacation Rentals in Winter Haven HomeEscape Vacation Rentals in Winter Haven

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