Winter Haven Vacation Rentals

Compare 66 available properties from 12 providers
Winter Haven
Anytime
2 guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
House
Resort
Camping
Distance to center
Max. 1 mi
Max. 2 mi
Max. 3 mi
Rating
Outstanding: 4.5+
Very Good: 4+
Good: 3.5+

Recommended Vacation Rentals in Winter Haven

Find your perfect vacation rental in Winter Haven: from $32 per night

House Winter Haven 3
House ∙ 3 guests ∙ 2 bedrooms
Winter Haven, Polk County, Florida, United States
from $54
Vrbo
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House Winter Haven 2
House ∙ 2 guests ∙ 1 bedroom
Winter Haven, Polk County, Florida, United States
from $32
Vrbo
5.0
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House Winter Haven 4
House ∙ 4 guests ∙ 1 bedroom
Winter Haven, Polk County, Florida, United States
from $44
Vrbo
4.9
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Apartment Winter Haven 3
Apartment ∙ 3 guests ∙ 1 bedroom
Winter Haven, Polk County, Florida, United States
from $65
Vrbo
5.0
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Apartment Winter Haven 3
Apartment ∙ 3 guests ∙ 1 bedroom
Winter Haven, Polk County, Florida, United States
from $75
Vrbo
5.0
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House Winter Haven 6
House ∙ 6 guests ∙ 3 bedrooms
Winter Haven, Polk County, Florida, United States
from $180
Vrbo
5.0
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House Winter Haven 6
House ∙ 6 guests ∙ 3 bedrooms
Winter Haven, Polk County, Florida, United States
from $85
Vrbo
5.0
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House Winter Haven 6
House ∙ 6 guests ∙ 3 bedrooms
Winter Haven, Polk County, Florida, United States
from $63
Vrbo
5.0
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House Winter Haven 7
House ∙ 7 guests ∙ 3 bedrooms
Winter Haven, Polk County, Florida, United States
from $63
Vrbo
5.0
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Vacation rentals with Wi-Fi

House Internet Winter Haven
Internet
House ∙ 6 guests ∙ 3 bedrooms
Winter Haven, Polk County, Florida, United States
from $195
Vrbo
5.0
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House Internet Winter Haven
Internet
House ∙ 4 guests ∙ 1 bedroom
Winter Haven, Polk County, Florida, United States
from $160
Vrbo
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House Internet Winter Haven
Internet
House ∙ 8 guests ∙ 3 bedrooms
Winter Haven, Polk County, Florida, United States
from $119
Vrbo
5.0
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Apartments and vacation rentals with a kitchen

House Kitchen Winter Haven
Kitchen
House ∙ 10 guests ∙ 3 bedrooms
Winter Haven, Polk County, Florida, United States
from $280
Vrbo
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House Kitchen Winter Haven
Kitchen
House ∙ 10 guests ∙ 4 bedrooms
Winter Haven, Polk County, Florida, United States
from $152
Vrbo
5.0
View deal
House Kitchen Winter Haven
Kitchen
House ∙ 10 guests ∙ 4 bedrooms
Winter Haven, Polk County, Florida, United States
from $366
Vrbo
5.0
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Vacation rentals and apartments with air conditioning

House Aircondition Winter Haven
-29%
Sep 18 - Sep 25
Aircondition
House ∙ 8 guests ∙ 4 bedrooms
Winter Haven, Polk County, Florida, United States
from $89 $125
Horizon Vacation Homes
4.8
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Apartment Aircondition Winter Haven
Aircondition
Apartment ∙ 4 guests ∙ 2 bedrooms
Winter Haven, Polk County, Florida, United States
from $82
Horizon Vacation Homes
4.8
View deal
House Aircondition Winter Haven
-50%
Sep 11 - Sep 18
Aircondition
House ∙ 8 guests ∙ 4 bedrooms
Winter Haven, Polk County, Florida, United States
from $89 $179
Horizon Vacation Homes
4.6
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Popular Rental Amenities in Winter Haven

  • Internet (38)
  • Parking (36)
  • No smoking (36)
  • Air conditioning (25)
  • Pool (22)
  • Kitchen (22)
  • Washer (21)
  • No pets (21)
  • TV (19)
  • Yard (17)
  • Microwave (16)
  • Grill (14)

Select a filter to find an accommodation meeting your criteria among the 66 properties in Winter Haven. Many vacation rentals in Winter Haven offer "internet" or "TVs," which makes it a great vacation spot if you can't imagine a vacation without internet or you want to tune out with some TV time. You could even look for accommodations if you need a crib for your baby (15 rentals include "cribs" in Winter Haven) or if you want a rental with a balcony or a patio (10 rentals in Winter Haven include "balconies/patios").

The Weather in Winter Haven

72°
52°
75°
55°
79°
59°
84°
64°
90°
68°
91°
73°
91°
75°
91°
75°
90°
73°
86°
68°
79°
59°
77°
59°
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 51° The rainiest month is July while the driest month is March.

Accommodations for your vacation in Winter Haven

Nearly half of the listings (45.33%) in Winter Haven are hotel rooms. They are the most typical accommodations in this destination. Interestingly, type of accommodation in particular, this type of property in particular is $111 per night, with an average area of 810 ft². Moreover, most hotel rooms in this destination can welcome 3 guests, which makes it a perfect destination for couples and small groups. If you would prefer to book another accommodation type, you could check house rentals, which are the other most frequent property type in Winter Haven. These properties cost $192 a night on average and have an average size of 1,880 ft².

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.

Show all 66 properties
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.

We compare more than 1,300 providers, including:

Booking.com Vacation Rentals in Winter Haven TripAdvisor Vacation Rentals in Winter Haven Vrbo Vacation Rentals in Winter Haven Airbnb Vacation Rentals in Winter Haven VacationRentals.com Vacation Rentals in Winter Haven HouseTrip Vacation Rentals in Winter Haven FlipKey Vacation Rentals in Winter Haven 9flats.com Vacation Rentals in Winter Haven PerfectPlaces.com 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 Bedycasa Vacation Rentals in Winter Haven Novasol Vacation Rentals in Winter Haven HomeEscape Vacation Rentals in Winter Haven

Get inspired for your vacation in Winter Haven

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