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Winter Haven Vacation Rentals

Find 284 available offers from 7 partners
Winter Haven
Anytime
Guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
Condo
House
Apartment
Distance to center
1 km
2 km
5 km
Rating
4.5+
4+
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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Best Vacation Home Deals in Winter Haven

Save up to 41%

House Winter Haven
Oct 16 - Oct 23
-41%
$460
$271 per night
House ∙ 11 guests ∙ 5 bedrooms
Family Friendly House in Winter Haven with Screened-In Patio + Great Views
Winter Haven, Polk County, Florida, United States
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House Winter Haven
Oct 21 - Oct 28
-34%
$139
$92 per night
House ∙ 8 guests ∙ 3 bedrooms
Vacation Home in Winter Haven
Winter Haven, Polk County, Florida, United States
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House Winter Haven
Oct 2 - Oct 9
-33%
$203
$135 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Winter Haven
4.4
Very good (15 ratings)
Winter Haven, Polk County, Florida, United States
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Find a rental that fits your preferences among the 284 fantastic options from more than 7 partner websites in Winter Haven. The website HomeToGo instantaneously compares all of these rentals so you can save up to 33%!

Top-Rated Rentals and Accommodations in Winter Haven

Book Vacation Rental Offers with the Highest User Rating

House Winter Haven
May 7 - May 14
$107 per night
House ∙ 6 guests ∙ 2 bedrooms
Vacation Home in Winter Haven with Wood-Burning Fireplace
4.7
Excellent (83 ratings)
Winter Haven, Polk County, Florida, United States
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House Winter Haven
Nov 11 - Nov 18
$140 per night
House ∙ 7 guests ∙ 3 bedrooms
Beautiful House in Winter Haven with Grill
4.9
Outstanding (60 ratings)
Winter Haven, Polk County, Florida, United States
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Cottage Winter Haven
Mar 16 - Mar 23
$90 per night
Cottage ∙ 3 guests ∙ 2 bedrooms
Cottage in Winter Haven
4.7
Excellent (41 ratings)
Winter Haven, Polk County, Florida, United States
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Recommended Vacation Rentals in Winter Haven

Find your perfect vacation rental in Winter Haven: from $47 per night

Boat Winter Haven
Sep 30 - Oct 7
$83 per night
Boat ∙ 3 guests ∙ 1 bedroom
Beautiful Boat in Winter Haven
4.5
Excellent (37 ratings)
Winter Haven, Polk County, Florida, United States
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Apartment Winter Haven
Sep 14 - Sep 21
$47 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Charming Apartment in Winter Haven with Yard
4.9
Outstanding (18 ratings)
Winter Haven, Polk County, Florida, United States
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House Winter Haven
Mar 23 - Mar 30
-26%
$124
$92 per night
House ∙ 6 guests ∙ 2 bedrooms
Vacation Home in Winter Haven
Winter Haven, Polk County, Florida, United States
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House Winter Haven
Aug 17 - Aug 24
$215 per night
House ∙ 8 guests ∙ 4 bedrooms
Wonderful Vacation Home in Winter Haven with Pool, Yard & Grill
4.7
Excellent (12 ratings)
Winter Haven, Polk County, Florida, United States
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House Winter Haven
Jan 10 - Jan 17
$272 per night
House ∙ 12 guests ∙ 4 bedrooms
House in Winter Haven with Large Pool
5.0
Outstanding (63 ratings)
Winter Haven, Polk County, Florida, United States
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Apartment Winter Haven
Aug 17 - Aug 24
-24%
$110
$83 per night
Apartment ∙ 3 guests ∙ 1 bedroom
Rental Apartment in Winter Haven with Grill & Yard
5.0
Outstanding (32 ratings)
Winter Haven, Polk County, Florida, United States
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House Winter Haven
Oct 24 - Oct 31
-43%
$237
$135 per night
House ∙ 8 guests ∙ 3 bedrooms
Vacation Home in Winter Haven with Electric Fireplace + Lake Views
4.7
Excellent (22 ratings)
Winter Haven, Polk County, Florida, United States
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Apartment Winter Haven
Sep 30 - Oct 7
-55%
$184
$83 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Nice Rental Apartment in Winter Haven with Grill
Winter Haven, Polk County, Florida, United States
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House Winter Haven
Dec 16 - Dec 23
$338 per night
House ∙ 12 guests ∙ 4 bedrooms
House in Winter Haven with Pool
5.0
Outstanding (24 ratings)
Winter Haven, Polk County, Florida, United States
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Budget-friendly Vacation Rentals in Winter Haven

Find Fantastic yet Inexpensive Offers

House Winter Haven
Aug 17 - Aug 24
-30%
$266
$187 per night
House ∙ 11 guests ∙ 3 bedrooms
Modern Vacation Home in Winter Haven with Grill & Yard
4.7
Excellent (43 ratings)
Winter Haven, Polk County, Florida, United States
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House Winter Haven
Jun 1 - Jun 8
$180 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Winter Haven with Outdoor Pool
4.5
Excellent (4 ratings)
Winter Haven, Polk County, Florida, United States
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House Winter Haven
Aug 17 - Aug 24
$215 per night
House ∙ 13 guests ∙ 6 bedrooms
Lovely House in Winter Haven with Friendly Pool
5.0
Outstanding (2 ratings)
Winter Haven, Polk County, Florida, United States
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Vacation rentals with Wi-Fi

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

House  Winter Haven
Nov 4 - Nov 11
-40%
$415
$250 per night
House ∙ 11 guests ∙ 5 bedrooms
Family Friendly Wonderful House in Winter Haven with Screened-In Patio + Great Views
4.8
Outstanding (30 ratings)
Winter Haven, Polk County, Florida, United States
Internet
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House  Winter Haven
Dec 16 - Dec 23
-15%
$265
$225 per night
House ∙ 6 guests ∙ 2 bedrooms
House in Winter Haven with Pool, Grill & Yard
5.0
Outstanding (21 ratings)
Winter Haven, Polk County, Florida, United States
Internet
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House  Winter Haven
Aug 17 - Aug 24
$518 per night
House ∙ 21 guests ∙ 7 bedrooms
Vacation Home in Winter Haven + Lakefront View
4.5
Excellent (2 ratings)
Winter Haven, Polk County, Florida, United States
Internet
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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  Winter Haven
Oct 1 - Oct 8
-52%
$180
$86 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Winter Haven with Yard, Pool & Grill
Winter Haven, Polk County, Florida, United States
Kitchen
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House  Winter Haven
Oct 21 - Oct 28
-31%
$208
$145 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Winter Haven with Pool
5.0
Outstanding (1 rating)
Winter Haven, Polk County, Florida, United States
Kitchen
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House  Winter Haven
Sep 30 - Oct 7
$296 per night
House ∙ 7 guests ∙ 3 bedrooms
Vacation Home in Winter Haven with Free Parking
5.0
Outstanding (7 ratings)
Winter Haven, Polk County, Florida, United States
Kitchen
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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.

Apartment  Winter Haven
Mar 23 - Mar 30
$90 per night
Apartment ∙ 5 guests ∙ 1 bedroom
Rental Apartment in Winter Haven + Bath View
4.6
Excellent (18 ratings)
Winter Haven, Polk County, Florida, United States
Air conditioning
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House  Winter Haven
Aug 17 - Aug 24
-21%
$350
$275 per night
House ∙ 12 guests ∙ 6 bedrooms
Lovely Vacation Home in Winter Haven with Yard & Grill
5.0
Outstanding (7 ratings)
Winter Haven, Polk County, Florida, United States
Air conditioning
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Villa  Winter Haven
Jan 13 - Jan 20
-24%
$465
$351 per night
Villa ∙ 8 guests ∙ 4 bedrooms
Villa in Winter Haven with Private Pool + Lake Views
5.0
Outstanding (4 ratings)
Winter Haven, Polk County, Florida, United States
Air conditioning
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Popular Rental Amenities in Winter Haven

  • Pool (165)
  • Pet-friendly (35)
  • WiFi (252)
  • Kitchen (139)
  • TV (223)
  • Air conditioning (230)
  • Washing machine (161)
  • Microwave (181)
  • Parking (12)
  • No smoking (177)
  • Fishing (43)
  • Balcony/patio (18)

Select a filter to find an accommodation meeting your criteria among the 284 properties in Winter Haven. Many vacation rentals in Winter Haven offer "Pool" or "Pets allowed," which makes it a great vacation spot if you want a rental with a pool or you travel with your pet. You could even look for accommodations if you want a rental providing a crib (54 rentals include "Crib" in Winter Haven) or if you need a fenced-in backyard (13 rentals in Winter Haven include "Fenced").

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.
Min.
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, 27 Sep
89°
73°

10%

8 h

8 mi/h

Thu, 28 Sep
89°
73°

10%

7 h

7 mi/h

Fri, 29 Sep
89°
73°

15%

6 h

9 mi/h

Sat, 30 Sep
87°
75°

15%

5 h

9 mi/h

Sun, 1 Oct
87°
77°

15%

6 h

14 mi/h

Mon, 2 Oct
86°
75°

15%

2 h

16 mi/h

Tue, 3 Oct
86°
68°

0%

10 h

6 mi/h

Accommodations for your vacation in Winter Haven

More than half of the listings (58.88%) 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 $291 per night, with an average area of 180 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 $154 a night on average and have an average size of 107 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 available 284 homes
💳 Possible discounts up to 33%
🌙 Nightly prices starting at $47
⭐ Popular amenities Pool, Pets allowed and Internet
🐾 Pet friendly homes 34 homes
🏊 Vacation rentals with pools 166 homes

Frequently Asked Questions

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

The nightly price of accommodations in Winter Haven starts at $47. If you are looking for a house rental, the nightly price is $291 on average. A apartment rental Winter Haven will cost $154 per night on average.

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

Currently there are 284 vacation rentals in Winter Haven to browse and book for your next trip.

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

Travelers search for Pool, Pets allowed, and Internet when booking a vacation rental in Winter Haven.

How many vacation rentals with a pool are there in Winter Haven?

Check out 166 vacation rentals available in Winter Haven for renting.

Are pets allowed in vacation homes in Winter Haven?

Finding a vacation home in Winter Haven that allows pets is easy, with 34 pet-friendly available.

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

Winter Haven has its warmest time of year around June and July, with average nightly prices around $47.

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