Apartments in Winter Haven

31 - 60 of 101 Results
4
$995 - 1,195
955 6th St SE Winter Haven, FL
1 BR | Available Now
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Dog Friendly
Cat Friendly
28
$2,275
Winter Haven, FL
3 BR | Oct. 5, 2026
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Dog Friendly
Cat Friendly
House
Balcony/Deck/Patio
Storage
12
$1,995
6147 Grey Heron Dr Winter Haven, FL
4 BR | Ask for Availability
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Air Conditioning
In Unit Laundry
Dishwasher
Pool
31
$857
Winter Haven, FL
1 BR | Ask for Availability
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Eloise Woods
41
$1,100
Winter Haven, FL
2 BR | Ask for Availability
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Orchid Springs
1
$1,599
2425 W Central Ave Winter Haven, FL
2 BR | Available Now
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Dog Friendly
Cat Friendly
House
Dishwasher
16
$1,550
Winter Haven, FL
1 BR | Available Now
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Dog Friendly
Cat Friendly
Air Conditioning
Balcony/Deck/Patio
Storage
1
$2,150
6030 Grey Heron Dr Winter Haven, FL
4 BR | Available Now
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Dog Friendly
Cat Friendly
House
Pool
22
$3,750
Winter Haven, FL
3 BR | Available Now
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Dog Friendly
Cat Friendly
House
Air Conditioning
Balcony/Deck/Patio
13
$1,500
Winter Haven, FL
3 BR | Available Now
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Dog Friendly
Cat Friendly
House
16
$1,300
Winter Haven, FL
1 BR | Available Now
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Cat Friendly
House
Reflections West
12
$2,200
Winter Haven, FL
4 BR | Available Now
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12
$1,799
1198 Sophia Blvd Winter Haven, FL
3 BR | Ask for Availability
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Air Conditioning
In Unit Laundry
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Eagle Crest
1
$1,595
876 Crestwood Dr Winter Haven, FL
3 BR | Available Now
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Dog Friendly
Cat Friendly
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Disability Access
6
$2,700
Winter Haven, FL
4 BR | Available Now
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Dog Friendly
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Dishwasher
1
$1,050
136 Avenue C NE APT 3 Winter Haven, FL
2 BR | Available Now
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Dog Friendly
Cat Friendly
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Disability Access
Biltmore Shores
18
$3,999
Winter Haven, FL
5 BR | Oct. 1, 2026
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Dog Friendly
Cat Friendly
House
15
$1,195
Winter Haven, FL
1 BR | Available Now
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Dog Friendly
Cat Friendly
Air Conditioning
Biltmore Shores
8
$1,825
2160 Oakhurst Dr Winter Haven, FL
3 BR | Ask for Availability
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House
Air Conditioning
In Unit Laundry
Fitness Center
Dishwasher
18
$1,150
Winter Haven, FL
Studio | Available Now
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Dog Friendly
Cat Friendly
Air Conditioning
Biltmore Shores
26
$2,000
Winter Haven, FL
4 BR | Available Now
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18
$1,400
Winter Haven, FL
2 BR | Available Now
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14
$1,199
Winter Haven, FL
3 BR | Available Now
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8
$1,100
Winter Haven, FL
2 BR | Ask for Availability
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Orchid Springs
35
$1,500
Winter Haven, FL
3 BR | Ask for Availability
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21
$2,500
Winter Haven, FL
3 BR | Available Now
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13
$1,895
2048 Lakeridge Dr Winter Haven, FL
3 BR | Ask for Availability
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House
Air Conditioning
In Unit Laundry
Dishwasher
1
$1,795
4347 Testana Ln Winter Haven, FL
3 BR | Oct. 1, 2026
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Dog Friendly
Cat Friendly
House
Biltmore Shores
1
$1,300
8302 Waterview Way Winter Haven, FL
2 BR | Available Now
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Dishwasher
Reflections West
12
$1,395
Winter Haven, FL
3 BR | Ask for Availability
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31 - 60 of 101 Results
  1. Home
  2. Winter Haven

How much does it cost to rent an apartment in Winter Haven?

Winter Haven Apartments
Bed Type Average Rent Range
Studio $1,350 $1,150 - $3,750
1BR $1,470 $780 - $1,760
2BR $1,700 $1,100 - $2,190
3BR $1,680 $1,360 - $2,610
4+BR $2,150 $1,860 - $2,650

Find a Winter Haven Apartment

Winter Haven is a smaller city tucked away in Polk County. Known as the "Chain of Lakes City", winter haven is home to a modest population of 35,000. Within the official boundaries of Winter Haven, there are more than 50 lakes. Above all else, these are what the town is known for, and why so many visit here on a regular basis. The bass fishing here is among the best in the country.

Athletics are also extremely important in Winter Haven. A number of professional athletes have lived here over the years, and certain sports like baseball and water skiing are extremely important to the local community. Winter Haven was a spring training location for 80 years, from 1928 through until 2008 when the Cleveland Indians moved their training to Arizona.

When to Search

Looking during the winter is a bad idea in the aptly named Winter Haven. This is a very busy time of year for the town as there are many people who spend the winters only here. Looking during the hotter months is likely to give you a few more options in terms of apartments.

Staying in the Know

When you apply for an apartment in Winter Haven, pay attention to how you conduct yourself. Although 35,000 people might sound like a lot, you don't have anywhere near the anonymity here you might have in a larger city. If you behave poorly or give a bad impression during an interview with a landlord, you might be surprised at how quickly word gets around.

Life in Winter Haven

Transportation

Winter Haven is a smaller town, which means that a car it the best way to navigate. Just remember that most addresses will be designated NE, SE, NW or SW, and you need to know the difference before you set out. The Winter Haven Area Transit also provides a handful of bus routes through the town.

Where to play

A great Florida tourist attraction is located near Winter Haven, and a visit to Legoland can be fun for people of all ages. Most of the entertainment takes place on the local lakes. Water Skiing and fishing are just a couple of ideas for what you can do on the water. Many different businesses rent boats and equipment if you don't have your own. Wine lovers should head to Grape Expectations, and fans of the craft beer movement should enjoy Jessie's.

Neighborhoods

Search Cities Near Winter Haven, FL

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Winter Haven:
September Rent Report

Welcome to the September 2026 Winter Haven Apartment Report. In this assessment of the local rental market, Rentable data scientists and rental experts break down the September 2026 key findings and figures for the Winter Haven rental landscape.

Our experts analyze the pricing trends — one-bedroom, two-bedroom, year-over-year and month-over-month — in Winter Haven and surrounding areas and provide comparisons to the entire metro area, nearby cities and some of the most desirable and expensive cities in the United States. Take a look at the last 12 months of Winter Haven average rent prices in the chart below.

Monthly Rent Report

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1 BR       2 BR

Winter Haven Rent Prices Decrease From August to September

Winter Haven rent prices decreased over the last month. From August to September, the city experienced a 0% decrease for the price of a one-bedroom apartment. The rent price for a Winter Haven one-bedroom apartments currently stands at $.

When we take a look at the two-bedroom comparison from August to September, Winter Haven experienced a 0% decrease for the price of a two-bedroom apartment. The rent price for a Winter Haven two-bedroom apartments currently stands at $.

September Prices: Winter Haven vs. Surrounding Areas

Rent Prices in Winter Haven and Surrounding Areas

Rent prices have decreased in Winter Haven over the last month. But how have the surrounding areas fared when it comes to the recent volatility in apartment prices? Rent prices in 0 of the Winter Haven suburbs increased last month. On the other hand, 0 local areas experienced a decrease in the price of a one-bedroom apartment.

More key findings include:

  • Rents did not increase in any of the Winter Haven suburbs

  • Rents did not decrease in any of the Winter Haven suburbs.

September 2026 Pricing Trends: Winter Haven vs. National Comparisons

Winter Haven Rent Prices More Affordable Than Major Cities

Rent growth in Winter Haven over the past year has been declining. When compared to major cities nearby, along with some of the most expensive cities in the country, Winter Haven average rent prices appear to be relatively affordable for local residents.

The price for a Winter Haven one-bedroom apartment remains vastly more affordable than four of the largest cities in the United States — New York City, Washington, D.C. San Francisco and Los Angeles. And pricing compares quite similarly to nearby Midwest cities.

For more information about Winter Haven and surrounding area rent prices, take a look at the complete data set below.

Data set for Winter Haven and suburbs

1 BR September 1 BR M/M % Change 2 BR September 2 BR M/M % Change

Methodology

Each month, using over 1 million Rentable listings across the United States, we calculate the median 1-bedroom and 2-bedroom rent prices by city, state, and nation, and track the month-over-month percent change. To avoid small sample sizes, we restrict the analysis for our reports to cities meeting minimum population and property count thresholds.