Winter Haven, FL rental listings

359 rentals

Sort:

Recommended

ABOUT THIS HOME
Winter Haven, FL Rental Listings
Golfers Paradise! Right on the 18th Fairway...This 2 BD, 2 BA single family home on the golf course offers the perfect blend of comfort, ease and resort-style living. With an open-concept layout, this

$3,500/mo

2 beds2 baths1,981 sq ft

4148 Dunmore Dr, Lake Wales, FL 33859

Pets welcome • Parking • A/C

ABOUT THIS HOME
Winter Haven, FL Rental Listings
3+ bedroom 2 bathroom single family home, plus additional 11x13 bonus room( great for office, study or play room), large kitchen with center island, granite counter tops, stainless steel appliances, l

$1,750/mo

3 beds2 baths1,580 sq ft

1220 Salisbury Dr, Winter Haven, FL 33881

Pets welcome • Parking • A/C

ABOUT THIS HOME
Winter Haven, FL Rental Listings
Welcome to your perfect home away from home in beautiful Winter Haven, Florida! This fully furnished rental is located in a private, peaceful community just 5 miles from LEGOLAND Florida and approxima

$1,700/mo

1 bed1 bath559 sq ft

8307 Waterview Way #8307, Winter Haven, FL 33884

Pets welcome • A/C • Car-dependent

ABOUT THIS HOME
Winter Haven, FL Rental Listings
Discover the perfect blend of comfort, style, and value at Terra Hill Estates, where our charming 2-bedroom, 1-bath apartments are designed to fit your lifestyle--whether you prefer classic layouts, m

$1,350/mo

2 beds1 bath950 sq ft

3135 Woodhill Rd, Winter Haven, FL 33881

Pets welcome • Laundry in unit

ABOUT THIS HOME
Winter Haven, FL Rental Listings
Special Offer! $200 OFF Your First Month's Rent!!!! This beautifully maintained 2-bedroom, 2-bath ground-floor condo is nestled within the highly sought-after gated community of Winterset. Step insi

$1,550/mo

2 beds2 baths1,090 sq ft

403 Laurel Cove Way #403, Winter Haven, FL 33884

Pets welcome • Parking • A/C

ABOUT THIS HOME
Winter Haven, FL Rental Listings
This beautiful 3-bedroom, 2-bathroom home is nestled in the sought-after Whispering Trails neighborhood of Winter Haven. Inside, you'll find an open floor plan that creates a bright, airy flow from th

$1,900/mo

3 beds2 baths1,553 sq ft

2845 Whispering Trails Dr, Winter Haven, FL 33884

Pets welcome • Laundry in unit • Parking

Property at 2924 Whispering Trails Dr, Winter Haven, FL, 33884, 1 bed, 1 bath, [object Object]

$950/mo

1 bed1 bath600 sq ft

2924 Whispering Trails Dr, Winter Haven, FL 33884

Property at 1542 Jessica Blvd, Winter Haven, FL, 33884, 5 beds, 2.5 baths, [object Object]

$2,300/mo

5 beds2.5 baths2,112 sq ft

1542 Jessica Blvd, Winter Haven, FL 33884

Property at 503 Avenue B NW #503, Winter Haven, FL, 33881, 2 beds, 2.5 baths, [object Object]

$1,995/mo

2 beds2.5 baths1,408 sq ft

503 Avenue B NW #503, Winter Haven, FL 33881

Property at 935 Summer Glen Dr, Winter Haven, FL, 33880, 4 beds, 2 baths, [object Object]

$1,979/mo

4 beds2 baths1,846 sq ft

935 Summer Glen Dr, Winter Haven, FL 33880

Property at 505 Kensington View Dr, Winter Haven, FL, 33880, 3 beds, 2 baths, [object Object]

$1,749/mo

3 beds2 baths1,528 sq ft

505 Kensington View Dr, Winter Haven, FL 33880

Property at 57 Saint Kitts Cir Unit 57, Winter Haven, FL, 33884, 3 beds, 2 baths, [object Object]

$1,700/mo

3 beds2 baths1,537 sq ft

57 Saint Kitts Cir Unit 57, Winter Haven, FL 33884

Property at 1309 26th St NW, Winter Haven, FL, 33881, 3 beds, 2 baths, [object Object]

$2,100/mo

3 beds2 baths1,687 sq ft

1309 26th St NW, Winter Haven, FL 33881

Property at 5635 Struthers Ct, Winter Haven, FL, 33884, 3 beds, 2 baths, [object Object]

$2,100/mo

3 beds2 baths1,726 sq ft

5635 Struthers Ct, Winter Haven, FL 33884

Property at 125 Lake Smart Cir, Winter Haven, FL, 33881, 4 beds, 2 baths, [object Object]

$2,300/mo

4 beds2 baths— sq ft

125 Lake Smart Cir, Winter Haven, FL 33881

Property at 2664 Rutledge Ct Unit 2664, Winter Haven, FL, 33884, 2 beds, 2 baths, [object Object]

$1,950/mo

2 beds2 baths1,419 sq ft

2664 Rutledge Ct Unit 2664, Winter Haven, FL 33884

Property at 295 Lake Smart Cir, Winter Haven, FL, 33881, 3 beds, 2 baths, [object Object]

$2,300/mo

3 beds2 baths1,725 sq ft

295 Lake Smart Cir, Winter Haven, FL 33881

Property at 77 Lake Ring Dr, Winter Haven, FL, 33884, 3 beds, 2 baths, [object Object]

$2,099/mo

3 beds2 baths1,611 sq ft

77 Lake Ring Dr, Winter Haven, FL 33884

Property at 237 St Georges Cir, Eagle Lake, FL, 33839, 3 beds, 2 baths, [object Object]

$1,952/mo

3 beds2 baths1,690 sq ft

237 St Georges Cir, Eagle Lake, FL 33839

Property at 3011 Totem RD, Eagle Lake, FL, 33839, 3 beds, 2 baths, [object Object]

$2,000/mo

3 beds2 baths1,487 sq ft

3011 Totem RD, Eagle Lake, FL 33839

Property at 1481 Haines Dr, Winter Haven, FL, 33881, 3 beds, 2 baths, [object Object]

$1,750/mo

3 beds2 baths1,302 sq ft

1481 Haines Dr, Winter Haven, FL 33881

Property at 861 Cambridge Dr, Winter Haven, FL, 33881, 3 beds, 2.5 baths, [object Object]

$1,999/mo

3 beds2.5 baths1,447 sq ft

861 Cambridge Dr, Winter Haven, FL 33881

Property at 3240 Country Walk Club Cir, Winter Haven, FL, 33881, 4 beds, 2 baths, [object Object]

$2,200/mo

4 beds2 baths1,851 sq ft

3240 Country Walk Club Cir, Winter Haven, FL 33881

Property at 1543 Jessica Blvd, Winter Haven, FL, 33884, 3 beds, 2 baths, [object Object]

$1,900/mo

3 beds2 baths1,487 sq ft

1543 Jessica Blvd, Winter Haven, FL 33884

Property at 567 Eagle Landing Blvd, Winter Haven, FL, 33880, 4 beds, 2.5 baths, [object Object]

$2,495/mo

4 beds2.5 baths2,193 sq ft

567 Eagle Landing Blvd, Winter Haven, FL 33880

Property at 904 Vienna Dr, Winter Haven, FL, 33884, 3 beds, 2 baths, [object Object]

$1,900/mo

3 beds2 baths1,778 sq ft

904 Vienna Dr, Winter Haven, FL 33884

Property at 565 Vittorio Dr, Winter Haven, FL, 33884, 4 beds, 2 baths, [object Object]

$2,000/mo

4 beds2 baths1,730 sq ft

565 Vittorio Dr, Winter Haven, FL 33884

Property at 3126 Totem Rd, Eagle Lake, FL, 33839, 3 beds, 2.5 baths, [object Object]

$2,050/mo

3 beds2.5 baths1,880 sq ft

3126 Totem Rd, Eagle Lake, FL 33839

Property at 28610 US Hwy 27, Dundee, FL, 33838, 10 beds, 10 baths, [object Object]

$6,500/mo

10 beds10 baths8,000 sq ft

28610 US Hwy 27, Dundee, FL 33838

Property at 1801 3rd Ct SE Unit C, Winter Haven, FL, 33880, 3 beds, 2 baths, [object Object]

$1,575/mo

3 beds2 baths— sq ft

1801 3rd Ct SE Unit C, Winter Haven, FL 33880

Property at 300 Arbuthnot St, Winter Haven, FL, 33881, 3 beds, 2 baths, [object Object]

$1,950/mo

3 beds2 baths1,787 sq ft

300 Arbuthnot St, Winter Haven, FL 33881

Property at 4510 Rapallo Ave, Winter Haven, FL, 33884, 4 beds, 2.5 baths, [object Object]

$2,295/mo

4 beds2.5 baths2,029 sq ft

4510 Rapallo Ave, Winter Haven, FL 33884

Property at 1204 Golden Eagle Ln, Winter Haven, FL, 33880, 4 beds, 2 baths, [object Object]

$1,800/mo

4 beds2 baths1,632 sq ft

1204 Golden Eagle Ln, Winter Haven, FL 33880

Property at 1128 Eagle Claw Ln, Winter Haven, FL, 33880, 4 beds, 2.5 baths, [object Object]

$2,250/mo

4 beds2.5 baths2,265 sq ft

1128 Eagle Claw Ln, Winter Haven, FL 33880

Property at 1875 Carnostie Rd, Winter Haven, FL, 33884, 3 beds, 2.5 baths, [object Object]

$1,680/mo

3 beds2.5 baths1,715 sq ft

1875 Carnostie Rd, Winter Haven, FL 33884

Property at 1534 Marksman Rd, Eagle Lake, FL, 33839, 4 beds, 2.5 baths, [object Object]

$2,200/mo

4 beds2.5 baths2,050 sq ft

1534 Marksman Rd, Eagle Lake, FL 33839

Property at 122 Inman Blvd, Winter Haven, FL, 33881, 4 beds, 2 baths, [object Object]

$2,200/mo

4 beds2 baths1,853 sq ft

122 Inman Blvd, Winter Haven, FL 33881

Property at 308 Lake Smart Cir #308, Winter Haven, FL, 33881, 3 beds, 2 baths, [object Object]

$1,900/mo

3 beds2 baths— sq ft

308 Lake Smart Cir #308, Winter Haven, FL 33881

Property at 1812 Carnostie Rd, Winter Haven, FL, 33884, 4 beds, 2 baths, [object Object]

$2,400/mo

4 beds2 baths2,170 sq ft

1812 Carnostie Rd, Winter Haven, FL 33884

Property at 674 Avenue L SE Unit 674, Winter Haven, FL, 33880, 3 beds, 2 baths, [object Object]

$1,600/mo

3 beds2 baths1,080 sq ft

674 Avenue L SE Unit 674, Winter Haven, FL 33880

Property at 223 Inman Blvd, Winter Haven, FL, 33881, 4 beds, 2 baths, [object Object]

$1,995/mo

4 beds2 baths1,867 sq ft

223 Inman Blvd, Winter Haven, FL 33881

Viewing page 5 of 9

Based on information submitted to the MLS GRID as of Mon Dec 01 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

The MLS data provided for the property above is provided courtesy of Redfin Corporation. Source: Southeast Florida MLS. Information is deemed reliable but not guaranteed. © 2025. The listing data on this page comes in part from the Internet Data Exchange (IDX), a collaboration between the following REALTOR(R) associations in the Southeast Florida Multiple Listing Service (MLS): Miami Association of REALTORS®, REALTOR® Association of Greater Ft. Lauderdale and South Broward Board of REALTORS®. All rights reserved. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Use of search facilities of data on the site, other than a consumer looking to purchase real estate, is prohibited.

More to explore in Winter Haven, FL

Property Types
Bedrooms
Amenities
Price

Rentals near Winter Haven, FL

Apartments for rent near Winter Haven, FL

Cities
Rental Buildings

Neighborhoods
Zip Codes

Popular rental markets in Florida

Rentals
Apartments

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

Winter Haven, FL rental listings

More to explore in Winter Haven, FL

Rentals near Winter Haven, FL

Cities

Apartments for rent near Winter Haven, FL

Popular rental markets in Florida

Related searches in Winter Haven, FL