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Apartments Under $1,500 in Winter Haven, FL

90 rentals available

730 26th St Nw - Photo 1 of 1

5d+ ago

Under 1500 house for rent in Winter Haven

730 26th St Nw, Winter Haven, FL 33881

Ceiling fan | Concierge service | On-site management

2 beds

1 bath

$1,295

House for rent

Available Jun 1

Description

One Month Free Rent Available!* Welcome to this charming 2-bedroom, 1-bathroom property offering you the perfect blend of comfort and convenience, with a spacious layout and inviting living areas providing plenty of room to relax, an a well-equipped kitchen. Enjoy the serene, fenced backyard – perfect for outdoor gatherings or simply unwinding after a long day. Don't miss your chance to make this delightful property your new home! Rent is $1295/month, security deposit is $1300 ***we Offer Security Deposit Payment Options!***. The application fee is only $80/adult. In addi

1800 31st St Nw #1 - Photo 1 of 1

5d+ ago

Under 1500 house for rent in Winter Haven

1800 31st Street NW, Unit A - 1

1800 31st St Nw #1, Winter Haven, FL 33881

Air conditioning | Microwave

3 beds

2 baths

$1,450

House for rent

Available Aug 17

Charming Duplex with Spacious Backyard Retreat

This adorable 3-bedroom, 2-bathroom duplex offers a delightful living space with an additional small office area. Spanning 1,450 sqft, it features a large kitchen, an attached 2-car carport, and a fenced-in yard, perfect for outdoor enjoyment. With a comfortable layout and ample room for relaxation, this home is designed for both convenience and comfort in a welcoming setting.

1328 37th St Nw - Photo 1 of 1

5d+ ago

Under 1500 house for rent in Winter Haven

Residential Lease, WINTER HAVEN, FL

1328 37th St Nw, Winter Haven, FL 33881

Outdoor space

1 bed

1 bath

$1,100

House for rent

Description

Property Status: Active Enjoy comfort and privacy in this cozy 1-bedroom, 1-bathroom rear unit located in a quiet Winter Haven neighborhood. This home features its own fully fenced private backyard, perfect for relaxing, entertaining, or enjoying outdoor space. Inside, you'll find a functional layout with a bright living area, a comfortable bedroom, and a well-appointed kitchen. Conveniently located near shopping, dining, schools, and major roadways, this home offers easy access to everything Winter Haven has to enjoy. Don't miss this affordable rental with the added bonus

139 Avenue D Sw - Photo 1 of 1

5d+ ago

Under 1500 South College apartment for rent in Winter Haven

Residential Lease, WINTER HAVEN, FL

139 Avenue D Sw, Winter Haven, FL 33880

Dishwasher

2 beds

1 bath

$1,350

Apartment for rent

Description

Property Status: Active Virtually Staged. This inviting two-bedroom, one-bath home places you just moments from First Street and the lively downtown Winter Haven district, giving you quick access to local restaurants, coffee shops, lakes, parks, and the growing downtown scene. Inside, the bright living area leads into a kitchen with a comfortable eating space that's perfect for casual meals or a quiet start to your day. The home features two bedrooms and a bathroom with a tub and shower, offering the essentials you need in a convenient, central location. With everyday erra

1100 Martinique Dr #106 - Photo 1 of 1

5d+ ago

Under 1500 condo for rent in Winter Haven

Residential Lease, WINTER HAVEN, FL

1100 Martinique Dr #106, Winter Haven, FL 33884

On-site laundry | Swimming pool | Fitness center

2 beds

1 bath

$1,400

Condo for rent

Description

Property Status: Active Virtually Staged. Nestled within the peaceful and highly desirable Orchid Springs Village, this beautifully renovated ground-floor condominium offers the perfect blend of modern style, low-maintenance living, and an unbeatable Winter Haven location. Designed with comfort and functionality in mind, the bright open floor plan seamlessly connects the living and dining areas, creating an inviting space filled with abundant natural light. Beautiful luxury vinyl plank flooring flows throughout the home, while the updated kitchen showcases crisp white cabi

1484 32nd St Nw - Photo 1 of 1

5d+ ago

Under 1500 apartment for rent in Winter Haven

Residential Lease, WINTER HAVEN, FL

1484 32nd St Nw, Winter Haven, FL 33881

Ceiling fan

2 beds

1 bath

$1,100

Apartment for rent

Description

Property Status: Active Discover this charming duplex in the heart of Winter Haven, FL, offering 2 bedrooms and 1 bathroom in a thoughtfully designed layout. Step inside to find a bright and functional kitchen equipped with essential appliances, including a refrigerator and range, making meal preparation effortless. The kitchen flows seamlessly into the living area, creating an open and welcoming space that combines dining and relaxation, ideal for everyday living or entertaining friends and family. The first bedroom is spacious and conveniently located near the main livin

521 20th St Sw #C - Photo 1 of 1

5d+ ago

Under 1500 apartment for rent in Winter Haven

20th Street Southwest 521 - C

521 20th St Sw #C, Winter Haven, FL 33880

Dishwasher

2 beds

1 bath

$1,075

Apartment for rent

Available Jun 2

2-bed apartment with pool access near Lake Howard

Set in Winter Haven, FL, this 2-bed, 1-bath second-floor apartment offers 732 sqft with an open floor plan and large enclosed porch. The kitchen includes all appliances, plus shared laundry room access and an in-ground pool. Located directly across from Lake Howard with covered parking and minutes from major shopping and dining.

428 Avenue E Se - Photo 1 of 1

5d+ ago

Under 1500 apartment for rent in Winter Haven

Apartment for rent

Description

Cute 1-Bedroom, 1-Bathroom Apartment in Winter Haven just minutes from down town!! Lessee(s) are required to provide proof of liability insurance in the amount of $100,000, prior to occupancy. Real Property Management Lakeside can provide the required coverage for an additional charge of $13.00 per month or you can purchase coverage from your preferred provider. To see all of our available properties check our primary site at www RPMLakeside com Please call Kyle Byram to for more information 863-877-1669 or emial **** or to set up a self showing please follow this link.

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2371 Edwin St Ne - Photo 1 of 1

5d+ ago

Under 1500 house for rent in Winter Haven

House for rent

Remodeled 2-bed duplex near Winter Haven schools

Right in Winter Haven, FL, this remodeled 2-bed, 1-bath duplex features tile floors throughout and an updated kitchen. Walking distance to local schools makes it convenient for families, with first month's rent, last month's rent, and security deposit required to move in.

8302 Waterview Way - Photo 1 of 1

5d+ ago

Under 1500 condo for rent in Winter Haven

2 beds

2 baths

$1,400

Condo for rent

Description

Cute and clean downstairs end unit in Winterset, a gated community. Features wood laminate flooring in living area and bedrooms and ceramic tile in the wet areas. Open floor plan, kitchen with breakfast bar overlooking living room with mirror wall and dining area. Master bedroom has sliding glass doors to a private 6x7 screened in patio. Master suite includes walk-in closet, stackable washer & dryer, tile walk-in shower with shelving in the bathroom, plus another lien closet or storage space outside. Guest bath also has a tile walk-in shower. Enjoy the amenities Winterset

209 Avenue B Se - Photo 1 of 1

5d+ ago

Under 1500 apartment for rent in Winter Haven

Residential Lease, WINTER HAVEN, FL

209 Avenue B Se, Winter Haven, FL 33880

In-unit laundry | Ceiling fan | Dishwasher

2 beds

1 bath

$1,500

Apartment for rent

2-bed duplex near Winter Haven Hospital

Set in Winter Haven, FL, this 2-bed, 1-bath duplex offers 720 sqft with in-unit laundry and dishwasher. Located minutes from Winter Haven Hospital, supermarkets, and restaurants, with top-rated schools within walking distance - the nearest middle school just 0.1 miles away. Central air and ceiling fans keep the space comfortable year-round.

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333 Lake Howard Dr Nw #312C - Photo 1 of 1
Age restricted

5d+ ago

Under 1500 condo for rent in Winter Haven

Residential Lease, WINTER HAVEN, FL

333 Lake Howard Dr Nw #312C, Winter Haven, FL 33880

Assigned parking | Swimming pool | Elevator

2 beds

2 baths

$1,425

Condo for rent

2-bed 55+ condo with pool and Lake Howard views

Set in Winter Haven, FL, this 2-bed, 2-bath condo at Imperial Harbours serves the 55+ community with generously sized bedrooms and an enclosed porch facing the garden area. The 1,030 sqft unit includes all appliances, in-unit laundry, and assigned parking. Community amenities feature a pool with tiki bar, elevator access, and sunrise views over Lake Howard.

140 Avenue W Nw #3 - Photo 1 of 1

5d+ ago

Under 1500 apartment for rent in Winter Haven

Residential Lease, WINTER HAVEN, FL

140 Avenue W Nw #3, Winter Haven, FL 33881

Walk-in closets | Ceiling fan

2 beds

1 bath

$1,100

Apartment for rent

Updated 2-bed Winter Haven apartment near schools

Set in Winter Haven, FL, this updated 2-bed, 1-bath apartment offers 800 sqft with generous room sizes and a functional layout. Central air, ceiling fans, and a walk-in closet add comfort to the unit. Conveniently located near shopping, dining, and major roadways for easy commutes, with a top-rated middle school just half a mile away.

118 Oak Crest Dr Nw - Photo 1 of 1

5d+ ago

Under 1500 apartment for rent in Winter Haven

Residential Lease, WINTER HAVEN, FL

118 Oak Crest Dr Nw, Winter Haven, FL 33881

Ceiling fan

1 bed

1 bath

$1,100

Apartment for rent

Updated 1-bed Winter Haven apt with parking

This 1-bed, 1-bath apartment in Winter Haven features updated cabinets, crown molding, and modern light fixtures throughout the 600 sqft layout. Private off-street parking and central air add convenience, while the quiet street location with no through traffic keeps things peaceful. Minutes from shopping, dining, and parks.

136 Avenue C Ne - Photo 1 of 1

5d+ ago

Under 1500 apartment for rent in Winter Haven

Apartment for rent

Pet-friendly 2-bed Winter Haven apartment

A pet-friendly 2-bed, 1-bath apartment in Winter Haven, FL, offering 750 sqft of living space with utility concierge service included. The unit requires HOA approval and comes with a resident benefits package that includes HVAC filter delivery and credit reporting for $25 monthly. Pet owners pay a $300 fee plus $30 monthly rent per pet.

730 W Central Ave - Photo 1 of 1

5d+ ago

Under 1500 apartment for rent in Winter Haven

Apartment - WINTER HAVEN, FL

730 W Central Ave, Winter Haven, FL 33880

Air conditioning | Walk-in closets | Ceiling fan

2 beds

1 bath

$1,200

Apartment for rent

Brightly Renovated Apartment Steps from Lake Howard

This beautifully updated 2-bedroom, 1-bathroom apartment offers a warm atmosphere with spacious bedrooms featuring walk-in closets. Enjoy the airy living space with oversized windows and a modern kitchen equipped with stainless steel appliances. Located just minutes from downtown Winter Haven's dining and shopping, this charming home includes lawn care and water in the rent, ensuring hassle-free living. Perfect for those seeking comfort and convenience near the scenic shores of Lake Howard.

2h ago

8.4

Very good

2850 Lake Alfred Road

2850 Lake Alfred Rd, Winter Haven, FL 33881

1 bed

1 bath

$995

Apartment for rent

Lakeside Living with Utilities Included

Beautiful lakefront apartment offers a carefree lifestyle with included power and water. Newly updated appliances and cabinetry enhance the charm of this one-bedroom haven. Enjoy tile flooring throughout, abundant natural light, and a private kitchen off the living area. The bathroom features a floor-to-ceiling shower and stylish vanity lights. This serene retreat is ready for immediate move-in, providing an ideal escape by Lake Ida.

13h ago

Under 1500 Downtown Winter Haven apartment for rent in Winter Haven

669 Avenue B NW Apt 7

669 Avenue B Nw, Winter Haven, FL 33881

Studio

1 bath

$1,150

Apartment for rent

Description

Welcome to the Lucia Apartments, where historic character and charm meet thoughtful modern updates. This beautifully refreshed 585-square-foot, second-story studio apartment offers a bright and inviting living space with an abundance of natural light, new flooring throughout, and unique architectural details that give the home a personality you simply don't find in a typical apartment. The spacious and versatile floor plan offers a separate area that can be used as a sleeping area, home office, or additional living space, allowing you to make the apartment work for your li

13h ago

Under 1500 Downtown Winter Haven apartment for rent in Winter Haven

669 Avenue B NW Apt 9

669 Avenue B Nw, Winter Haven, FL 33881

1 bed

1 bath

$1,195

Apartment for rent

Description

Welcome to this beautifully renovated first-floor apartment in Winter Haven! This charming 1-bedroom, 1-bathroom apartment offers approximately 595 square feet of comfortable living space and has been completely updated from top to bottom. The open floor plan creates a spacious and inviting feel, with the living area flowing seamlessly into the dining area located just off the kitchen, making the space perfect for both everyday living and entertaining. The apartment features brand-new flooring throughout, fresh interior paint, new kitchen cabinets, and new countertops, cre

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13h ago

Under 1500 Downtown Winter Haven apartment for rent in Winter Haven

669-Avenue B NW Apt 10

669 Avenue B Nw, Winter Haven, FL 33881

1 bed

1 bath

$1,195

Apartment for rent

Description

Welcome to Lucia Apartments, where comfort and modern updates come together in this beautifully refreshed second-story apartment in Winter Haven. This 1-bedroom, 1-bathroom apartment features fresh interior paint, brand-new flooring, new kitchen cabinets, and new countertops, creating a clean and modern space that is move-in ready. The open living area offers a comfortable layout with plenty of room for relaxing and entertaining, while the large windows throughout the apartment fill the home with an abundance of natural light, creating a bright and welcoming atmosphere. Th

Rent special

1d ago

7.8

Very good

Country Place Apartment Homes

3950 Country Pl, Winter Haven, FL 33880

2–3 beds

1–2 baths

$999–$1,275

Apartment for rent

2d ago

8.1

Very good

5657 Struthers Court

5657 Struthers Ct, Winter Haven, FL 33884

2 beds

1 bath

$1,475

Apartment for rent

Renovated 2BR duplex near Cypress Gardens Blvd

Set in Winter Haven, FL, this renovated 2-bedroom, 1-bathroom duplex includes a brand-new roof, screened-in lanai, washer and dryer, new stove, and large deep freezer. The property sits on an oversized lot with 2 parking spaces in a quiet area off Cypress Gardens Boulevard, minutes from shopping, restaurants, and major highways. No fee listing at $1,475/month.

Showing 51 - 72 of 72 results
Home > Apartments in Winter Haven
Updated: September 4, 2026

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Looking for under $1,500 apartments in Winter Haven, FL near you?

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💰Best rent deal428 Avenue E Se
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🧦In-unit laundry
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