Zumper

Apartments Under $1,500 in Winter Haven, FL

131 rentals

907 Lake Jessie Dr #B - Photo 1 of 1

5d+ ago

Under 1500 apartment for rent in Winter Haven

907 Lake Jessie Dr #B, Winter Haven, FL 33881

Carpet | Outdoor space

1 bed

1 bath

$1,200

Apartment for rent

Available Dec 30

Beautiful Duplex with Lake Views & No Carpet

This stunning 1-bed, 1-bath duplex features no carpet and a large backyard, perfect for outdoor enjoyment. Enjoy private covered parking and a secured hallway entry. With breathtaking lake views just across the street and a location close to shopping and dining, this home combines convenience and charm for a delightful living experience.

907 Lake Jessie Dr #A - Photo 1 of 1

5d+ ago

Under 1500 apartment for rent in Winter Haven

907 Lake Jessie Dr #A, Winter Haven, FL 33881

On-site laundry | Carpet | Outdoor space

1 bed

1 bath

$1,200

Apartment for rent

Available Dec 30

Charming Duplex with Lake Views & Spacious Yard

This delightful 1-bed, 1-bath duplex offers a bright and inviting atmosphere with NO CARPET throughout. Enjoy a large backyard, shared laundry, and a secure entryway. The stunning lake view just across the street enhances the charm of this home, conveniently located near shops and dining. Perfect for a cozy, low-maintenance lifestyle in sunny Winter Haven!

1300 Virginia Dr Sw - Photo 1 of 1

5d+ ago

Under 1500 Tranquility Park apartment for rent in Winter Haven

2BR/1.0BA

1300 Virginia Dr Sw, Winter Haven, FL 33880

2 beds

1 bath

$1,175

Apartment for rent

147 Palm Dr - Photo 1 of 1

5d+ ago

Under 1500 house for rent in Winter Haven

Single Family Residence - WINTER HAVEN, FL

147 Palm Dr, Winter Haven, FL 33880

Ceiling fan | Outdoor space

2 beds

1 bath

$1,275

House for rent

Charming Home with Screened Porch & Fenced Yard

This inviting 2-bedroom, 1-bath home spans 1,184 sq ft and features a bonus room and utility space. Freshly painted with all-new flooring, it offers a screened-in porch and a spacious, fenced backyard. Conveniently located near the Polk Parkway and minutes from Highway 27 and LEGOLAND, this lovely home is ideal for those seeking comfort and accessibility in a vibrant community.

2065 Isle Royale Ct Se - Photo 1 of 1

5d+ ago

Under 1500 condo for rent in Winter Haven

2065 Isle Royale Ct Se, Winter Haven, FL 33880

Assigned parking | Swimming pool | Dishwasher

1 bed

1 bath

$1,149

Condo for rent

Bright and Cozy Condo with Lakefront Access

This charming 1-bedroom, 1-bathroom condo offers a comfortable living space with large windows filling the home with natural light. The functional kitchen boasts ample cabinetry, while the spacious living area is perfect for relaxation. Conveniently located near shopping, dining, and the beautiful Chain of Lakes, this pet-friendly home includes access to a community pool and assigned parking. Ideal for effortless everyday living.

1103 Cypress Gardens Blvd #C106 - Photo 1 of 1

5d+ ago

Under 1500 condo for rent in Winter Haven

Condominium - WINTER HAVEN, FL

1103 Cypress Gardens Blvd #C106, Winter Haven, FL 33884

Ceiling fan

1 bed

1 bath

$1,100

Condo for rent

Charming Ground Floor Condo with Lake Access

Experience lakeside living in this delightful 1-bedroom, 1-bathroom ground floor condo, boasting 475 sq. ft. of cozy space. Newly updated with luxury vinyl plank flooring and fresh paint, it offers modern comfort with a ceiling fan and central air. Enjoy easy access to Lake Roy on the Winter Haven Chain of Lakes, perfect for relaxation and outdoor activities. Ideal for those seeking a tranquil retreat in a convenient location.

902 25th St Nw - Photo 1 of 1

5d+ ago

Under 1500 apartment for rent in Winter Haven

Half Duplex - WINTER HAVEN, FL

902 25th St Nw, Winter Haven, FL 33881

In-unit laundry | On-site laundry | Dishwasher

2 beds

1 bath

$1,295

Apartment for rent

Fully Remodeled Apartment with Spacious Yard

This stylish 2-bedroom, 1-bath apartment features a completely remodeled interior with vinyl plank flooring throughout. The living room flows into an eat-in area or TV room, complemented by a separate laundry space. Enjoy a large backyard perfect for outdoor activities, and take advantage of ample parking. Located just blocks from the lake, this vibrant space combines modern living with the charm of the outdoors.

730 W Central Ave #7 - Photo 1 of 1

5d+ ago

Under 1500 apartment for rent in Winter Haven

Apartment - WINTER HAVEN, FL

730 W Central Ave #7, Winter Haven, FL 33880

In-unit laundry | Walk-in closets | Dishwasher

2 beds

1 bath

$1,200

Apartment for rent

Updated Apartment Steps from Lake Howard

This charming second-floor 2-bedroom, 1-bath apartment offers 800 sq ft of modern living just moments from Lake Howard. Enjoy a bright, open layout with large windows, a well-equipped kitchen with stainless steel appliances, and a spacious walk-in closet. The dual-access bathroom adds privacy for guests. Located near vibrant downtown restaurants and shops, with lawn care and water included for added convenience. Experience the best of downtown living in this inviting space!

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1100 Martinique Dr #203 - Photo 1 of 1

5d+ ago

Under 1500 condo for rent in Winter Haven

Condominium - WINTER HAVEN, FL

1100 Martinique Dr #203, Winter Haven, FL 33884

In-unit laundry | Ceiling fan | Dishwasher

2 beds

1 bath

$1,500

Condo for rent

Turn-Key Condo Near LegoLand & Shopping Excitement

Spacious and updated 2-bed, 1-bath condo featuring modern appliances and ceiling fans, designed for comfort. Nestled in the vibrant Orchid Springs area, this turn-key home is perfect for those seeking convenience near shopping, golf, and LegoLand, all without age restrictions. Enjoy a casual lifestyle in this welcoming community!

2001 San Marcos Dr Se - Photo 1 of 1

5d+ ago

Under 1500 condo for rent in Winter Haven

1 BR, 1 BA in Winter Haven

2001 San Marcos Dr Se, Winter Haven, FL 33880

Outdoor space

1 bed

1 bath

$1,300

Condo for rent

Available Dec 11

Stylish First-Floor Condo with Pool Access

This charming 1-bedroom, 1-bathroom condo on the first floor features unique designer concrete floors that elevate the style. The cozy bedroom and well-designed bathroom provide comfort and convenience. Enjoy community amenities, including a sparkling swimming pool, perfect for unwinding or socializing. With its prime location near Cypress Gardens Blvd, this inviting space is an ideal choice for comfortable living.

2040 San Marcos Dr Se - Photo 1 of 1

5d+ ago

Under 1500 condo for rent in Winter Haven

2 BR, 2 BA in Winter Haven

2040 San Marcos Dr Se, Winter Haven, FL 33880

High ceilings | Outdoor space

2 beds

2 baths

$1,400

Condo for rent

Available Nov 26

Bright & Inviting First-Floor Condo with Pool Access

This spacious 2-bed, 2-bath first-floor condo offers high ceilings in the living area, creating an airy feel. Enjoy the convenience of an ensuite master bedroom, along with access to a sparkling community pool perfect for relaxation. Nestled in a peaceful community, this property combines comfort and accessibility, just moments away from shopping, dining, and entertainment. Pet-friendly and ready to welcome you home!

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2824 Avenue G Nw - Photo 1 of 1

5d+ ago

Under 1500 apartment for rent in Winter Haven

Apartment - WINTER HAVEN, FL

2824 Avenue G Nw, Winter Haven, FL 33880

Ceiling fan | Outdoor space

1 bed

1 bath

$1,100

Apartment for rent

Charming Lakeside Apartment with Modern Upgrades

This beautifully updated 1-bedroom, 1-bath apartment spans 680 sq. ft. and features stylish ceramic tile flooring, newer cabinets, and appliances. Enjoy serene views overlooking Deer Lake from the spacious backyard, with lawn care included. Perfect for relaxed living in a convenient space, this inviting unit offers both comfort and modern amenities in a peaceful setting.

1995 5th St Ne #1995 - Photo 1 of 1

5d+ ago

Under 1500 apartment for rent in Winter Haven

3 BR, 1 BA in Florence Villa

1995 5th St Ne #1995, Winter Haven, FL 33881

Outdoor space

3 beds

1 bath

$1,195

Apartment for rent

Available Dec 1

Spacious 3-Bed Home with Fenced Yard for Pets

This charming 3-bedroom, 1-bath home is designed for comfortable living with an open floor plan that seamlessly connects the living and dining areas. The fenced-in backyard offers a perfect space for outdoor gatherings or relaxing in the fresh air. Enjoy easy-to-clean flooring throughout and a supportive application process for all pet lovers. With plenty of room for family fun, this residence is inviting and ready for its next chapter.

1595 28th St Nw - Photo 1 of 1
3D tour

5d+ ago

Under 1500 house for rent in Winter Haven

1595 28th St Nw, Winter Haven, FL 33881

Concierge service | Package service

2 beds

1 bath

$1,450

House for rent

Available Oct 1

Charming 2-Bedroom Haven Close to Local Amenities

This inviting 2-bedroom, 1-bath house features 1,117 sq. ft. of comfortable living space in a serene neighborhood. Enjoy nearby shopping, parks, and local conveniences. Tenants can benefit from a package offering identity theft protection and more, making this home a perfect blend of comfort and convenience.

845 Orchid Springs Dr - Photo 1 of 1

5d+ ago

Under 1500 apartment for rent in Winter Haven

Condominium - WINTER HAVEN, FL

845 Orchid Springs Dr, Winter Haven, FL 33884

In-unit laundry | Swimming pool | Ceiling fan

2 beds

1 bath

$1,285

Apartment for rent

Charming Apartment with Pool Access Near Legoland

This well-maintained 2-bedroom, 1.5-bath apartment offers 888 sq ft of comfort and convenience in Winter Haven. Equipped with essential appliances and in-unit laundry, it provides hassle-free living. Enjoy community amenities like a refreshing swimming pool and easy access to dining and recreation, just minutes from Legoland and Lake Hamilton. Perfect for long-term stays in a vibrant setting!

208 Sears Ave Ne - Photo 1 of 1

5d+ ago

Under 1500 house for rent in Winter Haven

House for rent

Charming Home with Fenced Yard and New Carpet

A delightful 3-bedroom, 1-bathroom single-family home featuring newer carpet throughout and a fenced yard for added privacy. This cozy retreat is perfect for gardening or outdoor activities. Enjoy the convenience of a refrigerator and range as part of your new living space. Embrace the comfort and tranquility this welcoming home offers.

2001 San Marcos Dr Se #3 - Photo 1 of 1

5d+ ago

Under 1500 condo for rent in Winter Haven

Condominium - WINTER HAVEN, FL

2001 San Marcos Dr Se #3, Winter Haven, FL 33880

In-unit laundry | Swimming pool | Outdoor space

1 bed

1 bath

$1,300

Condo for rent

Stylish First-Floor Condo with Pool Access

This charming 1-bedroom, 1-bath condo features designer concrete floors that add flair to the living space. With 792 square feet, the unit offers a cozy bedroom and a functional bathroom for everyday needs. Residents enjoy a sparkling swimming pool, perfect for relaxing and social gatherings. Located conveniently off Cypress Gardens Blvd, this inviting condo is an ideal place to call home in a welcoming community.

2241 9th St Se - Photo 1 of 1

5d+ ago

Under 1500 townhouse for rent in Winter Haven

Apartment - WINTER HAVEN, FL

2241 9th St Se, Winter Haven, FL 33880

In-unit laundry | Air conditioning | Balcony

2 beds

2 baths

$1,350

House for rent

Modern Townhome with Move-In Incentive & Updates

Enjoy contemporary living in this 2-bedroom, 2-bath townhome featuring a stylish updated kitchen with stainless steel appliances, LVP flooring downstairs, and cozy carpeting upstairs. Appreciate the vaulted ceilings in the bathrooms, a back screen porch for relaxation, and a private balcony off the master bedroom. The included lawn care and unique financial flexibility with deposit-free living through Obligo enhance this rental's appeal. Plus, the second month’s rent is free!

2251 9th St Se - Photo 1 of 1

5d+ ago

Under 1500 townhouse for rent in Winter Haven

Apartment - WINTER HAVEN, FL

2251 9th St Se, Winter Haven, FL 33880

In-unit laundry | Air conditioning | Walk-in closets

2 beds

2 baths

$1,250

House for rent

Modern Townhome with Unique Move-In Incentives

Enjoy the charm of this 2-bedroom, 2-bath corner unit townhome featuring an open layout, formal dining room, and spacious master suite with vaulted ceilings and double walk-in closets. The property also includes a 2-car carport and washer/dryer hookups. With a special offer of one month free on approved leases and deposit-free living options, this residence not only offers contemporary comfort but also financial flexibility. Experience worry-free living with included amenities like maintenance support and tenant rewards.

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2210 Avenue C Nw - Photo 1 of 1

5d+ ago

Under 1500 apartment for rent in Winter Haven

2210 Ave C NW, apt b

2210 Avenue C Nw, Winter Haven, FL 33880

Air conditioning

1 bed

1 bath

$1,120

Apartment for rent

Description

Welcome to this beautiful 1 Bed 1 Bathroom Apartment centrally located on the heart of Winter haven by Lake Howard Rental Terms * Rent: $1,120.00 * Utilities: $30.00 * Application Fee: $19.99 per adult 18 and over (non-refundable) * Available to move-in: Immediate Move In * Renters Insurance Required All applicants 18 and over must each submit an application, upload copies of Identification, Social Security, and Proof of Income (current last three months of paystubs) to process your application. Please contact us so we can discuss the requirements for this rental proper

2854 Lake Alfred Rd #LOT5 - Photo 1 of 1

5d+ ago

Under 1500 house for rent in Winter Haven

2 beds

1 bath

$797

House for rent

Available Oct 7

Updated Mobile Home with Charming Outdoor Space

This cozy 2-bedroom, 1-bath mobile home boasts modern updates and a welcoming ambiance throughout. With stylish finishes, new flooring, and an open layout, the space is bright and inviting. The kitchen features sleek stainless steel appliances, while a private covered patio offers a perfect spot for relaxation or entertaining. Assigned off-street parking adds convenience, making this pet-friendly residence ideal for comfortable living.

523 Winter Terrace #1 - Photo 1 of 1

5d+ ago

Under 1500 condo for rent in Winter Haven

523 Winter Terrace - 1

523 Winter Terrace #1, Winter Haven, FL 33881

In-unit laundry | Air conditioning | Central heat

3 beds

2 baths

$1,450

Condo for rent

Available Dec 9

Charming Lakeview Condo with Florida Room

This beautifully maintained 3-bedroom, 2-bathroom condo features a spacious 1,073 sq. ft. layout with an open floor plan and split design for privacy. The enclosed Florida Room adds versatility, perfect for relaxation or entertaining. Enjoy community amenities like lake access with a private dock, a clubhouse, and pool. Centrally located near shopping and dining, this pet-friendly home is ideal for enjoying the Florida lifestyle!

817 Orchid Springs Dr #817 - Photo 1 of 1

5d+ ago

Under 1500 condo for rent in Winter Haven

Garden,Low-rise, Condo - Winter Haven, FL

817 Orchid Springs Dr #817, Winter Haven, FL 33884

In-unit laundry | Garage parking | Hardwood floor

2 beds

1 bath

$1,300

Condo for rent

Charming Ground Floor Condo Minutes from Adventure

This inviting ground floor condo features 2 bedrooms and 1.5 baths across 851 sqft of open living space, highlighted by ceramic tile and laminate wood flooring. The cozy living and dining areas lead to a lovely terrace, perfect for relaxation. Rental includes all kitchen appliances and an in-unit washer/dryer. Located just minutes from LEGOLAND and local amenities, this affordable retreat promises convenience and fun in sunny Central Florida.

5605 Struthers Ct #5605 - Photo 1 of 1

5d+ ago

Under 1500 apartment for rent in Winter Haven

2 BR, 2 BA in Winter Haven

5605 Struthers Ct #5605, Winter Haven, FL 33884

In-unit laundry

2 beds

2 baths

$1,495

Apartment for rent

Available Nov 14

Bright & Spacious Duplex Minutes from LEGOLAND

This roomy 2-bedroom, 2-bath duplex boasts an open living and dining area, creating a warm and inviting atmosphere. The well-equipped kitchen leads to a large screened lanai, perfect for outdoor enjoyment. Both bedrooms offer generous closet space, complemented by two full bathrooms for added convenience. A full-sized washer and dryer are included for easy chores. With easy access to LEGOLAND and nearby amenities, this lovely home is ready for immediate move-in.

2600 Lucerne Park Rd - Photo 1 of 1
Age restricted

5d+ ago

Under 1500 condo for rent in Winter Haven

2 BR, 2 BA in Winter Haven

2600 Lucerne Park Rd, Winter Haven, FL 33881

In-unit laundry | Walk-in closets | Dishwasher

2 beds

2 baths

$1,395

Condo for rent

Available Nov 19

Inviting Lakefront Condo in 55+ Community

Enjoy serene lakefront living in this charming 2-bed, 2-bath condo offering stunning canal views. The unit features a cozy Florida Sunroom perfect for relaxation, a well-equipped kitchen, and a spacious primary suite with a walk-in closet. LED lighting and durable flooring optimize the living space. Located just steps from community amenities like a pool and boating and close to pristine nature parks, this well-maintained condo is ideal for embracing the Florida lifestyle.

523 Winter Terrace - Photo 1 of 1

5d+ ago

Under 1500 condo for rent in Winter Haven

523 Winter Terrace, Winter Haven, FL 33881

In-unit laundry | Air conditioning | Assigned parking

3 beds

2 baths

$1,450

Condo for rent

Cozy Lakefront Condo with Enclosed Florida Room

This charming 3-bedroom, 2-bath single-story condo offers 1,073 sq. ft. of comfort in the desirable Winter Ridge community. The open floorplan and enclosed Florida Room create versatile living spaces, perfect for relaxation or entertaining. Enjoy convenient amenities such as lake access with a private dock, a clubhouse, pool, and shuffleboard courts. Centrally located for quick access to shopping and dining, this pet-friendly condo is a delightful retreat in Florida.

351 Avenue N Ne #1 - Photo 1 of 1

5d+ ago

Under 1500 apartment for rent in Winter Haven

351 Ave N NE, Unit 1

351 Avenue N Ne #1, Winter Haven, FL 33881

In-unit laundry | Ceiling fan

Studio

1 bath

$1,000

Apartment for rent

Available Dec 2

Freshly Renovated Studio with Modern Finishes

This chic 400 sq. ft. studio boasts modern updates, featuring luxury vinyl plank flooring, updated lighting, and a stylish kitchen with stainless steel appliances. Convenient in-unit washer and dryer hookups make life easier. With designated parking and a prime location near downtown Winter Haven, grocery stores, and restaurants, this compact yet efficient space is perfect for those seeking comfort and convenience in a vibrant area.

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351 Avenue N Ne #2 - Photo 1 of 1

5d+ ago

Under 1500 apartment for rent in Winter Haven

351 Avenue N NE, Unit 2

351 Avenue N Ne #2, Winter Haven, FL 33881

In-unit laundry | Ceiling fan

Studio

1 bath

$1,000

Apartment for rent

Available Dec 2

Modern Studio Retreat with Updated Features

This freshly renovated studio offers a chic living space with luxury vinyl plank flooring and contemporary finishes. The kitchen boasts sleek cabinetry and stainless-steel appliances, while in-unit washer and dryer hookups add convenience. Located near downtown Winter Haven, enjoy easy access to grocery stores, restaurants, and more. Ideal for those seeking a modern, efficient layout without the fuss. Perfect for comfortable living in a practical setting!

1010 4th St Se - Photo 1 of 1

5d+ ago

Under 1500 apartment for rent in Winter Haven

Apartment for rent

Spacious & Bright 3-Bedroom Haven

This airy 3-bed, 2-bath apartment in Winter Haven offers ample space with an open floor plan perfect for relaxing or entertaining. Located in a desirable neighborhood, it features 1,250 sq. ft. of living space. The pet-friendly unit includes an HOA approval and a Resident Benefits Package for added convenience. Don't miss out on this fantastic rental opportunity!

1995 5th St Ne - Photo 1 of 1

5d+ ago

Under 1500 house for rent in Winter Haven

Single Family Residence - WINTER HAVEN, FL

1995 5th St Ne, Winter Haven, FL 33881

Outdoor space

3 beds

1 bath

$1,195

House for rent

Charming 3-Bed Home with Fenced-In Backyard

This inviting 3-bedroom, 1-bath home features a spacious open floor plan perfect for relaxed living. Enjoy a fenced-in backyard ideal for gatherings and outdoor activities. With easy-to-clean flooring throughout and a layout that encourages comfort, this residence is a delightful escape in Winter Haven. Don't miss the opportunity to enjoy this charming space!

1702 Recker Highway #D - Photo 1 of 1

5d+ ago

Under 1500 condo for rent in Winter Haven

Newly Remodeled - 2 Bed/1 Bath Apartment in Winter Haven - Available 10/22

1702 Recker Highway #D, Winter Haven, FL 33880

On-site laundry | Ceiling fan

2 beds

1 bath

$1,450

Condo for rent

Available Dec 1

Stylishly Remodeled Condo Minutes from Downtown

This chic 2-bedroom, 1-bath condo has been beautifully remodeled with plank flooring, wood cabinetry, and stunning granite countertops. Enjoy new light fixtures, a ceiling fan in the bedrooms, and easy access to shopping, restaurants, and LEGOLAND. With 800 sq ft of comfortable living space, this condo combines modern updates with convenience, making it an ideal choice for those seeking a vibrant lifestyle in Winter Haven.

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.

2040 San Marcos Dr Se #103 - Photo 1 of 1

5d+ ago

Under 1500 condo for rent in Winter Haven

Condominium - WINTER HAVEN, FL

2040 San Marcos Dr Se #103, Winter Haven, FL 33880

In-unit laundry | Swimming pool | Ceiling fan

2 beds

2 baths

$1,400

Condo for rent

Bright First-Floor Condo with Pool Access

Experience spacious living in this inviting 2-bedroom, 2-bath first-floor condo boasting high ceilings and an airy ambiance. The master suite features a private ensuite for added comfort. Located in a well-kept community, enjoy access to a sparkling pool perfect for relaxation. With its prime location near shopping, dining, and entertainment, this condo blends comfort and convenience in a vibrant setting.

301 Avenue B Se #301-4 - Photo 1 of 1

5d+ ago

Under 1500 apartment for rent in Winter Haven

1 BR, 1 BA in East College

301 Avenue B Se #301-4, Winter Haven, FL 33880

1 bed

1 bath

$1,000

Apartment for rent

Available Sep 1

Charming 1-Bedroom Retreat Near Legoland

This cozy 1-bedroom, 1-bathroom unit offers a comfortable layout in a peaceful quadruplex, ideal for singles or couples. With 1,052 sq. ft. of living space, it’s just 10 minutes from Legoland. Enjoy pet-friendly living in a quiet environment with manageable lease terms. Minimum credit score and other qualification requirements apply. Perfect for those seeking a charming getaway in Winter Haven!

612 Lake Ned Rd - Photo 1 of 1

5d+ ago

Under 1500 house for rent in Winter Haven

Single Family Residence - WINTER HAVEN, FL

612 Lake Ned Rd, Winter Haven, FL 33884

In-unit laundry | Air conditioning | Garage parking

2 beds

1 bath

$1,460

House for rent

Charming Home Near Lakes & Adventure Awaits

This inviting 2-bed, 1-bath residence offers a fantastic location in SE Winter Haven, just minutes from Legoland and Orlando. Enjoy fresh paint, new AC (2017), an oversized two-car garage, and a screened lanai. Explore the beauty of the Winter Haven Chain of Lakes with nearby public boat ramps. With deposit-free living options and added resident benefits, this home combines comfort, convenience, and ease for modern living.

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1020 4th St Se - Photo 1 of 1

5d+ ago

Under 1500 apartment for rent in Winter Haven

1020 4th St Se, Winter Haven, FL 33880

In-unit laundry | Assigned parking

3 beds

2 baths

$1,400

Apartment for rent

Bright & Spacious 3-Bed Apartment for Families

Offering ample room for relaxation and entertaining, this airy 3-bedroom, 2-bath apartment features an open floor plan with generous square footage. Conveniently located in a desirable neighborhood, it includes in-unit laundry and assigned parking. With its welcoming atmosphere, this pet-friendly home is perfect for families looking to make lasting memories. Don't miss the chance to call this charming space your own!

44 Stebbins Dr #44 - Photo 1 of 1

5d+ ago

Under 1500 apartment for rent in Winter Haven

Mobile Home, Residential - Winter Haven, FL

44 Stebbins Dr #44, Winter Haven, FL 33884

Garage parking

2 beds

2 baths

$1,250

Apartment for rent

Charming 2-Bed Home in a Peaceful Community

Own a delightful 2-bedroom, 2-bath home in a well-kept neighborhood that feels like a daily getaway. This inviting property boasts spacious living areas and has been updated for modern comfort. Situated in the Grove Shores community, it offers a tranquil environment with convenient amenities. Take advantage of special incentive programs and experience the joys of easy living in this lovely residence!

20 Stebbins Dr #20 - Photo 1 of 1

5d+ ago

Under 1500 apartment for rent in Winter Haven

Mobile Home, Residential - Winter Haven, FL

20 Stebbins Dr #20, Winter Haven, FL 33884

Garage parking

2 beds

1 bath

$1,200

Apartment for rent

Cozy Living in a Tranquil Community Setting

This 2-bedroom, 1-bath home is perfect for enjoying a serene lifestyle in a well-maintained neighborhood. Featuring plenty of living space, this updated residence offers a vacation-like feel every day. Residents will benefit from a professionally managed community with special incentive programs available. Don’t miss out on this opportunity!

1733 2nd St Nw #B - Photo 1 of 1

5d+ ago

Under 1500 apartment for rent in Winter Haven

Half Duplex - WINTER HAVEN, FL

1733 2nd St Nw #B, Winter Haven, FL 33881

Ceiling fan | Outdoor space

2 beds

1 bath

$1,200

Apartment for rent

Cozy Remodeled Duplex with Spacious Yard

This beautifully renovated 2-bedroom, 1-bath duplex offers a perfect blend of comfort and convenience. Spanning 750 square feet, it features a spacious backyard ideal for relaxation and play. Ideally located minutes from local shopping and entertainment, this cozy home is perfect for those who relish a vibrant lifestyle. Enjoy central air, ceiling fans, and a bright atmosphere in this inviting space. A wonderful opportunity for easy living awaits!

723 Jenny Wren Rd #723 - Photo 1 of 1
New construction

5d+ ago

Under 1500 apartment for rent in Winter Haven

Mobile Home, Mobile/Manufactured - Winter Haven, FL

723 Jenny Wren Rd #723, Winter Haven, FL 33881

In-unit laundry | Garage parking | Swimming pool

2 beds

2 baths

$1,100

Apartment for rent

Brand New Senior Living with Modern Comfort

Experience modern comfort in this brand new 2-bed, 2-bath mobile home in a vibrant senior community. Enjoy stainless steel kitchen appliances and a screened room, with a carport in the works. Washer/dryer hook-ups available. Complete with air conditioning and walk-in closet, community amenities include garage parking and a swimming pool. Perfect for long-term rental.

514 Avenue C Ne #4 - Photo 1 of 1

5d+ ago

Under 1500 apartment for rent in Winter Haven

514 Avenue C Ne #4, Winter Haven, FL 33881

2 beds

1 bath

$1,150

Apartment for rent

Bright Renovated Apartment Near Parks & Schools

This charming 2-bedroom, 1-bathroom apartment features a recent renovation and is ideally located just a short walk from Rotary and Kiwanis Parks. With 468 square feet of cozy living space and water included in the rent, it's perfect for comfortable living. Close proximity to schools like Jewett School of the Arts makes it an ideal choice for families seeking convenience and vibrant community life. Enjoy the cozy atmosphere and easy access to outdoor activities!

1303 Eagle Pond Dr - Photo 1 of 1

5d+ ago

Under 1500 condo for rent in Winter Haven

2 beds

2 baths

$1,300

Condo for rent

Bright Condo with Comfort & Resort-Like Amenities

Experience a vibrant lifestyle in this spacious 2-bed, 2-bath ground-level condo in the gated Cypresswood community. With an open layout and ample closet space, this home offers comfort and convenience. Residents enjoy access to a sparkling pool, tennis and pickleball courts, an on-site restaurant, and a welcoming clubhouse. Perfect for relaxation or socializing, this condo is ideal for those seeking both privacy and a community atmosphere.

433 Flamingo Way #433 - Photo 1 of 1
Age restricted

5d+ ago

Under 1500 apartment for rent in Winter Haven

Mobile Home, Mobile/Manufactured - Winter Haven, FL

433 Flamingo Way #433, Winter Haven, FL 33881

In-unit laundry | Garage parking | Swimming pool

2 beds

1 bath

$1,200

Apartment for rent

Senior Living Oasis with Modern Updates & Porch

This delightful 2-bed, 1.5-bath doublewide home offers a serene living environment for seniors with modern upgrades like new flooring and fresh paint. Enjoy the bright bay window, ceiling fans, and a screened porch. Includes fridge, stove, dishwasher, and microwave. Savor convenience with in-unit laundry hookups, garage parking, and a community swimming pool. Rent-to-own option available with 25% down.

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1480 32nd St Nw - Photo 1 of 1

5d+ ago

Under 1500 apartment for rent in Winter Haven

1480 32nd St Nw, Winter Haven, FL 33881

Ceiling fan

2 beds

1 bath

$1,000

Apartment for rent

Bright and Functional Duplex in Winter Haven

This charming duplex features 2 bedrooms and 1 bathroom within a thoughtful 950 sq ft layout. The bright kitchen, equipped with essential appliances, flows into an inviting living area, perfect for relaxation or entertaining. The spacious first bedroom ensures comfort, while the second bedroom offers flexibility for guests or a home office. Enjoy easy access to nearby shopping, dining, and parks, combining quiet living with city conveniences. Monthly pest control for just $20.

1d ago

7.7

Very good

Country Place Apartment Homes

3950 Country Pl, Winter Haven, FL 33880

2–3 beds

1–3 baths

$1,150–$1,275

Apartment for rent

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Updated: January 20, 2026

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

🔑Available apartment rentals131
💰Best rent deal2854 Lake Alfred Rd #LOT5
Popular amenities, ,
🧦In-unit laundry
🍽With dishwasher
🏠With photos

For more in depth rent prices, check out our Winter Haven, FL rent data, which covers average and median rents in Winter Haven, FL.

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