Zumper

Apartments Under $1,500 in Winter Haven, FL

157 rentals available

407 Eagle Pond Dr #407 - Photo 1 of 1

4h ago

Under 1500 condo for rent in Winter Haven

407 Eagle Pond Dr #407, Winter Haven, FL 33884

Swimming pool | Walk-in closets | Ceiling fan

2 beds

2 baths

$1,450

Condo for rent

Description

Property Status: Active Upstairs 2 bedroom 2 bath corner unit condo located in the Eagle Pond neighborhood at Cypresswood Golf and Country Club. The country club amenities include access to the clubhouse with bar and grill, jr. Olympic swimming pool and pickleball/tennis courts. The championship 18 hole golf course is open to the public. As an added bonus, Publix just opened a brand new location just a mile down the road which is sure to attract other popular businesses. Office Phone: (863) 224-2297 Copyright © 2026 Stellar MLS. All rights reserved. All information provide

104 Mayfair Pl Sw - Photo 1 of 1

4h ago

Under 1500 house for rent in Winter Haven

SINGLE_FAMILY - WINTER HAVEN, FL

104 Mayfair Pl Sw, Winter Haven, FL 33880

Air conditioning | On-site laundry | Ceiling fan

2 beds

2 baths

$1,395

House for rent

Description

Property Status: Active Virtually Staged. Wonderful 2 bedroom/2 bath unit with spacious, soaring ceilings, neutral colors, and very ENERGY EFFICIENT: Brand New A/C system, Brand New Gas Hot Water Heater, Brand New Gas Heat Furnace---so low utility bills! Just professionally painted inside, new door hardware, new bathroom light fixtures & sink faucets. Easy-to-maintain ceramic tile floors throughout, STAINLESS appliances and any chef's delight, a gas range. There's a large inside laundry, plenty of storage, and ceiling fans in every room. Primary bedroom has sliders opening

The Breeze - Photo 1 of 1
Rent special
New construction

5h ago

8.7

Very good

The Breeze

265 Avenue E Sw, Winter Haven, FL 33880

Swimming pool | Fitness center | Elevator

Studio–1 bed

1 bath

$1,340–$1,865

Apartment for rent

Pet-friendly Winter Haven apartments with pool

Set in South College, Winter Haven, FL, these new construction apartments feature gourmet-inspired kitchens, stainless steel appliances, and controlled access. The community includes a pool, fitness center, business center, EV charging, and valet trash service - near Central Park Downtown Winter Haven and top-rated schools within half a mile.

Raindance - Photo 1 of 1
Rent special

5h ago

8.5

Very good

Raindance

200 Avenue C Sw, Winter Haven, FL 33880

Swimming pool | Fitness center | Elevator

1 bed

1 bath

$1,295–$1,700

Apartment for rent

Downtown Winter Haven apartments with pool & gym

Located in Downtown Winter Haven, these modern apartments feature designer interiors, expansive windows, and controlled-access grounds. The community includes a fitness center, pool, recreation room with pool table, EV charging, coffee bar, and valet service. Near Central Park Downtown Winter Haven and top-rated schools within half a mile.

Dream Winter Haven - Photo 1 of 1

7h ago

8

Very good

Dream Winter Haven

5004 Dream Dr, Winter Haven, FL 33880

1 bed

1 bath

$1,299–$1,519

Price drop

Apartment for rent

Tranquil Living with Stunning Water Views

Residents of Dream Winter Haven enjoy serene water views and a pet-friendly atmosphere in this vibrant community. With multiple floor options, each unit boasts captivating sights that enhance everyday living. A perfect retreat for those seeking a peaceful lifestyle while still being nestled in a lively environment.

710 Avenue C SW - Photo 1 of 1

10h ago

7.7

Very good

710 Avenue C SW

710 Avenue C Sw, Winter Haven, FL 33880

On-site laundry | Walk-in closets

1 bed

1 bath

$1,050

Apartment for rent

Cozy Living Near Downtown Winter Haven

Residents of 710 Avenue C SW enjoy a delightful 14-unit apartment complex conveniently located near Downtown Winter Haven, FL. Enjoy proximity to local shops, dining, and entertainment.

Nearby rental good for eco-living

Nearby rental good for pet owners

Lake Silver Apartments - Photo 1 of 1

17h ago

Under 1500 apartment for rent in Winter Haven

Lake Silver Apartments

207 S Lake Silver Dr Nw, Winter Haven, FL 33881

Dishwasher

1 bed

1 bath

$1,125

Apartment for rent

Serene Lakeside Living with Stunning Views

Experience tranquil lakeside living in this cozy 2-bedroom, 2-bathroom apartment. Residents enjoy breathtaking lakefront views and peaceful surroundings. The community features convenient on-site laundry and a lovely Community Dock for relaxation by the water. Embrace the beauty and serenity of this unique living space in Winter Haven, FL, where comfort meets nature. Pet-friendly options available based on screening results.

64 Stebbins Dr #64 - Photo 1 of 1

23h ago

Under 1500 house for rent in Winter Haven

SINGLE_FAMILY - Winter Haven, FL

64 Stebbins Dr #64, Winter Haven, FL 33884

2 beds

2 baths

$875

House for rent

New 2-bed, 2-bath with garage in Winter Haven

Located in Winter Haven, FL, this 2-bed, 2-bath unit in Grove Shores offers 896 sqft of updated living space from 2022. The professionally managed community includes garage parking, and a top-rated elementary school sits within 0.6 miles for families with school-age children.

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1484 32nd St Nw - Photo 1 of 1

1d ago

Under 1500 house for rent in Winter Haven

2 beds

1 bath

$1,100

House for rent

Description

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 living areas, providing both

350 Winter Ridge Blvd - Photo 1 of 1

2d ago

Under 1500 condo for rent in Winter Haven

350 Winter Ridge Blvd, Winter Haven, FL 33881

Air conditioning | Assigned parking | Swimming pool

2 beds

2 baths

$1,399

$1,299

Price drop

Condo for rent

Available Jul 20

Description

This beautifully updated 2-bedroom, 2-bathroom condo in the sought-after Winter Ridge community offers a perfect blend of modern comfort and tranquil lakeside living. Located just minutes from downtown Winter Haven, this move-in-ready home is designed for those who appreciate a low-maintenance lifestyle with premium views. Featuring 1,073 sq. ft. of bright, open living space with a great room/dining combo perfect for entertaining. Enjoy stylish luxury vinyl flooring throughout and a fresh, neutral paint palette. A functional galley-style kitchen equipped with a closet pant

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

2d 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

$1,100

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.

1800 3rd Ct SE - Photo 1 of 1

3d ago

8

Very good

1800 3rd Ct SE

1800 3rd Ct Se, Winter Haven, FL 33880

Dishwasher

1 bed

1 bath

$1,025

Apartment for rent

Description

One-Bedroom, one-bathroom close to it all. This all-tile apartment home offers ample cabinet storage in the kitchen along with stainless-steel appliances. With its prime location, this rental provides easy access to local shops, restaurants, and public transportation, making it an ideal choice for anyone seeking a simple, low-maintenance home in a convenient area. Community laundry space. Pets Allowed Based on PetScreening. com Results. Fees/rents based on results. Tenants are required to sign up for our Resident Benefits Package that includes renter's insurance, A/C fi

The Haven Place - Photo 1 of 1

3d ago

7.8

Very good

The Haven Place

955 6th St Se, Winter Haven, FL 33880

1 bed

1 bath

$1,075–$1,190

Apartment for rent

Pet-friendly apartment near Winter Haven High

Located in Winter Haven, FL, this corner unit features laminate floors throughout, modern kitchen cabinets, and includes stove, microwave, and refrigerator. The apartment comes with high-efficiency AC, modern lighting, and security cameras on property. Walking distance to Winter Haven High School, bus line, restaurants, and shopping, with downtown Winter Haven just two blocks away.

The Landings Apartment Homes - Photo 1 of 1
Highly rated
Rent special

3d ago

8.8

Very good

The Landings Apartment Homes

102 Landings Way, Winter Haven, FL 33880

In-unit laundry | Air conditioning | Balcony

1–2 beds

1–2 baths

$1,100–$1,385

Apartment for rent

Pet-friendly Winter Haven apartments with laundry

Located in Winter Haven, FL, these smoke-free apartments include in-unit laundry, air conditioning, and balconies or patios. Units come with high-speed internet access and outdoor spaces. Near South Lake Howard Nature Park, Eagle Lake Sports facilities, and top-rated schools within 0.4 miles - a good fit for pet owners with nearby pet supply stores and outdoor areas.

Summary of resident reviews

The Landings Apartment Homes receives praise for being a nice, tranquil community with exceptional staff. Residents consistently highlight helpful leasing staff like Candace/Candice for their patience and authentic service. Maintenance, particularly Jeff, earns outstanding reviews for quick, friendly service.

The Jade - Photo 1 of 1

3d ago

9

Excellent

The Jade

1150 3rd St Sw, Winter Haven, FL 33880

In-unit laundry | Air conditioning | On-site laundry

1 bed

1 bath

$1,200–$1,670

Apartment for rent

Smart 1-bed apartments near downtown Winter Haven

Located in South College, these smart-enabled 1-bedroom apartments include in-unit laundry, stainless steel appliances, and free high-speed WiFi. The community features a 24/7 fitness center, heated spa, outdoor cinema, coworking lounge with coffee bar, and pickleball courts - a good fit for remote workers and fitness enthusiasts.

New Year Kick Off 2026 at the same rate! - Photo 1 of 1

3d ago

8.1

Very good

New Year Kick Off 2026 at the same rate!

3135 Woodhill Rd, Winter Haven, FL 33881

2 beds

1 bath

$1,350

Apartment for rent

2-bed apartments with granite counters & specials

Located in Winter Haven, FL, these 2-bedroom, 1-bath apartments feature granite countertops and stainless steel appliances in renovated units, plus in-unit washer and dryer in every apartment. Move-in specials include 1-2 months free with a 14-month lease and no admin fees, near Lake Cannon Park and top-rated schools within half a mile.

Review from the web

Goog

- Drucellia Reynolds on Jul 18, 2017
2366 Lake Dr Nw - Photo 1 of 1

4d ago

Under 1500 house for rent in Winter Haven

2366 Lake Dr Nw, Winter Haven, FL 33881

Garage parking | Ceiling fan | Dishwasher

2 beds

2 baths

$1,250

House for rent

Available Jun 11

Updated 2-bed Winter Haven house with garage

Set in Winter Haven, FL, this freshly updated 2-bed, 2-bath house offers modern flooring, clean tile finishes, and a well-equipped kitchen with dishwasher and range. The 1,003 sqft layout includes a garage, utility area, and ceiling fans throughout. Move-in ready condition with landscaping included, close to schools and shopping.

955 6th St Se #5 - Photo 1 of 1

4d ago

Under 1500 apartment for rent in Winter Haven

955 6th St Se #5, Winter Haven, FL 33880

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

1 bed

1 bath

$1,190

Apartment for rent

Description

Property Status: Active The renovated first-floor apartment features laminate floors throughout, beautiful kitchen cabinets, appliances include a stove, microwave, and refrigerator and Washer & Dryer It also features an A/C unit Hight efficiency, modern lighting lamps and blinds. Security cameras on property exteriors. Great location offering walking distance to the bus line, Winter Haven High School, municipal offices, restaurants, shopping areas, Hospitals, and a short drive distance to Sunny Beaches. Office Phone: (321) 939-3748 Copyright © 2026 My State MLS. All rights

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Aqua Apartment Homes - Photo 1 of 1

4d ago

8.3

Very good

Aqua Apartment Homes

2000 15th Ct Nw, Winter Haven, FL 33881

In-unit laundry | Swimming pool | Outdoor space

2 beds

1 bath

$1,385

Apartment for rent

Pet-friendly apartments with pool and dog park

Located in Winter Haven, FL, these apartments feature spacious kitchens with upgraded countertops, tile backsplash, and washer/dryer combo units. The community includes an inground pool, dog park, and picnic area with views from select units. Close to Publix, Winter Haven Hospital, and top-rated schools - a good fit for pet owners with the on-site dog park and pet supply stores nearby.

Summary of resident reviews

Aqua Apartment Homes receives mixed feedback from residents. Some appreciate the quiet environment, but many express concerns about value for the rental rates. Common complaints include pest issues, maintenance response times and fees, parking availability, and grounds upkeep. Residents note renovation quality concerns and utility costs not being included in rent. Management responsiveness varies according to different experiences.

Brandywyne Apartment Homes - Photo 1 of 1
Rent special

4d ago

8.8

Very good

Brandywyne Apartment Homes

418 19th St Se, Winter Haven, FL 33884

In-unit laundry | Air conditioning | Balcony

1–2 beds

1–2 baths

$1,100–$1,285

Apartment for rent

Pet-friendly apartments near top-rated schools

Set in Winter Haven, FL, these pet-friendly apartments include in-unit laundry, dishwasher, and patios or balconies. Units feature air conditioning and walk-up access, with outdoor space and picnic areas on-site. Top-rated elementary and middle schools sit within half a mile - a good fit for pet owners with nearby veterinary care, grooming, and pet supply options.

5665-67 Struthers Ct - Photo 1 of 1

4d ago

8.4

Very good

5665-67 Struthers Ct

5665 Struthers Ct, Winter Haven, FL 33884

2 beds

1 bath

$1,300

Apartment for rent

2-bed duplex near Legoland with HWY 27 access

In Winter Haven, FL, this clean 2-bedroom, 1-bathroom duplex features wood laminate flooring, newer kitchen cabinets, and comes with range/oven and refrigerator. Both bedrooms include ceiling fans and ample space, plus washer/dryer hookups. Near Walmart, Publix, and Legoland with quick highway access to Orlando and Tampa.

Kimberly Cove - Photo 1 of 1

5d+ ago

8.6

Very good

Kimberly Cove

Avenue G Nw, Winter Haven, FL 33881

In-unit laundry

2 beds

1 bath

$1,099

Apartment for rent

Pet-friendly 2BR with W/D hookups near downtown

Located in Winter Haven, FL, this spacious 2-bedroom, 1-bathroom apartment includes 832 square feet, fresh paint, easy-to-clean flooring, and washer/dryer hookups. The community sits near Central Park Downtown Winter Haven, restaurants, and shopping with $500 off first month's rent - a good fit for pet owners and remote workers.

1016 East Lake Silver Drive NE - Photo 1 of 1

5d+ ago

8

Very good

1016 East Lake Silver Drive NE

1016 E Lake Silver Dr Ne, Winter Haven, FL 33881

2 beds

1 bath

$1,400

Apartment for rent

2BR/1BA apartment near Winter Haven Hospital

Located in Winter Haven, FL, this 2-bedroom, 1-bathroom apartment includes ceramic tile floors, central AC, and water in the rent. Near Winter Haven Hospital for healthcare workers, plus close to Central Park Downtown Winter Haven, restaurants, and top-rated schools within a mile.

151 Avenue C SE - Photo 1 of 1

5d+ ago

7.9

Very good

151 Avenue C SE

151 Avenue C Se, Winter Haven, FL 33880

Air conditioning | Microwave

2 beds

1 bath

$1,300

Apartment for rent

513 Avenue J SE - Photo 1 of 1

5d+ ago

7.7

Very good

513 Avenue J SE

513 Avenue J Se, Winter Haven, FL 33880

2 beds

1 bath

$1,269

Apartment for rent

3823 Avenue J Nw - Photo 1 of 1
3D tour

5d+ ago

Under 1500 house for rent in Winter Haven

Charming 3-Bedroom Home in Winter Haven, FL

3823 Avenue J Nw, Winter Haven, FL 33881

Storage | On-site management | Outdoor space

3 beds

1 bath

$1,575

$1,495

Price drop

House for rent

Move-in ready 3-bed house near Legoland

Set in Winter Haven, FL, this pet-friendly 3-bed, 1-bath house offers 1,050 sqft of refreshed living space with LVP flooring and stainless steel appliances. The gated entry leads to an open layout with extensive kitchen storage, covered carport parking, and spacious yard. Located minutes from downtown Winter Haven, Legoland Florida, and a top-rated middle school just 0.08 miles away.

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20 on Second - Photo 1 of 1

5d+ ago

8.3

Very good

20 on Second

240 2nd St Sw, Winter Haven, FL 33880

In-unit laundry | Dishwasher | Microwave

1 bed

1 bath

$1,399

Apartment for rent

Downtown 2BR with quartz counters & walkability

Located in Downtown Winter Haven, this 2-bedroom, 2-bathroom apartment features polished concrete floors, quartz countertops, stainless steel appliances, and in-unit washer/dryer. The open-concept layout includes high ceilings and modern finishes, with walkable access to local shops, dining, and entertainment - a good fit for pet owners with nearby grooming services and pet supply stores.

1802 3rd Ct SE - Photo 1 of 1

5d+ ago

7.8

Very good

1802 3rd Ct SE

1802 3rd Ct Se, Winter Haven, FL 33880

2 beds

1 bath

$1,205

Apartment for rent

2BR/1BA apartment near shopping with parking

Located in Winter Haven, FL, this single-level 2-bedroom, 1-bathroom apartment features an open living area, updated kitchen with ample cabinet space, and central A/C. The unit includes on-site parking, with landlord covering lawn care and pest control. No fee listing near Walmart, Publix, and Cypress Gardens Boulevard for convenient shopping and highway access.

428 Avenue E Se #C - Photo 1 of 1

5d+ ago

Under 1500 apartment for rent in Winter Haven

1-Bedroom studio , 1-Bathroom Apt in Winter Haven

428 Avenue E Se #C, Winter Haven, FL 33880

Concierge service | On-site management | Package service

1 bed

1 bath

$900

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 $12.00 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 **** All residents are enrolled in the Resident Benefits

850 17th Ter Ne - Photo 1 of 1
Rent special
3D tour

5d+ ago

Under 1500 house for rent in Winter Haven

Comfortable 2-Bedroom Home

850 17th Ter Ne, Winter Haven, FL 33881

Ceiling fan | On-site management

2 beds

1 bath

$1,395

House for rent

Move-in ready 2-bed house with covered patio

In Winter Haven, FL, this pet-friendly 2-bed, 1-bath house offers 1,206 sqft with hard surface flooring and an attached carport for convenience. The layout includes a functional kitchen with stainless steel appliances and wood cabinetry, plus a covered back patio for outdoor living - a fit for pet owners with nearby grooming services and pet supply stores.

3062 Saint Paul Dr - Photo 1 of 1

5d+ ago

Under 1500 apartment for rent in Winter Haven

Spacious 2 Bed, 1 Bath Apartment with Essential Conveniences | Pet Friendly | Available Now!

3062 Saint Paul Dr, Winter Haven, FL 33880

Air conditioning | On-site laundry | On-site management

2 beds

1 bath

$1,145

Apartment for rent

Pet-friendly 2-bed apartment with laundry hookups

Sitting in Winter Haven, FL, this pet-friendly 2-bed, 1-bath apartment offers 1,100 sqft with tile flooring and laundry hookups. The kitchen includes a refrigerator, stove/oven, and vent-hood, while central air and forced air heating keep things comfortable year-round. A fit for pet owners with dogs and cats welcome, plus parking pad and on-street options available.

1203 Eagle Pond Dr - Photo 1 of 1

5d+ ago

Under 1500 condo for rent in Winter Haven

1203 Eagle Pond Dr

1203 Eagle Pond Dr, Winter Haven, FL 33884

Carpet | Outdoor space

2 beds

2 baths

$1,500

Condo for rent

Available Jul 14

Description

Spacious 2 Bedroom 2 Bathroom beautifully kept 1st floor condo at Eagle Pond in the Cypresswood Golf & Country Club. New LVP in living area and new carpet in bedrooms, an outdoor seating area, and a great floor plan. 24 hour manned security and all of the amenities you need including golf, tennis, pool, and clubhouse with restaurant and bar. Call today! This unit will not last!!! Resident Benefits Package, including renter's insurance, air filter replacements, et cetera, for $50.00 monthly. Please see the flyer in the property photos* 24 Hour Security Gate Community Poo

Tropical Gardens - Photo 1 of 1

5d+ ago

8.6

Very good

Tropical Gardens

3101 Avenue V Nw, Winter Haven, FL 33881

2 beds

1 bath

$1,335

Apartment for rent

Pet-friendly first-floor apartment with patio

Located in Winter Haven, FL, this first-floor apartment features tile throughout, vaulted ceilings, a private patio, and washer/dryer hookups. The unit includes complete appliances, central A/C, and $1,335 rent with move-in specials available - a good fit for pet owners with nearby pet services and outdoor space.

163 Avenue A SE - Photo 1 of 1

5d+ ago

7.7

Very good

163 Avenue A SE

163 Avenue A Se, Winter Haven, FL 33880

2 beds

1 bath

$1,250

Apartment for rent

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1246 31st St Nw - Photo 1 of 1

5d+ ago

Under 1500 house for rent in Winter Haven

House for rent

Description

Welcome to a freshened up 2 bed 1 bath home ready for its next tenants. Washer and dryer hook up available, large back yard, covered parking and so much more. Professionally managed to insure your needs as a tenant are addressed. Come view this home today!

The Arbours at Garden Grove - Photo 1 of 1

5d+ ago

8.4

Very good

The Arbours at Garden Grove

4900 Cypress Gardens Rd, Winter Haven, FL 33884

In-unit laundry | Air conditioning | Garage parking

1–3 beds

1–2 baths

$1,100–$1,825

Apartment for rent

1-3 bedroom apartments with pool and fitness

Floor plans at The Arbours at Garden Grove range from one to three bedrooms in Winter Haven, FL, with vaulted ceilings, wet bars, air conditioning, and walk-in closets. The community features a pool, state-of-the-art fitness center, basketball court, playground, and garage parking - a good fit for pet owners with nearby pet supply stores and grooming services.

Summary of resident reviews

The Arbours at Garden Grove receives praise for excellent management, particularly office staff responsiveness and timely maintenance. Residents appreciate the quiet atmosphere, well-maintained grounds, convenient location near schools and main roads, plus on-site storage units. Many highlight the accommodating staff and strong sense of community, with several recommending it to family members.

2407 6th St NE - Photo 1 of 1

5d+ ago

7.7

Very good

2407 6th St NE

2407 6th St Ne, Winter Haven, FL 33881

2 beds

1 bath

$1,050

Apartment for rent

Multi-family home near top schools in Winter Haven

Located in Winter Haven, FL, this multi-family residential property includes a brand new refrigerator and stove. The community sits within a quarter-mile of top-rated elementary and middle schools, with convenient access to local dining like Miami Style Grill and Simply Bahamian Food nearby.

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.

638 W Central Ave - Photo 1 of 1

5d+ ago

Under 1500 Downtown Winter Haven apartment for rent in Winter Haven

638 W Central Avenue

638 W Central Ave, Winter Haven, FL 33880

In-unit laundry | Carpet

2 beds

2 baths

$1,400

Apartment for rent

Available Jul 7

Modern 2-Bedroom Apartment Near Downtown Fun

Experience convenient living in this fully updated upstairs apartment featuring 2 bedrooms and 2 bathrooms within 1,000 sq. ft. Enjoy brand new vinyl flooring, modern appliances, and an en suite bedroom. The unit includes in-unit laundry with no carpet, providing a fresh, stylish atmosphere. Ideally situated just steps from Downtown Winter Haven’s vibrant dining and shopping scene, this pet-friendly home is ready for its next resident!

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.

235 Palmetto Ave Nw - Photo 1 of 1

5d+ ago

Under 1500 apartment for rent in Winter Haven

235 Palmetto Ave NW

235 Palmetto Ave Nw, Winter Haven, FL 33881

Air conditioning

2 beds

1.5 baths

$1,195

Apartment for rent

Charming 2-Bed Apartment in Heart of Winter Haven

This pet-friendly apartment offers 1,024 sq. ft. of comfortable living with 2 bedrooms and 1.5 baths. Centrally located, it features air conditioning for your comfort. Ideal for immediate move-in, this space welcomes Section 8 vouchers and is ready to become your new home. Enjoy the vibrant lifestyle of Winter Haven in a charming setting!

242 Winter Ridge Blvd - Photo 1 of 1

5d+ ago

Under 1500 condo for rent in Winter Haven

Condo for rent

2-bed Winter Haven condo with pool & patio

Set in Winter Haven, FL, this pet-friendly 2-bed, 2-bath condo offers 1,073 sqft with tile flooring throughout and a fully enclosed tile patio. The quiet community includes a pool and shuffle board courts, just minutes from downtown Winter Haven. Pet fee $300 with $30 monthly rent per pet.

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168 Rebecca Dr Ne - Photo 1 of 1

5d+ ago

Under 1500 Lake Buckeye Estates house for rent in Winter Haven

House for rent

Description

This 2-Bedroom, 1-Bathroom home is located just minutes from downtown Winter Haven and features tile floors throughout the common areas, as well as a new AC, refrigerator & stove, and an enclosed patio!! LAWNCARE INCLUDED!! All residents are enrolled in the Resident Benefits Package (RBP) at a cost of $25/per month, which includes HVAC air filter delivery (for applicable properties), utility concierge service making utility connection a breeze during your move-in, our best-in-class resident rewards program, credit reporting, and much more! More details upon application.

76 Stebbins Dr #76 - Photo 1 of 1

5d+ ago

Under 1500 house for rent in Winter Haven

SINGLE_FAMILY - Winter Haven, FL

76 Stebbins Dr #76, Winter Haven, FL 33884

2 beds

2 baths

$1,325

House for rent

2019 2-bed manufactured home with garage parking

Other with 2 beds in Winter Haven, FL, this 2019 manufactured home in the Grove Shores community offers 896 sqft with 2-bed, 2-bath layout and garage parking. The professionally managed community provides a well-maintained setting, with a top-rated elementary school within a mile. Priced $275 below the median for comparable properties in the area.

3076 Saint Paul Dr - Photo 1 of 1

5d+ ago

Under 1500 apartment for rent in Winter Haven

Affordable 2 Bedroom / 1 Bathroom Home for Rent - Winter Haven, FL

3076 Saint Paul Dr, Winter Haven, FL 33880

High ceilings | On-site management | Outdoor space

2 beds

1 bath

$1,159

Apartment for rent

Available Jul 11

Pet-friendly 2-bed home near Publix plaza

Set in Winter Haven, FL, this pet-friendly 2-bed, 1-bath home offers 860 sqft with vaulted ceilings and tile flooring. Walking distance from Publix plaza for shopping and dining, the layout includes washer/dryer hookups, off-street parking, and outdoor space with a lawn - a fit for pet owners with nearby grooming and veterinary services.

2405 Avenue C Sw #B - Photo 1 of 1

5d+ ago

Under 1500 condo for rent in Winter Haven

2405 Avenue C Sw #B, Winter Haven, FL 33880

In-unit laundry | Carpet | Outdoor space

2 beds

1 bath

$1,399

Condo for rent

Available Jun 29

Description

This adorable duplex is available immediately. This home offers 930 sf with 2BR/1BA with tile and vinyl flooring, no carpet! All stainless steel appliances included in the kitchen, as well as a stacked washer and dryer. Neutral colors throughout and lots of modern finishes. Owner pays for lawn care.

400 El Camino Dr #203 - Photo 1 of 1
Age restricted

5d+ ago

Under 1500 apartment for rent in Winter Haven

400 El Camino Dr #203, Winter Haven, FL 33884

In-unit laundry | Air conditioning | Balcony

2 beds

2 baths

$1,500

Apartment for rent

Available Jun 28

Description

Property Id: 2712857 ***55+ Senior Community*** Amazing 2 bedroom, 2 bathroom apartment in Winter Haven. Amenities included: balcony, central air, central heat, and dishwasher. No Utilities included. Is pet friendly. Date Available: Jun 27th 2026. $1,500/month rent. $1,500 security deposit required. Please submit the form on this page or contact Oscar at 385-286-8290 to learn more. This property is managed by a responsible landlord using Avail landlord software. Bedrooms: 2 Primary Bedroom Dimensions: 16 X 11 Primary Bedroom Level: First Other Rooms Total Rooms: 3 Livin

3039 Saint Paul Dr - Photo 1 of 1

5d+ ago

Under 1500 condo for rent in Winter Haven

3039 Saint Paul Dr, Winter Haven, FL 33880

In-unit laundry | On-site laundry | High ceilings

2 beds

1 bath

$1,095

Condo for rent

Available May 29

2-bed condo with vaulted ceilings & pet-friendly

Quietly set in Winter Haven, FL, this 2-bed, 1-bath condo features vaulted ceilings with exposed beams and a granite-counter kitchen with breakfast bar. The 864 sqft layout includes washer/dryer hookups and comes with lawn care included. A fit for pet owners with up to 2 small pets welcome (30 lbs or less) and outdoor space available.

663 Avenue J Nw #2 - Photo 1 of 1

5d+ ago

Under 1500 apartment for rent in Winter Haven

Charming 1BR Winter Haven Unit

663 Avenue J Nw #2, Winter Haven, FL 33881

Assigned parking

1 bed

1 bath

$950

Apartment for rent

Description

Discover the perfect blend of comfort, privacy, and convenience in this well-maintained Winter Haven residence. Ideally suited for anyone seeking a low-maintenance, independent living space, this cozy 1-bedroom, 1-bathroom apartment delivers a peaceful residential feel with excellent functional perks Lease and Move-In Details: Availability: Ready for immediate move-in. Parking: Driveway and designated off-street parking included. Move-In Costs: First month's rent, security deposit, and $199 admin fee. Applications are $75 per adult.

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

$1,350

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 $1350/month, security deposit is $1400 ***we Offer Security Deposit Payment Options!***. The application fee is only $80/adult. In addi

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Updated: July 21, 2026

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💰Best rent deal64 Stebbins Dr #64
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🧦In-unit laundry
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