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Apartments for Rent in Cypress Grove, Winter Haven, FL

Average rent

$1,875
decreased by44%

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757 Reggie Rd #NA - Photo 1 of 1

5d+ ago

House for rent in Winter Haven

$2,100 - 3 Bedroom 2 Bathroom House In Winter Haven With Great Amenities

757 Reggie Rd #NA, Winter Haven, FL 33884

In-unit laundry | Air conditioning | Garage parking

3 beds

2 baths

$2,100

House for rent

Available Sep 2

Description

Amazing 3 bedroom, 2 bathroom house in Winter Haven. Amenities included: central air, central heat, dishwasher, pool, stainless steel appliance, updated kitchen, updated bathroom, storage, washer dryer, and yard. No Utilities included. Is pet friendly. Date Available: Sep 2nd 2025. $2,100/month rent. $2,100 security deposit required. Please submit the form on this page or contact Maria Cendon at 407-536-0778 to learn more.

2239 CHRIS DRIVE - Photo 1 of 1
New construction

5d+ ago

House for rent in Winter Haven

Single Family Residence - WINTER HAVEN, FL

2239 CHRIS DRIVE, Winter Haven, FL 33884

In-unit laundry | Garage parking | Dishwasher

4 beds

3 baths

$2,100

$2,000

Price drop

House for rent

Description

Property Status: Active Great Deal! RENTAL PRICE JUST REDUCED – Catch this Deal while you can! Pet Friendly!! Get one month FREE with a 12-month lease. This stunning Brand-New Home has never been lived in and comes with the bonus of no rear neighbors. Office Phone: (407) 380-2800 Copyright © 2025 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

565 Reggie Road - Photo 1 of 1
New construction

5d+ ago

Apartment for rent in Winter Haven

565 Reggie Road, Winter Haven, FL 33884

Air conditioning | On-site laundry | Assigned parking

5 beds

3 baths

$2,250

Apartment for rent

Description

Welcome to your new home in Winter Haven, Florida! This charming property offers an ideal location, just a short drive away from a department store and only 9 minutes from IMA Medical Clinic of Lake Wales, making it convenient for both shopping and healthcare needs. With spacious bedrooms and bathrooms, this residence provides ample space for relaxation and living. The floor area ensures comfort, making it easy to personalize your space as you settle in. While this property does not include utilities such as gas, electricity, cable, internet, water, heat, or trash servic

2219 CHRIS DRIVE - Photo 1 of 1
New construction

5d+ ago

House for rent in Winter Haven

Single Family Residence - WINTER HAVEN, FL

2219 CHRIS DRIVE, Winter Haven, FL 33884

In-unit laundry | Garage parking | Walk-in closets

4 beds

2 baths

$2,100

$1,990

Price drop

House for rent

Description

Property Status: Pending One or more photo(s) has been virtually staged. ** Lawn Mower included** Spacious 4-Bedroom Home with Loft for Rent in Winter Haven! Brand-new construction - Be the first tenant! Discover the perfect blend of comfort, style, and quality living in this beautiful home located in the Peace Creek Reserve community of Winter Haven. Featuring 4 bedrooms, 2.5 bathrooms in a corner lot, and a versatile loft, this property offers a modern open floor plan ideal for families and those who love to entertain. The kitchen seamlessly connects to the din

972 972 Harold Pass - Photo 1 of 1

5d+ ago

House for rent in Winter Haven

972 972 Harold Pass, Winter Haven, FL 33884

In-unit laundry | Swimming pool | Storage

3 beds

2 baths

$1,900

House for rent

Available Jun 30

Description

Modern and Efficient Home in a Prime Winter Haven Community Welcome to your new home in the vibrant community of VillaMar. This modern, ranch-style residence features 3 bedrooms and 2 full bathrooms across 1,555 square feet of thoughtfully designed space. The home is centered around a bright, open-concept floor plan that seamlessly connects the kitchen and living areas. You’ll appreciate the brand-new refrigerator, washer, and dryer, along with the spa-inspired owner's bathroom and a large pantry for extra storage. This property is designed for both comfort and an active

668 REGGIE ROAD - Photo 1 of 1
New construction

5d+ ago

House for rent in Winter Haven

Single Family Residence - WINTER HAVEN, FL

668 REGGIE ROAD, Winter Haven, FL 33884

In-unit laundry | Furnished | Garage parking

3 beds

2 baths

$1,850

House for rent

Description

Property Status: Pending One or more photo(s) has been virtually staged. WELCOME TO THIS BEAUTIFULLY UNFURNISHED HOME LOCATED IN THE HIGHLY DESIRABLE PEACE CREEK RESERVE COMMUNITY IN POLK COUNTY. This charming and fully equipped residence features 3 spacious bedrooms, 2 full bathrooms, and a versatile workspace ideal for working from home or studying. The open-concept layout seamlessly blends the modern kitchen, dining area, and living room, creating a bright, welcoming atmosphere that’s perfect for both daily living and entertaining guests. Enjoy the outdoors in your pri

Find rentals with popular amenities

Storage

Dishwasher

Garage Parking

In-Unit Laundry

956 Harold Pass - Photo 1 of 1
New construction

5d+ ago

House for rent in Winter Haven

956 Harold Pass, Winter Haven, FL 33884

In-unit laundry | Assigned parking | Swimming pool

5 beds

2 baths

$2,399

House for rent

Description

Welcome to your new home in the heart of Winter Haven! This stunning five-bedroom, two-and-a-half-bathroom single-family home, built in 2024, offers a perfect blend of modern living and community charm. With a spacious floor area of 2,216 square feet, this property features a striking two-story exterior and a welcoming front porch. The open-concept kitchen boasts stainless steel appliances and a large island, perfect for gatherings. Enjoy a bright living room enhanced by large windows and a neutral color palette throughout. This home comes equipped with convenient unit am

607 Sweet Bay Cir #607 - Photo 1 of 1

5d+ ago

Condo for rent in Winter Haven

$2100-2 Bedroom 2 Bathroom Condo In Winter Haven With Great Amenities

607 Sweet Bay Cir #607, Winter Haven, FL 33884

In-unit laundry | Furnished | Air conditioning

2 beds

2 baths

$2,100

Condo for rent

Available Nov 1

Description

This beautiful 2 bed 2 bath fully furnished condo is located in the gated community of Winterset and boasts spectacular views of lake Winterset and the Legoland fireworks. This fully renovated condo is heaped in upgrades and is move in ready. As you enter the condo via your private entrance you will love the curved steps up to the brand new front door with ring doorbell. As you enter you will immediately notice the modern upgraded tiles throughout the unit, the 5 inch baseboards and amazingly tall ceilings ranging from 12 to 24ft. The glass sliding patio doors from the liv

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150 Morning Glory Cir - Photo 1 of 1

5d+ ago

House for rent in Winter Haven

150 Morning Glory Circle

150 Morning Glory Cir, Winter Haven, FL 33884

Outdoor space

3 beds

2 baths

$2,100

House for rent

Available Jul 29

Description

***Professionally Managed*** GORGEOUS HOME AVAILABLE FOR LONG-TERM LEASE IN WINTERSET! This 3 bed 2 bath home features tile flooring, a huge kitchen that leads right out to a massive living space, a screened-in porch, and a stunning master bedroom with an oversized closet and master bathroom. The gated community of Winterset features amenities like a community pool, grounds care, tennis courts, and a clubhouse! Conveniently located close to good food, shopping, and LEGOLAND, this residence is can't miss! Call today, this won't last long! ***FINANCIAL INFORMATION*** The mo

57 Saint Kitts Cir - Photo 1 of 1

5d+ ago

House for rent in Winter Haven

57 Saint Kitts Circle - 1

57 Saint Kitts Cir, Winter Haven, FL 33884

Air conditioning | Garage parking | On-site management

3 beds

2 baths

$1,795

House for rent

Available Aug 1

Description

Beautiful 3-Bedroom, 2-Bath Home with Garage in Quiet, Secluded Neighborhood This well-maintained home features an open floor plan with 3 spacious bedrooms and 2 full bathrooms. Enjoy modern living with attached garage, stainless steel appliances, dishwasher, garbage disposal, and elegant quartz countertops, new roof and new air conditioner. Tenant responsible for lawn maintenance and utilities No pets allowed Application Details: A comprehensive background check is required through the management company and TransUnion SmartMove. $65 application fee per adult. Call o

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The Arbours at Garden Grove - Photo 1 of 1
Rent special

1d ago

8.5

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

$1,250–$1,825

Apartment for rent

810 Marcia Loop - Photo 1 of 1

2d ago

Our team has verified this company

Verified

810 Marcia Loop, Winter Haven, FL 33884

Balcony | Swimming pool | On-site management

3 beds

2 baths

$1,860

House for rent

Description

We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home is currently occupied and coming soon; please respect the current resident’s privacy and do not disturb. Please note that the advertised price may exclude additional fees. These in

3338 Fox Ridge Dr - Photo 1 of 1

1d ago

Our team has verified this company

Verified

3338 Fox Ridge Dr, Winter Haven, FL 33884

Swimming pool | On-site management | Outdoor space

2 beds

2 baths

$1,730

$1,625

Price drop

House for rent

Description

We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home is currently occupied and coming soon; please respect the current resident’s privacy and do not disturb. Please note that the advertised price may exclude additional fees. These in

541 Heather Glen Dr - Photo 1 of 1

1d ago

House for rent in Winter Haven

Single Family Residence - WINTER HAVEN, FL

541 Heather Glen Dr, Winter Haven, FL 33884

In-unit laundry | Air conditioning | Garage parking

3 beds

2 baths

$2,500

House for rent

Description

Property Status: Active Welcome to Heather Glen, a gated community in the heart of Winter Haven! This charming 3 bedroom, 2 bathroom home with an attached 2-car garage offers comfort, security, and convenience with a flexible move-in date starting October 15, 2025. Featuring neutral gray walls, wood-look tile flooring, and plantation shutters throughout, this open-concept home is filled with natural light and boasts a spacious master suite with walk-in closet and private bath, two additional bedrooms with a guest bath, and a bright kitchen with plenty of counter space, a w

620 Reflections Loop - Photo 1 of 1

3d ago

House for rent in Winter Haven

Garage parking | Dishwasher | Outdoor space

3 beds

2 baths

$1,950

House for rent

Description

Welcome to this spacious 3/2 near Legoland! Nestled in the heart of Winter Haven, FL, this home boasts three generously sized bedrooms and two full bathrooms. The split bedroom floor plan ensures privacy, while the eat-in kitchen nook provides a cozy space for meals. The master suite is a true retreat, complete with a luxurious garden tub. The entire home is outfitted with ceramic tiled flooring, adding a touch of elegance and ease of maintenance. The property also features a large yard, perfect for outdoor activities, and a two-car garage for your vehicles or extra storag

8507 Waterview Way - Photo 1 of 1

5d+ ago

Condo for rent in Winter Haven

Condominium - WINTER HAVEN, FL

8507 Waterview Way, Winter Haven, FL 33884

In-unit laundry | On-site laundry | Swimming pool

1 bed

1 bath

$1,650

Condo for rent

Description

Property Status: Active 5 MINUTES FROM LEGOLAND !!! Experience the perfect combination of charm, style, and convenience in this stunning multi-level condo! This unique home features 1 spacious bedroom, 1 full bath, and an open-concept living area, plus a versatile third-level loft with its own half bath—ideal for a guest space, home office, or media room. Nestled within a highly sought-after 24-hour gated community with water access to a lake, this rare gem offers tranquility and security in an unbeatable location. Step inside to find modern upgrades throughout, including

Find sweet deals near Cypress Grove

These rentals are 10%-30% cheaper than the local average price for similar rentals.

44 Stebbins Dr #44 - Photo 1 of 1

5d+ ago

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

Description

Property Status: Active Own your own home in a quiet, well-maintained neighborhood! This 2 bed/2 bath home has plenty of living space. Every day could feel like a vacation! Call us today to schedule a showing and see all the benefits of living in Grove Shores, a professionally managed community. Ask about our special incentive programs! This one won't last long! Office Phone: (863) 880-1980 Copyright © 2025 My State MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

631 Reflections Loop - Photo 1 of 1

5d+ ago

House for rent in Winter Haven

631 Reflections Loop W

631 Reflections Loop, Winter Haven, FL 33884

In-unit laundry | Assigned parking | Outdoor space

3 beds

2 baths

$1,900

House for rent

Available Aug 12

Description

Welcome to your new home in the highly sought-after Reflections community! This well-maintained property is move-in ready and offers the perfect blend of comfort, convenience, and location. Property Features: • 3 Spacious Bedrooms and 2 Full Bathrooms • Open-Concept Living Area with plenty of natural light • Modern Kitchen with ample cabinet space and breakfast bar • Two-Car Garage with extra driveway parking • Fully Fenced Backyard – perfect for pets, entertaining, or relaxing • Washer & Dryer Hookups for your convenience • Fresh, Clean, and Ready for Immediate Move-In

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2212 Garden Lake Dr - Photo 1 of 1

4d ago

Townhouse for rent in Winter Haven

Townhouse - WINTER HAVEN, FL

2212 Garden Lake Dr, Winter Haven, FL 33884

In-unit laundry | Garage parking | On-site laundry

3 beds

2 baths

$1,750

House for rent

Description

Property Status: Active Welcome to your new home in the highly sought-after gated community of Winter Haven, FL! This spacious 3-bedroom residence offers a functional and inviting floor plan with pond views and two screened-in patios—perfect for enjoying Florida’s beautiful weather both upstairs and downstairs. Inside, the home features: 3 comfortable bedrooms and 1.5 bathrooms Convenient downstairs laundry room and loads of storage throughout 1-car garage for secure parking and additional storage Open living area with easy access to the screened patio overl

8307 Waterview Way #8307 - Photo 1 of 1
3D tour

5d+ ago

Condo for rent in Winter Haven

Condominium - WINTER HAVEN, FL

8307 Waterview Way #8307, Winter Haven, FL 33884

In-unit laundry | Furnished | Balcony

1 bed

1 bath

$1,700

Condo for rent

Description

Property Status: Active 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 approximately 45 miles from Orlando. Ideal for traveling professionals or anyone seeking a relaxing retreat, this cozy unit offers access to a community clubhouse, pool, and scenic lake access for added leisure. Enjoy your morning coffee on the private outdoor balcony or take a short 4-mile drive to Winter Haven Hospital for easy convenience. Whether you're her

3406 Fox Ridge St - Photo 1 of 1

5d+ ago

House for rent in Winter Haven

3 beds

2 baths

$1,795

House for rent

Description

You will love this charming home centrally located in Winter Haven near Legoland. This home offers spacious bedrooms, updated cabinets, flooring, bathrooms and more! Lawn care is included in the rent amount. Move in costs include $50 application fee per person 18 and over, $100 tenant set up fee, $1795 rent, $2400 security deposit. No pets allowed.

108 Lantern Ln - Photo 1 of 1
Rent special

5d+ ago

House for rent in Winter Haven

3 Bedroom Pet-Friendly Home in winter haven, FL with Main Street Renewal

108 Lantern Ln, Winter Haven, FL 33884

Swimming pool | Storage | Outdoor space

3 beds

2 baths

$1,745

$1,670

Price drop

House for rent

Description

Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening! Take advantage of the incredible location, nestled in a great neighborhood with access to schools, parks, dining and more. Don't miss a chance to make this house your next home! Beyond the home, experience the ease of our technology

Listings within 5 miles
677 Lake Dexter Cir - Photo 1 of 1

5d+ ago

House for rent in Winter Haven

Single Family Residence - WINTER HAVEN, FL

677 Lake Dexter Cir, Winter Haven, FL 33884

In-unit laundry | Garage parking | Swimming pool

3 beds

2 baths

$2,000

House for rent

Description

Property Status: Pending LAKEFRONT!! LAKE DEXTER! Enjoy spectacular lake views and water activities right in our own back yard. Fish, ski, paddleboard, kayak, float on a tube...or just enjoy the serene waterviews and plentiful wildlife such as ducks, turtles, osprey and the occasional fly by of the resident bald eagle located in the cove. Enjoy the community pool and boat ramp. Office Phone: (863) 293-1234 Copyright © 2025 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be indepe

522 Lake Dexter Blvd - Photo 1 of 1

5d+ ago

House for rent in Winter Haven

Single Family Residence - WINTER HAVEN, FL

522 Lake Dexter Blvd, Winter Haven, FL 33884

In-unit laundry | Furnished | Air conditioning

3 beds

2 baths

$2,250

House for rent

Description

Property Status: Active TURN KEY! FULLY FURNISHED! Welcome to this beautifully renovated 3-bedroom, 2-bathroom single-family home located in a peaceful, safe and family-friendly community neighborhood in Winter Haven. This move-in-ready home features all brand-new furnishings, modern appliances, and versatile living spaces ideal for families, traveling professionals, or roommates sharing a lease. The lease structure is flexible and can accommodate couple of tenants or parties. Enjoy convenient access to a community pool within a short 2-minute walk from the property.

7185 Summit Dr - Photo 1 of 1

5d+ ago

House for rent in Winter Haven

Single Family Residence - WINTER HAVEN, FL

7185 Summit Dr, Winter Haven, FL 33884

In-unit laundry | Garage parking | Walk-in closets

3 beds

2 baths

$1,990

House for rent

Description

Property Status: Active PRICE IMPROVEMENT! This delightful 3-bedroom, 2-bathroom home at 7185 Summit Dr in Winter Haven, FL offers a perfect blend of comfort and sustainability. Equipped with a fully functional SOLAR system, this home helps significantly reduce your utility costs, making it an eco-friendly and budget-conscious choice. The spacious, light-filled interior provides a welcoming atmosphere, with a functional layout ideal for everyday living. Don’t miss out on this opportunity to lease a home with lower energy bills in a tranquil, sought-after neighborhood. Sche

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Home > Apartments in Winter Haven > Cypress Grove Apartments For Rent
Updated: September 26, 2025

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Learn more about renting in Cypress Grove, Winter Haven, FL

Methodology: How we got this data

Zumper’s proprietary rental data fuels our analysis. Rent and market trends, availability, neighborhood popularity, and lifestyle scores are all calculated using real-time and 2024 rental inventory and prices.

Our Lifestyle Categories ("great for eco-living," "great for social life," "great for pet owners," etc.) are determined by set criteria, against which we score each listing and its available features. At the neighborhood level, we calculate the listing count for each category to determine which lifestyles best fit each area.

Zumper, founded in 2012, is North America’s largest privately-owned rental platform, offering over 1 million listings across the U.S. and Canada. Stay informed on the latest trends and shifts in the rental market with our monthly National Rent Report, your go-to resource for key insights into the evolving rental landscape.

Cypress Grove Apartments for rent FAQ

What is the average size of an apartment in Cypress Grove, FL?

The average size of a 3 bedroom apartment rental in Cypress Grove is 1428 square feet.

Can I afford an apartment for rent in Cypress Grove, FL?

To help you better understand how much rent you can afford, check out Zumper's rent calculator. Our rent calculator can help you learn more about Cypress Grove average rent prices.

What type of apartment rental is most common in Cypress Grove, Winter Haven, FL?

3 bedroom apartments are the most common type of rentals in Cypress Grove, Winter Haven, FL right now.

What type of apartment rental is least common in Cypress Grove, Winter Haven, FL?

3 bedroom apartments are the least common type of rentals in Cypress Grove, Winter Haven, FL right now.

Looking for an apartment in Cypress Grove, Winter Haven, FL?

🔑Available apartment rentals25
💰Best rent deal44 Stebbins Dr #44
Popular amenities, ,
🍽With dishwasher
🏠With photos