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Luxury Apartments for Rent in Winter Haven, FL

85 rentals

39 Enclave Dr #1 - Photo 1 of 1

1d ago

Luxury townhouse for rent in Winter Haven

39 Enclave Dr

39 Enclave Dr #1, Winter Haven, FL 33884

Luxury | Outdoor space

2 beds

2 baths

$1,850

House for rent

Available Oct 21

513 Winter Ter - Photo 1 of 1

1d ago

Luxury house for rent in Winter Haven

513 Winter Ter, Winter Haven, FL 33881

Luxury | Swimming pool

2 beds

2 baths

$1,450

House for rent

Aqua Apartment Homes - Photo 1 of 1

1d ago

8.3

Very good

Aqua Apartment Homes

2000 15th Ct Nw, Winter Haven, FL 33881

Luxury | Swimming pool | In-unit laundry

2 beds

1 bath

$1,445–$1,495

Apartment for rent

Top amenities
In-Unit Laundry
Dream Winter Haven - Photo 1 of 1

1d ago

8

Very good

Dream Winter Haven

5004 Dream Dr, Winter Haven, FL 33880

Luxury

1–3 beds

1–2 baths

$1,399–$2,139

Apartment for rent

2000 15th Ct Nw #10 - Photo 1 of 1

2d ago

Luxury apartment for rent in Winter Haven

2000 15th Ct Nw #10, Winter Haven, FL 33881

Luxury | Walk-in closets | Swimming pool

2 beds

1 bath

$1,475

Apartment for rent

Top amenities
In-Unit Laundry
On-Site Laundry
Swimming Pool
907 Lake Jessie Drive - Photo 1 of 1

2d ago

8.3

Very good

907 Lake Jessie Drive

907 Lake Jessie Dr, Winter Haven, FL 33881

Luxury | On-site laundry

1 bed

1 bath

$1,299

Price drop

Apartment for rent

Top amenities
On-Site Laundry

Nearby rental good for eco-living

$1,295

405 Avenue M Ne

Nearby rental good for pet owners

2850 Lake Alfred Road - Photo 1 of 1

5d+ ago

8.4

Very good

2850 Lake Alfred Road

2850 Lake Alfred Rd, Winter Haven, FL 33881

Luxury

1 bed

1 bath

$895

Apartment for rent

1125 Evergreen Court - Photo 1 of 1

5d+ ago

8.3

Very good

1125 Evergreen Court

1125 Evergreen Ct, Winter Haven, FL 33881

Luxury | Swimming pool | Controlled access

2–3 beds

2 baths

$1,690–$1,790

Apartment for rent

Top amenities
Storage
Swimming Pool
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1925 Avenue O Sw #204 - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Haven

Cozy 1 Bed / 1 Bath (Upstairs) - In-Unit W/D, Stainless Appliances - Near Downtown Winter Haven

1925 Avenue O Sw #204, Winter Haven, FL 33880

Luxury | In-unit laundry | On-site laundry

1 bed

1 bath

$1,150

Condo for rent

Available Oct 13

Top amenities
Ceiling Fan
In-Unit Laundry
On-Site Laundry
3355 Dexter Dell Se - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Haven

Luxury | Dishwasher | Microwave

2 beds

2 baths

$1,649

House for rent

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Find sweet deals in Winter Haven

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

$1,099–$1,299

350 24th St Nw

$1,100–$1,360

418 19th St Se

$1,195

955 6th St Se

$1,749

240 2nd St Sw

541 Heather Glen Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Haven

Single Family Residence - WINTER HAVEN, FL

541 Heather Glen Dr, Winter Haven, FL 33884

Luxury | Walk-in closets | In-unit laundry

3 beds

2 baths

$2,500

$2,200

Price drop

House for rent

Top amenities
Air Conditioning
Ceiling Fan
High Ceilings
In-Unit Laundry
On-Site Laundry
402 Terranova St - Photo 1 of 1

5d+ ago

Luxury Terranova house for rent in Winter Haven

402 Terranova St, Winter Haven, FL 33884

Luxury | Swimming pool | In-unit laundry

4 beds

3 baths

$3,250

House for rent

Available Oct 14

Top amenities
Dishwasher
In-Unit Laundry
Swimming Pool
1280 1280 Delani Drive - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Haven

1280 1280 Delani Drive, Winter Haven, FL 33880

Luxury | Swimming pool | In-unit laundry

3 beds

2 baths

$2,500

House for rent

Top amenities
Dishwasher
In-Unit Laundry
Microwave
5432 Hogan Ln - Photo 1 of 1
Age restricted

5d+ ago

Luxury Lake Ashton West house for rent in Winter Haven

Single Family Residence - WINTER HAVEN, FL

5432 Hogan Ln, Winter Haven, FL 33884

Luxury | Walk-in closets | Swimming pool

2 beds

2 baths

$2,400

House for rent

Top amenities
Ceiling Fan
Dishwasher
Garage Parking
In-Unit Laundry
900 Lake Jessie Dr #NA - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Haven

Rare Waterfront 3 bed 3 bath Home on Chain of Lakes

900 Lake Jessie Dr #NA, Winter Haven, FL 33881

Luxury | In-unit laundry | Furnished

3 beds

3 baths

$3,000

House for rent

Available Oct 1

Top amenities
Air Conditioning
Furnished
Hardwood Floor
In-Unit Laundry
689 Lake Howard Dr Nw #3B - Photo 1 of 1
Age restricted

5d+ ago

Luxury condo for rent in Winter Haven

Condominium - WINTER HAVEN, FL

689 Lake Howard Dr Nw #3B, Winter Haven, FL 33880

Luxury | Swimming pool | In-unit laundry

2 beds

2 baths

$2,150

$1,850

Price drop

Condo for rent

Top amenities
In-Unit Laundry
Swimming Pool
3353 Dexter Shores Dr Se - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Haven

3353 Dexter Shores Dr Se, Winter Haven, FL 33884

Luxury | Walk-in closets | In-unit laundry

2 beds

2 baths

$1,600

House for rent

Top amenities
In-Unit Laundry
1240 6th St Ne - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Haven

House for rent

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1925 Avenue O Sw #102 - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Haven

2 Bed / 2 Bath (Downstairs) - In-Unit W/D, Stainless Appliances - Near Downtown Winter Haven

1925 Avenue O Sw #102, Winter Haven, FL 33880

Luxury | In-unit laundry | Ceiling fan

2 beds

2 baths

$1,450

Condo for rent

Available Oct 31

Top amenities
Ceiling Fan
In-Unit Laundry
2924 Whispering Trails Dr - Photo 1 of 1
New construction

5d+ ago

Luxury house for rent in Winter Haven

Great private studio all included

2924 Whispering Trails Dr, Winter Haven, FL 33884

Luxury | Walk-in closets | Fitness center

1 bed

1 bath

$1,200

House for rent

Available Oct 8

Top amenities
Dishwasher
In-Unit Laundry
Microwave
5607 Struthers Ct - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Haven

Luxury | Dishwasher

2 beds

2 baths

$1,550

Apartment for rent

208 E Lake Howard Dr #101 - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Haven

208 E Lake Howard Dr #101, Winter Haven, FL 33881

Luxury | Balcony | Walk-in closets

2 beds

2 baths

$1,875

Condo for rent

Available Oct 1

Top amenities
Assigned Parking
Dishwasher
Elevator
In-Unit Laundry
2445M Gerber Dairy Rd - Photo 1 of 1
New construction

5d+ ago

Luxury house for rent in Winter Haven

2445M Gerber Dairy Rd, Winter Haven, FL 33880

Luxury | In-unit laundry | Furnished

3 beds

2 baths

$2,800

House for rent

Top amenities
High Ceilings
In-Unit Laundry
503 Avenue B Nw #503 - Photo 1 of 1

5d+ ago

Luxury Downtown Winter Haven condo for rent in Winter Haven

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

Luxury | Swimming pool | In-unit laundry

2 beds

2 baths

$1,995

Condo for rent

Top amenities
Dishwasher
In-Unit Laundry
Swimming Pool
2445 Gerber Dairy Rd - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Haven

2445 Gerber Dairy Rd, Winter Haven, FL 33880

Luxury | Furnished | Garage parking

4 beds

4 baths

$4,200

House for rent

Top amenities
Furnished
730 W Central Ave #6 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Haven

Apartment - WINTER HAVEN, FL

730 W Central Ave #6, Winter Haven, FL 33880

Luxury | Walk-in closets | Ceiling fan

1 bed

1 bath

$965

Apartment for rent

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5635 Struthers Ct - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Haven

Half Duplex - WINTER HAVEN, FL

5635 Struthers Ct, Winter Haven, FL 33884

Luxury | Balcony | In-unit laundry

3 beds

2 baths

$2,145

Apartment for rent

Top amenities
Ceiling Fan
Garage Parking
In-Unit Laundry
1228 Evergreen Ct - Photo 1 of 1

5d+ ago

Luxury Lake Buckeye Estates townhouse for rent in Winter Haven

1228 Evergreen Ct, Winter Haven, FL 33881

Luxury | Swimming pool | Fitness center

2 beds

2 baths

$1,690

House for rent

Available Oct 1

Top amenities
Carpet
Fitness Center
Garage Parking
Hardwood Floor
On-Site Laundry
Residents Lounge
1297 Evergreen Ct - Photo 1 of 1

5d+ ago

Luxury Lake Buckeye Estates townhouse for rent in Winter Haven

1297 Evergreen Ct, Winter Haven, FL 33881

Luxury | Swimming pool | Fitness center

2 beds

2 baths

$1,690

House for rent

Available Oct 1

Top amenities
Carpet
Controlled Access
Garage Parking
Hardwood Floor
On-Site Laundry
Swimming Pool
1335 Evergreen Ct - Photo 1 of 1

5d+ ago

Luxury Lake Buckeye Estates townhouse for rent in Winter Haven

Evergreen Court

1335 Evergreen Ct, Winter Haven, FL 33881

Luxury | Swimming pool | Controlled access

2 beds

2 baths

$1,690

House for rent

Available Aug 29

Top amenities
Carpet
Dishwasher
Garage Parking
On-Site Laundry
Swimming Pool
1595 28th St Nw - Photo 1 of 1
3D tour

5d+ ago

Luxury house for rent in Winter Haven

1595 28th St Nw, Winter Haven, FL 33881

Luxury | Concierge service | Package service

2 beds

1 bath

$1,550

House for rent

Available Oct 1

2480 Avenue B Sw #B - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Haven

2480 Avenue B Sw #B, Winter Haven, FL 33880

Luxury | Ceiling fan

2 beds

1 bath

$1,450

Apartment for rent

383 Winter Ridge Blvd - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Haven

383 Winter Ridge Blvd, Winter Haven, FL 33881

Luxury | Walk-in closets | Swimming pool

2 beds

2 baths

$1,600

Condo for rent

Available Oct 1

Top amenities
In-Unit Laundry
208 E Lake Howard Dr #104 - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Haven

208 E Lake Howard Dr #104, Winter Haven, FL 33881

Luxury | Balcony | Assigned parking

2 beds

2 baths

$1,775

Condo for rent

Available Sep 29

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3309 Verbena Ave - Photo 1 of 1
3D tour

5d+ ago

Luxury Poinsettia Park house for rent in Winter Haven

3309 Verbena Ave, Winter Haven, FL 33881

Luxury | Swimming pool | Garage parking

3 beds

2 baths

$2,350

House for rent

Available Sep 18

Top amenities
On-Site Laundry
1925 Avenue O Sw #205 - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Haven

1 Bed / 1 Bath (Upstairs) - In-Unit W/D, Stainless Appliances - Near Downtown Winter Haven

1925 Avenue O Sw #205, Winter Haven, FL 33880

Luxury | In-unit laundry | On-site laundry

1 bed

1 bath

$1,200

Condo for rent

Available Oct 7

Top amenities
Dishwasher
In-Unit Laundry
On-Site Laundry
8507 Waterview Way - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Haven

Condominium - WINTER HAVEN, FL

8507 Waterview Way, Winter Haven, FL 33884

Luxury | Walk-in closets | Swimming pool

1 bed

1 bath

$1,650

Condo for rent

Top amenities
In-Unit Laundry
On-Site Laundry
Swimming Pool
113 Avenue C Se #B - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Haven

Single Family Residence - WINTER HAVEN, FL

113 Avenue C Se #B, Winter Haven, FL 33880

Luxury | In-unit laundry | Ceiling fan

1 bed

1 bath

$1,095

House for rent

Top amenities
Dishwasher
In-Unit Laundry
346 Sand Pine Trl - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Haven

Single Family Residence - WINTER HAVEN, FL

346 Sand Pine Trl, Winter Haven, FL 33880

Luxury | In-unit laundry | Furnished

2 beds

2 baths

$1,450

House for rent

Top amenities
Ceiling Fan
In-Unit Laundry
4207 San Rocco Way - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Haven

4207 San Rocco Way - 1

4207 San Rocco Way, Winter Haven, FL 33884

Luxury | In-unit laundry | Package service

3 beds

2 baths

$2,150

House for rent

Available Oct 15

Top amenities
In-Unit Laundry
3483 Costello Cir - Photo 1 of 1
New construction

5d+ ago

Luxury house for rent in Winter Haven

Single Family Residence - WINTER HAVEN, FL

3483 Costello Cir, Winter Haven, FL 33884

Luxury | Walk-in closets | In-unit laundry

3 beds

2 baths

$2,150

House for rent

Top amenities
Dishwasher
Garage Parking
In-Unit Laundry
912 Lake Jessie Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Haven

Lake Jessie

912 Lake Jessie Dr, Winter Haven, FL 33881

Luxury

1 bed

1 bath

$1,800

House for rent

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912 Lake Jessie Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Haven

Lake Front Living

912 Lake Jessie Dr, Winter Haven, FL 33881

Luxury

2 beds

1 bath

$2,000

House for rent

912 Lake Jessie Dr #3 - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Haven

Single Family Residence - WINTER HAVEN, FL

912 Lake Jessie Dr #3, Winter Haven, FL 33881

Luxury | In-unit laundry | On-site laundry

1 bed

1 bath

$2,000

House for rent

Top amenities
In-Unit Laundry
On-Site Laundry
912 Lake Jessie Dr #2 - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Haven

Single Family Residence - WINTER HAVEN, FL

912 Lake Jessie Dr #2, Winter Haven, FL 33881

Luxury | Walk-in closets | In-unit laundry

1 bed

1 bath

$1,800

House for rent

Top amenities
In-Unit Laundry
912 Lake Jessie Dr #1 - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Haven

Single Family Residence - WINTER HAVEN, FL

912 Lake Jessie Dr #1, Winter Haven, FL 33881

Luxury | In-unit laundry | Dishwasher

2 beds

1 bath

$2,000

House for rent

Top amenities
In-Unit Laundry
722 W Central Ave Apt A #Apt A - Photo 1 of 1
3D tour

5d+ ago

Luxury condo for rent in Winter Haven

722 W Central Ave Apt A #Apt A, Winter Haven, FL 33880

Luxury | Package service | Outdoor space

1 bed

1 bath

$995

Condo for rent

Available Aug 11

726 W Central Ave - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Haven

726 W Central Ave, Winter Haven, FL 33880

Luxury | Outdoor space

1 bed

1 bath

$995

Condo for rent

Available Aug 4

351 Avenue N Ne #1 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Haven

Luxury | In-unit laundry | On-site laundry

Studio

1 bath

$1,000

Apartment for rent

Available Oct 6

Top amenities
Ceiling Fan
In-Unit Laundry
On-Site Laundry
550 Woodpecker Pike - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Haven

550 Woodpecker Pike, Winter Haven, FL 33881

Luxury | Swimming pool | Fitness center

1 bed

1 bath

$1,195

House for rent

Available Jun 27

Top amenities
Fitness Center
In-Unit Laundry
On-Site Laundry
Residents Lounge
Swimming Pool
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Updated: October 23, 2025

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Looking for luxury apartments in Winter Haven, FL near you?

🔑Available apartment rentals85
💰Best rent deal2850 Lake Alfred Rd
✨Popular amenities, ,
🧦In-unit laundry
🏠With photos

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