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Houses for Rent in Winter Haven FL with a Swimming Pool - 12 Homes

2069 Whispering Trails Blvd

2069 Whispering Trails Blvd, Winter Haven, FL 33884
1 / 5
$2,060

4 Beds, 2.5 Baths, 2,203 sq ft

Pets Allowed Pool Patio Gated

(833) 252-8444
2752 San Marco Wy

2752 San Marco Wy, Winter Haven, FL 33884
1 / 5
$2,199

4 Beds, 3 Baths, 1,988 sq ft

Pets Allowed Pool

(877) 300-6995
3917 Cypress Landing N

3917 Cypress Landing N, Winter Haven, FL 33884
1 / 5
$1,600

2 Beds, 2 Baths, 1,248 sq ft

Pool Walk-In Closets

(863) 328-4343
1922 Sarah St

1922 Sarah St, Winter Haven, FL 33884
1 / 5
$1,898

3 Beds, 2 Baths, 1,486 sq ft

Cats Allowed Pool Walk-In Closets

(863) 622-9533
2135 Cartgate Ln

2135 Cartgate Ln, Winter Haven, FL 33884
1 / 5
$2,400

3 Beds, 2 Baths, 2,000 sq ft

Dogs Allowed Pool

(863) 280-3106
4148 Dunmore Dr

4148 Dunmore Dr, Lake Wales, FL 33859
1 / 5
$2,400

2 Beds, 2 Baths, 2,341 sq ft

Pool Walk-In Closets Gated Tennis Court Fitness Center

(863) 312-0133
1306 Diego Ter

1306 Diego Ter, Winter Haven, FL 33884
1 / 13
$945

1 Bed, 1 Bath, 450 sq ft

Pool Playground

(760) 477-4641
433 Flamingo Way

433 Flamingo Way, Winter Haven, FL 33881
1 / 5
$1,200

2 Beds, 1.5 Baths

Pets Allowed Pool Gated Fireplace Smoke Free Fitness Center Clubhouse

(863) 294-1844
320 Kayden Cv

320 Kayden Cv, Winter Haven, FL 33884
1 / 5
$1,800

3 Beds, 2 Baths, 2,109 sq ft

Pool

(954) 445-4632
1024 Cambridge Dr

1024 Cambridge Dr, Winter Haven, FL 33881

For Rent

By Owner
$1,950

3 Beds, 2 Baths, 1,725 sq ft

Pool Playground

(863) 474-9138
$2,180

4 Beds, 2.5 Baths, 1,879 sq ft

1658 Teagan Ln, Winter Haven, FL 33884
$2,199

4 Beds, 3 Baths, 1,988 sq ft

2752 San Marco Wy, Winter Haven, FL 33884

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Winter Haven, FL Homes with Pool for Rent

Find the perfect house for rent with a pool in Winter Haven. Whether you're looking for houses with neighborhood swimming areas or a home with a private pool, you can experience comfort, convenience, and relaxation just steps from your back door. Elevate your lifestyle by unwinding in the sun after a long day or hosting poolside gatherings with friends and family. Stay active with invigorating swims or simply enjoy a moment of tranquility by the glistening water.

Dive in at your leisure - when you rent a house with a pool, you make the schedule. You won't have to adhere to restricted swimming hours or wait for summer crowds to thin out. Embrace the freedom of having a pool at your fingertips, available for you to enjoy whenever you want! If you're hoping to swim even when the summer heat begins to cool off, consider searching for rentals with an indoor pool for year-round access. Start searching now. Browse 12 houses for rent with a pool and find your new home today.