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Houses for Rent in Winter Haven FL with a Swimming Pool - 9 Homes

1661 Teagan Ln

1661 Teagan Ln, Winter Haven, FL 33884
1 / 20
$1,880

3 Beds, 2 Baths, 1,287 sq ft

Dogs Allowed Pool
1343 Benevento Dr

1343 Benevento Dr, Winter Haven, FL 33884
1 / 5
$2,000

4 Beds, 2 Baths, 1,849 sq ft

Pool Walk-In Closets
2520 Ave A SW

2520 Ave A SW, Winter Haven, FL 33880
1 / 16
$1,825

3 Beds, 2 Baths, 1,310 sq ft

Pool
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
548 Woodpecker Pike

548 Woodpecker Pike, Winter Haven, FL 33881
1 / 5
$1,200

2 Beds, 2 Baths

Pets Allowed Pool Gated Fireplace Smoke Free Fitness Center Clubhouse
1019 State Rd 540 W

1019 State Rd 540 W, Winter Haven, FL 33880
1 / 5
$3,500

4 Beds, 3.5 Baths, 3,195 sq ft

Pets Allowed Pool Fireplace Waterfront
425 Greenfield Rd

425 Greenfield Rd, Winter Haven, FL 33884

For Rent

By Owner
1 / 17
$1,700

2 Beds, 2 Baths, 1,500 sq ft

Pets Allowed Pool Gated Smoke Free
2443 Taloncrest Ct

2443 Taloncrest Ct, Eagle Lake, FL 33839
1 / 5
$2,600

5 Beds, 3 Baths, 2,447 sq ft

Pool Walk-In Closets Fireplace Playground Smoke Free
246 Cove At Eagle Lake Cir

246 Cove At Eagle Lake Cir, Eagle Lake, FL 33839
1 / 5
$3,300

4 Beds, 2 Baths, 2,224 sq ft

Pets Allowed Pool
More Rentals Near Winter Haven, FL

We found 16 more rentals that closely match your search.
1100 W Commerce Ave

1100 W Commerce Ave, Haines City, FL 33844
1 / 13
$1,200

1 Bed, 1.5 Baths, 800 sq ft

Pets Allowed Pool Furnished Fitness Center
185 Brooke's Pl

185 Brooke's Pl, Haines City, FL 33844
1 / 20
$2,800

3 Beds, 2 Baths, 1,548 sq ft

Pets Allowed Pool Furnished Fitness Center
920 Serchio St

920 Serchio St, Haines City, FL 33844
1 / 20
$2,100

3 Beds, 2 Baths, 1,440 sq ft

Pets Allowed Pool
2912 Poppy Ave

2912 Poppy Ave, Haines City, FL 33844
1 / 11
$2,250

3 Beds, 2 Baths, 1,401 sq ft

Pets Allowed Pool
2660 Hemingway Ave

2660 Hemingway Ave, Haines City, FL 33844
1 / 14
$2,200

3 Beds, 2 Baths, 1,130 sq ft

Pets Allowed Pool
5736 Mast Ave

5736 Mast Ave, Haines City, FL 33844
1 / 20
$2,000

3 Beds, 2 Baths, 1,491 sq ft

Dogs Allowed Pool
185 Piave St

185 Piave St, Haines City, FL 33844

For Rent

By Owner
1 / 14
$1,895

4 Beds, 2 Baths, 1,722 sq ft

Pool Patio Walk-In Closets Island Kitchen
753 W Main St

753 W Main St, Haines City, FL 33844
1 / 5
$1,150

1 Bed, 1 Bath

Pets Allowed Pool Furnished Fireplace Smoke Free Clubhouse
2660 Hemingway Ave

2660 Hemingway Ave, Haines City, FL 33844
1 / 5
$2,200

3 Beds, 2 Baths, 1,130 sq ft

Pets Allowed Pool
185 Brooke's Pl

185 Brooke's Pl, Haines City, FL 33844
1 / 5
$2,200

3 Beds, 2 Baths, 1,548 sq ft

Pets Allowed Pool
664 Tanaro Ln

664 Tanaro Ln, Haines City, FL 33844
1 / 5
$3,300

4 Beds, 3 Baths, 2,080 sq ft

Pets Allowed Pool
1115 Mariner Cay Dr

1115 Mariner Cay Dr, Haines City, FL 33844
1 / 5
$2,500

4 Beds, 3 Baths, 1,644 sq ft

Pool Furnished
1113 Mariner Cay Dr

1113 Mariner Cay Dr, Haines City, FL 33844
1 / 5
$2,400

4 Beds, 3 Baths, 1,644 sq ft

Pool Furnished
$1,900

3 Beds, 2 Baths, 1,500 sq ft

1949 Harrods Pl, Haines City, FL 33844
$2,300

3 Beds, 3 Baths, 2,265 sq ft

957 Silverlake Blvd, Lake Alfred, FL 33850
$1,745

3 Beds, 2 Baths, 1,504 sq ft

1516 Ellesmere Ave, Haines City, FL 33844

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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 9 houses for rent with a pool and find your new home today.