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

533 Legacy Park Dr

533 Legacy Park Dr, Casselberry, FL 32707
1 / 5
$3,100

4 Beds, 3 Baths, 2,630 sq ft

Dogs Allowed Pool Patio Walk-In Closets

(321) 215-7507
205 San Gabriel St

205 San Gabriel St, Winter Springs, FL 32708

For Rent

By Owner
1 / 10
$2,100

3 Beds, 2 Baths, 1,102 sq ft

Pets Allowed Pool Smoke Free Security System

(321) 471-1364
249 Long Creek Cove E

249 Long Creek Cove E, Longwood, FL 32750
1 / 39
$2,400

3 Beds, 2 Baths, 1,400 sq ft

Pets Allowed Pool Security System Double Vanities

(724) 404-7020
916 Puma Trail

916 Puma Trail, Winter Springs, FL 32708
1 / 5
$3,899

4 Beds, 3 Baths, 2,851 sq ft

Pool

(407) 967-3976
219 Broadmoor Rd

219 Broadmoor Rd, Lake Mary, FL 32746
1 / 12
$1,300

1 Bed, 1 Bath, 500 sq ft

Pool Furnished Patio

(321) 346-5614
349 Little Springs Ln

349 Little Springs Ln, Longwood, FL 32750
1 / 5
$3,250

4 Beds, 2 Baths, 2,278 sq ft

Pool Fireplace Waterfront

(407) 687-0634
4592 Old Carriage Trail

4592 Old Carriage Trail, Oviedo, FL 32765
1 / 5
$6,500

6 Beds, 4.5 Baths, 4,616 sq ft

Pets Allowed Pool Fireplace

(407) 505-9864
1260 Seminola Blvd

1260 Seminola Blvd, Casselberry, FL 32707
1 / 5
$2,500

3 Beds, 2 Baths, 1,412 sq ft

Dogs Allowed Pool Waterfront

(321) 947-0424
$1,395

2 Beds, 1 Bath, 768 sq ft

3772 Idlebrook Cir, Casselberry, FL 32707
More Rentals Near Winter Springs, FL

We found 16 more rentals that closely match your search.
120 Heatherhill

120 Heatherhill, Longwood, FL 32750
1 / 5
$2,720

4 Beds, 2 Baths, 1,791 sq ft

Pool Fireplace

(407) 284-4494
2446 Waxwing Wy

2446 Waxwing Wy, Sanford, FL 32773
1 / 5
$2,299

3 Beds, 2 Baths, 1,349 sq ft

Pets Allowed Pool Walk-In Closets Gated

(833) 742-0874
222 Washington Ave

222 Washington Ave, Lake Mary, FL 32746
1 / 5
$2,885

4 Beds, 2 Baths, 1,780 sq ft

Pets Allowed Pool Patio Hardwood Floors Yard Fenced Lot

(833) 252-8444
2627 Ambergate Rd

2627 Ambergate Rd, Winter Park, FL 32792

For Rent

By Owner
1 / 5
$5,990

4 Beds, 3 Baths, 1,805 sq ft

Pets Allowed Pool Furnished Hardwood Floors Yard Smoke Free Security System

(727) 201-0451
120 Heatherhill

120 Heatherhill, Longwood, FL 32750
1 / 5
$2,720

4 Beds, 2 Baths, 1,791 sq ft

Pets Allowed Pool

(813) 335-6008
380 Cypress Knee Ln

380 Cypress Knee Ln, Lake Mary, FL 32746
1 / 5
$2,850

4 Beds, 2 Baths, 1,956 sq ft

Pets Allowed Pool

(407) 260-8800
1006 Albamonte Ct

1006 Albamonte Ct, Oviedo, FL 32765
1 / 5
$2,900

3 Beds, 2 Baths, 1,778 sq ft

Pool

(407) 575-7011
120 Heatherhill

120 Heatherhill, Longwood, FL 32750
1 / 5
$2,720

4 Beds, 2 Baths, 1,791 sq ft

Pets Allowed Pool

(904) 563-0108
1340 Chestnut Ave

1340 Chestnut Ave, Winter Park, FL 32789
1 / 5
$7,500

6 Beds, 5.5 Baths, 4,182 sq ft

Pets Allowed Pool Furnished

(407) 547-9242
1245 Wellington Terrace

1245 Wellington Terrace, Maitland, FL 32751
1 / 5
$4,500

5 Beds, 3 Baths, 2,800 sq ft

Pool Fireplace

(321) 666-0301
970 Burlwood Ct

970 Burlwood Ct, Longwood, FL 32750
1 / 5
$3,950

4 Beds, 3.5 Baths, 2,478 sq ft

Pets Allowed Pool Fireplace

(321) 750-8498
1749 Harvest Cove

1749 Harvest Cove, Winter Park, FL 32792
1 / 5
$2,599

3 Beds, 2 Baths, 1,368 sq ft

Pool

(407) 702-5547
1310 Ridge Rd

1310 Ridge Rd, Longwood, FL 32750
1 / 5
$3,200

3 Beds, 2 Baths, 1,520 sq ft

Pool Fireplace

(407) 617-0067
1823 Dover Rd

1823 Dover Rd, Winter Park, FL 32792
1 / 5
$2,990

4 Beds, 2 Baths, 1,808 sq ft

Pets Allowed Pool

(321) 208-4649
$2,200

3 Beds, 2 Baths, 1,467 sq ft

2611 Antilles Dr, Winter Park, FL 32792
$2,900

3 Beds, 2.5 Baths, 1,857 sq ft

478 Wishbone Ln, Lake Mary, FL 32746

Houses Florida Seminole County

Winter Springs, FL Homes with Pool for Rent

Find the perfect house for rent with a pool in Winter Springs. 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.