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Houses for Rent in Winter Springs FL with a Swimming Pool - 8 Homes

423 Sandringham Ct

423 Sandringham Ct, Winter Springs, FL 32708
1 / 16
$4,100

5 Beds, 4.5 Baths, 3,512 sq ft

Pool Walk-In Closets Hardwood Floors Gated Playground Lounge Tennis Court
219 Broadmoor Rd

219 Broadmoor Rd, Lake Mary, FL 32746

For Rent

By Owner
1 / 14
$1,327

1 Bed, 1 Bath, 500 sq ft

Pool Furnished Patio
303 Freedom's Ring Dr

303 Freedom's Ring Dr, Winter Springs, FL 32708
1 / 19
$2,095

3 Beds, 2.5 Baths, 1,468 sq ft

Pool Patio Gated
526 Seasons Ct

526 Seasons Ct, Winter Springs, FL 32708
1 / 20
$2,300

3 Beds, 2 Baths, 1,161 sq ft

Pool Vaulted Ceiling
510 Spoonbill Ct

510 Spoonbill Ct, Winter Springs, FL 32708
1 / 5
$3,000

3 Beds, 2.5 Baths, 1,695 sq ft

Pets Allowed Pool
530 Webster St

530 Webster St, Lake Mary, FL 32746
1 / 5
$2,690

3 Beds, 2 Baths, 1,796 sq ft

Pool
450 Longwood Cir

450 Longwood Cir, Longwood, FL 32750
1 / 5
$2,150

4 Beds, 1.5 Baths, 1,426 sq ft

Dogs Allowed Pool
$1,327

1 Bed, 1 Bath, 500 sq ft

219 Broadmoor Rd, Lake Mary, FL 32746
More Rentals Near Winter Springs, FL

We found 25 more rentals that closely match your search.
523 E Livingston St

523 E Livingston St, Orlando, FL 32803
1 / 23

Videos
$3,950

3 Beds, 2.5 Baths, 1,250 sq ft

Pets Allowed Pool Furnished
1542 Almond Avenue

1542 Almond Avenue, Orlando, FL 32814
1 / 25
$3,950

3 Beds, 2.5 Baths, 2,000 sq ft

Pets Allowed Pool Walk-In Closets Hardwood Floors Yard Security System Fitness Center
2550 N Alafaya Trl

2550 N Alafaya Trl, Orlando, FL 32826

For Rent

By Owner
1 / 17
$1,500

2 Beds, 2 Baths, 1,000 sq ft

Pool Patio Fitness Center
7431 Portside Ct

7431 Portside Ct, Winter Park, FL 32792
1 / 16
$2,490

3 Beds, 2 Baths, 1,448 sq ft

Pets Allowed Pool
1197 W Lakeview Cir

1197 W Lakeview Cir, Altamonte Springs, FL 32714
1 / 16
$2,890

4 Beds, 3 Baths, 2,881 sq ft

Pets Allowed Pool
12846 Maribou Cir

12846 Maribou Cir, Orlando, FL 32828
1 / 20
$2,300

3 Beds, 2 Baths, 1,611 sq ft

Pets Allowed Pool Patio Fitness Center
413 E Citrus St

413 E Citrus St, Altamonte Springs, FL 32701
1 / 14
$2,620

4 Beds, 2 Baths, 2,458 sq ft

Pets Allowed Pool Fireplace
216 Lochmond Dr

216 Lochmond Dr, Casselberry, FL 32730
1 / 16
$2,320

3 Beds, 2 Baths, 1,188 sq ft

Pets Allowed Pool
409 Riverwoods Cir

409 Riverwoods Cir, Orlando, FL 32825
1 / 16
$2,625

3 Beds, 2 Baths, 1,878 sq ft

Pets Allowed Pool Yard Fenced Lot
14834 Oldham Dr

14834 Oldham Dr, Orlando, FL 32826
1 / 16
$3,250

4 Beds, 3 Baths, 2,357 sq ft

Pets Allowed Pool Yard Fireplace Fenced Lot Double Vanities
748 Tomlinson Terrace

748 Tomlinson Terrace, Lake Mary, FL 32746
1 / 16
$3,090

4 Beds, 3 Baths, 2,100 sq ft

Pets Allowed Pool Yard Fireplace Fenced Lot Double Vanities
165 Walnut Crest Run

165 Walnut Crest Run, Sanford, FL 32771
1 / 14
$2,300

3 Beds, 2 Baths, 1,684 sq ft

Pets Allowed Pool Yard Fenced Lot Deck Vaulted Ceiling Double Vanities
238 Afton Square

238 Afton Square, Altamonte Springs, FL 32714
1 / 6
$1,350

1 Bed, 1 Bath, 552 sq ft

Pets Allowed Pool Fitness Center
2309 Hidden Palm Dr

2309 Hidden Palm Dr, Sanford, FL 32773
1 / 20
$2,950

5 Beds, 3 Baths, 2,465 sq ft

Pets Allowed Pool
1118 Overdale St

1118 Overdale St, Orlando, FL 32825
1 / 5
$3,200

3 Beds, 1 Bath, 1,175 sq ft

Pets Allowed Pool Furnished Fenced Lot Security System
2851 Dorell Ave

2851 Dorell Ave, Orlando, FL 32814
1 / 5
$8,650

5 Beds, 5 Baths, 4,953 sq ft

Dogs Allowed Pool Patio Walk-In Closets Hardwood Floors Deck Tennis Court
523 E Livingston St

523 E Livingston St, Orlando, FL 32803
1 / 19
$4,200

3 Beds, 2.5 Baths, 1,250 sq ft

Pool Furnished Security System
1890 Emerald Green Cir

1890 Emerald Green Cir, Oviedo, FL 32765
1 / 5
$4,000

5 Beds, 3.5 Baths, 2,935 sq ft

Pets Allowed Pool
1636 Lawndale Cir

1636 Lawndale Cir, Winter Park, FL 32792
1 / 5
$3,995

3 Beds, 2.5 Baths, 1,990 sq ft

Pets Allowed Pool
8676 Hillside Dr

8676 Hillside Dr, Orlando, FL 32810
1 / 5
$2,600

3 Beds, 2 Baths, 1,666 sq ft

Pool
229 Flame Ave

229 Flame Ave, Maitland, FL 32751
1 / 5
$4,550

4 Beds, 4 Baths, 4,055 sq ft

Pets Allowed Pool Fireplace
1511 Leeway Ave

1511 Leeway Ave, Orlando, FL 32810
1 / 5
$2,550

3 Beds, 2 Baths, 1,628 sq ft

Pool
315 Lazy Acres Ln

315 Lazy Acres Ln, Longwood, FL 32750
1 / 5
$5,800

5 Beds, 3.5 Baths, 5,473 sq ft

Pets Allowed Pool Fireplace
2619 Hendy Ct

2619 Hendy Ct, Orlando, FL 32817
1 / 5
$2,550

3 Beds, 2 Baths, 1,032 sq ft

Pets Allowed Pool
2627 Verona Trail

2627 Verona Trail, Winter Park, FL 32789
1 / 5
$5,050

4 Beds, 3 Baths, 2,422 sq ft

Pool Fireplace

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