Houses for Rent in Winter Park FL with a Swimming Pool - 6 Homes

2019 Soaring Oak Way

2019 Soaring Oak Way, Winter Park, FL 32792
1 / 25
$5,000

4 Beds, 3 Baths, 3,050 sq ft

Pets Allowed Pool Gated Playground Clubhouse Double Vanities

(321) 257-2784
1461 Vía Tuscany

1461 Vía Tuscany, Winter Park, FL 32789
1 / 5
$45,000

5 Beds, 5 Baths, 8,353 sq ft

Pets Allowed Pool Fireplace Waterfront

(407) 629-4446
2809 Bower Rd

2809 Bower Rd, Winter Park, FL 32792
1 / 5
$3,200

3 Beds, 2 Baths, 1,488 sq ft

Pets Allowed Pool Fireplace

(407) 450-0840
1741 Glencoe Rd

1741 Glencoe Rd, Winter Park, FL 32789
1 / 5
$13,000

4 Beds, 4.5 Baths, 4,692 sq ft

Pool Fireplace

(407) 304-6458
1749 Harvest Cove

1749 Harvest Cove, Winter Park, FL 32792
1 / 5
$2,800

3 Beds, 2 Baths, 1,368 sq ft

Pool

(407) 702-5547
5424 Kingswood Dr

5424 Kingswood Dr, Orlando, FL 32810
1 / 5
$2,695

4 Beds, 2 Baths, 1,895 sq ft

Pool

(407) 325-3593
More Rentals Near Winter Park, FL

We found 19 more rentals that closely match your search.
1446 Pon Pon Ct

1446 Pon Pon Ct, Orlando, FL 32825
1 / 5
$2,240

3 Beds, 2 Baths, 1,583 sq ft

Pets Allowed Pool Patio Yard Fenced Lot Double Vanities

(833) 252-8444
5264 Hidden Cypress Ln

5264 Hidden Cypress Ln, Oviedo, FL 32765
1 / 5
$2,000

3 Beds, 2 Baths, 1,502 sq ft

Pool Furnished Security System

(516) 859-2475
1026 Piedmont Lakes Blvd

1026 Piedmont Lakes Blvd, Apopka, FL 32703
1 / 5
$2,630

3 Beds, 2.5 Baths, 1,817 sq ft

Pets Allowed Pool Yard Fenced Lot Double Vanities

(833) 252-8444
205 San Gabriel St

205 San Gabriel St, Winter Springs, FL 32708
1 / 10
$2,100

3 Beds, 2 Baths, 1,102 sq ft

Pets Allowed Pool Smoke Free
4002 Bolinas Ct

4002 Bolinas Ct, Orlando, FL 32817
1 / 17
$2,350

3 Beds, 2 Baths, 1,300 sq ft

Pool Waterfront

(321) 594-7216
1532 Hunters Mill Pl

1532 Hunters Mill Pl, Oviedo, FL 32765
1 / 5
$5,749

4 Beds, 4.5 Baths, 4,896 sq ft

Pets Allowed Pool Fireplace

(407) 505-9864
1407 Berwyn Rd

1407 Berwyn Rd, Orlando, FL 32806
1 / 5
$2,799

3 Beds, 2 Baths, 1,585 sq ft

Pets Allowed Pool

(407) 461-8637
1223 Harbour Island Rd

1223 Harbour Island Rd, Orlando, FL 32809
1 / 5
$6,750

4 Beds, 3.5 Baths, 4,346 sq ft

Pool

(407) 675-3098
311 Streamview Way

311 Streamview Way, Winter Springs, FL 32708
1 / 5
$2,975

2 Beds, 2 Baths, 1,519 sq ft

Pets Allowed Pool

(321) 231-2262
3876 Biscayne Dr

3876 Biscayne Dr, Winter Springs, FL 32708
1 / 5
$2,774

3 Beds, 2 Baths, 1,950 sq ft

Pets Allowed Pool

(754) 204-5431
1004 Grayson Dr

1004 Grayson Dr, Orlando, FL 32825
$2,600

3 Beds, 1 Bath, 828 sq ft

Pets Allowed Pool

(407) 202-2640
6700 Crescent Ridge Rd

6700 Crescent Ridge Rd, Orlando, FL 32810
1 / 5
$2,200

5 Beds, 2 Baths, 1,988 sq ft

Pool

(407) 575-1355
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
10336 Jane Eyre Dr

10336 Jane Eyre Dr, Orlando, FL 32825
1 / 5
$3,000

4 Beds, 2 Baths, 1,812 sq ft

Pets Allowed Pool

(407) 360-4435
10708 Fallow Trl

10708 Fallow Trl, Orlando, FL 32817
1 / 5
$2,450

3 Beds, 2.5 Baths, 1,630 sq ft

Pool Fireplace

(407) 791-7768
10538 Stradford Row

10538 Stradford Row, Orlando, FL 32817
1 / 5
$2,575

4 Beds, 2.5 Baths, 2,143 sq ft

Pets Allowed Pool Fireplace

(407) 466-3058
$1,100

1 Bed, 1 Bath, 542 sq ft

5505 Hernandes Dr, Orlando, FL 32808
$1,400

1 Bed, 1 Bath, 675 sq ft

3998 Atrium Dr, Orlando, FL 32822
$2,450

5 Beds, 2 Baths, 2,018 sq ft

4113 Seybold Ave, Orlando, FL 32808

Houses Florida Orange County

Winter Park, FL Homes with Pool for Rent

Find the perfect house for rent with a pool in Winter Park. 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 6 houses for rent with a pool and find your new home today.