Houses for Rent in Winter Garden FL with a Swimming Pool - 17 Homes

17002 Tradewind Pt

17002 Tradewind Pt, Winter Garden, FL 34787
1 / 5
$3,500

4 Beds, 4 Baths, 2,983 sq ft

Pool Walk-In Closets Fireplace Waterfront Fitness Center

(321) 346-5308
16253 Pebble Bluff Loop

16253 Pebble Bluff Loop, Winter Garden, FL 34787
1 / 7
$2,550

3 Beds, 2 Baths, 1,700 sq ft

Pool Walk-In Closets Waterfront Smoke Free Fitness Center Clubhouse

(689) 407-8375
14990 Lebeau Loop

14990 Lebeau Loop, Winter Garden, FL 34787

For Rent

By Owner
1 / 29
$3,100

3 Beds, 2.5 Baths, 1,944 sq ft

Pool Playground

(862) 348-2474
15986 Johns Lake Overlook Dr

15986 Johns Lake Overlook Dr, Winter Garden, FL 34787
1 / 5
$9,000

5 Beds, 5 Baths, 4,498 sq ft

Pool Waterfront

(407) 432-9767
15763 Shorebird Ln

15763 Shorebird Ln, Winter Garden, FL 34787
1 / 5
$6,950

5 Beds, 4.5 Baths, 3,816 sq ft

Pool

(407) 675-3098
13509 Lake Luntz Dr

13509 Lake Luntz Dr, Winter Garden, FL 34787
1 / 5
$6,000

4 Beds, 3 Baths, 2,752 sq ft

Pool Fireplace

(407) 901-9939
10207 Atwater Bay Dr

10207 Atwater Bay Dr, Winter Garden, FL 34787
1 / 5
$8,500

5 Beds, 4.5 Baths, 3,354 sq ft

Pets Allowed Pool Waterfront

(407) 360-0822
14681 Scott Key Dr

14681 Scott Key Dr, Winter Garden, FL 34787
1 / 5
$5,500

4 Beds, 3.5 Baths, 2,935 sq ft

Pets Allowed Pool

(407) 963-2139
223 Valencia Shores Dr

223 Valencia Shores Dr, Winter Garden, FL 34787
1 / 5
$3,500

3 Beds, 2 Baths, 1,998 sq ft

Dogs Allowed Pool

(407) 590-6192
12138 Stoneleigh Aly

12138 Stoneleigh Aly, Winter Garden, FL 34787
1 / 37
$2,850

3 Beds, 2 Baths, 1,588 sq ft

Pets Allowed Pool Furnished Playground Lounge Fitness Center Clubhouse

(321) 352-3446
13849 Lanyard Way

13849 Lanyard Way, Winter Garden, FL 34787
1 / 30
$3,400

4 Beds, 3.5 Baths, 2,900 sq ft

Dogs Allowed Pool Balcony Patio Yard High Ceilings

(628) 237-4719
101 N Starr St

101 N Starr St, Oakland, FL 34760
1 / 5
$5,900

3 Beds, 3.5 Baths, 2,502 sq ft

Pets Allowed Pool Furnished Fireplace

(256) 283-8747
364 Belhaven Falls Dr

364 Belhaven Falls Dr, Ocoee, FL 34761
1 / 5
$3,000

4 Beds, 3 Baths, 2,587 sq ft

Pool

(407) 242-7758
1238 Glenheather Dr

1238 Glenheather Dr, Windermere, FL 34786
1 / 39
$4,900

4 Beds, 3 Baths, 2,924 sq ft

Dogs Allowed Pool Balcony Patio Gated Waterfront Basketball Court

(628) 261-6110
$3,000

4 Beds, 2.5 Baths, 2,114 sq ft

4991 Railroad Ave, Winter Garden, FL 34787
$2,995

3 Beds, 3 Baths, 2,719 sq ft

585 Setting Sun Dr, Winter Garden, FL 34787
$3,000

4 Beds, 2.5 Baths, 2,114 sq ft

5081 Railroad Ave, Winter Garden, FL 34787

Houses Florida Orange County

Winter Garden, FL Homes with Pool for Rent

Find the perfect house for rent with a pool in Winter Garden. 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 17 houses for rent with a pool and find your new home today.