Houses for Rent in Oakland FL with a Swimming Pool - 3 Homes

15041 Summer Harvest St

15041 Summer Harvest St, Oakland, FL 34787
1 / 5
$3,750

4 Beds, 4.5 Baths, 2,687 sq ft

Pool Walk-In Closets Fireplace Smoke Free Clubhouse

(407) 930-3530
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
$3,400

4 Beds, 3.5 Baths, 2,500 sq ft

16754 Oakboro St, Oakland, FL 34787
More Rentals Near Oakland, FL

We found 24 more rentals that closely match your search.
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
4434 Davos Dr

4434 Davos Dr, Clermont, FL 34711
1 / 5
$2,650

4 Beds, 4 Baths, 1,987 sq ft

Cats Allowed Pool Walk-In Closets

(352) 706-9843
4370 Davos Dr

4370 Davos Dr, Clermont, FL 34711
1 / 5
$2,600

4 Beds, 2 Baths, 1,654 sq ft

Pets Allowed Pool

(941) 218-7227
7793 Marsala Street

7793 Marsala Street, Clermont, FL 34714
1 / 5
$3,755

4 Beds, 2.5 Baths, 2,903 sq ft

Pets Allowed Pool

(224) 202-1826
6391 Blissful St

6391 Blissful St, Clermont, FL 34787
1 / 5
$2,599

3 Beds, 3 Baths, 1,782 sq ft

Dogs Allowed Pool Patio Walk-In Closets Fitness Center

(321) 359-8514
3100 Ambersweet Pl

3100 Ambersweet Pl, Clermont, FL 34711
1 / 29
$2,450

3 Beds, 2 Baths, 1,820 sq ft

Dogs Allowed Pool Patio Walk-In Closets Yard Gated Waterfront

(689) 407-2764
3846 Beacon Ridge Way

3846 Beacon Ridge Way, Clermont, FL 34711
1 / 5
$3,000

4 Beds, 2.5 Baths, 2,180 sq ft

Pool Walk-In Closets Gated Fireplace Playground Sauna Smoke Free

(407) 614-5158
11415 Waterstone Loop Dr

11415 Waterstone Loop Dr, Windermere, FL 34786
1 / 5
$10,500

5 Beds, 6 Baths, 4,845 sq ft

Pets Allowed Pool Waterfront

(407) 616-5098
11050 Coniston Way

11050 Coniston Way, Windermere, FL 34786
1 / 5
$11,500

5 Beds, 4.5 Baths, 4,291 sq ft

Dogs Allowed Pool Furnished Fireplace

(407) 900-0771
11263 Ledgement Ln

11263 Ledgement Ln, Windermere, FL 34786
1 / 5
$4,999

5 Beds, 3.5 Baths, 3,360 sq ft

Pool

(407) 967-3976
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
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
804 Starke Lake Cir

804 Starke Lake Cir, Ocoee, FL 34761
1 / 5
$2,250

3 Beds, 2 Baths, 1,609 sq ft

Dogs Allowed Pool

(407) 864-0505
9525 Lavill Ct

9525 Lavill Ct, Windermere, FL 34786
1 / 5
$10,500

4 Beds, 3.5 Baths, 4,097 sq ft

Pool Fireplace Waterfront

(321) 332-3000
13419 Zori Ln

13419 Zori Ln, Windermere, FL 34786
1 / 5
$4,500

3 Beds, 3 Baths, 2,415 sq ft

Pool

(321) 286-6065
307 W 4th Ave

307 W 4th Ave, Windermere, FL 34786
1 / 5
$6,500

4 Beds, 3 Baths, 3,190 sq ft

Pets Allowed Pool

(407) 779-6677
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
705 Vandergrift Dr

705 Vandergrift Dr, Ocoee, FL 34761
1 / 5
$2,800

4 Beds, 2.5 Baths, 1,880 sq ft

Pool

(321) 947-4014
223 Valencia Shores Dr

223 Valencia Shores Dr, Winter Garden, FL 34787
1 / 5
$4,000

3 Beds, 2 Baths, 1,998 sq ft

Dogs Allowed Pool

(407) 590-6192
776 S Grand Hwy

776 S Grand Hwy, Clermont, FL 34711

For Rent

By Owner
1 / 8
$1,600

2 Beds, 2 Baths, 900 sq ft

Pool

(386) 961-4188
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
$4,890

6 Beds, 5 Baths, 3,860 sq ft

2292 Juniper Berry Dr, Minneola, FL 34756
$3,000

4 Beds, 2.5 Baths, 2,114 sq ft

5081 Railroad Ave, Winter Garden, FL 34787
$3,000

4 Beds, 2.5 Baths, 2,114 sq ft

4991 Railroad Ave, Winter Garden, FL 34787

Houses Florida Orange County

Oakland, FL Homes with Pool for Rent

Find the perfect house for rent with a pool in Oakland. 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 3 houses for rent with a pool and find your new home today.