Houses for Rent in Oakland Hills, FL

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ABOUT THIS HOME
House for Rent in Oakland Hills:
Welcome to Rotonda West. This is a beautiful, well maintained 4 bedrooms, 2 bathrooms, 1 car garage in a well-sought-out area. Close to shopping, schools, and many other activities. All bedrooms hav

$1,800/mo

4 beds2 baths1,890 sq ft

20 Annapolis Ln, Rotonda West, FL 33947

Pets welcome • Parking • A/C

ABOUT THIS HOME
House for Rent in Oakland Hills:
Introducing Caddy Shack, the perfect abode for your short-term stay. This delightful 2 bed, 2 bath waterfront home has been thoughtfully remodeled to exude a beachy atmosphere. Spanning 2,230 square f

$3,700/mo

2 beds2 baths1,337 sq ft

241 Caddy Rd, Rotonda West, FL 33947

Parking • A/C • Car-dependent

ABOUT THIS HOME
House for Rent in Oakland Hills:
Welcome to Rotunda West. You will find this furnished 4 bedroom pool home near Gulf Beaches and Golf Courses. This waterfront home would be the perfect interim option for a family who only needs 6 mon

$2,999/mo

4 beds2 baths1,819 sq ft

231 Caddy Rd, Rotonda West, FL 33947

Dogs welcome • Parking • A/C

ABOUT THIS HOME
House for Rent in Oakland Hills:
Welcome Home!Experience the best of Southwest Florida living in this beautifully maintained rental home located on Rotonda Circle within the highly desirable Rotonda West community. Known for its uniq

$4,000/mo

3 beds2 baths1,350 sq ft

173 Rotonda Cir, Rotonda West, FL 33947

Available 12/01 • Dogs welcome • Parking

ABOUT THIS HOME
House for Rent in Oakland Hills:
Step into this beautifully updated 2-bedroom, 2-bathroom home featuring a brand-new roof (2024), along with a completely remodeled kitchen and bathrooms. Designed for both style and durability, the ho

$2,100/mo

2 beds2 baths1,459 sq ft

66 Oakland Hills Ct, Rotonda West, FL 33947

Pets welcome • Laundry in unit • Parking

ABOUT THIS HOME
House for Rent in Oakland Hills:
"Luxurious 4-Bed Furnished Home with Pool - Minutes from Beaches! 45 Oakland Hills Court, Rotonda West, FL 33947"Your Dream Florida Getaway Awaits!! This beautifully furnished 4-bedroom, 2-bathroom Po

$2,700/mo

4 beds2 baths1,536 sq ft

45 Oakland Hills Ct, Rotonda West, FL 33947

Dogs welcome • Parking • A/C

Property at 33 Caddy Rd, Rotonda West, FL, 33947, 3 beds, 2 baths, [object Object]

$2,600/mo

3 beds2 baths1,490 sq ft

33 Caddy Rd, Rotonda West, FL 33947

Property at 118 Caddy Rd, Rotonda West, FL, 33947, 3 beds, 2 baths, [object Object]

$4,750/mo

3 beds2 baths1,828 sq ft

118 Caddy Rd, Rotonda West, FL 33947

Property at 98 Caddy Rd, Rotonda West, FL, 33947, 2 beds, 2 baths, [object Object]

$4,000/mo

2 beds2 baths1,167 sq ft

98 Caddy Rd, Rotonda West, FL 33947

Property at 13 Oakland Hills Rd, Rotonda West, FL, 33947, 3 beds, 2 baths, [object Object]

$3,900/mo

3 beds2 baths1,694 sq ft

13 Oakland Hills Rd, Rotonda West, FL 33947

Property at 37 Oakland Hills Pl, Rotonda West, FL, 33947, 3 beds, 2 baths, [object Object]

$3,900/mo

3 beds2 baths1,321 sq ft

37 Oakland Hills Pl, Rotonda West, FL 33947

Property at 64 Golfview Rd, Rotonda West, FL, 33947, 4 beds, 2 baths, [object Object]

$2,095/mo

4 beds2 baths1,697 sq ft

64 Golfview Rd, Rotonda West, FL 33947

Property at 65 Oakland Hills Pl, Rotonda West, FL, 33947, 2 beds, 2 baths, [object Object]

$4,500/mo

2 beds2 baths1,444 sq ft

65 Oakland Hills Pl, Rotonda West, FL 33947

Property at 18 Golfview Ct, Rotonda West, FL, 33947, 3 beds, 2 baths, [object Object]

$3,000/mo

3 beds2 baths1,686 sq ft

18 Golfview Ct, Rotonda West, FL 33947

Property at 60 Golfview Rd, Rotonda West, FL, 33947, 3 beds, 2 baths, [object Object]

$5,550/mo

3 beds2 baths1,336 sq ft

60 Golfview Rd, Rotonda West, FL 33947

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ABOUT THIS HOME
House for Rent in Oakland Hills:
RENT TO OWN! This lovely house is near a great beach and an award-winning high school. It is tiled throughout with a fully fenced backyard and a new hot water heater. Lease Duration is as long as it i

$1,250/mo

2 beds1 bath— sq ft

8283 Pelican Rd, Englewood, FL 34224

Pets welcome • Parking • A/C

ABOUT THIS HOME
House for Rent in Oakland Hills:
Live the vacation life daily in this 3-bedroom gem near beaches and Lemon Bay High School! Available now, with no credit issues too big for us to assist. This home features a new Central HVAC, upgrade

$1,500/mo

3 beds1 bath1,000 sq ft

8289 Pelican Rd, Englewood, FL 34224

Pets welcome • A/C • Car-dependent

ABOUT THIS HOME
House for Rent in Oakland Hills:
3 bedroom, 2 bath pool home in Rotonda West available as an unfurnished annual rental. Offering a split bedroom floor-plan, with the primary bedroom suite separated from the other two bedrooms & bathr

$2,000/mo

3 beds2 baths1,306 sq ft

125 Sportsman Rd, Rotonda West, FL 33947

Pets welcome • Parking • A/C

ABOUT THIS HOME
House for Rent in Oakland Hills:
THIS IS AN ANNUAL UNFUNISHED RENTAL PROPERTY.........50 + COMMUNITY......PETS ARE NOT PERMITTED.... Located in the great community of Clubhouse Condominium complex. A deed restricted community. This i

$1,525/mo

2 beds2 baths1,540 sq ft

177 Boundary Blvd, Rotonda West, FL 33947

Laundry in unit • Parking

ABOUT THIS HOME
House for Rent in Oakland Hills:
Beautiful 3 Bedroom, 2 Bathroom Home in Rotonda West This well-maintained single-family home offers comfort and convenience in a peaceful Rotonda West neighborhood. Featuring a new roof and new A/C, t

$2,600/mo

3 beds2 baths— sq ft

137 Sportsman Rd, Rotonda West, FL 33947

Dogs welcome • Laundry in unit • Parking

ABOUT THIS HOME
House for Rent in Oakland Hills:
Leave those Winter blues behind as the sun is shining and the temperatures are perfect here in Southwest FL. Located in the well sought Rotonda community, this home is the perfect escape. Do not forge

$4,500/mo

3 beds2 baths1,598 sq ft

155 Long Meadow Ln, Rotonda West, FL 33947

Parking • A/C • Car-dependent

Property at 123 Marker Rd, Rotonda West, FL, 33947, 3 beds, 2 baths, [object Object]

$2,250/mo

3 beds2 baths2,006 sq ft

123 Marker Rd, Rotonda West, FL 33947

Property at 168 Marker Rd, Rotonda West, FL, 33947, 3 beds, 2 baths, [object Object]

$2,900/mo

3 beds2 baths2,000 sq ft

168 Marker Rd, Rotonda West, FL 33947

Property at 8340 Roosevelt St Unit B, Englewood, FL, 34224, 2 beds, 2 baths, [object Object]

$950/mo

2 beds2 baths1,165 sq ft

8340 Roosevelt St Unit B, Englewood, FL 34224

Property at 8238 Harborside Cir, Englewood, FL, 34224, 3 beds, 3 baths, [object Object]

$2,200/mo

3 beds3 baths1,590 sq ft

8238 Harborside Cir, Englewood, FL 34224

Property at 20 Pebble Beach Rd, Rotonda West, FL, 33947, 3 beds, 2 baths, [object Object]

$1,499/mo

3 beds2 baths1,308 sq ft

20 Pebble Beach Rd, Rotonda West, FL 33947

Property at 71 Mark Twain Ln, Rotonda West, FL, 33947, 3 beds, 2 baths, [object Object]

$2,050/mo

3 beds2 baths1,622 sq ft

71 Mark Twain Ln, Rotonda West, FL 33947

Property at 84 Boundary Blvd, Rotonda West, FL, 33947, 2 beds, 2 baths, [object Object]

$2,900/mo

2 beds2 baths1,100 sq ft

84 Boundary Blvd, Rotonda West, FL 33947

Property at 87 Mark Twain Ln, Rotonda West, FL, 33947, 3 beds, 2 baths, [object Object]

$2,500/mo

3 beds2 baths1,235 sq ft

87 Mark Twain Ln, Rotonda West, FL 33947

Property at 42 Mark Twain Ln, Rotonda West, FL, 33947, 3 beds, 2.5 baths, [object Object]

$2,800/mo

3 beds2.5 baths1,677 sq ft

42 Mark Twain Ln, Rotonda West, FL 33947

Property at 18 Bunker Pl, Rotonda West, FL, 33947, 3 beds, 2 baths, [object Object]

$2,500/mo

3 beds2 baths1,591 sq ft

18 Bunker Pl, Rotonda West, FL 33947

Property at 19 Medalist Way, Rotonda West, FL, 33947, 3 beds, 3 baths, [object Object]

$5,450/mo

3 beds3 baths2,413 sq ft

19 Medalist Way, Rotonda West, FL 33947

Property at 181 Bunker Rd, Rotonda West, FL, 33947, 2 beds, 2 baths, [object Object]

$4,600/mo

2 beds2 baths1,355 sq ft

181 Bunker Rd, Rotonda West, FL 33947

Property at 119 Bunker Rd, Rotonda West, FL, 33947, 3 beds, 2 baths, [object Object]

$6,680/mo

3 beds2 baths1,620 sq ft

119 Bunker Rd, Rotonda West, FL 33947

Property at 80 Mariner Ln, Rotonda West, FL, 33947, 3 beds, 2 baths, [object Object]

$4,800/mo

3 beds2 baths2,052 sq ft

80 Mariner Ln, Rotonda West, FL 33947

The information is being provided by Southwest Florida Multiple Listing Service. Information deemed reliable but not guaranteed. Information is provided for consumers' personal, non-commercial use, and may not be used for any purpose other than the identification of potential properties for purchase. Copyright 2025 Southwest Florida Multiple Listing Service. All Rights Reserved.

Based on information submitted to the MLS GRID as of Sun Nov 30 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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