Location: Rotonda West Oakland Hills, Rotonda West
Do Not Show Listings
231 CADDY RD, ROTONDA WEST, FL 33947
$4,10027 Days on yellowkey MLS ID: C7527190
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1819 Built: 1980Community: Rotonda West Oakland HillsSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: None
High School: None
Tax Year:
Middle School: None
Remarks: 4-Bedroom, 2-Bath Fully Furnished Home in Oakland Hills, Rotonda West. Enjoy a Heated Pool & waterfront setting. Ask about weekly & monthly pricing! Rates change in and out of snowbird season. May - Nov 2026 - $3200/month plus taxes and fees Dec 2026 - Mar 2027 - $4100/month plus taxes and fees
Listing is courtesy of: R & R CONSULTING LLC (941-916-1662)
Listing Agent: Ruth Keiling (941-916-1662)
98 CADDY RD, ROTONDA WEST, FL 33947
$4,0003540 Days on yellowkey MLS ID: D5914648
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1167 Built: 1974 Tax: $2,918 (2021)Community: Rotonda West Oakland HillsSingle Family
Taxes:$2,918
Tax Year: 2021
Remarks: Seasonal/Short-Term Rental available throughout the year. Posted rate is winter/peak season rate. Off-season rate is $2,200/month. Looking for that "beachy cottage" feel in your Florida vacation home? Look no further - you've found it in this adorable 2 bedroom, 2 bathroom pool home, with electrically heated, saltwater pool. The spacious master bedroom features a king size bed and newly updated walk-in shower in the master bath. The roomy 2nd bedroom has a queen bed, and there is a queen and a twin inflatable mattress available if you have additional visitors during your stay. The bright and airy living room and dining room combo are perfect for entertaining guests. The expansive lanai and pool area overlook the 5th fairway of The Hill's golf course. The home has 3 televisions - one in the living room and one in each of the bedrooms. Electric heat pump and solar cover for the pool. Live streaming TV. Fireplace does not work, and will not be repaired, decoration only.
Listing is courtesy of: TALL PINES REALTY (941-475-5015)
Listing Agent: Madelene Waterhouse (941-276-6015)
113 BOUNDARY BLVD #2, ROTONDA WEST, FL 33947
$1,595120 Days on yellowkey MLS ID: A4685608
REDUCED by $30 (1.8%) on 06/16/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1323 Built: 2022Community: Rotonda West Oakland HillsTownhouse
Elementary School: Vineland Elementary
High School: Lemon Bay High
Middle School: L.A. Ainger Middle
Remarks: McCall Road or Placida Road to Rotonda Drive North or West. Proceed to Boundary Blvd then west to the site. Welcome to this well-maintained and comfortable condo located at 113 Boundary Blvd Unit B, offering the perfect combination of convenience, privacy, and Florida lifestyle. Situated in a quiet residential community, this unit provides easy access to shopping, dining, golf, and the beautiful Gulf Coast beaches. Inside, the home features a bright and functional layout with comfortable living space and plenty of natural light. The living and dining areas flow together nicely, creating an inviting space for relaxing or entertaining. The kitchen offers ample cabinet and counter space, making meal preparation easy and efficient. The bedrooms are spacious and comfortable, providing a peaceful retreat at the end of the day. Large windows allow for plenty of natural light while maintaining privacy. Residents will enjoy the peaceful surroundings and convenient location, with nearby access to local amenities, parks, golf courses, and waterfront activities. The property is also just a short drive from downtown Punta Gorda, Fishermen’s Village, and area marinas. Property Highlights • Comfortable and functional floor plan • Quiet and well-maintained community • Convenient location near shopping, dining, and golf • Easy access to Punta Gorda and surrounding areas • Close to Gulf Coast beaches and waterfront activities This home offers a great opportunity to enjoy relaxed Florida living in a convenient location.
Listing is courtesy of: STRINGER MANAGEMENT INC (941-922-4959)
Listing Agent: Mike Sorensen (941-380-2900)
125 BOUNDARY BLVD #2, ROTONDA WEST, FL 33947
$1,59990 Days on yellowkey MLS ID: A4689500
REDUCED by $100 (5.9%) on 06/11/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1323 Built: 2023Community: Rotonda West Oakland HillsHalf Duplex
Remarks: LARGE 3 beds and 2 baths UNIT AVAILABLE ! LAWN CARE included! This unit is part of a duplex building (2 units) built in 2022. Large size unit, perfect for a family or multi-generation. Unit is completely PRIVATE with a SEPARATED entrance. Master Bedroom with master bathroom (SHOWER) and large walk-in closet. Two additional rooms with built-in closet and an additional/guest bathroom bath(Tub) . Fully equipped and premium kitchen: Newer stainless steel appliances, stone counter tops. Large Main room (open concept) with a dining area. Washer and Dryer connection in unit. One LARGE Car garage. Very LARGE common driveway. Property is seated and an oversized piece of land perfect for privacy. Very Quiet area and unit canal view. very close to Golfs, country club and minutes to shops and beaches. Rotonda West is a deeded restricted area providing calm, confort and a premium lifestyle. Pet friendly. One month security deposit and first month rent only. APPLY TODAY !
Listing is courtesy of: RAYNARD REALTY GROUP LLC (786-201-8463)
Listing Agent: Julien Raynard (786-201-8463)
249 ROTONDA BLVD W, ROTONDA WEST, FL 33947
$2,45034 Days on yellowkey MLS ID: C7526962
REDUCED by $249 (9.2%) on 06/08/2026
Bed: 4 Bath: 2.0 Gar: 3 Liv Area Sq Ft: 1755 Built: 2021Community: Rotonda West Oakland HillsSingle Family
Remarks: Fully furnished 4-bedroom, 2-bath home available for a long-term 12-month lease in the desirable Oakland Hills section of Rotonda West. Built in 2021, this spacious home offers 1,755 square feet of comfortable living space, a 3-car garage, and an oversized 0.37-acre lot. Inside, the home features an open and functional floor plan with cathedral ceilings, tray ceiling accents, stone countertops, upgraded cabinetry, and a bright kitchen/family room combination. The main living areas feature tile flooring, while the bedrooms provide comfortable private spaces. The primary suite includes a walk-in closet and a private bathroom with a tiled shower. The home is fully furnished, making it a convenient option for tenants looking for a move-in-ready rental. Enjoy Florida living from the covered rear lanai overlooking the spacious backyard. Additional features include hurricane shutters, irrigation system, public water and sewer, and a low-maintenance layout. Located in Rotonda West, this home is close to area golf courses, parks, boating, fishing, shopping, dining, and Gulf beaches. Clean, newer, furnished, and well located — this Rotonda West home is ready for its next long-term tenant.
Listing is courtesy of: REALTY ONE GROUP MVP (800-896-8790)
Listing Agent: Oleg Lisitsyn (941-441-5277)
118 CADDY RD, ROTONDA WEST, FL 33947
$2,795440 Days on yellowkey MLS ID: A4650143
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1828 Built: 1973Community: Rotonda West Oakland HillsSingle Family
Remarks: Luxurious 3BR Home with Heated Pool on Hills Golf Course – Fully Furnished! Enjoy resort-style living in this fully furnished and equipped 3-bedroom, 2-bathroom home featuring a 2-car garage, heated pool, and enclosed lanai. Nestled right on the Rotonda West Hills Golf Course, this stunning property offers comfort and convenience in a prime location. 30 Day Minimum - Rented for the 2027 season.
Listing is courtesy of: FLORIDA DREAMIN' REALTY GROUP INC (941-303-0855)
Listing Agent: Bill Williams (941-303-0855)
239 ANNAPOLIS LN, ROTONDA WEST, FL 33947
$2,00050 Days on yellowkey MLS ID: TB8510276
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1747 Built: 1974Community: Rotonda West Oakland HillsSingle Family
Remarks: Welcome to this charming home located at 239 Annapolis Ln in the desirable community of Rotonda West. This well-maintained property offers comfortable Florida living with a spacious layout, natural light, and a peaceful neighborhood setting. Enjoy nearby golf courses, beaches, boating, shopping, and dining, all just a short drive away. this home combines convenience, comfort, and the relaxed Southwest Florida lifestyle. Don’t miss your opportunity to own a piece of paradise in Rotonda West!
Listing is courtesy of: REALTY ONE GROUP PLUS (305-742-0520)
Listing Agent: Faisal Awan (352-219-1528)
230 ANNAPOLIS LN, ROTONDA WEST, FL 33947
$1,80070 Days on yellowkey MLS ID: N6144143
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1768 Built: 1974Community: Rotonda West Oakland HillsSingle Family
Remarks: Waterfront 3-Bedroom Home in Rotonda West – $1,800/month (Annual Lease) This charming 3-bedroom, 2-bath split floor plan home is nestled along Oakland Hills Creek in the desirable Rotonda West community. As you enter through the double-entry foyer, you're welcomed into a spacious living and dining area with beautiful views overlooking the tranquil canal. Out back, enjoy direct water access—perfect for casting a fishing line from your own backyard or setting off on a peaceful kayak trip through the creek. Whether you’re relaxing by the water or exploring the surrounding nature, this home offers the ideal Florida lifestyle. Just minutes away are the sandy shores of Englewood’s Manasota Key Beach and the vibrant island of Boca Grande. Golf lovers will appreciate being close to five golf courses located right within the Rotonda West community. Available now for an annual lease at $1,800 per month.
Listing is courtesy of: KELLER WILLIAMS ISLAND LIFE REAL ESTATE (941-254-6467)
Listing Agent: Laurie Shaffer (330-565-5651)
37 OAKLAND HILLS PL, ROTONDA WEST, FL 33947
$4,0002323 Days on yellowkey MLS ID: D6111147
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1321 Built: 1974Community: Rotonda West Oakland HillsSingle Family
Remarks: Annual or Seasonal Rental located in the Rotonda West community. This 3/2 single family home overlooks the golf course, is approximately 12 minutes from Englewood Beach, shopping and restaurants and is PET FRIENDLY. 12-month lease available for $2500 per month and includes water, sewer, electric, basic cable, internet and lawn maintenance.
Listing Agent: Danielle Jones (941-270-0475)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.