Houses for Rent in Osprey, FL

This lovely 2-bedroom, 2-bathroom residence boasts a spacious den and great room with double tray ceilings and crown molding. The well-appointed kitchen features ample storage with pull-out shelves and two pantries, perfect for entertaining. Enjoy stunning water views from the lanai and a low-maintenance lifestyle, with lawn care included. Located near the Legacy Trail and Oscar Scherer State Park, outdoor enthusiasts will adore easy access to nature and local beaches.

This beautifully maintained 4-bedroom, 2-bathroom home spans 1,861 sq ft and features an open kitchen layout complete with a brand-new refrigerator. Enjoy tile flooring in communal areas and engineered wood vinyl in bedrooms. A large covered lanai provides a perfect spot for relaxation or entertainment, alongside a private backyard. Located near top-rated Pine View School and just minutes from Casey Key Beach, this home offers comfort, community, and convenience. Pet-friendly with ample amenities!

Experience ultimate relaxation in this beautifully furnished 3-bedroom, 2.5-bath pool home offering 2,691 sqft of living space. Nestled in Stoneybrook Golf & Country Club, enjoy a screened-in heated pool overlooking a serene lake. The spacious kitchen and living areas are perfect for entertaining. Access to fantastic amenities like golf, tennis, and dining awaits, while the stunning beaches of Siesta Key are just a quick drive away. Ideal for both vacations and long-term stays!

Enjoy Florida living in this custom-built 3-bedroom, 2-bathroom home featuring 2,298 sq. ft. of light-filled space, volume tray ceilings, and crown molding. The master suite boasts double walk-in closets and a cozy sitting area. Relax on the screened lanai overlooking the heated pool and tranquil lake. Located in the desirable Willow Bend community, amenities include a clubhouse, fitness area, and more, with maintenance-free living close to schools, parks, and beaches.

This beautifully remodeled 3-bedroom, 2-bath home boasts 1,977 sq ft of elegant coastal living. A spacious open living area and split floor plan provide ample room for relaxation and entertaining. Enjoy stunning bay views from the primary bedroom and a large screened pool in the expansive backyard. Direct access to a private sandy beach enhances the tropical paradise experience. Recent upgrades include a new metal roof and impact windows, ensuring resilience and modern comfort.

This beautiful one-story home spans 2,008 square feet, featuring an open-concept design with three bedrooms and two bathrooms. An open lanai extends from the living room, perfect for enjoying the Florida sunshine. Conveniently located near world-renowned beaches and Pine View school, it offers easy access to US41 and I-75. Ample space and a two-car garage complete this inviting residence, ideal for those seeking comfort and convenience in a vibrant coastal setting.

This stunning home behind the gates of The Oaks Country Club features 3 bedrooms, 3.5 bathrooms, and over 4,500 sq. ft. of luxurious living space. Enjoy the spacious open floor plan, marble and wood flooring, and a chef's kitchen with top-of-the-line appliances. The expansive primary suite boasts a bonus room and lavish ensuite. Outdoor living is a dream with a screened lanai, PebbleTec pool, spa, and outdoor kitchen overlooking the 17th fairway.

This beautifully updated 3-bedroom, 1.5-bath home features an open layout with vaulted ceilings and a brand-new kitchen, complete with granite countertops and stainless steel appliances. Recent renovations include stylish flooring and a refreshed bathroom. Enjoy the fully fenced yard and outdoor areas, including a side porch and spacious deck, perfect for entertaining. Located minutes from the stunning Gulf Coast beaches, this home is ideal for comfortable living and vibrant Florida lifestyle.

Embrace luxury living in this spacious 3,183 sq ft, 4-bedroom home with scenic preserve and pond views. The flexible leasing options include lease purchase or lease with an option to buy. Highlights include a private pool, an oversized lot for maximum privacy, and an upstairs bonus room perfect for guests or an office. Located in a top-rated school district, just minutes from Casey Key Beach, this Willowbend community also features resort-style amenities for a vibrant lifestyle.

This stunning 9,000+ sq ft golf course estate in The Oaks offers expansive living with 4 beds, 4.5 baths, a gourmet kitchen, large primary suite, theater, and office. Enjoy the outdoor kitchen, heated pool, and spa with golf course views. Featuring high-end finishes, it's perfect for entertaining. Situated in a secure, distinguished country club community, close to top schools and beaches.

This stunning 3-bed, 2-bath home in the gated Oaks Preserve boasts a chef's kitchen, luxurious owner's suite, and premium finishes. Enjoy 2,271 sq. ft. of elegant living with tray ceilings, crown moldings, and a private screened lanai with wet bar. Perfectly located near top schools, beaches, and biking trails, this rare rental offers an exceptional Florida lifestyle.

This stunning 5-bedroom, 4.5-bathroom home spans 3,981 sq ft and boasts a premium chef's kitchen and an inviting floor plan perfect for relaxation and entertaining. The luxurious heated pool is perfect for enjoying sunny days, making every moment special. With ample space for everyone, including furry friends, this luxury turnkey rental is ideal for those seeking comfort and elegance by the water. Minimum 3-month rental available from May to October 2025.

Experience luxury in this stunning townhome featuring 2 bedrooms, each with its own en-suite bath, and an inviting open floor plan. The spacious living and dining areas lead to a serene outdoor space overlooking a preserve. Enjoy access to a community pool within an exclusive enclave of 12 homes. Located near shopping, dining, and the beautiful Siesta Key Beach, this residence combines comfort with a vibrant lifestyle in a traditional architectural style, offering 1,890 sq. ft. of living space.

This beautifully designed 3BR/2.5BA corner townhouse offers a bright, airy atmosphere with vaulted ceilings and a custom eat-in kitchen. Enjoy a private screened patio with tranquil nature views. Located in a friendly community, amenities include two heated pools, tennis, and pickleball courts. Just steps from the Gulf of Mexico and the Legacy Bike Trail, this home is perfect for those seeking a laid-back Florida lifestyle in a prime location.

Experience vibrant living in this exquisite 2-bed, 2.5-bath villa in the gated Stoneybrook Golf & Country Club. Enjoy a renovated golf course, tennis courts, fitness center, and elegant clubhouse. With 2,368 sq ft, this furnished home features a screened lanai with a pool and spa, a loft, an office, and ample parking. Proximity to stunning beaches and local amenities make this a prime, seasonal retreat. No pets allowed.

This beautifully appointed 4-bedroom, 3-bathroom pool home offers a resort-like experience in the vibrant Willowbend community. Enjoy serene lake views, a heated caged pool, and a spacious patio perfect for indoor/outdoor entertaining. The community features a clubhouse, exercise room, and a pool, enhancing the active lifestyle. Just minutes from the stunning Casey Key Beach and Sarasota's entertainment, this home is a fantastic seasonal rental opportunity.