Houses for Rent in Osprey, FL

This pristine rental offers 3 bedrooms and 3.5 baths, showcasing a spacious layout with a private office. The stylish kitchen features gas cooking, an oversized island, and walk-in pantry. Enjoy the luxury of en suite bathrooms for all guest rooms and a beautifully landscaped outdoor space with a heated pool, spa, and outdoor kitchen complete with a gas fireplace. A tandem 3-car garage provides ample storage for kayaks and bikes, while access to kayaking and beautiful beaches ensures endless adventure.

Experience upscale living in this luxurious, turnkey furnished Georgian-style villa, featuring 2 en-suite bedrooms and a charming wet bar. Set in the secure Oaks Preserve, enjoy access to a community pool and clubhouse just steps away. Surrounded by lush vegetation, this serene retreat offers 1,678 sq. ft. of beautifully maintained space, while being conveniently located near the Legacy Trail, shopping, and stunning local beaches. The perfect blend of comfort and convenience awaits!

Experience luxurious living in this stunning 3-bed, 2-bath home featuring 2,306 sq. ft. of elegantly designed space. Highlights include a chef's kitchen, an expansive primary suite, and a resort-style heated pool with a cascading waterfall. Perfect for entertaining, the screened lanai boasts an outdoor kitchen, while the lush backyard creates a serene retreat. Located in a gated community near Siesta Key, this property combines comfort and sophistication.

This inviting 3-bedroom, 2-bathroom home spans 1,371 square feet, offering a perfect blend of comfort and convenience. The bright living space features a modern kitchen with an electric stove, dishwasher, and more. Located in serene Osprey, it offers easy access to parks, shopping, and dining. Small dogs are welcome, making it a perfect space for pet lovers. Showings begin March 15, with move-in on March 16. Explore this fantastic rental opportunity and elevate your living experience!

Nestled in a serene cul-de-sac, this beautifully revitalized 4-bedroom, 6-bath estate offers 9,081 sq ft of refined Florida living. A chef's kitchen flows seamlessly to the spacious lanai, showcasing heated pool and spa with stunning golf course views. The first-floor primary suite offers an elegant sanctuary, while the second-story guest wing features a loft and theater room. Enjoy a split four-car garage and luxury amenities in this premier country club community.

Enjoy the Florida lifestyle in this turnkey, furnished 3-bedroom, 2-bathroom townhouse with a garage. Featuring hurricane windows and located in a gated community, residents have access to a pool, clubhouse, and gym. Just minutes from Siesta Key and Nokomis Beach, and with restaurants and shopping nearby, this vibrant home is perfect for easy living. A minimum lease ensures comfort and convenience in this sought-after location.

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.

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 stunning 4-bedroom, 3-bathroom pool home offers a fully furnished retreat with breathtaking views of Oscar Scherer State Park. Spanning 2,290 sq ft, it features a luxurious kitchen equipped with premium GE Café appliances. Enjoy private relaxation by the screened pool and the convenience of low-maintenance living with included lawn care and pool maintenance. Located steps from Pine View School and the Legacy Trail, this residence combines serene living with easy access to local amenities and beautiful beaches.

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 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 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.

This elegant 3-bed, 2-bath home spans 2,172 sq ft in Willowbend, offering a bright open layout perfect for relaxation. Enjoy a spacious kitchen, large primary suite, and serene screened lanai. Community amenities include a pool, fitness center, and scenic walking paths, all just moments from beautiful beaches, shopping, and dining. This seasonal rental is fully furnished and ready for your Florida getaway!

This meticulously maintained 3-bedroom, 2-bath home features an airy open floor plan with a spacious great room and dedicated dining area. Cathedral ceilings and pocket sliding doors enhance the light and airy atmosphere. The eat-in kitchen boasts ample cabinetry and a new stainless-steel refrigerator. The oversized primary suite includes a walk-in closet and ensuite bathroom. A covered porch overlooks a stunning paver patio, ideal for relaxation and entertaining.

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.