Osprey, FL Houses for Rent with Pool

New to the rental market, very nice light and bright 4 bedroom pool home with private secluded lot in the quaint community of Oak Bay Estates in Osprey. Great access to Sarasota and Venice without having to get on I-75. Brand new interior paint and brand new ceiling fans throughout. Enjoy this great home and the private pool in your spare time as the pool care and lawn and landscaping are done

Brian ODonnell,PLLC REALTY BY DESIGN LLC

Annual unfurnished single-family home is available in the Willowbend community of Osprey! With some of the best lake views in Willowbend, this two-bedroom plus den, two-bath home features a large primary bedroom with dual sink main bath, walk-in shower and separate soaking tub. Additional features include stainless steel kitchen appliances, gas range, pantry and laundry room with utility sink.

Alex Lane PREMIER SOTHEBY'S INTERNATIONAL

SouthBay Yacht & Raquet Club one of the most desirable communities in Osprey! This beautiful well maintained home welcomes you with the circular driveway! Brand new roof in August 2024, newer a/c in 2024. Lush landscaping makes this property very inviting. Three bedroom 3 bath home with a dedicated office space is waiting for you arrival. Super large kitchen with a large island and plenty of

Angela Bailey MONARCH PROPERTY GROUP LLC

This luxuriously FULLY furnished 4 Bedroom Pool home is available starting April 15, 2025! It backs right onto the tropical preserves of Oscar Scherer Park and nestled in the sought-after community of The Woodlands at Rivendell providing the perfect blend of comfort, convenience, and natural beauty. Within the 400+ acres of lush landscapes in the neighborhood, enjoy the numerous scenic lakes,

Chantelle Edalgo KELLER WILLIAMS ON THE WATER S

Welcome to this bright and spacious 4 Bed, 3 Bath home with an office and a private pool located within the highly sought-after intracoastal waterfront community of Southbay Yacht & Racquetball Club. Upon entry, you are greeted with by the formal living and dining room with 10 foot ceilings and large sliding glass doors that reveal the pool lanai. From here, you can access the office/study,

Chantelle Edalgo KELLER WILLIAMS ON THE WATER S

Mint-condition, immaculate pool home nestled within an exclusive Osprey, FL community. This pristine 3-bedroom, 3.5-bath residence boasts over 2,400 sq. ft. of elegant living space, offering a perfect blend of style and comfort. Step into a spacious layout featuring a gourmet kitchen, expansive family room, and formal living and dining areas. Each bedroom is a private suite, ensuring ultimate

John Michailidis REAL PROPERTY MANAGEMENT

An Ascendia Property! **Available beginning January 15, 2025, for a 90-night minimum stay or longer. The rental rate in the listing does not include additional fees and taxes. The rental rate will be discounted for a long-term lease (6-12 months). Please note, a long-term lease of 6-12 months DOES NOT include utilities such as electric, water, sewer or internet.** This 3-bedroom, 2-bathroom

Beth Dilley ASCENDIA REAL ESTATE

**RENTAL OPPORTUNITY (unfurnished)** SPACIOUS, LUXURIOUS and BEAUTIFULLY RENOVATED, GOLF COURSE ESTATE situated behind the SECURE GATES of The Oaks Country Club Community, Boasting OVER 9,000sf and located on a prominent, private cul de sac lot of Over 3/4 Acres. Expansive room abounds in this LIGHT and BRIGHT Open Floorplan consisting of 4 Beds + 4/2 Baths + Office/Library + Home Theater + Game

Mark Lyda GENEROUS PROPERTY

RENTED , FEBRUARY, MARCH & APRIL 2026. AVAILABLE JUNE THROUGH DECEMBER 2025: Exceptional villa, open floor plan, recently updated with new flooring and furnishings, large master suite with king bed, garden tub and separate shower. Twin beds in the guest room and a sleeper sofa in den. Flat-screen TVs and internet access, a well-equipped kitchen, laundry room, and a crystal clear pool on the

Victoria Reilly BERKSHIRE HATHAWAY HOMESERVICE