Osprey, FL Houses for Rent with Community Pool

Enjoy the Florida lifestyle in this beautifully updated and fully furnished 3-bedroom, 2-bath pool home in sought-after Southbay Yacht & Racquet Club. With nearly 2,500 square feet of living space, the home features a desirable split-bedroom floor plan, with the primary suite on one side and two guest bedrooms on the other, offering privacy for family and guests.At the heart of the home

Carolyn Yates COLDWELL BANKER SARASOTA CENT.

This FULLY FURNISHED 4 bedroom, 3 bathroom rental home is available for an ANNUAL LEASE in a quiet HOA community with a PRIVATE HEATED POOL, HOT TUB, 3-CAR GARAGE, and great access to everything Sarasota/Osprey has to offer!This home has the perfect Florida living setup with a backyard overlooking natural Florida views that you can enjoy from your SCREENED-IN LANAI.Inside, enjoy

Benjamin Schwab KEYRENTER SARASOTA PROPERTY MANAGEMENT

Southbay Yacht & Racquet Club where the true Florida lifestyle is alive and well! This three-bedroom two bath pool home is located in an active community with unmatched amenities such as an active social atmosphere, heated community pool, playground, fitness room, tennis, pickleball courts, and fishing. All for you to enjoy! Walk, bike or take your golf cart to restaurants, shopping or the

Sharon Lewis GOLF & BAY PROPERTIES LLC

Stylish 3BR Pool Home w/ Office – 10 Mins to Beach -- 90 Day minimum stay, Peak Season at $7,900/mo plus taxes and fees; Off Season at $5,900/mo plus taxes and fees. NOTE: Jan, Feb and March 2027 are Not Available. Your Gulf Coast getaway awaits at this beautifully furnished 3-bedroom, 3-bath pool home in the scenic Willowbend community of Osprey, FL. Ideal for mid-term stays, this spacious

Dave Holt PMI SOUTHWEST FLORIDA

**CHARMING and PRIVATE, GOLF COURSE ESTATE** is located behind the Secure Gates of the highly sought after Oaks Country Club community and offers a Lovely, Golf Course View of the 17th Fairway of the interior, Heron Golf Course. This Spacious, Light and Bright, Open Floorplan of OVER 4500sf entails 3-BEDS, 3 FULL and 1 HALF BATHS, Study/Den, Bonus Room / Entertaining area with Fireplace and

Mark Lyda GENEROUS PROPERTY

AVAILABLE AUGUST 25, 2026 AS UNFURNISHED RENTAL. 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. New interior paint and new ceiling fans throughout. Enjoy this great home and the private pool in your spare time as the pool care and lawn and landscaping

Brian ODonnell,PLLC REALTY BY DESIGN LLC

RENTED FEBRUARY & MARCH 2027, NOT AVAILABLE OFF-SEASON: Spacious single-family home at Stoneybrook Golf & Country Club situated in the center of the cul-de-sac offers stunning views from the amazing, seamlessly screened pool cage, creating a virtual oasis with overflow spa, underwater lighting, outdoor kitchen, and ample covered seating and dining area. Double entry doors greet you as you enter

Victoria Reilly BERKSHIRE HATHAWAY HOMESERVICES FLORIDA REALTY