Newest Homes for Rent in Osprey, FL

Welcome to this beautifully maintained 4-bedroom, 3-bathroom home with a 2-car garage, ideally situated on a desirable corner lot in The Palms of Casey Key, just a short walk to the nationally ranked Pine View School. Built in 2018, this residence offers thoughtful upgrades throughout, including updated flooring in every room, custom window treatments, and elegant light fixtures. The open-concept

Klara Mrcela COMPASS FLORIDA, LLC

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

Experience elevated coastal living in this beautifully furnished waterfront residence, available for seasonal (DEC-APR - $8500) or long-term rental (off-season rental $5500 MAY-NOV) in the exclusive Blackburn Harbor community. Located on the second floor with elevator access, this spacious 3-bedroom plus den, 3-bath condominium offers over 3,700 square feet of elegant living space with

Angelic Tassos CORCORAN DWELLINGS REALTY

Come lounge around in one of the finest golf communities where everyday can feel like a vacation. This elegant loft has a lovely view of the lake with the rolling green right behind it. Enjoy endless summer days basking in the sun at the pool which is only steps away! This loft is equipped with granite countertops, a full size washer and dryer, stainless steel appliances, fixtures and fittings, a

Deserea Hardy ROSSI & COMPANY INC

The unit is available for rent from June 15 till December 15, 2026. The minimum rental period is 3 month. The monthly rent is $2150. The tenant is responsible for electricity and internet costs. INCLUDED IN THE LEASE : Water, sewer. If you are looking for the perfect Florida lifestyle, this is it. Conveniently located between Sarasota and Venice with #1 Siesta Key beach close by, this darling

Claudia Dybala DALTON WADE INC

3, 6, 9 or 12 month 6 Lease Available. Experience the beauty of Florida’s Gulf Coast from this spacious, fully furnished 3-bedroom, 2.5-bath waterfront condominium overlooking Little Sarasota Bay. Thoughtfully designed for both comfort and flexibility, the home includes a private den or home office, convenient in-unit laundry, and generous living spaces perfect for relaxing or entertaining.

Jaime Barcelo GULF COAST REALTY & MANAGEMENT

Welcome to this immaculate 2-bedroom, 2-bathroom condo with a private 1-car garage, offering beautiful pond views from every window and a peaceful, resort-style setting. Ideally located just minutes from some of Florida’s most beautiful Gulf Coast beaches: 10 minutes to Nokomis Beach and Casey Key15 minutes to the world-famous Siesta Key BeachOutdoor enthusiasts will love the easy access

Tim Weller EXIT KING REALTY

For Lease at THE OAKS CLUB WINDSOR LODGE. Private sanctuary rarely available for rent at one of Sarasota's most exclusive private country clubs. This lovely sunny Second floor end unit is fully turnkey furnished and ready for MOVE IN. Completely updated one bedroom, resort suite style studio, condominium with sweeping Water Views of the Lakefront of the 18th fairway on the Eagle Course. A

Patrice Ivan WAGNER REALTY

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

Welcome home to this charming and beautifully maintained 3-bedroom, 2-bath residence located on a great community. Step inside to a spacious open floor plan featuring a generous great room, a dedicated dining area, and a large primary suite. Cathedral ceilings, pocket sliding doors, and fluid room transitions create an airy atmosphere perfect for easy living and entertaining. The bright, eat-in

Kenia Rivas PREFERRED SHORE 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

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

CLOSE TO NOKOMIS BEACH! BOOKED JAN/FEB/MAR 2027. AVAILABLE APR 2027 $7,000/MONTH. Beautiful direct waterfront 5th Floor condo located in Blackburn Harbor Residences with breathtaking panoramic water views of Little Sarasota Bay, which can be seen from the living room, kitchen, primary bedroom suite, and spacious balcony! The condo comes turnkey furnished and has 3 bedrooms (3rd bedroom was

Chrissie Cummings JENNETTE PROPERTIES INC

Now AVAILABLE FOR LEASE PINE RUN Condominiums in OSPREY, Florida! 3BR/2.5BA Great SARASOTA Vacation Location! West of the Trail, Pine Run is an active community set in a tropical oasis of 20+ acres of wooded Florida landscape. This spacious corner unit townhouse is well FURNISHED. Beautifully decorated and full of light and color with vaulted ceiling in the main Great Room. Custom designed

Patrice Ivan WAGNER REALTY

**FURNISHED, 3-BED / 3-FULL BATH, Over 2500sf CONDO with FANTASTIC VIEW** features an Open Floorplan and is located behind the Secure Gates of the highly sought after Oaks-Preserve, Country Club neighborhood. As you emerge from your private elevator lobby, you will be enthralled by the Spacious interior which boasts beautiful Crown Moldings, Hardwood Floors, a well-equipped Kitchen with granite

Mark Lyda GENEROUS PROPERTY

AVAILABLE FOR SEASON 2027 - 2 MONTH MIN REQUIRED. MINUTES TO CASEY KEY & NOKOMIS BEACH! Welcome to BELLAGIO at Osprey Harbor Village, offering luxurious waterfront living! This turnkey direct waterfront condo has 3 beds/2 baths plus a den is the perfect place for your next Florida vacation, located in a private gated community. As you step off the elevator, you are basically outside this 3rd

Chrissie Cummings JENNETTE PROPERTIES INC

**RARE RENTAL OPPORTUNITY (UNFURNISHED)** This STUNNING, UPDATED, MAINTENANCE-FREE Home is located in EMERALD WOODS, behind the SECURE GATES of the Distinguished OAKS PRESERVE Neighborhood. Offering 3-Beds (or 2-Beds plus Den), 2-Baths and 2-Car Garage, Premium finishes abound throughout this home and include a Chef’s Kitchen, Tray Ceilings, Crown Moldings, Beautiful Luxury Vinyl Wood Plank,

Mark Lyda GENEROUS PROPERTY

BACIK ON THE MARKET HIGH SEASON NOW AVAILABLE!! Seasonal and short term rental Get out of the cold and into the sunshine in this newer 3/2 condo in the gated community of Bay Street Village in Osprey. This condo is an end unit with an open floor plan for ease of entertaining and family time. The extra windows flood the unit with natural sun light. The kitchen is a natural gathering point with

Cody Smith RENT SARASOTA

Property available for $2300 from April 1,2024 till November 30,2024. Tenant pays electricity and internet. Available for season 2024/2025 for $4500. If you are looking for the perfect Florida lifestyle, this is it. Conveniently located between Sarasota and Venice with #1 Siesta Key beach close by, this darling two-bedroom, two-bath, impeccably maintained, property move-in ready. Located on the

Claudia Dybala DALTON WADE INC