Osprey Single Family Homes For Rent - 10 homes

Remarks: 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 HIGH/VAULTED CEILINGS, tile & hardwood flooring and a comfortable layout that includes a DINING ROOM and BREAKFAST NOOK and plenty of natural light. The kitchen features MARBLE COUNTERTOPS, a KITCHEN ISLAND, PREMIUM GE CAFE STAINLESS STEEL APPLIANCES, and great cabinet/counter space. The laundry room also includes MARBLE COUNTERS. Fully stocked and TRULY TURN-KEY with cookware, linens, towels, and more The primary suite includes a WALK-IN CLOSET, DOUBLE VANITIES, a separate TUB, walk-in SHOWER, and plenty of space to feel comfortable at home. Enjoy extra features like an electric car/TESLA CHARGING STATION, ALARM SYSTEM, HURRICANE SHUTTERS, and an EXTRA FRIDGE IN THE GARAGE. NO PETS ALLOWED. No Cats. No Dogs. Lawn Care and Pool Maintenance INCLUDED! distance to Pine View School and Legacy Trail * Direct access to I-75 and medical offices * 1 mile from Walmart, gas stations, and everyday essentials * 5 minute drive to Costco, Total Wine, Sprouts, Ulta, Hidden Harbor Marina, and more! * 10-12 minute drive to Casey Key and Siesta Key BEACHES * Easy access to Downtown Venice and Downtown Sarasota

Listing is courtesy of: KEYRENTER SARASOTA PROPERTY MANAGEMENT (561-889-2308)

Listing Agent: Benjamin Schwab (561-889-2308)

Remarks: 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 floor plan is designed for both everyday living and effortless entertaining. The gourmet kitchen features a large granite island, stainless steel appliances, a pantry, and seamlessly connects to the great room and dining area. The spacious primary suite overlooks the private, tree-lined backyard and offers dual vanities, a generous walk-in closet, and convenient access to the laundry room. Three additional bedrooms and two full bathrooms provide flexibility for family, guests, or a home office. Step outside to the screened lanai and enjoy peaceful views of the lush natural surroundings. The backyard features a paved patio and a variety of mature fruit trees, including mango and dragon fruit, creating a private outdoor retreat. Additional highlights include a whole-house water filtration and softener system, an electric vehicle charging station in the oversized garage, and a paved walkway surrounding the home. Ideally located near the Legacy Trail, Historic Spanish Point, Oscar Scherer State Park, shopping, dining, and Gulf Coast beaches, this home also offers the rare convenience of being able to walk to and from Pine View School, combining comfort, functionality, and an exceptional location.

Listing is courtesy of: COMPASS FLORIDA, LLC (305-851-2820)

Listing Agent: Klara Mrcela (216-971-0750)

Remarks: 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 retreat features a private screened-in pool, open-concept living, and a dedicated office workspace—perfect for remote work and extended relaxation. The fully equipped kitchen boasts granite countertops and stainless steel appliances, flowing into a bright living area and a covered lanai for outdoor dining and lounging. The master suite offers direct pool access and a spa-like bath for ultimate comfort. Beach gear provided: chairs, umbrella, cooler, and towels Dedicated home office setup with desk, chair, and fast Wi-Fi Distance to beaches: - Nokomis Beach – 10 minutes - Casey Key – 12 minutes - Siesta Key – 20 minutes Guests enjoy full access to Willowbend’s resort-style amenities: a heated pool and spa, fitness center, pickleball and basketball courts, and peaceful walking trails. Please Note: This home is part of an HOA that requires guest registration. After booking, we will request basic information to complete and submit the application. All HOA application fees are included in the rental cost—no surprises.

Listing is courtesy of: PMI SOUTHWEST FLORIDA (941-237-0011)

Listing Agent: David Holt (941-677-8090)

Remarks: 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 are done for you and included in the rent. This home is located in a very nice neighborhood with easy access to many restaurants, shopping and the Florida lifestyle including the Legacy Trail for biking, walking or jogging. Only 10 minutes to two of the finest beaches on the Gulf Coast at Siesta key and Nokomis beach. First and last months rent and security deposit due upfront. pets are possible and are considered on a case by case basis.

Listing is courtesy of: REALTY BY DESIGN LLC (941-779-4509)

Listing Agent: Brian Odonnell (941-779-4509)

Remarks: Perfect Family Pool Home in a Location you can't ignore. Just a few blocks from The Oaks, one of the most exclusives areas in Sarasota, this impeccable home has 4 bedrooms and 3 bathrooms, 3 car garage, with just under 2,300 square feet of living area for your quiet enjoyment or entertaining friends and family. The home offers a designer pool and spa with lake and preserve views, located in the desirable Rivendell neighborhood, blocks from Pine View School - one of the top-rated schools in Florida! This home offers upgrades by design and include 10’ ceilings, rich engineered hardwood floors and tile throughout living areas, a formal living room and dining room that open to the pool and lanai, accenting arches throughout, great room opening to pool with the kitchen providing a breakfast bar and nook. A sizable Master Suite with a convenient door to the pool area, Master Bath includes a large glass enclosed shower, two walk-in closets, dual sinks and soaking tub. Enjoy the Florida living with the screen enclosed pool with a swim out for the little ones -or- visit the heated community pool, playground, and nature trails. Close proximity to Shopping, Beaches, Oscar Scherer State Park, and just 20 minutes to all of the amenities of Sarasota! ~Included in Rent: Landscaping and Pool Maintenance. ~Association: Application is required.

Listing is courtesy of: COMPASS PROPERTY MANAGEMENT LLC (941-444-6185)

Listing Agent: Jeremy Myers (941-444-6185)

Remarks: **RENT JUST LOWERED**Impressive three-bedroom, two-bathroom home with heated pool designed for both comfortable family living and grand-scale entertaining. High-speed internet is now included. Ideally situated on a quiet cul-de-sac in Emerald Woods at The Oaks, this gated, beautifully landscaped community features serene lakes throughout and offers a prime location just minutes from Siesta Key and the Gulf of Mexico. This exceptional home showcases spacious, well-appointed rooms highlighted by elegant architectural details, custom built-ins, and abundant natural light. The expansive primary suite is a private retreat featuring rich wood flooring, a relaxing sitting area, and a luxurious en-suite bathroom complete with a soaking tub, walk-in shower, double vanities, private water closet, and three large, professionally organized closets. The chef-inspired kitchen is both functional and elegant, featuring stainless steel appliances, solid wood cabinetry, slab granite countertops, a wine cellar, breakfast bar, butler’s pantry, and a charming breakfast nook overlooking the pool and waterfall. Step outside to your private outdoor oasis. The screened lanai includes a fully equipped outdoor kitchen with a gas grill, refrigerator, and sink — perfect for entertaining. The resort-style heated pool and spa feature a stunning cascading waterfall, creating a relaxing and luxurious atmosphere. Beyond the lanai, the tropical backyard showcases a beautifully designed rock-paved pathway leading to additional patio areas, surrounded by lush landscaping and enhanced by enchanting evening lighting that transforms the yard into a magical retreat. This home is also located close to several excellent schools, including Pine View School for the Gifted, Laurel Nokomis School, and Venice High School. Schedule your private tour today and experience luxury Florida living at its finest. This community is governed by a homeowners' association (HOA). The HOA charges fees for lease applicants, which may include application processing, background screening, and common area deposits. Please contact the agent for specific HOA fee details.

Listing is courtesy of: RENT SARASOTA (941-328-8999)

Listing Agent: Cody Smith (404-991-0209)

Remarks: Brand-new construction single-family home available for rent in a prime Osprey location! This spacious residence offers 5 bedrooms + 2 dedicated office/study rooms + 4.5 bathrooms + a 2-car garage, also All windows are impact-rated, eliminating the hassle of putting up hurricane shutters while providing extra security, energy efficiency, and storm protection. and ideal for large families or those working from home. Enjoy an open-concept layout with a modern kitchen, high-end finishes, and abundant natural light throughout. The flexible floor plan provides ample space for living, working, and entertaining. Conveniently located just minutes from Pine View School, shopping, dining, and the beautiful Gulf beaches including Siesta Key Beach. Easy access to U.S. Route 41 and I-75 makes commuting simple. Move-in ready. Don’t miss this exceptional rental opportunity!

Listing is courtesy of: FLORIDA MORNING REALTY LLC (941-441-5990)

Listing Agent: Phoebe Zhang (727-458-5188)

Remarks: Brand-new construction single-family home available for rent in a prime Osprey location! This spacious residence offers 5 bedrooms + 2 dedicated office/study rooms + 4.5 bathrooms + a 2-car garage, also All windows are impact-rated, eliminating the hassle of putting up hurricane shutters while providing extra security, energy efficiency, and storm protection. and ideal for large families or those working from home. Enjoy an open-concept layout with a modern kitchen, high-end finishes, and abundant natural light throughout. The flexible floor plan provides ample space for living, working, and entertaining. Conveniently located just minutes from Pine View School, shopping, dining, and the beautiful Gulf beaches including Siesta Key Beach. Easy access to U.S. Route 41 and I-75 makes commuting simple. Move-in ready. Don’t miss this exceptional rental opportunity!

Listing is courtesy of: FLORIDA MORNING REALTY LLC (941-441-5990)

Listing Agent: Phoebe Zhang (727-458-5188)

Remarks: **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 Wetbar, 3-CAR GARAGE, etc. Premium features abound including Crown moldings, Marble and wood floors, Coffered ceiling, Custom built-ins, a well-equipped kitchen with Granite countertops, Stainless Steel Appliances including KitchenAid and Fisher & Paykel, and much more! An Expansive Primary Bedroom Suite features a Bonus Room, Walk-In Closet, dual vanities, soaking tub and custom-tiled shower. Enjoy OUTDOOR LIVING at its FINEST in an Expansive, Screened Lanai with PEBBLETEC Pool & Spa and Outdoor Kitchen in a serene setting. NEW HURRICANE IMPACT SLIDING DOORS and WINDOWS; ROOF (2015). THE OAKS is a distinguished country club community which boasts many accolades including: Platinum Club of America, Emerald Club of the World and Elite Distinguished Club of the World. The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. **ENJOY VIEWING THE 3D VIRTUAL TOUR**

Listing is courtesy of: GENEROUS PROPERTY (941-275-9399)

Listing Agent: Mark Lyda (941-586-2670)

Remarks: **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, Plantation Shutters, an Oversized, Owner’s Bedroom Suite with Multiple walk-in closets and sitting area and much more! Enjoy the expansive and private outdoor living area in a screened lanai with wet bar and southern exposure overlooking a Garden and Tranquil Preserve. Mostly NEW Hurricane Impact Windows/Door. The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer.

Listing is courtesy of: GENEROUS PROPERTY (941-275-9399)

Listing Agent: Mark Lyda (941-586-2670)