20

Osprey, FL Houses for Rent

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  • /2

    $5,500 Per Month

    • 3 Beds
    • 2 Baths
    • 2,172 Sq Ft
    • House for Rent

    557 Crane Prairie Way, Osprey, FL 34229

    Welcome to this beautiful fully furnished 3-bed, 2-bath home in the gated community of Willowbend in Osprey. With 2,172 sq ft of bright, open living space, this seasonal rental offers comfort, style, and plenty of room to relax. Enjoy a spacious kitchen, a large primary suite, and a peaceful screened lanai perfect for morning coffee or evening sunsets.The community features a pool, fitness

    Agent Photo

    Craig McCoy

    PREFERRED SHORE LLC

    (941) 392-7290

    557 Crane Prairie Way, Osprey, FL 34229
  • /8

    $775 Per Month

    • 1 Bed
    • 1 Bath
    • House for Rent

    8 Bay Ave, Osprey, FL 34229

    Property Id: 1524644Unfurnished Room with private bath for rent, for 1 person, utilities included. No pets, no alcohol drinks, no drugs, no visitors allowed inside the house. House rules to follow, NO EXCEPTIONSLandlord requires 1st, last month rent plus $455 security deposit due at the sign of the lease. Information to verify employment, references from previous landlord and

    (914) 281-2489

    8 Bay Ave, Osprey, FL 34229
  • /45

    $3,150 Per Month

    • 3 Beds
    • 2 Baths
    • 1,897 Sq Ft
    • House for Rent

    341 Bayshore Dr, Osprey, FL 34229

    This fully renovated classic-style residence blends Old Florida charm with modern finishes and spacious living areas throughout. Featuring 3 Bedrooms and 2 Bathrooms, the home offers a functional layout designed for comfort and privacy. Conveniently located near Blackburn Boat Ramp with plenty of on-site parking. Just under 1900 sqft of living space, the kitchen flows seamlessly into the dining

    Agent Photo

    Jeremy Myers

    COMPASS PROPERTY MANAGEMENT LLC

    (941) 957-2561

    341 Bayshore Dr, Osprey, FL 34229
  • /20

    $4,000 Per Month

    • 4 Beds
    • 3.5 Baths
    • 2,970 Sq Ft
    • House for Rent

    759 Fordingbridge Way, Osprey, FL 34229

    Property Id: 779624This is a very nice luxury Neighborhood of Rivendell community walking path to Pineview get to school. The house has four large bedrooms with a office den and 3 1/2 bath there is travertine floor for the first floor and vinyl hardwood for the second floor all the bathrooms are newly renovated with granite marble light with a beautiful Italian bathroom design. The house

    (858) 988-5943

    759 Fordingbridge Way, Osprey, FL 34229
  • /18

    $1,850

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 950 Sq Ft
    • House for Rent

    455 Pennsylvania Ave, Osprey, FL 34229

    Fully Furnished 2BR/1BA Turnkey Home in Osprey, FLUnique, peaceful property with native wildflower garden, beach gear, and old-Florida charm. Located in the quiet fishing village of Osprey, this FULLY FURNISHED home includes:•Upgraded kitchen with stainless steel appliances, granite counters, and all essentials•New washer/dryer•Enclosed lanai•High-speed WiFi, water, sewer,

    455 Pennsylvania Ave, Osprey, FL 34229
  • /48

    $4,999 Per Month

    • 3 Beds
    • 2 Baths
    • 2,306 Sq Ft
    • House for Rent

    124 Turquoise Ln, Osprey, FL 34229

    **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

    Cody Smith RENT SARASOTA

    124 Turquoise Ln, Osprey, FL 34229
  • /46

    $14,000 Per Month

    • 4 Beds
    • 6 Baths
    • 9,081 Sq Ft
    • House for Rent

    854 MacEwen Dr, Osprey, FL 34229

    Set on a quiet private cul-de-sac in The Oaks, this beautifully revitalized estate embodies the elegance of refined Florida living. Bright, open interiors and thoughtful updates create a welcoming flow from the chefs kitchen through the main living areas and out to the lanai, where sweeping golf course views frame the heated pool, spa, and fully equipped outdoor kitchen perfect for year-round

    854 MacEwen Dr, Osprey, FL 34229
  • /32

    $5,750 Per Month

    • 3 Beds
    • 2 Baths
    • 2,271 Sq Ft
    • House for Rent

    293 Turquoise Ln, Osprey, FL 34229

    **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

    293 Turquoise Ln, Osprey, FL 34229
  • /33

    $8,000 Per Month

    • 3 Beds
    • 3 Baths
    • 3,681 Sq Ft
    • House for Rent

    600 Eagle Watch Ln, Osprey, FL 34229

    Beautifully UPDATED AND MOVE IN READY, this stunning golf course estate in the highly sought-after Oaks Country Club offers ideal southern exposure and sweeping views across the 3rd fairway of the Heron Course. Set on an oversized lot with a circular driveway and lush, manicured landscaping, this extensively renovated home features 3 bedrooms + study/den, 3 full baths, high ceilings, crown

    600 Eagle Watch Ln, Osprey, FL 34229
  • /38

    $4,800 Per Month

    • 4 Beds
    • 3 Baths
    • 2,290 Sq Ft
    • House for Rent

    956 Scherer Way, Osprey, FL 34229

    Stunning 4-bedroom, fully furnished pool home backing directly to the tropical preserve of Oscar Scherer State Park in the highly desirable Woodlands at Rivendell. Enjoy privacy, serene views, and resort-style living within a beautifully maintained community featuring 400+ acres of lakes, walking trails, playground, and heated community pool. Prime location — walking distance to Pine View School

    Chantelle Edalgo EXIT KING REALTY

    956 Scherer Way, Osprey, FL 34229
  • /45

    $4,500 Per Month

    • 4 Beds
    • 3 Baths
    • 2,290 Sq Ft
    • Annual Rental: Luxurious 4 Bedroom 3 bath POOL home in Woodlands of Rivendell! Just Blocks form P...

    919 Scherer Way, Osprey, FL 34229

    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

    919 Scherer Way, Osprey, FL 34229
  • /46

    $3,980 Per Month

    • 5 Beds
    • 4.5 Baths
    • 3,050 Sq Ft
    • House for Rent

    246 Burney Rd, Osprey, FL 34229

    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

    xiaoying zhang FLORIDA MORNING REALTY LLC

    246 Burney Rd, Osprey, FL 34229
  • /48

    $5,000 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,950 Sq Ft
    • Annual Turnkey 3/3 penthouse on waterfront in Osprey

    260 Hidden Bay Dr, Osprey, FL 34229

    Annual Turnkey Furnished or seasonal Penthouse on the Bay! If you want mesmerizing views of intracoastal waterway, Little Sarasota Bay, Casey Key, and the Gulf of Mexico in a beautiful, comfortable and roomy penthouse, then this could be your next home. This natural light filled delight is 2 bedrooms, each with en suite bathroom, separate office with large closet and glass French doors, and

    260 Hidden Bay Dr, Osprey, FL 34229
  • /46

    $3,980 Per Month

    • 5 Beds
    • 4.5 Baths
    • 3,050 Sq Ft
    • House for Rent

    254 Burney Rd, Osprey, FL 34229

    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

    xiaoying zhang FLORIDA MORNING REALTY LLC

    254 Burney Rd, Osprey, FL 34229
  • /15

    $3,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,648 Sq Ft
    • House for Rent

    2068 Preymore St, Osprey, FL 34229

    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

    2068 Preymore St, Osprey, FL 34229
  • /31

    $4,500 Per Month

    • 3 Beds
    • 2 Baths
    • 2,367 Sq Ft
    • House for Rent

    1355 Southbay Dr, Osprey, FL 34229

    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

    1355 Southbay Dr, Osprey, FL 34229
  • /44

    $6,500 Per Month

    • 3 Beds
    • 3 Baths
    • 2,266 Sq Ft
    • House for Rent

    521 Habitat Blvd, Osprey, FL 34229

    Stylish 3BR Pool Home w/ Office – 10 Mins to Beach ****SEASONAL RENTAL ONLY**** 90 Day minimum stay, Peak Season at $8,900/mo plus fees; Off Season at $6,500/mo plus 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

    521 Habitat Blvd, Osprey, FL 34229
  • /51

    $7,000 Per Month

    • 3 Beds
    • 3.5 Baths
    • 4,519 Sq Ft
    • House for Rent

    852 MacEwen Dr, Osprey, FL 34229

    **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

    852 MacEwen Dr, Osprey, FL 34229
  • /19

    $2,100 Per Month

    • 2 Beds
    • 2 Baths
    • 2,052 Sq Ft
    • House for Rent

    4062 Westbourne Cir, Sarasota, FL 34238

    AVAILABLE JUNE THROUGH OCTOBER 2026: SINGLE-FAMILY HOME in gated community of Stoneybrook estates: Need a place while you look for a place or build your dream home or just want to get away for a few months? This fully furnished single-family home located on Palmer Ranch might be just what you're looking for; two bedrooms, two baths, kitchen, dining area, family room and living room plus a large

    Victoria Reilly BERKSHIRE HATHAWAY HOMESERVICE

    4062 Westbourne Cir, Sarasota, FL 34238
  • /51

    $13,000 Per Month

    • 4 Beds
    • 3 Baths
    • 2,546 Sq Ft
    • House for Rent

    9477 Cedar Ridge Ln, Sarasota, FL 34238

    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 HOMESERVICE

    9477 Cedar Ridge Ln, Sarasota, FL 34238

Frequently Asked Questions

How much does it cost to rent a single-family home in Osprey, FL?
The median rent for a single-family home in Osprey, FL is $3,980 per month, though prices vary by neighborhood, size, and property type. As of June 2026, townhouses tend to be the most affordable option while condos and single-family homes are currently more expensive.
How much do you need to make to afford rent in Osprey, FL?
To comfortably afford the median rent in Osprey, FL, a household needs to earn roughly $159,200 per year. This is based on the common guideline that households should spend no more than 30% of gross income on housing. Most landlords require monthly household income of at least 3x the monthly rent, and with a median rent of $3,980 per month in Osprey, FL, renters typically need to show $11,940 per month in gross income to qualify. Actual affordability will vary depending on household debts, other living expenses, and overall budget.
Is it more affordable to rent or buy in Osprey, FL?
In Osprey, FL, the price-to-rent ratio is 13.7, which generally favors renting. This ratio divides the median home price by the annual median rent: below 15 typically favors buying, 15 to 20 is balanced, and above 20 typically favors renting. Your finances, how long you plan to stay, and costs like mortgage rates, taxes, and maintenance all factor into the decision.
What neighborhoods in Osprey, FL are best for renting a single-family home?
The best neighborhood for renting in Osprey, FL depends on your priorities: commute, walkability, budget, and lifestyle all play a role. Popular areas for renting a single-family home include Casey Key, Vamo, Coral Cove/Holiday Harbor, East Sarasota and South Gate Ridge, each with its own character and price range.

Rental Home Trends in Osprey, FL

Rental Home Trends

Number of Houses for Rent
20
Median Single Family Home Rent
$3,980
Median 3 Bedroom Single Family Home Rent
$3,875
Median 4 Bedroom Single Family Home Rent
$4,250
Median 5 Bedroom Single Family Home Rent
$3,980
How to Rent a Home