47

Newest Homes for Rent in Osprey, FL

Section Image Section Image
  • /14

    $1,995

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,300 Sq Ft
    • Condo for Rent

    188 Explorer Dr Unit 188, Osprey, FL 34229

    Location, Location, Location. Beautiful, quiet, safe & secure, Newer 2 Bed, 2 Bath, for rent annually, All amenities including all Stainless Steel Appliances, Washer, Dryer, Stove, Refrigerator. Gorgeous Pool, Exercise Room, Clubhouse, great area, five minutes to Sarasota Square Mall, Costco, shopping, and medical facilities. Close to Siesta Key Beach and fabulous restaurants. Special Hurricane

    188 Explorer Dr Unit 188, 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
  • /45

    $4,850 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,168 Sq Ft
    • Coastal Luxury at Hidden Bay | 3BR Waterfront Condo with Bay Views

    260 Hidden Bay Dr, Osprey, FL 34229

    6 Month Minimum 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. Nestled

    260 Hidden Bay Dr, 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
  • /15

    $3,500 Per Month

    • 2 Beds
    • 2 Baths
    • 950 Sq Ft
    • Condo for Rent

    8 Bay Acres Ave Unit 8 Bay Acres Ave, Osprey, FL 34229

    Property Id: 2540106Welcome to Osprey, FL! This 2 bed, 2 bath fully furnished unit with a fenced back yard is perfect for families and small pets. Relax in a private lanai or binge-watch Netflix; Whatever your past time, this home has what you need. You will be walking distance to a Breeze bus stop route 17, and situated in the middle of the best beaches in southwest Florida as well as

    (941) 946-7190

    8 Bay Acres Ave Unit 8 Bay Acres Ave, Osprey, FL 34229
  • /15

    $3,500 Per Month

    • 2 Beds
    • 2 Baths
    • 950 Sq Ft
    • Condo for Rent

    6 Bay Acres Ave Unit 6 Bay Acres Ave, Osprey, FL 34229

    Property Id: 2376171Welcome to Osprey, FL! This 2 bed, 2 bath fully furnished unit with a fenced back yard is perfect for families and small pets. Relax in a private lanai or binge-watch Netflix; Whatever your past time, this home has what you need. You will be walking distance to a Breeze bus stop route 17, and situated in the middle of the best beaches in southwest Florida as well as

    (941) 207-8462

    6 Bay Acres Ave Unit 6 Bay Acres Ave, Osprey, FL 34229
  • /45

    $3,200 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
  • /45

    $4,850 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,168 Sq Ft
    • Condo for Rent

    260 Hidden Bay Dr Unit B 401, Osprey, FL 34229

    6 Month Minimum 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. Nestled

    Jaime Barcelo GULF COAST REALTY & MANAGEMENT

    260 Hidden Bay Dr Unit B 401, Osprey, FL 34229
  • /41

    $2,400 Per Month

    • 2 Beds
    • 2 Baths
    • 1,244 Sq Ft
    • Condo for Rent

    4219 Frontier Ln Unit 105, Osprey, FL 34229

    2 bedrooms. 2 baths, 1 car garage. Condo Unfurnished. Available July 1, 2026. Tenant Occupied until June 22, 2026. 2nd floor. Close to Beaches! Located 10 minutes to Nokomis Beach/Casey Key Beach or 15 minutes to Siesta Key Beach. Minutes by bike to Legacy Trail and Casey Key. Water, Sewer & trash included in the rent. This maintenance free community includes gated entry, resort style community

    Tim Weller EXIT KING REALTY

    4219 Frontier Ln Unit 105, 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

    $4,500 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
  • /46

    $4,500 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
  • /21

    $1,695 Per Month

    • 2 Beds
    • 2 Baths
    • 1,224 Sq Ft
    • Condo for Rent

    354 Pine Run Dr, Osprey, FL 34229

    This is an unfurnished 2 bedroom, 2 bathroom condo located in the Pine Run community in Osprey! This upper-level unit features vaulted ceilings, a mix of hardwood and tile flooring, and a distinctive courtyard-style layout that brings the outdoors inside. The kitchen features granite countertops, maple shaker-style cabinets with glass-front uppers, stainless steel appliances, a tile backsplash,

    Todd Roughton SARASOTA MANAGEMENT & LEASING

    354 Pine Run Dr, Osprey, FL 34229
  • /45

    $7,500 Per Month

    • 4 Beds
    • 3 Baths
    • Osprey, FL 4BR/3BA Single Family Pool Home

    605 Crane Prairie Way, Osprey, FL 34229

    3 month minimum rental. Just 10 minutes to the amazing clear waters of Casey Key Beach. You are only a few minutes away from all the entertainment you can handle in Sarasota. This beautifully appointed 4 bedroom, 3 bathroom pool home in the very active community of Willowbend, Osprey, FL has lake views from inside and outside with the caged in pool and patio area. With indoor/outdoor

    605 Crane Prairie Way, 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
  • /27

    $2,599 Per Month

    • 2 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • The Residences of Blackburn Bay

    2090 S Tamiami Trail Unit 303, Osprey, FL 34229

    2090 S Tamiami Trail Unit 303, 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
  • /20

    $2,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,371 Sq Ft
    • House for Rent

    253 Glenwood Ave, Osprey, FL 34229

    Welcome to your new oasis in Osprey! This charming 3-bedroom, 2-bathroom house offers a perfect blend of comfort and convenience, making it an ideal place to call home. With a spacious 1,371 square feet, there's plenty of room for you to spread out and enjoy life.Step inside to discover a bright and inviting living space, complete with modern amenities that make daily living a breeze. The

    (941) 335-5525

    253 Glenwood Ave, 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

    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 outdoor lanai with a scenic view of

    Victoria Reilly BERKSHIRE HATHAWAY HOMESERVICE

    4062 Westbourne Cir, Sarasota, FL 34238
  • /31

    $2,250 Per Month

    • 1 Bed
    • 1 Bath
    • 623 Sq Ft
    • Condo for Rent

    51 MacEwen Dr Unit 12, Osprey, FL 34229

    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

    51 MacEwen Dr Unit 12, Osprey, FL 34229
  • /36

    $2,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,528 Sq Ft
    • Townhouse for Rent

    80 Navigation Cir, Osprey, FL 34229

    Turnkey fully furnished newer built 3 bedroom 2 bathroom one car garage townhouse on the second floor. Hurricane windows, gated community, with community pool, club house and gym room. 15-20 minutes to Siesta Key and about 10-15 to Nokomis Beach, Legacy Trail at the end of the street, Dogpark across the street. Walking distance to 4-5 Restaurants. Walmart across the street 3 Publixes and a Target

    Krisztian Kecskes M&M PROPERTY MANAGEMENT GROUP

    80 Navigation Cir, 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
  • /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
  • /32

    $3,595 Per Month

    • 3 Beds
    • 2 Baths
    • 1,937 Sq Ft
    • Condo for Rent

    280 Hidden Bay Dr Unit 202, Osprey, FL 34229

    Be the first to call this brand-new condo in Edgewater at Hidden Bay home. The kitchen showcases a sleek, modern design, complemented by solid wood cabinetry and quartz countertops, creating an ideal space for both everyday living and effortless entertaining. Appliances include a stainless-steel refrigerator, microwave, range, and dishwasher. Large windows bring in an abundance of natural light

    Nancy Guerrero PMI SOUTHWEST FLORIDA

    280 Hidden Bay Dr Unit 202, Osprey, FL 34229
  • /35

    $3,795 Per Month

    • 3 Beds
    • 2 Baths
    • 1,937 Sq Ft
    • Condo for Rent

    280 Hidden Bay Dr Unit 203, Osprey, FL 34229

    This second-story unit in Edgewater at Hidden Bay is ready for move-in and is offered furnished or unfurnished. The apartment includes 3 bedrooms, 2 bathrooms, modern finishes, and steady natural light throughout. The kitchen provides ample cabinet storage, a breakfast bar, quartz countertops, and all major appliances, including a stainless-steel refrigerator, microwave, dishwasher, and range.

    Nancy Guerrero PMI SOUTHWEST FLORIDA

    280 Hidden Bay Dr Unit 203, Osprey, FL 34229
  • /36

    $3,795 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,168 Sq Ft
    • Condo for Rent

    280 Hidden Bay Dr Unit 201, Osprey, FL 34229

    Be the first to live in this brand-new stunning condo in the community of Edgewater at Hidden Bay! Sorry, no pets for renters. The kitchen features a sleek and modern look, equipped with stainless steel appliances, including a refrigerator, microwave, stove, and dishwasher, paired with solid wood cabinetry and elegant quartz countertops, creating an ideal space for both everyday living and

    Nancy Guerrero PMI SOUTHWEST FLORIDA

    280 Hidden Bay Dr Unit 201, 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
  • /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
  • /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
  • /53

    $5,000 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,950 Sq Ft
    • Condo for Rent

    260 Hidden Bay Dr Unit B-504, Osprey, FL 34229

    Annual Turnkey Furnished or short term 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

    Cody Smith RENT SARASOTA

    260 Hidden Bay Dr Unit B-504, 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
  • /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
  • /87

    $6,950 Per Month

    • 3 Beds
    • 2 Baths
    • 2,143 Sq Ft
    • Condo for Rent

    5100 Jessie Harbor Dr Unit 504, Osprey, FL 34229

    CLOSE TO NOKOMIS BEACH! BOOKED JAN/FEB/MAR 2027. AVAILABLE APR 2027 $6,950/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

    5100 Jessie Harbor Dr Unit 504, Osprey, FL 34229
  • /18

    $3,500 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,937 Sq Ft
    • Condo for Rent

    260 Hidden Bay Dr Unit 204, Osprey, FL 34229

    Property Id: 18124583 bedroom 2.5 bath waterfront condo is immaculate and the perfect place for a seasonal snow bird rental, annual rental or Florida vacation (1 month minimum). Lanai that reveals a view of the bay and AMAZING SUNSETS. The unit has laundry room with washer, dryer, sink. The kitchen has granite counter tops ,fully equipped. . The master suite has a king size bed, 2 large

    (270) 813-2485

    260 Hidden Bay Dr Unit 204, Osprey, FL 34229
  • /39

    $6,950 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,839 Sq Ft
    • Townhouse for Rent

    101 Woodland Place, Osprey, FL 34229

    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

    101 Woodland Place, 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
  • /36

    $1,800

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,100 Sq Ft
    • Condo for Rent

    1847 Highland Rd Unit 1839 Highland Rd, Osprey, FL 34229

    Spacious Duplex Villa with community pool in a great area. Close to beaches, shopping & restaurants. Right across Oscar Scherer State Park. Shoreland Park is down the street, where you can launch your kayak.

    1847 Highland Rd Unit 1839 Highland Rd, Osprey, FL 34229
  • /42

    $5,900 Per Month

    • 3 Beds
    • 3 Baths
    • 2,545 Sq Ft
    • Condo for Rent

    3603 N Point Rd Unit 602, Osprey, FL 34229

    **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

    3603 N Point Rd Unit 602, Osprey, FL 34229
  • /20

    $1,900 Per Month

    • 2 Beds
    • 2 Baths
    • 1,325 Sq Ft
    • Condo for Rent

    236 Woodland Dr, Osprey, FL 34229

    Property Id: 310276AVAILABLE JUNE 15 to AUGUST 15, 2026 Light, airy home in Pine Run overlooks established native landscaping. Copious sliding doors, windows & high ceilings. Beautifully updated kitchen offer views to outdoors. Carport + 1 visitor parking space. A nature lovers paradise, this laid-back, quiet & desirable community is close to Casey Key, Blackburn Point Park &

    (941) 845-6331

    236 Woodland Dr, Osprey, FL 34229

Showing Results 1 - 40, Page 1 of 2

Frequently Asked Questions

How much does it cost to rent a home in Osprey, FL?
The median rent for a home in Osprey, FL is $4,000 per month, though prices vary by neighborhood, size, and property type. As of May 2026, condos tend to be the most affordable option while townhouses 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 $160,000 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 $4,000 per month in Osprey, FL, renters typically need to show $12,000 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 13.8, 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 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 home include Casey Key, Vamo, East Sarasota, Coral Cove/Holiday Harbor and South Gate Ridge, each with its own character and price range.

Rental Home Trends in Osprey, FL

Rental Home Trends

Number of Homes for Rent
47
Median Rent
$4,000
Median Single Family Home Rent
$3,950
Median Townhouse Rent
$2,500
Median Condo Rent
$2,400
How to Rent a Home