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2-Bedroom Homes for Rent in Osprey, FL

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  • /48

    $3,950 per month

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

    5100 Jessie Harbor Dr Unit 602, Osprey, FL 34229

    Enjoy luxury waterfront living in this beautifully updated 6th-floor condo at Blackburn Harbor Residences on the West side of Tamiami Trail, overlooking the Blackburn bay. This 2-bedroom, 2-bath unit includes a den/flex room and offers panoramic water views from the main rooms. The fully remodeled kitchen features quartz countertops, stainless steel appliances, and two refrigerators—perfect for

    Agent Photo

    Jeremy Myers

    COMPASS PROPERTY MANAGEMENT LLC

    (941) 770-3963

    5100 Jessie Harbor Dr Unit 602, Osprey, FL 34229
  • /284

    $2,025 - $3,495 per month

    Alton Osprey

    1 - 3 Beds

    174 E Bay St, Osprey, FL 34229

    Arriving Spring 2025, discover stunning one-, two-, and three-bedroom apartment homes coming to Osprey, FL. With high-end finishes outfitting each residence, offering the perfect blend of comfort and sophistication, coming home will feel like a daily retreat. Our best-in-class amenity spaces allow you the opportunity to live beyond your expectations - from our sleek business center that works for

    174 E Bay St, Osprey, FL 34229
  • /32

    $2,195 per month

    • 2 Beds
    • 2 Baths
    • 1,599 Sq Ft
    • Property for Rent

    291 Hidden Bay Dr Unit 201, Osprey, FL 34229

    Spacious 2nd-floor end-unit with one car garage (22x11) provides nearly 1,600 sq. ft. and stunning lake and courtyard views. This updated 2BR + den/office (can be 3rd BR) features the largest floor plan in the building, no carpet (tile & laminate throughout), an open-concept layout, and tons of natural light. Kitchen has granite counters, stainless appliances, and upgraded cabinets. Master suite

    Terri Lindsay LINDSAY LEASING LLC

    291 Hidden Bay Dr Unit 201, 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 AUG 1 to SEP 30 / $100 discount for term of 2 or more months: 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,

    236 Woodland Dr, Osprey, FL 34229
  • /25

    $2,200 per month

    • 2 Beds
    • 2 Baths
    • 1,135 Sq Ft
    • Townhouse for Rent

    184 Explorer Dr, Osprey, FL 34229

    The unit is available for rent from August 1 ,2025.The minimum rental period is 2months. The monthly rent is $2200. The tenant is responsible for electricity and internet costs. NO PETS! 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

    184 Explorer Dr, Osprey, FL 34229
  • /18

    $1,850 per month

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

    455 Pennsylvania Ave, Osprey, FL 34229

    Available Now – 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,

    455 Pennsylvania Ave, Osprey, FL 34229
  • /33

    $3,695 per month

    • 2 Beds
    • 3.5 Baths
    • 1,890 Sq Ft
    • Townhouse for Rent

    60 Bishops Court Rd Unit 114, Osprey, FL 34229

    This is a rare opportunity to rent a luxury, unfurnished townhome located in the heart of the Oaks Preserve. Showcasing charming architectural details and quality finishes, this traditional-style home offers an inviting floor plan with two bedrooms, each featuring its own en-suite bath. The gracious living and dining areas flow seamlessly into a spacious and private outdoor living space that

    Heidi Thompson STRINGER MANAGEMENT INC

    60 Bishops Court Rd Unit 114, Osprey, FL 34229
  • /32

    $1,750 per month

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

    1847 Highland Rd Unit 1865 Shoreland, 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 1865 Shoreland, Osprey, FL 34229
  • /21

    $2,300 per month

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

    184 Explorer Dr Unit 184, Osprey, FL 34229

    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

    184 Explorer Dr Unit 184, Osprey, FL 34229
  • /20

    $2,550 per month

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

    8 Bay Acres Ave Unit ID1228251P, Osprey, FL 34229

    Relax in this stylish 2-bedroom and 2-bathroom retreat just 5 minutes from Nokomis Beach. Feel at home with a private lanai, fast Wi-Fi, a full kitchen, and a Smart TV with Netflix. Perfect for couples, families, or mid-term stays, this apartment is close to Siesta Key, Venice, and St. Armands, comfortably sleeping up to 6 people.Welcome to your Florida retreat. Whether you're here for

    8 Bay Acres Ave Unit ID1228251P, Osprey, FL 34229
  • /47

    $5,000 per month

    • 2 Beds
    • 2 Baths
    • 1,568 Sq Ft
    • Condo for Rent

    293 Hidden Bay Dr Unit 203, Osprey, FL 34229

    RENTED JANUARY TILL MARCH 2026. TURNKEY FURNISHED RENTAL! GATED, WATER VIEWS! WATERFRONT COMMUNITY IN OSPREY! 2 Bedroom 2 bath plus den. Den has French doors. Lots of light from this second-floor end unit condo. Front door has disappearing screen for fresh Air. TURNKEY FURNISHED. Completely renovated. NO CARPET. Porcelain tile thru out. Granite counters and high ceilings. Front loading washer &

    Alba Lange WAGNER REALTY

    293 Hidden Bay Dr Unit 203, Osprey, FL 34229
  • /20

    $3,020 per month

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

    6 Bay Acres Ave Unit ID1228250P, Osprey, FL 34229

    Step into a sunlit, single-story retreat with two inviting bedrooms and two modern bathrooms. Designed for families or groups of friends, this home seamlessly blends comfort with elegance. Located just moments away, dive into the vibrant St. Armand's Circle or unwind on the pristine sands of Siesta Key and Nokomis Beaches.This space includes everything needed for a quality and memorable

    6 Bay Acres Ave Unit ID1228250P, Osprey, FL 34229
  • /42

    $4,500 per month

    • 2 Beds
    • 2 Baths
    • 1,682 Sq Ft
    • House for Rent

    5305 Bartolomeo St, Sarasota, FL 34238

    Annual lease (no short term) turn-key furnished 3 bedroom two bath w/private heated pool and spa. Life-style community with all the resort amenities and activities: Clubhouse, pickleball, tennis courts, fitness gym, exercise rooms, day spa, Bahama Bar, resort pool, resistance pool, pool side spa, trails, & direct access to the Legacy Bike Trail.Primary suite is a peaceful retreat with a tray

    Leonard Giarrano RE/MAX ALLIANCE GROUP

    5305 Bartolomeo St, Sarasota, FL 34238
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