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2-Bedroom Homes for Rent in Osprey, FL

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  • /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 &

    Agent Photo

    Alba Lange

    WAGNER REALTY

    (941) 207-9375

    293 Hidden Bay Dr Unit 203, Osprey, FL 34229
  • /49

    $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
  • /269

    $1,599 - $3,025 per month

    Alton Osprey

    1 - 3 Beds

    4000 Destination Dr, 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

    4000 Destination Dr, Osprey, FL 34229
  • /41

    $2,500 per month

    • 2 Beds
    • 2 Baths
    • 1,391 Sq Ft
    • Condo for Rent

    2313 Jessie Harbor Dr Unit 2302, Osprey, FL 34229

    ANNUAL UNFURNISHED VILLA AVAILABLE FOR LEASE IN BLACKBURN HARBOR IN OSPREY! This beautiful 2BR 2BA villa has a large lanai with peaceful views over Blackburn Harbor and features Brazilian Cherry hardwood floors, stainless steel appliances and a private one car garage. The entire condo has been freshly painted. Blackburn Harbor is a gated community and offers many amenities, which include a

    Alex Lane PREMIER SOTHEBY'S INTERNATIONAL REALTY

    2313 Jessie Harbor Dr Unit 2302, Osprey, FL 34229
  • /18

    $1,850 per month

    • 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
  • /36

    $2,900 per month

    • 2 Beds
    • 2 Baths
    • 1,069 Sq Ft
    • House for Rent

    305 Bay Vista Ave, Osprey, FL 34229

    Welcome to this stunning two-bedroom, two-bathroom retreat, perfectly designed for relaxation and entertainment!As you step inside, you'll notice the bright and airy open-plan living area, flooded with natural light pouring in through the large windows.But the true showstopper is the incredible backyard oasis! The expansive fenced yard beckons you to unwind and enjoy the fresh

    Jennifer . STOCKTON REALTY ADVISORS LLC

    305 Bay Vista Ave, Osprey, FL 34229
  • /20

    $2,763 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
  • /9

    $2,395 per month

    • 2 Beds
    • 2 Baths
    • 1,145 Sq Ft
    • Townhouse for Rent

    1817 Highland Rd, Osprey, FL 34229

    Lovely 2 bed/2 bth well maintained townhouse with a 2 car garage Set in a private enclave in the desirable West of Trail Osprey location with a Community pool. Close to beaches, restaurants and shopping.

    Steven Koleno BEYCOME OF FLORIDA LLC

    1817 Highland Rd, Osprey, FL 34229
  • /20

    $2,748 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, 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, a centrally located 2-bedroom,

    8 Bay Acres Ave Unit ID1228251P, Osprey, FL 34229
  • /34

    $2,200 per month

    • 2 Beds
    • 2 Baths
    • 1,729 Sq Ft
    • Condo for Rent

    304 Pine Run Dr, Osprey, FL 34229

    Stunning annual unfurnished 2 bed/2 bath ground floor condo located at Pine Run in Osprey, FL. Water, sewer/trash, lawn maintenance, washer/dryer, and pest control included. Available now for $2,200 a month. Application fee for each adult $50, association application fee of $50(10-day association approval process), $ 2,200 security deposit, and $100 administrative fee. 1 pet allowed

    AnaElizabeth Fernandez A & R PROPERTY MGMT, LLC

    304 Pine Run Dr, Osprey, FL 34229
  • /39

    $2,100 per month

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

    294 Hidden Bay Dr Unit 203, Osprey, FL 34229

    Unfurnished light and airy 2 Bedroom 2 Bath with Den condo on 2nd floor. Lease terms negotiable with 7 months minimum. In the Lovely gated Hidden Bay Community that covers 12 beautiful acres located on Little Sarasota Bay with waterfront access for kayaking (including storage) and boardwalk to fishing pier. Recreational center includes pool, spa, fitness center, library, clubhouse,

    294 Hidden Bay Dr Unit 203, 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 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 powder room in an

    Henry Rossi RENT SARASOTA

    260 Hidden Bay Dr Unit B-504, 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 MAY 15 to SEP 15, 2026 / $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

    236 Woodland Dr, Osprey, FL 34229
  • /15

    $3,000 per month

    • 2 Beds
    • 2 Baths
    • 1,738 Sq Ft
    • House for Rent

    1363 New Forest Ln, Osprey, FL 34229

    Welcome to The Woodlands At Rivendell! This beautiful home is on a large corner lot in the Patio Section of the Woodlands. It has TWO Bedrooms + a DEN, Great Room, double tray ceilings w/ crown molding. The den has double pocket doors! The kitchen is central in the house for entertaining, with plenty of storage, pull-out shelves, and 2 pantries! The Lanai has glimmering water views! Some nice

    Pamela Strom RE/MAX PALM

    1363 New Forest Ln, Osprey, FL 34229
  • /25

    $1,995 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 September 15 till December 25 ,2025.The minimum rental period is 2 months. The monthly rent is $1995. 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

    Claudia Dybala DALTON WADE INC

    184 Explorer Dr, 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
  • /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
  • /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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