14

Homes for Rent in Osprey, FL with 2-Bedrooms

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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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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

Rental Home Trends in Osprey, FL

Rental Home Trends

Number of 2 Bedroom Homes for Rent
14
Median 2 Bedroom Condo Rent
$2,300
Median 2 Bedroom Townhouse Rent
$3,295
How to Rent a Home