20

Osprey, FL Condos for Rent

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  • /30

    $10,050 per month

    • 3 Beds
    • 3.5 Baths
    • 2,716 Sq Ft
    • Condo for Rent

    14021 Bellagio Way Unit 401, Osprey, FL 34229

    2025 AVAILABLE: DEC.2026 AVAILABLE: MAR, APR.BOOK AT: $10,050/PER MONTH (SEASON IS DEC-APRIL, 1 MONTH MINIMUM)*PRICES MAY VARY DEPENDING ON NUMBER OF NIGHTS BOOKED*This is your chance to enjoy the Florida Coastal lifestyle that you've been dreaming about! This rarely available very quiet, 3 bedroom, 3 1/2 bath 2,700 square foot penthouse suite is the epitome of luxury. This condo impresses from

    Agent Photo

    Jeremy Myers

    274501900

    (941) 274-3817

    14021 Bellagio Way Unit 401, 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
  • /35

    $4,400 per month

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

    280 Hidden Bay Dr Unit 303, Osprey, FL 34229

    One or more photo(s) has been virtually staged. Annual Rental. This newly constructed 3rd floor condo is available for immediate occupancy at Hidden Bay in Osprey. This gorgeous 3 Bedroom PLUS a Home Office is light, bright and very spacious! Wood and tile floors throughout- NO CARPETING! The Primary suite features 2 walk-in closets, sliding glass doors leading to the lanai and an ensuite with a

    Jaime Barcelo GULF COAST REALTY & MANAGEMENT

    280 Hidden Bay Dr Unit 303, Osprey, FL 34229
  • /20

    $2,850 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. Whether you're here for sunshine,

    8 Bay Acres Ave Unit ID1228251P, Osprey, FL 34229
  • /21

    $2,400 per month

    • 3 Beds
    • 2 Baths
    • 1,430 Sq Ft
    • Condo for Rent

    4248 Expedition Way Unit 4248, Osprey, FL 34229

    Apply within 24 hours of your conducted showing and once approved you will be credited your application fees towards your first full month's rent! Welcome home to this beautiful 3-bedroom, 2-bathroom condo in the sought after gated community of Bay Street Village! Neutral paint, ceiling fans throughout, tile flooring in the main living areas and carpet in the bedrooms make decorating a breeze!

    Colbey Mason RYNTAL

    4248 Expedition Way Unit 4248, Osprey, FL 34229
  • /20

    $3,320 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
  • /48

    $2,450 per month

    • 3 Beds
    • 2.5 Baths
    • 1,655 Sq Ft
    • Condo for Rent

    4209 Expedition Way Unit 102, Osprey, FL 34229

    This lovely 3 bedroom, 2 1⁄2 bath townhome. This unfurnished unit has (2) Separate Single car garages-Storage and Parking. Located Close to Beaches, Shopping and Dining. Like New, Freshly Painted, Built in 2016. The kitchen has granite, nice cabinets, and stainless appliances. Beautiful Water View w/ fountain! Large open kitchen, dining and living room. All bedrooms are upstairs and are great

    Tim Weller EXIT KING REALTY

    4209 Expedition Way Unit 102, Osprey, FL 34229
  • /37

    $1,750 per month

    • 2 Beds
    • 2 Baths
    • 1,000 Sq Ft
    • Condo for Rent

    1847 Highland Rd Unit 1869, Osprey, FL 34229

    Beautiful Duplex Villa with community pool in a great area. Close to beaches, shopping & restaurants.

    1847 Highland Rd Unit 1869, Osprey, FL 34229
  • /36

    $4,000 per month

    • 3 Beds
    • 2 Baths
    • 1,799 Sq Ft
    • Condo for Rent

    14041 Bellagio Way Unit 214, Osprey, FL 34229

    One or more photo(s) has been virtually staged. ANNUAL or Short Term (3 Months Minimum) CONDO/VILLA AVAILABLE FOR LEASE with Option to Purchase! Short Term Rent is $6000 /month. Annual Lease is $4000/Month. Villas at the Harbor Village boasts luxurious amenities and waterfront living on Little Sarasota Bay with access to the Intracoastal Waterway and the Gulf, just across from Casey Key. Enjoy

    Veronica Lee FINE PROPERTIES

    14041 Bellagio Way Unit 214, Osprey, FL 34229
  • /49

    $2,995 per month

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

    127 Explorer Dr Unit 127 Explorer Dr, Osprey, FL 34229

    Great location - short drive to the best Florida beaches, golf clubs, Oscar Schrer State park, Legacy trail, right between cultural and culinary wealth of downtown Sarasota and Venice. Walking distance to Pine View School, playground and dog park across the street. Gated community with heated pool, fitness center and club house, newer buildings with hurricane -withstand features. One car garage

    127 Explorer Dr Unit 127 Explorer Dr, Osprey, FL 34229
  • /87

    $7,000 per month

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

    5100 Jessie Harbor Dr Unit 504, Osprey, FL 34229

    This beautiful 5th Floor condo located in Blackburn Harbor Residences is now available for Season 2026! There are 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 converted from a den) and 2 bathrooms. As you step inside the

    Chrissie Cummings JENNETTE PROPERTIES INC

    5100 Jessie Harbor Dr Unit 504, Osprey, FL 34229
  • /42

    $6,000 per month

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft
    • Condo for Rent

    260 Hidden Bay Dr Unit View of Casey Key, Osprey, FL 34229

    Beautiful penthouse (fifth floor) condominium, newly furnished in active gated community. Nestled between Venice and Sarasota. Stunning unobstructed views of Little Sarasota Bay and Casey Key available for rent starting July 1, 2025. Elevator and stairs in building. Large master suite with two closets and access to porch. Guest suite in back of condo offers privacy when family and friends come to

    260 Hidden Bay Dr Unit View of Casey Key, Osprey, FL 34229
  • /43

    $6,000 per month

    • 3 Beds
    • 2 Baths
    • 2,374 Sq Ft
    • Condo for Rent

    14041 Bellagio Way Unit 218, Osprey, FL 34229

    If you're looking for a place that offers a rent to own opportunity, now is your chance! Welcome to your coastal sanctuary in the gated community of Villas at Osprey Harbor Village. Located just minutes from the newly reopened Midnight Pass beach, and walking distance to Casey Key fish house. This impeccably remodeled 3 bedroom, 2 bathroom residence offers an elegant, light-filled living space

    Kelli Eggen COLDWELL BANKER REALTY

    14041 Bellagio Way Unit 218, Osprey, FL 34229
  • /41

    $2,400 per month

    • 2 Beds
    • 2 Baths
    • 1,574 Sq Ft
    • Condo for Rent

    4214 Frontier Ln Unit 102, Osprey, FL 34229

    Apply within 24 hours of your conducted showing and once approved you will be credited your application fees towards your first full month's rent! Welcome to this lovely, fully furnished, 2-bedroom, 2-bathroom condo in Osprey! This condo is ready to welcome your entire family, complete with bright and airy spaces, spacious bedrooms, and a coastal vibe perfect for the ideal Florida lifestyle! Not

    Colbey Mason RYNTAL

    4214 Frontier Ln Unit 102, Osprey, FL 34229
  • /17

    $2,150 per month

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

    4223 Frontier Ln, Osprey, FL 34229

    This 1,135-square-foot condo features 2 bedrooms, 2 bathrooms, and a 1-car garage and will be available for an annual lease starting June 1, 2025. First and last month’s rent, along with a security deposit (3x$2,150), are required before move-in. A credit and background check is required, with a $50 application fee per person. Rent includes water, sewer, trash, access to amenities and

    Anna Bridinger PELICAN REALTY CORP

    4223 Frontier Ln, 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
  • /74

    $7,900 per month

    • 3 Beds
    • 2 Baths
    • 2,058 Sq Ft
    • Condo for Rent

    14041 Bellagio Way Unit 316, Osprey, FL 34229

    NOW AVAILABLE FOR APRIL AND OFF-SEASON MONTHS 2025 AND JAN-APRIL 2026! Welcome to BELLAGIO at Osprey Harbor Village, offering luxurious waterfront living! This turnkey direct waterfront condo has 3 beds/2 baths plus a den is the perfect place for your next Florida vacation, located in a private gated community. As you step off the elevator, you are basically outside this 3rd floor end unit. Upon

    Chrissie Cummings JENNETTE PROPERTIES INC

    14041 Bellagio Way Unit 316, Osprey, FL 34229
  • /10

    $2,500 per month

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

    51 Mac Ewen Dr Unit 1, Osprey, FL 34229

    ***AVAILABLE NOVEMBER 2025 THRU JANUARY 2026*** Welcome to THE OAK community, it's gated 24/7. private as private can be. Drenched in value and a fantastic community located in South Sarasota. Open plan, easy to show! Close to Siesta Key, Costco restaurants very convenient to all the amenities Sarasota has to offer.

    Anthony DeLuca AUDREY RAIN RENTALS, INC

    51 Mac Ewen Dr Unit 1, Osprey, FL 34229
  • /25

    $4,500 per month

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

    152 Navigation Cir Unit 107, Osprey, FL 34229

    Seasonal and short term rental Get out of the cold and into the sunshine in this newer 3/2 condo in the gated community of Bay Street Village in Osprey. This condo is an end unit with an open floor plan for ease of entertaining and family time. The extra windows flood the unit with natural sun light. The kitchen is a natural gathering point with solid wooden cabinetry, topped with slab granite

    Henry Rossi RENT SARASOTA

    152 Navigation Cir Unit 107, 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

    AVAILABLE ANNUAL OR 2026 SEASON. 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
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