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Osprey, FL Condos for Rent

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  • /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
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    $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
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    $3,200 per month

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

    14041 Bellagio Way Unit 414, Osprey, FL 34229

    Annual turn-key furnished rental opportunity at Osprey Harbor Village, a gated waterfront community along Florida’s Intracoastal Waterway. This 3 bedroom, 2 bath penthouse offers nearly 2,000 square feet of living space plus a 290 square foot tiled terrace with sweeping views of the marina, Intracoastal, and Sarasota Bay. Soaring ceilings, an open floor plan, and walls of windows fill the

    Agent Photo

    Dawn Bear

    WILLIAM RAVEIS REAL ESTATE

    (941) 246-2954

    14041 Bellagio Way Unit 414, Osprey, FL 34229
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    $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
  • /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
  • /20

    $2,775 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
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    $2,500 per month

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

    4256 Expedition Way Unit 107, Osprey, FL 34229

    Welcome to Bay Street in Osprey! This 3-bedroom, 2-bath condominium offers the comfort of single-level living on the second floor of a two-story building. Enjoy an open layout filled with natural light and peaceful lake and fountain views from nearly every room. The kitchen is equipped with newer stainless steel appliances, plus a washer and dryer. Additional features include ceiling fans

    Geri Scheckner BRIGHT REALTY

    4256 Expedition Way Unit 107, Osprey, FL 34229
  • /20

    $2,742 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
  • /38

    $6,000 per month

    • 3 Beds
    • 3 Baths
    • 2,055 Sq Ft
    • Condo for Rent

    409 N Point Rd Unit 802, Osprey, FL 34229

    **TURNKEY FURNISHED, PENTHOUSE Condo Unit has been FULLY RENOVATED** This 8TH FLOOR, Light and Bright, 3-BEDROOM plus 3 FULL BATH dwelling with screened balcony is available beginning in September, 2025. The 2055sf floorplan is tastefully furnished and offers superb views of the Intracoastal Waterway and Gulf. This unit was fully renovated in 2023 with updated oak hardwood flooring, new kitchen

    Mark Lyda GENEROUS PROPERTY

    409 N Point Rd Unit 802, 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
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    $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
  • /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
  • /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
  • /30

    $4,200 per month

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

    280 Hidden Bay Dr Unit 202, Osprey, FL 34229

    READY FOR IMMEDIATE OCCUPANCY! Modern Elegance at Edgewater: A Luxurious Haven Overlooking Little Sarasota Bay Step into a world of contemporary sophistication with this new construction condominium nestled in the eminent enclave of Edgewater at Hidden Bay. Boasting 1937 square feet, this meticulously crafted residence offers three bedrooms, two bathrooms, and an inviting office space for your

    Mike Aveni KELLER WILLIAMS ISLAND LIFE REAL ESTATE

    280 Hidden Bay Dr Unit 202, Osprey, FL 34229
  • /20

    $2,350 per month

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

    205 Navigation Cir Unit 205, Osprey, FL 34229

    town home style condo at Bay Street, with beautiful lakefront view. Enjoy coastal breezes & the Florida lifestyle in maintenance free community. open design concept with great room, kitchen & dinning on the 1st floor, Cherry spice cabinets, stainless appliances, granite counter tops, with a private covered entry porch & 2 separate garages. Luxury waterproof floor on the second floor. Master suite

    Qi Wang HAUZS INC

    205 Navigation Cir Unit 205, Osprey, FL 34229
  • /39

    $4,200 per month

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

    280 Hidden Bay Dr Unit 302, Osprey, FL 34229

    NOW AVAILABLE FOR RENT – READY FOR IMMEDIATE OCCUPANCYModern Elegance at Edgewater | Stunning Condo with Bay ViewsLive the luxury lifestyle in this brand-new 3-bedroom, 2-bathroom + office condominium in the exclusive Edgewater at Hidden Bay community. Offering 1,937 sq ft of modern design, this elegant residence features a gourmet kitchen with top-tier LG appliances, solid wood

    Jim Xarras, Jr BERKSHIRE HATHAWAY HOMESERVICE

    280 Hidden Bay Dr Unit 302, Osprey, FL 34229
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    $4,200 per month

    • 3 Beds
    • 2.5 Baths
    • 2,166 Sq Ft
    • Condo for Rent

    Unlisted Address

    NOW AVAILABLE FOR RENT – READY FOR IMMEDIATE OCCUPANCYModern Elegance at Edgewater | Stunning Condo with Bay ViewsLive the luxury lifestyle in this brand-new 3-bedroom, 2-bathroom + office condominium in the exclusive Edgewater at Hidden Bay community. Offering 1,937 sq ft of modern design, this elegant residence features a gourmet kitchen with top-tier LG appliances, solid wood

    Jim Xarras, Jr BERKSHIRE HATHAWAY HOMESERVICE

    Unlisted Address
  • /39

    $4,200 per month

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

    Unlisted Address

    NOW AVAILABLE FOR RENT – READY FOR IMMEDIATE OCCUPANCYModern Elegance at Edgewater | Stunning Condo with Bay ViewsLive the luxury lifestyle in this brand-new 3-bedroom, 2-bathroom + office condominium in the exclusive Edgewater at Hidden Bay community. Offering 1,937 sq ft of modern design, this elegant residence features a gourmet kitchen with top-tier LG appliances, solid wood

    Jim Xarras, Jr BERKSHIRE HATHAWAY HOMESERVICE

    Unlisted Address
  • /35

    $4,250 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
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    $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
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    $5,000 per month

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

    14041 Bellagio Way Unit 218, Osprey, FL 34229

    Welcome to your coastal sanctuary in the gated community of Villas at Osprey Harbor Village. Located just minutes from Midnight Pass beach, Snake Island and walking distance to Casey Key fish house. This impeccably remodeled 3 bedroom, 2 bathroom residence offers an elegant, light-filled living space with breath taking harbor and sunset views from every room. Designed with both comfort and style

    Kelli Eggen COLDWELL BANKER REALTY

    14041 Bellagio Way Unit 218, Osprey, FL 34229
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    $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
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    $7,500 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
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