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Osprey, FL Condos for Rent

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  • /83

    $2,200 per month

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Condo for Rent

    129 Woodland Place, Osprey, FL 34229

    One or more photo(s) has been virtually staged. AVAILABLE FURNISHED FOR $3,300. Step into the serene lifestyle at 129 Woodland Place, a charming 2-bedroom, 2-bathroom condo in the peaceful Pine Run community of Osprey, Florida. Spanning 1,223 square feet, this home boasts an open layout with soaring ceilings that invite natural light to fill the space. The living and dining areas seamlessly

    Agent Photo

    Paulina Vasiliev

    KELLER WILLIAMS ON THE WATER S

    (941) 394-8767

    129 Woodland Place, Osprey, FL 34229
  • /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

    Agent Photo

    Jeremy Myers

    COMPASS PROPERTY MANAGEMENT LLC

    (941) 274-3817

    14021 Bellagio Way Unit 401, Osprey, FL 34229
  • /18

    $4,500 per month

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

    260 Hidden Bay Dr Unit 204, Osprey, FL 34229

    Property Id: 18124583 bedroom 2.5 bath waterfront condo is immaculate and the perfect place for a seasonal snow bird rental, annual rental or Florida vacation (1 month minimum). Lanai that reveals a view of the bay and AMAZING SUNSETS. The unit has laundry room with washer, dryer, sink. The kitchen has granite counter tops ,fully equipped. . The master suite has a king size bed, 2 large

    260 Hidden Bay Dr Unit 204, Osprey, FL 34229
  • /23

    $2,200 per month

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

    137 Navigation Cir Unit 137, 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! Don't miss this beautiful 3-bedroom, 2-bathroom fully furnished condo in Osprey! Complete with modern furniture, art, and fixtures that will make you feel like you're living the life of luxury. The state of the art kitchen is complete with granite

    Christopher Plemenos

    137 Navigation Cir Unit 137, Osprey, FL 34229
  • /23

    $2,000 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 SEPTEMBER 15: Light, airy home in Pine Run overlooks established native landscaping. Copious sliding doors, windows & high ceilings. Beautifully updated kitchen offer views to outdoors. A nature lovers paradise, this laid-back, quiet & desirable community is close to Casey Key, Blackburn Point Park & Intracoastal Waterway. A rare find & well-kept

    236 Woodland Dr, Osprey, FL 34229
  • /53

    $4,900 per month

    • 3 Beds
    • 3.5 Baths
    • 2,214 Sq Ft
    • Condo for Rent

    14021 Bellagio Way Unit 410, Osprey, FL 34229

    Enjoy STUNNING sunsets 365 days a year in this LUXURIOUS WATERFRONT CONDO in Osprey, FL. From the moment you step out of your PRIVATE ELEVATOR and into this PENTHOUSE UNIT you’ll be amazed by the SPECTACULAR VIEWS overlooking Little Sarasota Bay and the Intracoastal Waterway (ICW). This 3 bed/3.5bath, TURNKEY FURNISHED unit, has been freshly painted inside and features newer flooring, crown

    Adam Waxler UKEEPCOMMISSION REAL ESTATE

    14021 Bellagio Way Unit 410, Osprey, FL 34229
  • /34

    $1,850 per month

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

    1847 Highland Rd Unit 1859, Osprey, FL 34229

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

    1847 Highland Rd Unit 1859, Osprey, FL 34229
  • /31

    $2,900 per month

    • 3 Beds
    • 2.5 Baths
    • 1,950 Sq Ft
    • Condo for Rent

    260 Hidden Bay Dr Unit B-202, Osprey, FL 34229

    Edgewater at Hidden Bay Annual Rental available now. This pristine 3-bedroom, 2.5-bath condo features a spacious lanai, offering a glimpse of the bay over the serene preserve views—perfect for enjoying breathtaking sunsets. King murphy bed in 2nd guest room, living room wall unit and patio furniture are included. Additional details that make this unit feel more like a home than a condo include an

    Terri Lindsay LINDSAY LEASING LLC

    260 Hidden Bay Dr Unit B-202, 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
  • /11

    $2,300 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 $2,300), 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
  • /46

    $2,800 per month

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

    758 Sarabay Rd Unit 5, Osprey, FL 34229

    ANNUAL UNFURNISED CONDO/VILLA WITH BOAT DOCK AVAILABLE FOR LEASE IN HERON BAY! Heron Bay is a secluded waterfront community on Little Sarasota Bay with access to the Intracoastal Waterway and the Gulf. Heron Bay is an intimate and peaceful 10-acre community across from the northern section of Casey Key. The home has waterfront views along with views of the community pond with a custom

    Alex Lane PREMIER SOTHEBY'S INTERNATIONAL

    758 Sarabay Rd Unit 5, Osprey, FL 34229
  • /20

    $1,695 per month

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

    51 MacEwen Dr Unit 14, Osprey, FL 34229

    Windsor Lodge in The Oaks - Gorgeous turnkey furnished studio apartment available now for lease! This charming 595 sq ft second-floor studio is located in the desirable Windsor Lodge within the exclusive Oaks community. It features top-of-the-line finishes, all brand new, and is accessible by both elevator and stairs. The unit includes a full kitchen equipped with a full-size refrigerator,

    Terri Lindsay LINDSAY LEASING LLC

    51 MacEwen Dr Unit 14, Osprey, FL 34229
  • /21

    $2,200 per month

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

    116 Revolution Way Unit 116, Osprey, FL 34229

    ONE MONTH FREE RENT with a 24-MONTH LEASE - Ask about our security deposit alternative to help with the upfront move in cost! You are just going to love this stunning, 2-bedroom, 2-bathroom condo located in Osprey! Located in the gated community of Bay Street, it iclose to Sarasota's top-rated, and nationally recognized, Pine View School. This second floor unit is situated on a quiet cul-de-sac,

    Christopher Plemenos

    116 Revolution Way Unit 116, 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
  • /47

    $5,500 per month

    • 3 Beds
    • 3 Baths
    • 2,203 Sq Ft
    • Condo for Rent

    385 N Point Rd Unit 503, Osprey, FL 34229

    **TURN-KEY, MOVE IN READY 5TH FLOOR CONDO WITH WATERFRONT AND PRESERVE VIEWS RIVALING HIGHER FLOORS** - JUST BRING YOUR SUITCASE AND ENJOY PARADISE! Over 2200sf in the Luxury, High-Rise, Meridian Condo Complex which features 3 BEDROOMS + 3 FULL BATHS, with new furnishings throughout, behind the Secure Gates of the highly sought after OAKS-PRESERVE, COUNTRY CLUB neighborhood. This light, bright

    Mark Lyda GENEROUS PROPERTY

    385 N Point Rd Unit 503, Osprey, FL 34229
  • /37

    $2,350 per month

    • 2 Beds
    • 2 Baths
    • 1,379 Sq Ft
    • Condo for Rent

    754 Pine Run Dr Unit 754, Osprey, FL 34229

    Exceptional Ground-Level 2/2 Condo with Modern Features and Prime LocationThis rarely available ground-level 2-bedroom, 2-bathroom condo offers a unique blend of space, style, and an unbeatable location within the community. Its thoughtfully designed floorplan features a central open-air atrium, accessible through 8-foot glass doors on three sides, creating a seamless connection to nature.

    Sasha Volosevych CALL IT CLOSED INTL REALTY

    754 Pine Run Dr Unit 754, Osprey, FL 34229
  • /30

    $2,200 per month

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

    51 MacEwen Dr Unit 12, Osprey, FL 34229

    For Lease at THE OAKS CLUB WINDSOR LODGE. Private sanctuary rarely available for rent at one of Sarasota's most exclusive private country clubs. This lovely sunny Second floor end unit is fully turnkey furnished and ready for MOVE IN. Completely updated one bedroom, resort suite style studio, condominium with sweeping Water Views of the Lakefront of the 18th fairway on the Eagle Course. A

    Patrice Ivan WAGNER REALTY

    51 MacEwen Dr Unit 12, Osprey, FL 34229
  • /74

    $8,000 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
  • /55

    $2,400 per month

    • 2 Beds
    • 2 Baths
    • 1,479 Sq Ft
    • Condo for Rent

    291 Hidden Bay Dr Unit 102, Osprey, FL 34229

    This lease is available starting MAY 2025. This spacious first floor unit is fully furnished, with two bedrooms and two bathrooms. The view overlooks a tranquil pond. Hidden Bay condominium is a 12-acre, gated community on Sarasota Bay in Osprey with beautiful views of Casey Key.The community includes a clubhouse that features a fully-stocked library, an entertainment/media room, kitchen,

    Anthony DeLuca AUDREY RAIN RENTALS, INC

    291 Hidden Bay Dr Unit 102, 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 February 1, 2025 thru July 31, 2025*** 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 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 & dryer

    Alba Lange WAGNER REALTY

    293 Hidden Bay Dr Unit 203, Osprey, FL 34229
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