10

Fully Furnished Homes for Rent in Osprey, FL

Section Image Section Image
  • /2

    $5,500 per month

    • 3 Beds
    • 2 Baths
    • 2,172 Sq Ft
    • House for Rent

    557 Crane Prairie Way, Osprey, FL 34229

    Welcome to this beautiful fully furnished 3-bed, 2-bath home in the gated community of Willowbend in Osprey. With 2,172 sq ft of bright, open living space, this seasonal rental offers comfort, style, and plenty of room to relax. Enjoy a spacious kitchen, a large primary suite, and a peaceful screened lanai perfect for morning coffee or evening sunsets.The community features a pool, fitness

    Agent Photo

    Craig McCoy

    PREFERRED SHORE LLC

    (941) 392-7290

    557 Crane Prairie Way, Osprey, FL 34229
  • /49

    $3,750 per month

    • 3 Beds
    • 2.5 Baths
    • 2,155 Sq Ft
    • House for Rent

    221 Lookout Point Dr, Osprey, FL 34229

    Stunning 3 Bedrooms and 3 Baths for rent in Southwest Florida,located on the Intracoastal waterway with easy access to nearby beaches,cultural attractions and golf ,The community-owned marina is for the exclusive use of the Southbay Homeowners.This home is available on May,15th,2026.Last year was remodeled and upgraded troughout featuring a modern kitchen with granite countertops and wine

    Elizabeth Anzellini KELLER WILLIAMS ON THE WATER S

    221 Lookout Point Dr, Osprey, FL 34229
  • /31

    $2,250 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
  • /35

    $3,795 per month

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

    280 Hidden Bay Dr Unit 203, Osprey, FL 34229

    This second-story unit in Edgewater at Hidden Bay is ready for move-in and is furnished or unfurnished. The apartment includes 3 bedrooms, 2 bathrooms, modern finishes, and steady natural light throughout. The kitchen provides ample cabinet storage, a breakfast bar, quartz countertops, and all major appliances, including a stainless-steel refrigerator, microwave, dishwasher, and range. The open

    Nancy Guerrero PMI SOUTHWEST FLORIDA

    280 Hidden Bay Dr Unit 203, Osprey, FL 34229
  • /24

    $6,000 per month

    • 3 Beds
    • 3.5 Baths
    • 2,570 Sq Ft
    • House for Rent

    32 Bayhead Ln, Osprey, FL 34229

    Stunning 3 bedroom, 3 1⁄2 bath professionally redesigned home in the Oaks Preserve. This exceptional property features a spacious chef’s kitchen with top-of-the-line appliances, a large prep island, quartz countertops throughout, and an open concept for ease in entertaining. The family/gathering has a panoramic view overlooking the lanai, lake and fountain. and lake with a fountain. The Owners’

    Christian Higgins ANDRE LECLAIR PROPERTIES LLC

    32 Bayhead Ln, Osprey, FL 34229
  • /31

    $4,500 per month

    • 3 Beds
    • 2 Baths
    • 2,367 Sq Ft
    • House for Rent

    1355 Southbay Dr, Osprey, FL 34229

    Southbay Yacht & Racquet Club where the true Florida lifestyle is alive and well! This three-bedroom two bath pool home is located in an active community with unmatched amenities such as an active social atmosphere, heated community pool, playground, fitness room, tennis, pickleball courts, and fishing. All for you to enjoy! Walk, bike or take your golf cart to restaurants, shopping or the

    Sharon Lewis GOLF & BAY PROPERTIES LLC

    1355 Southbay Dr, Osprey, FL 34229
  • /44

    $6,500 per month

    • 3 Beds
    • 3 Baths
    • 2,266 Sq Ft
    • House for Rent

    521 Habitat Blvd, Osprey, FL 34229

    Stylish 3BR Pool Home w/ Office – 10 Mins to Beach ****SEASONAL RENTAL ONLY**** 90 Day minimum stay, Peak Season at $8,900/mo plus fees; Off Season at $6,500/mo plus fees. NOTE: Jan, Feb and March 2027 are Not Available. Your Gulf Coast getaway awaits at this beautifully furnished 3-bedroom, 3-bath pool home in the scenic Willowbend community of Osprey, FL. Ideal for mid-term stays, this spacious

    Dave Holt PMI SOUTHWEST FLORIDA

    521 Habitat Blvd, Osprey, FL 34229
  • /39

    $6,950 per month

    • 3 Beds
    • 2.5 Baths
    • 1,839 Sq Ft
    • Townhouse for Rent

    101 Woodland Place, Osprey, FL 34229

    Price Reduction and Now AVAILABLE FOR LEASE for FEBRUARY through APRIL 2026 at PINE RUN Condominiums in OSPREY, Florida! One month availability. 3BR/2.5BA Great SARASOTA Vacation Location! West of the Trail, Pine Run is an active community set in a tropical oasis of 20+ acres of wooded Florida landscape. This spacious corner unit townhouse is well FURNISHED. Beautifully decorated and full of

    Patrice Ivan WAGNER REALTY

    101 Woodland Place, 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
  • /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 MAY 2026 THRU JULY 2026 AND THEN AGAIN IN NOVEMBER 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
How to Rent a Home