$5,000

1438 LANDVIEW LANE

OSPREY FL 34229

3,602 sqft
4 Beds
3 Baths
0.24 Acres

Welcome to this bright, sunny and spacious 4 Bed, 3 Bath home with an office and a private pool — perfect for Florida living! Nestled …

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$4,900

14021 BELLAGIO WAY UNIT 410

OSPREY FL 34229

2,555 sqft
3 Beds
3.5 Baths
4.02 Acres

Enjoy STUNNING sunsets 365 days a year in this LUXURIOUS WATERFRONT CONDO in Osprey, FL. From the moment you step out of your PRIVATE ELEVAT…

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$4,800

956 SCHERER WAY

OSPREY FL 34229

3,182 sqft
4 Beds
3 Baths
0.25 Acres

This luxuriously FULLY furnished 4 Bedroom Pool home is available starting April 15, 2025! It backs right onto the tropical preserves of Os…

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$4,500

152 NAVIGATION CIRCLE UNIT 107

OSPREY FL 34229

1,889 sqft
3 Beds
2 Baths
0 Acres

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 Villag…

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$4,400

1768 S CREEK LANE

OSPREY FL 34229

3,662 sqft
3 Beds
2 Baths
0.29 Acres

One or more photo(s) has been virtually staged. Home for rent in the coveted, gated community of South Creek. This home has 3 bedrooms and 2…

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$4,200

534 OAK BAY DRIVE

OSPREY FL 34229

2,787 sqft
4 Beds
3 Baths
0 Acres

New to the rental market, very nice light and bright 4 bedroom pool home with private secluded lot in the quaint community of Oak Bay Estate…

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$4,000

6100 JESSIE HARBOR DRIVE UNIT 202

OSPREY FL 34229

4,209 sqft
3 Beds
3.5 Baths
0 Acres

This beautiful waterfront condo looks over Blackburn Harbor and offers plenty of space with 3,771 square feet with 3 bedrooms + a den and 2 …

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$3,695

60 BISHOPS COURT ROAD UNIT 114

OSPREY FL 34229

2,154 sqft
2 Beds
3.5 Baths
1.62 Acres

This is a rare opportunity to rent a luxury, unfurnished townhome located in the heart of the Oaks Preserve. Showcasing charming architectur…

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$3,250

531 LATITUDE LANE

OSPREY FL 34229

2,430 sqft
2 Beds
2 Baths
0.18 Acres

Annual unfurnished single-family home is available in the Willowbend community of Osprey! With some of the best lake views in Willowbend, t…

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$3,199

591 OAK BAY DRIVE

OSPREY FL 34229

2,698 sqft
3 Beds
3.5 Baths
0.28 Acres

Mint-condition, immaculate pool home nestled within an exclusive Osprey, FL community. This pristine 3-bedroom, 3.5-bath residence boasts ov…

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$2,900

260 HIDDEN BAY DRIVE UNIT 202

OSPREY FL 34229

2,109 sqft
3 Beds
2.5 Baths
1.06 Acres

Edgewater at Hidden Bay Annual Rental available now. This pristine 3-bedroom, 2.5-bath condo features a spacious lanai, offering a glimpse o…

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$2,800

758 SARABAY ROAD UNIT 5

OSPREY FL 34229

1,974 sqft
2 Beds
2 Baths
10.75 Acres

ANNUAL UNFURNISED CONDO/VILLA WITH BOAT DOCK AVAILABLE FOR LEASE IN HERON BAY! Heron Bay is a secluded waterfront community on Little Saras…

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$2,500

51 MAC EWEN DRIVE UNIT 1

OSPREY FL 34229

623 sqft
1 Beds
1 Baths
0 Acres

***AVAILABLE November 1, 2024 thru July 31, 2025*** Welcome to THE OAK community, it’s gated 24/7. private as private can be. Drenched in v…

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$2,400

291 HIDDEN BAY DRIVE UNIT 102

OSPREY FL 34229

1,597 sqft
2 Beds
2 Baths
0 Acres

This lease is available starting May 1, 2024 through October 31, 2024. This spacious first floor unit is fully furnished, with two bedrooms …

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$2,350

754 PINE RUN DRIVE UNIT 754

OSPREY FL 34229

1,529 sqft
2 Beds
2 Baths
0 Acres

Exceptional Ground-Level 2/2 Condo with Modern Features and Prime Location This rarely available ground-level 2-bedroom, 2-bathroom condo o…

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$2,300

4223 FRONTIER LANE

OSPREY FL 34229

1,219 sqft
2 Beds
2 Baths
0 Acres

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,…

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$2,245

221 GLENWOOD AVENUE

OSPREY FL 34229

1,412 sqft
3 Beds
2 Baths
0.14 Acres

Looking for your dream home? Through our seamless leasing process, this beautifully designed home is move-in ready. Our spacious layout …

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$2,200

184 EXPLORER DRIVE

OSPREY FL 34229

1,450 sqft
2 Beds
2 Baths
30.5 Acres

FULLY FURNISHED Property available for $2200 from April 15, 2025 till December 15 ,2025. Tenant pays electricity and internet. INCLUDED IN…

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$2,200

116 REVOLUTION WAY UNIT 116

OSPREY FL 34229

1,219 sqft
2 Beds
2 Baths
30.5 Acres

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 g…

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$2,200

129 WOODLAND PLACE UNIT 129

OSPREY FL 34229

1,200 sqft
2 Beds
2 Baths
4.39 Acres

One or more photo(s) has been virtually staged. AVAILABLE FURNISHED FOR $3,300. Step into the serene lifestyle at 129 Woodland Place, a char…

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$2,200

51 MACEWEN DRIVE UNIT 12

OSPREY FL 34229

623 sqft
1 Beds
1 Baths
0 Acres

For Lease at THE OAKS CLUB WINDSOR LODGE. Private sanctuary rarely available for rent at one of Sarasota’s most exclusive private country c…

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$2,200

137 NAVIGATION CIRCLE UNIT 137

OSPREY FL 34229

1,510 sqft
3 Beds
2 Baths
30.5 Acres

Apply within 24 hours of your conducted showing and once approved you will be credited your application fees towards your first full month’s…

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$1,850

1835 HIGHLAND ROAD

OSPREY FL 34229

1,066 sqft
2 Beds
2 Baths
0 Acres

Charming 2 bedroom 2 bathroom villa in GREAT location just across the street from Oscar Scherer Park in Osprey! Nice and Bright with open fl…

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$1,695

51 MACEWEN DRIVE UNIT 14

OSPREY FL 34229

595 sqft
1 Beds
1 Baths
4.53 Acres

Windsor Lodge in The Oaks – Gorgeous turnkey furnished studio apartment available now for lease! This charming 595 sq ft second-floor studio…

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