$2,500 per month
- 1 Bed
- 1 Bath
- 623 Sq Ft
- Condo for Rent
51 Mac Ewen Dr Unit 1, Osprey, FL 34229
51 Mac Ewen Dr Unit 1, Osprey, FL 34229$2,500 per month
51 Mac Ewen Dr Unit 1, Osprey, FL 34229
51 Mac Ewen Dr Unit 1, Osprey, FL 34229$5,000 per month
293 Hidden Bay Dr Unit 203, Osprey, FL 34229
293 Hidden Bay Dr Unit 203, Osprey, FL 34229$5,500 per month
557 Crane Prairie Way, Osprey, FL 34229
557 Crane Prairie Way, Osprey, FL 34229$5,000 per month
716 Sarabay Rd, Osprey, FL 34229
716 Sarabay Rd, Osprey, FL 34229$1,599 - $2,925 per month
Alton Osprey
1 - 3 Beds
4000 Destination Dr, Osprey, FL 34229
$3,695 per month
280 Hidden Bay Dr Unit 202, Osprey, FL 34229
Be the first to call this brand-new condo in Edgewater at Hidden Bay home. The kitchen showcases a sleek, modern design, complemented by solid wood cabinetry and quartz countertops, creating an ideal space for both everyday living and effortless entertaining. Appliances include a stainless-steel refrigerator, microwave, range, and dishwasher. Large windows bring in an abundance of natural light
MJ LoParco PMI SOUTHWEST FLORIDA
$1,900 per month
236 Woodland Dr, Osprey, FL 34229
Property Id: 310276AVAILABLE MAY 15 to SEP 15, 2026 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, Blackburn Point Park & Intracoastal
$3,895 per month
280 Hidden Bay Dr Unit 202, 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
MJ LoParco PMI SOUTHWEST FLORIDA
$1,850 per month
1847 Highland Rd Unit 1855 Highland Rd, Osprey, FL 34229
Spacious Duplex Villa with community pool in a great area. Close to beaches, shopping & restaurants. Right across Oscar Scherer State Park. Shoreland Park is down the street, where you can launch your kayak.
$3,895 per month
280 Hidden Bay Dr Unit 201, Osprey, FL 34229
Be the first to live in this brand-new stunning condo in the community of Edgewater at Hidden Bay! The kitchen features a sleek and modern look, equipped with stainless steel appliances, including a refrigerator, microwave, stove, and dishwasher, paired with solid wood cabinetry and elegant quartz countertops, creating an ideal space for both everyday living and entertaining. Expansive windows
MJ LoParco PMI SOUTHWEST FLORIDA
$1,850 per month
455 Pennsylvania Ave, Osprey, FL 34229
Fully Furnished 2BR/1BA Turnkey Home in Osprey, FLUnique, peaceful property with native wildflower garden, beach gear, and old-Florida charm. Located in the quiet fishing village of Osprey, this FULLY FURNISHED home includes:•Upgraded kitchen with stainless steel appliances, granite counters, and all essentials•New washer/dryer•Enclosed lanai•High-speed WiFi, water, sewer,
$6,000 per month
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
$2,995 per month
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
$4,500 per month
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
$2,195 per month
1755 Highland Rd, Osprey, FL 34229
Spacious duplex in Osprey with a bonus room! This Townhouse boasts 2 bedrooms and a bonus room downstairs that can be used as an office, playroom or even additional bedroom. The unit features a single car garage, washer and dryer hook ups, a screened in patio out front, an oversized living room. This community is located off us highway 41 south, right across the street from beautiful Oscar
Jennifer . STOCKTON REALTY ADVISORS LLC
$3,950 per month
523 Habitat Blvd, Osprey, FL 34229
PRICE REDUCED!! Ready for you to move in! Immaculate home available as an annual rental, this pristine 4-bedroom, 3-bath residence is located in Willowbend, a sought-after, Lee Wetherington–built community known for quality construction and manicured surroundings. Ideally situated with convenient access to Sarasota, Venice, and the area’s renowned beaches, the home offers tranquil lake views from
Susan Brooks COLDWELL BANKER SUNSTAR REALTY
$3,300 per month
232 Hidden Bay Dr Unit 504, Osprey, FL 34229
Annual unfurnished condominium available in Hidden Bay! Discover luxurious waterfront living in this stunning 2,000-square-foot, three-bedroom, three-bath condominium with breathtaking views of the Intracoastal Waterway. Enjoy spectacular sunsets from the expansive screened balcony, ideal for dining and relaxation. The home also comes with a private two-car garage. At the beautiful, gated
Alex Lane PREMIER SOTHEBY'S INTERNATIONAL REALTY
$1,950 per month
758 Pine Run Dr Unit 758, Osprey, FL 34229
Welcome to your beautifully updated coastal retreat! This spacious 2-story condo offers 2 bedrooms, 2.5 bathrooms, and a fresh modern design throughout. Perfectly situated in a desirable community just minutes from the beach and with easy access to Blackburn Point Road, this home combines style, comfort, and convenience. Step inside to find a newly remodeled kitchen featuring shaker-style
Jaime Barcelo GULF COAST REALTY & MANAGEMENT
$3,500 per month
2068 Preymore St, Osprey, FL 34229
Welcome home to this charming and beautifully maintained 3-bedroom, 2-bath residence located on a great community. Step inside to a spacious open floor plan featuring a generous great room, a dedicated dining area, and a large primary suite. Cathedral ceilings, pocket sliding doors, and fluid room transitions create an airy atmosphere perfect for easy living and entertaining. The bright, eat-in
Kenia Nunez PREFERRED SHORE LLC
$4,250 per month
1308 Thornapple Dr, Osprey, FL 34229
Welcome home to Willow Bend, a tropical maintenance-free community located in middle of everything southwest Florida has to offer! Gorgeous turnkey 3 bedroom& 2 Bath Furnished annual rental near Nokomis Beach. Peaceful Lake views on an oversized lot. The pretty lanai features travertine marble tile and a HEATED POOL. Many upgrades include quartz kitchen counters, wood plank oak flooring, and
Rachel Tritschler RE/MAX ALLIANCE GROUP
$2,950 per month
4429 Conchfish Ln, Osprey, FL 34229
Steps from Pine View School, Florida's #1 public school, with 2,008 sq. ft. of living space, this home features brand-new thick waterproof laminate wood flooring in all bedrooms and closets, an ocean-inspired guest bathroom, and tile throughout the main living areas for easy maintenance.Enjoy the covered lanai overlooking a private backyard, perfect for relaxing or entertaining, and take
JIA SONG Jia Song Realty
$2,500 per month
305 Bay Vista Ave, Osprey, FL 34229
Welcome to this stunning two-bedroom, two-bathroom retreat, perfectly designed for relaxation and entertainment!As you step inside, you'll notice the bright and airy open-plan living area, flooded with natural light pouring in through the large windows.But the true showstopper is the incredible backyard oasis! The expansive fenced yard beckons you to unwind and enjoy the fresh
Jennifer . STOCKTON REALTY ADVISORS LLC
$2,250 per month
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
$6,000 per month
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
$5,000 per month
260 Hidden Bay Dr Unit B-504, Osprey, FL 34229
Annual Turnkey Furnished or short term seasonal 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
Henry Rossi RENT SARASOTA
$4,200 per month
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
$6,500 per month
521 Habitat Blvd, Osprey, FL 34229
REDUCED FOR THE SEASON! Stylish 3BR Pool Home w/ Office – 10 Mins to Beach ****SEASONAL RENTAL ONLY**** 60 Day minimum stay in Peak Season at $8,900/mo plus fees; Minimum 60 Day stay in Off Season at $6,500/mo plus fees. 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
$7,000 per month
852 MacEwen Dr, Osprey, FL 34229
**CHARMING and PRIVATE, GOLF COURSE ESTATE** is located behind the Secure Gates of the highly sought after Oaks Country Club community and offers a Lovely, Golf Course View of the 17th Fairway of the interior, Heron Golf Course. This Spacious, Light and Bright, Open Floorplan of OVER 4500sf entails 3-BEDS, 3 FULL and 1 HALF BATHS, Study/Den, Bonus Room / Entertaining area with Fireplace and
Mark Lyda GENEROUS PROPERTY
$6,000 per month
5100 Jessie Harbor Dr Unit 504, Osprey, FL 34229
CLOSE TO NOKOMIS BEACH! AVAILABLE JAN/FEB/MAR/APR 2026 $6,000/MONTH. Beautiful waterfront 5th Floor condo located in Blackburn Harbor Residences with 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
Chrissie Cummings JENNETTE PROPERTIES INC
$2,995 per month
60 Bishops Court Rd Unit 114, Osprey, FL 34229
This is a rare opportunity to rent a luxury, unfurnished townhome located in the heart of the Oaks Preserve. Showcasing charming architectural details and quality finishes, this traditional-style home offers an inviting floor plan with two bedrooms, each featuring its own en-suite bath. The gracious living and dining areas flow seamlessly into a spacious and private outdoor living space that
Heidi Thompson STRINGER MANAGEMENT INC
$6,950 per month
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
$5,900 per month
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
$7,000 per month
14041 Bellagio Way Unit 316, Osprey, FL 34229
*BOOKED DEC THROUGH JUNE 2026.* MINS TO CASEY KEY & NOKOMIS BEACH! 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
$5,750 per month
293 Turquoise Ln, Osprey, FL 34229
**RARE RENTAL OPPORTUNITY (UNFURNISHED)** This STUNNING, UPDATED, MAINTENANCE-FREE Home is located in EMERALD WOODS, behind the SECURE GATES of the Distinguished OAKS PRESERVE Neighborhood. Offering 3-Beds (or 2-Beds plus Den), 2-Baths and 2-Car Garage, Premium finishes abound throughout this home and include a Chef’s Kitchen, Tray Ceilings, Crown Moldings, Beautiful Luxury Vinyl Wood Plank,
Mark Lyda GENEROUS PROPERTY
$4,500 per month
152 Navigation Cir Unit 107, Osprey, FL 34229
BACIK ON THE MARKET HIGH SEASON NOW AVAILABLE!! 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
Henry Rossi RENT SARASOTA
$2,300 per month
184 Explorer Dr Unit 184, Osprey, FL 34229
Property available for $2300 from April 1,2024 till November 30,2024. Tenant pays electricity and internet. Available for season 2024/2025 for $4500. If you are looking for the perfect Florida lifestyle, this is it. Conveniently located between Sarasota and Venice with #1 Siesta Key beach close by, this darling two-bedroom, two-bath, impeccably maintained, property move-in ready. Located on the
Claudia Dybala DALTON WADE INC
$12,000 per month
9477 Cedar Ridge Ln, Sarasota, FL 34238
RENTED FEBRUARY 2026, NOT AVAILABLE OFF-SEASON: Spacious single-family home at Stoneybrook Golf & Country Club situated in the center of the cul-de-sac offers stunning views from the amazing, seamlessly screened pool cage, creating a virtual oasis with overflow spa, underwater lighting, outdoor kitchen, and ample covered seating and dining area. Double entry doors greet you as you enter the
Victoria Reilly BERKSHIRE HATHAWAY HOMESERVICE
Osprey, FL, a census-designated community on the Gulf Coast, is known for its vibrant outdoor spaces and waterfront living. Residents can start their day kayaking through mangroves, enjoy lunch at waterfront restaurants, and spend evenings at tiki bars on Casey Key. The area around Tamiami Trail offers numerous shopping and dining options, including fresh seafood. Osprey features a variety of home styles, from condos to Mediterranean-inspired properties and waterfront villas, often within gated communities with amenities like golf courses and clubhouses. The community is home to highly rated schools such as Gulf Gate Elementary, Pine View School, and Venice High. Outdoor enthusiasts can explore Oscar Scherer State Park, with its hiking trails and opportunities for canoeing and kayaking, or visit Bay Preserve for fishing and boating. Historic Spanish Point offers a glimpse into the region's past with its prehistoric mound and citrus packing house. For nightlife, The O Bar and Spanish Point Tiki Bar are popular spots. Osprey is car-dependent but has public transportation options and is conveniently located near major employers like Sarasota Memorial Hospital and PGT Innovations. Nearby beaches, including Nokomis Beach and Siesta Key Beach, are just a short drive away, and Sarasota Bradenton International Airport is 15 miles from the community.