$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
$4,500 per month
1308 Thornapple Dr, Osprey, FL 34229
1308 Thornapple Dr, Osprey, FL 34229
$6,000 per month
716 Sarabay Rd, Osprey, FL 34229
716 Sarabay Rd, Osprey, FL 34229
$3,500 per month
5100 Jessie Harbor Dr Unit 602, Osprey, FL 34229
5100 Jessie Harbor Dr Unit 602, 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
$1,599 - $3,025 per month
Alton Osprey
1 - 3 Beds
4000 Destination Dr, Osprey, FL 34229
$4,500 per month
4243 Expedition Way Unit 4243, Osprey, FL 34229
AVAILABLE THIS SEASON JANURY AND FEBRUARY 2026.***No smoking,no pets permitted. Due at signing - total rent,security deposit,cleaning fee of $250,HOA fee of $150 and sales tax applicable. Heated swimming pool,small club house,gym and cabana across the street from this condo. Positioned perfectly in the highly coveted community of Bay Street Village,this second-story turnkey condo has two bedrooms
Svatava Jurinova BRIGHT REALTY
$3,450 per month
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,
$3,500 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
$3,450 per month
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
$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
$3,345 per month
692 Stillwater Ct, Osprey, FL 34229
Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $3524.90. That covers your base rent, $3345.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Pool
$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
$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
$1,500 per month
137 Woodland Place, Osprey, FL 34229
Pine Run 2-bedroom, 2-bath condo West of the Trail, offered for annual lease. Unit is located on 2nd floor with stairs. Tucked among mature trees, the home offers a peaceful retreat with a private deck and three balconies that let you enjoy the surrounding natural setting from multiple vantage points. Inside, you’ll find spacious rooms filled with natural light, high ceilings, soft colors, NEW
Terri Lindsay LINDSAY LEASING LLC
$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.
$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
$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,
$2,900 per month
4417 Conchfish Ln, Osprey, FL 34229
This one-story home offers 1861 sqft living space, with four bedrooms, two bathrooms, and a two-car garage. Open-concept floor plan. Welcome to 4417 Conchfish Ln, a beautifully maintained 4-bedroom, 2-bathroom home located in the highly sought-after community of Osprey, FL just steps from the top-rated Pine View School. This spacious home features an open kitchen layout with a brand-new
JIA SONG Jia Song Realty
$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
$2,400 per month
163 Pennsylvania Ave, Osprey, FL 34229
Welcome to 163 Pennsylvania Avenue, nestled in the quaint community of Osprey, FL. This charming 3-bedroom, 2-bathroom home, built in 2018, offers a smart blend of style and energy efficiency. Spanning 1,346 square feet, the open floor plan showcases a modern grey color palette, creating an inviting ambiance throughout. Step into the kitchen, where sleek stainless steel appliances and light wood
Beth Harris COMPASS FLORIDA LLC
$2,600 per month
554 Pine Ranch East Rd, Osprey, FL 34229
ANNUAL/ GENTLY FURNISHED 4 BED/2.5 BATH. The home is gently furnished which will work perfectly for the family who has some furniture already.Available November1st - 9 month minimum - come stay here while your build your home.Master has a king bed with ensuite bathroom.- walk in shower, garden tub. Guest room has twin beds, 2nd guest room has a built in office and a Murphy bed. 4th
Annabelle Newland STOCKTON REALTY ADVISORS LLC
$3,550 per month
603 Pine Ranch East Rd, Osprey, FL 34229
*AVAILABLE NOVEMBER 15, 2025 — PREVIEW BY APPOINTMENT ONLY*Currently occupied — showings available by appointment only.This beautifully updated 3-bedroom, 2-bathroom home, features a desirable split floor plan and a spacious 2-car garage. Offered unfurnished, with pool and yard maintenance included in the rent.HIGHLIGHTS:Open-concept layout designed for comfort, entertaining,
Marina Yanovskiy ALL SEASONS REALTY LLC
$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
$3,800 per month
451 N Shore Dr, Osprey, FL 34229
Welcome to your new spacious home in the beautiful waterfront neighborhood of Sorrento Shores. As you approach this three bedroom, three bath POOL house you will notice the quiet charm that this highly sought-after neighborhood provides. The streets are lined with tropical fruit trees, palms, and plants that create a tranquil atmosphere. The open concept, split floor plan, and wonderfully updated
Justin Ulrich ZACHOS REALTY & DESIGN GROUP
$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
$2,395 per month
1817 Highland Rd, Osprey, FL 34229
Lovely 2 bed/2 bth well maintained townhouse with a 2 car garage Set in a private enclave in the desirable West of Trail Osprey location with a Community pool. Close to beaches, restaurants and shopping.
Steven Koleno BEYCOME OF FLORIDA LLC
$2,000 per month
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 $2,000 a month. Application fee for each adult $50, association application fee of $50(10-day association approval process), $ 2,000 security deposit, and $100 administrative fee. 1 pet allowed (small to
AnaElizabeth Fernandez A & R PROPERTY MGMT, LLC
$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
$3,000 per month
1363 New Forest Ln, Osprey, FL 34229
Welcome to The Woodlands At Rivendell! This beautiful home is on a large corner lot in the Patio Section of the Woodlands. It has TWO Bedrooms + a DEN, Great Room, double tray ceilings w/ crown molding. The den has double pocket doors! The kitchen is central in the house for entertaining, with plenty of storage, pull-out shelves, and 2 pantries! The Lanai has glimmering water views! Some nice
Pamela Strom RE/MAX PALM
$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
$4,000 per month
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
$2,000 per month
234 Patterson Ave, Osprey, FL 34229
Welcome to 234 Patterson Ave, a charming single-family home nestled in the heart of Osprey, Florida. This amazingly located residence offers 3 bedrooms, 1 and a half bathrooms, and 1,173 square feet of comfortable living space. The open-concept layout features vaulted ceilings and a NEW modern kitchen equipped with granite countertops, soft close drawers, a center island, and new Frigidaire
Sean Seward KELLER WILLIAMS ISLAND LIFE REAL ESTATE
$7,000 per month
Unlisted Address
NOW AVAILABLE FOR SEASONAL RENTAL – READY FOR IMMEDIATE OCCUPANCY AND FULLY FURNISHED!Modern 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
Jim Xarras, Jr BERKSHIRE HATHAWAY HOMESERVICE
$7,500 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
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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.
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