$1,599 - $3,025 per month
Alton Osprey
1 - 3 Beds
4000 Destination Dr, Osprey, FL 34229
$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
$4,500 per month
1308 Thornapple Dr, Osprey, FL 34229
1308 Thornapple Dr, Osprey, FL 34229
$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
$6,000 per month
716 Sarabay Rd, Osprey, FL 34229
716 Sarabay Rd, Osprey, FL 34229
$2,950 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
$2,500 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
$3,000 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
$3,200 per month
9528 Knightsbridge Cir, Sarasota, FL 34238
Beautiful 4BR/3BA home in the desirable Stoneybrook Estates at Palmer Ranch. Features an open floor plan, vaulted ceilings, and a spacious screened lanai. Primary suite includes walk-in closet and en-suite bath with soaking tub. Close to Siesta Key, Legacy Trail, shopping, dining, and top-rated schools.
Danny Shi DALTON WADE INC
$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 SARASOTA
$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
$3,500 per month
5100 Jessie Harbor Dr Unit 602, Osprey, FL 34229
5100 Jessie Harbor Dr Unit 602, Osprey, FL 34229
$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
$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
$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,
$7,000 per month
5100 Jessie Harbor Dr Unit 504, Osprey, FL 34229
CLOSE TO NOKOMIS BEACH! AVAILABLE DECEMBER 2025 $5,000 INCL UTILITIES, AND JAN/FEB/MAR/APR 2026 $7,000/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
Chrissie Cummings JENNETTE PROPERTIES INC
$3,695 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
$7,200 per month
101 Woodland Place, Osprey, FL 34229
Now AVAILABLE FOR LEASE WINTER SEASON 2026 at PINE RUN Condominiums in Osprey, Florida! 3BR/2.5BA Location! Location! West of the Trail, Pine Run is a waterfront tropical oasis of 20+ acres of wooded Florida landscape. This spacious corner unit townhouse is well FURNISHED. Beautifully decorated and full of light and color with vaulted ceiling in the main Great Room. Custom designed Kitchen is
Patrice Ivan WAGNER REALTY
$1,800 per month
1847 Highland Rd Unit 1869 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.
$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
$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,
$2,995 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
$7,000 per month
14041 Bellagio Way Unit 316, Osprey, FL 34229
MINS TO CASEY KEY & NOKOMIS BEACH! NOW AVAILABLE DEC 2025 $6,000 AND JAN-APRIL 2026 $7,000! 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
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
$2,500 per month
51 Mac Ewen Dr Unit 1, Osprey, FL 34229
51 Mac Ewen Dr Unit 1, Osprey, FL 34229
$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
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