$10,050 per month
14021 Bellagio Way Unit 401, Osprey, FL 34229
14021 Bellagio Way Unit 401, Osprey, FL 34229
$2,200 per month
129 Woodland Place, Osprey, FL 34229
129 Woodland Place, Osprey, FL 34229
$4,500 per month
260 Hidden Bay Dr Unit 204, Osprey, FL 34229
Property Id: 18124583 bedroom 2.5 bath waterfront condo is immaculate and the perfect place for a seasonal snow bird rental, annual rental or Florida vacation (1 month minimum). Lanai that reveals a view of the bay and AMAZING SUNSETS. The unit has laundry room with washer, dryer, sink. The kitchen has granite counter tops ,fully equipped. . The master suite has a king size bed, 2 large
$4,200 per month
534 Oak Bay Dr Unit 1, Osprey, FL 34229
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 Estates in Osprey. Great access to Sarasota and Venice without having to get on I-75. Brand new interior paint and brand new ceiling fans throughout. Enjoy this great home and the private pool in your spare time as the pool care and lawn and landscaping are done
Brian ODonnell,PLLC REALTY BY DESIGN LLC
$2,000 per month
236 Woodland Dr, Osprey, FL 34229
Property Id: 310276AVAILABLE MAY 15 to SEPTEMBER 15: Light, airy home in Pine Run overlooks established native landscaping. Copious sliding doors, windows & high ceilings. Beautifully updated kitchen offer views to outdoors. A nature lovers paradise, this laid-back, quiet & desirable community is close to Casey Key, Blackburn Point Park & Intracoastal Waterway. A rare find & well-kept
$2,200 per month
137 Navigation Cir Unit 137, Osprey, FL 34229
Apply within 24 hours of your conducted showing and once approved you will be credited your application fees towards your first full month's rent! Don't miss this beautiful 3-bedroom, 2-bathroom fully furnished condo in Osprey! Complete with modern furniture, art, and fixtures that will make you feel like you're living the life of luxury. The state of the art kitchen is complete with granite
Christopher Plemenos
$3,600 per month
508 Meadow Sweet Cir, Osprey, FL 34229
Property Id: 1775840Welcome to 508 Meadow Sweet Cir, Ospery - an elegantly furnished home with brand new Room and Board pieces. This stunning residence offers a bright, open floor plan with 2 bedrooms, 2 bathrooms and a study room. Conveniently located 5 MINUTES walking distance to the prestigious Pine View school, this home is also near pristine beaches, shopping, and dinning,
$4,900 per month
14021 Bellagio Way Unit 410, Osprey, FL 34229
Enjoy STUNNING sunsets 365 days a year in this LUXURIOUS WATERFRONT CONDO in Osprey, FL. From the moment you step out of your PRIVATE ELEVATOR and into this PENTHOUSE UNIT you’ll be amazed by the SPECTACULAR VIEWS overlooking Little Sarasota Bay and the Intracoastal Waterway (ICW). This 3 bed/3.5bath, TURNKEY FURNISHED unit, has been freshly painted inside and features newer flooring, crown
Adam Waxler UKEEPCOMMISSION REAL ESTATE
$1,850 per month
1847 Highland Rd Unit 1859, Osprey, FL 34229
Beautiful Duplex Villa with community pool in a great area. Close to beaches, shopping & restaurants.
$3,250 per month
531 Latitude Ln, Osprey, FL 34229
Annual unfurnished single-family home is available in the Willowbend community of Osprey! With some of the best lake views in Willowbend, this two-bedroom plus den, two-bath home features a large primary bedroom with dual sink main bath, walk-in shower and separate soaking tub. Additional features include stainless steel kitchen appliances, gas range, pantry and laundry room with utility sink.
Alex Lane PREMIER SOTHEBY'S INTERNATIONAL
$2,845 per month
124 Main St, Osprey, FL 34229
Furnished Seasonal or Annual Rental Steps from Water Access! Available April 20, 2025 | Pet-Friendly | Lawn Care IncludedRental Options:Peak Season (Jan Mar): $5,000/monthPre/Post Season (Dec & Apr): $4,000/monthOff-Peak (May Nov): $2,495/monthAnnual Lease: $2,845/month (12-month term)LOCATION, LOCATION, LOCATION Perfect for Outdoor
$2,200 per month
184 Explorer Dr, Osprey, FL 34229
FULLY FURNISHED Property available for $2200 from April 15, 2025 till December 15 ,2025. Tenant pays electricity and internet. INCLUDED IN THE LEASE :Water, sewer. 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
Claudia Dybala DALTON WADE INC
$1,850 per month
455 Pennsylvania Ave, Osprey, FL 34229
Available mid APRIL 2025 NO PETS ~ NO SMOKING Unique property has a style all its own, including native wildflower/herbal garden and beach gear. Nestled away in the ole' Florida fishing Village of Osprey is this quaint quiet FULLY FURNISHED TURN KEY 2/1 offers:~Upgraded kitchen fully equipped with all the necessary essentials, ~Stainless steel appliances including
$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
$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
$5,500 per month
228 Lookout Point Dr, Osprey, FL 34229
SouthBay Yacht & Raquet Club one of the most desirable communities in Osprey! This beautiful well maintained home welcomes you with the circular driveway! Brand new roof in August 2024, newer a/c in 2024. Lush landscaping makes this property very inviting. Three bedroom 3 bath home with a dedicated office space is waiting for you arrival. Super large kitchen with a large island and plenty of
Angela Bailey MONARCH PROPERTY GROUP LLC
$4,800 per month
956 Scherer Way, Osprey, FL 34229
This luxuriously FULLY furnished 4 Bedroom Pool home is available starting April 15, 2025! It backs right onto the tropical preserves of Oscar Scherer Park and nestled in the sought-after community of The Woodlands at Rivendell providing the perfect blend of comfort, convenience, and natural beauty. Within the 400+ acres of lush landscapes in the neighborhood, enjoy the numerous scenic lakes,
Chantelle Edalgo KELLER WILLIAMS ON THE WATER S
$1,750 per month
1835 Highland Rd, Osprey, FL 34229
Charming 2 bedroom 2 bathroom villa in GREAT location just across the street from Oscar Scherer Park in Osprey! Nice and Bright with lovely open floor plan, ceiling fans, spacious eat-in kitchen, plenty of cabinet space, large kitchen island and washer & dryer in the unit. Tile flooring in main living space, carpet in both the bedrooms. Master Bedroom has ensuite bath with double sinks and
Roxanne Klopp JENNETTE PROPERTIES, 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
$5,000 per month
1438 Landview Ln, Osprey, FL 34229
Welcome to this bright, sunny and spacious 4 Bed, 3 Bath home with an office and a private pool — perfect for Florida living! Nestled in the highly sought-after intracoastal waterfront community of Southbay Yacht & Racquetball Club, this home offers an ideal blend of comfort, convenience, and elegance. Upon entry, you'll be greeted by 10 foot ceilings and the separate formal living and dining
Chantelle Edalgo KELLER WILLIAMS ON THE WATER S
$4,000 per month
6100 Jessie Harbor Dr Unit 202, Osprey, FL 34229
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 dining rooms. Featuring natural tones, drop ceilings, stainless steel appliances, granite countertops, a lovely entryway with ambient lighting, walk-in closets, an oversized covered patio with a gorgeous water view perfect for your morning coffee and evening
Deserea Hardy ROSSI & COMPANY INC
$2,900 per month
260 Hidden Bay Dr Unit B-202, Osprey, FL 34229
Edgewater at Hidden Bay Annual Rental available now. This pristine 3-bedroom, 2.5-bath condo features a spacious lanai, offering a glimpse of the bay over the serene preserve views—perfect for enjoying breathtaking sunsets. King murphy bed in 2nd guest room, living room wall unit and patio furniture are included. Additional details that make this unit feel more like a home than a condo include an
Terri Lindsay LINDSAY LEASING LLC
$2,300 per month
4223 Frontier Ln, Osprey, FL 34229
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, 2025. First and last month’s rent, along with a security deposit (3x $2,300), are required before move-in. A credit and background check is required, with a $50 application fee per person. Rent includes water, sewer, trash, access to amenities and
Anna Bridinger PELICAN REALTY CORP
$2,800 per month
758 Sarabay Rd Unit 5, Osprey, FL 34229
ANNUAL UNFURNISED CONDO/VILLA WITH BOAT DOCK AVAILABLE FOR LEASE IN HERON BAY! Heron Bay is a secluded waterfront community on Little Sarasota Bay with access to the Intracoastal Waterway and the Gulf. Heron Bay is an intimate and peaceful 10-acre community across from the northern section of Casey Key. The home has waterfront views along with views of the community pond with a custom
Alex Lane PREMIER SOTHEBY'S INTERNATIONAL
$3,099 per month
591 Oak Bay Dr, Osprey, FL 34229
Mint-condition, immaculate pool home nestled within an exclusive Osprey, FL community. This pristine 3-bedroom, 3.5-bath residence boasts over 2,400 sq. ft. of elegant living space, offering a perfect blend of style and comfort. Step into a spacious layout featuring a gourmet kitchen, expansive family room, and formal living and dining areas. Each bedroom is a private suite, ensuring ultimate
John Michailidis REAL PROPERTY MANAGEMENT
$1,695 per month
51 MacEwen Dr Unit 14, Osprey, FL 34229
Windsor Lodge in The Oaks - Gorgeous turnkey furnished studio apartment available now for lease! This charming 595 sq ft second-floor studio is located in the desirable Windsor Lodge within the exclusive Oaks community. It features top-of-the-line finishes, all brand new, and is accessible by both elevator and stairs. The unit includes a full kitchen equipped with a full-size refrigerator,
Terri Lindsay LINDSAY LEASING LLC
$2,200 per month
116 Revolution Way Unit 116, Osprey, FL 34229
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 going to love this stunning, 2-bedroom, 2-bathroom condo located in Osprey! Located in the gated community of Bay Street, it iclose to Sarasota's top-rated, and nationally recognized, Pine View School. This second floor unit is situated on a quiet cul-de-sac,
Christopher Plemenos
$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
$5,500 per month
385 N Point Rd Unit 503, Osprey, FL 34229
**TURN-KEY, MOVE IN READY 5TH FLOOR CONDO WITH WATERFRONT AND PRESERVE VIEWS RIVALING HIGHER FLOORS** - JUST BRING YOUR SUITCASE AND ENJOY PARADISE! Over 2200sf in the Luxury, High-Rise, Meridian Condo Complex which features 3 BEDROOMS + 3 FULL BATHS, with new furnishings throughout, behind the Secure Gates of the highly sought after OAKS-PRESERVE, COUNTRY CLUB neighborhood. This light, bright
Mark Lyda GENEROUS PROPERTY
$2,350 per month
754 Pine Run Dr Unit 754, Osprey, FL 34229
Exceptional Ground-Level 2/2 Condo with Modern Features and Prime LocationThis rarely available ground-level 2-bedroom, 2-bathroom condo offers a unique blend of space, style, and an unbeatable location within the community. Its thoughtfully designed floorplan features a central open-air atrium, accessible through 8-foot glass doors on three sides, creating a seamless connection to nature.
Sasha Volosevych CALL IT CLOSED INTL REALTY
$2,200 per month
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
$2,245 per month
221 Glenwood Ave, Osprey, FL 34229
Looking for your dream home? Through our seamless leasing process, this beautifully designed home is move-in ready. Our spacious layout is perfect for comfortable living that you can enjoy with your pets too; we’re proud to be pet friendly. Our homes are built using high-quality, eco-friendly materials with neutral paint colors, updated fixtures, and energy-efficient appliances. Enjoy the
Nico Silva Vanegas MAIN STREET RENEWAL LLC
$7,000 per month
543 Pine Ranch Rd E, Osprey, FL 34229
An Ascendia Property! **Available beginning January 15, 2025, for a 90-night minimum stay or longer. The rental rate in the listing does not include additional fees and taxes. The rental rate will be discounted for a long-term lease (6-12 months). Please note, a long-term lease of 6-12 months DOES NOT include utilities such as electric, water, sewer or internet.** This 3-bedroom, 2-bathroom
Beth Dilley ASCENDIA REAL ESTATE
$8,000 per month
14041 Bellagio Way Unit 316, Osprey, FL 34229
NOW AVAILABLE FOR APRIL AND OFF-SEASON MONTHS 2025 AND JAN-APRIL 2026! 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
$2,400 per month
291 Hidden Bay Dr Unit 102, Osprey, FL 34229
This lease is available starting MAY 2025. This spacious first floor unit is fully furnished, with two bedrooms and two bathrooms. The view overlooks a tranquil pond. Hidden Bay condominium is a 12-acre, gated community on Sarasota Bay in Osprey with beautiful views of Casey Key.The community includes a clubhouse that features a fully-stocked library, an entertainment/media room, kitchen,
Anthony DeLuca AUDREY RAIN RENTALS, 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
$21,000 per month
854 MacEwen Dr, Osprey, FL 34229
**RENTAL OPPORTUNITY (unfurnished)** SPACIOUS, LUXURIOUS and BEAUTIFULLY RENOVATED, GOLF COURSE ESTATE situated behind the SECURE GATES of The Oaks Country Club Community, Boasting OVER 9,000sf and located on a prominent, private cul de sac lot of Over 3/4 Acres. Expansive room abounds in this LIGHT and BRIGHT Open Floorplan consisting of 4 Beds + 4/2 Baths + Office/Library + Home Theater + Game
Mark Lyda GENEROUS PROPERTY
$2,500 per month
51 Mac Ewen Dr Unit 1, Osprey, FL 34229
***AVAILABLE February 1, 2025 thru July 31, 2025*** 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
$4,500 per month
152 Navigation Cir Unit 107, Osprey, FL 34229
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 solid wooden cabinetry, topped with slab granite
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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