$7,500 per month
- 5 Beds
- 4.5 Baths
- 3,981 Sq Ft
- House for Rent
1216 Flying Bridge Ln, Osprey, FL 34229
1216 Flying Bridge Ln, Osprey, FL 34229$7,500 per month
1216 Flying Bridge Ln, Osprey, FL 34229
1216 Flying Bridge Ln, Osprey, FL 34229$3,950 per month
5100 Jessie Harbor Dr Unit 602, Osprey, FL 34229
5100 Jessie Harbor Dr Unit 602, Osprey, FL 34229$12,000 per month
600 Eagle Watch Ln, Osprey, FL 34229
600 Eagle Watch Ln, Osprey, FL 34229$2,025 - $3,495 per month
Alton Osprey
1-3 Beds
174 E Bay St, Osprey, FL 34229
$2,695 per month
607 Oak River Ct, Osprey, FL 34229
Don't miss out on this 3 bed/2bath with 2 car garage. Immaculate home. Light and bright.Great floor plan includes a formal living/dining room and a separate family room over the kitchen. Laundry room is inside with washer/dryer. Kitchen is fabulous with newer stainless steel appliances, and the whole house is tastefully painted. Both bathrooms have had a refresh recently and feature LED
Alex Corona PMI SOUTHWEST FLORIDA
$3,020 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
$4,200 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
$2,570 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. Whether you're here for sunshine,
$9,500 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
$1,900 per month
236 Woodland Dr, Osprey, FL 34229
Property Id: 310276AVAILABLE AUG 1 to SEP 30 / $100 discount for term of 2 or more months: 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,
$800 per month
570 Blackburn Point Rd Unit 25, Osprey, FL 34229
Welcome to The Dry Slips at Osprey Harbor Village. Onsite you'll enjoy access to the marina store with food, drinks, ice, and bait. Conveniently available are pump out, ethanol free fuel, work racks, and fish cleaning stations as well. This indoor slip is high and dry hurricane rated and secured Unit 25 of Longboat Row is 14.6' tall, 10.5' wide and 28' long on the bottom row for easy access. The
EJ Stukenborg KELLER WILLIAMS ON THE WATER S
$1,850 per month
455 Pennsylvania Ave, Osprey, FL 34229
Available Now – 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,
$3,750 per month
650 Crane Prairie Way, Osprey, FL 34229
Now Available – Lease Option or Lease Purchase Opportunity in Willowbend!Live large in this 3,183 sq ft Lee Wetherington-built pool home with preserve and pond views. Flexible lease terms now offered:Lease Option with option fee - OR - Lease Purchase with buyer commitment and possible rent creditSpacious layout with 4 true bedrooms on the main floor plus an upstairs bonus
Cheri Castro KELLER WILLIAMS ON THE WATER
$1,750 per month
1847 Highland Rd Unit 1865 Shoreland, 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.
$4,200 per month
510 Latitude Ln, Osprey, FL 34229
Custom, Lee Wetherington home with a private heated pool in the sought after, maintenance free community of Willow Bend. Located close to Pineview School, Legacy Trail, Oscar Scherer Park and our world-famous beaches. This home features volume tray ceilings with lots of natural light, natural gas cooking, crown molding, built in features and indoor laundry. The large master suite features double
Marisa Marino BRIGHT 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
$2,195 per month
291 Hidden Bay Dr Unit 201, Osprey, FL 34229
Spacious 2nd-floor end-unit with one car garage (22x11) provides nearly 1,600 sq. ft. and stunning lake and courtyard views. This updated 2BR + den/office (can be 3rd BR) features the largest floor plan in the building, no carpet (tile & laminate throughout), an open-concept layout, and tons of natural light. Kitchen has granite counters, stainless appliances, and upgraded cabinets. Master suite
Terri Lindsay LINDSAY LEASING LLC
$4,250 per month
280 Hidden Bay Dr Unit 303, Osprey, FL 34229
One or more photo(s) has been virtually staged. Annual Rental. This newly constructed 3rd floor condo is available for immediate occupancy at Hidden Bay in Osprey. This gorgeous 3 Bedroom PLUS a Home Office is light, bright and very spacious! Wood and tile floors throughout- NO CARPETING! The Primary suite features 2 walk-in closets, sliding glass doors leading to the lanai and an ensuite with a
Jaime Barcelo GULF COAST REALTY & MANAGEMENT
$2,299 per month
4248 Expedition Way Unit 4248, 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! Welcome home to this beautiful 3-bedroom, 2-bathroom condo in the sought after gated community of Bay Street Village! Neutral paint, ceiling fans throughout, tile flooring in the main living areas and carpet in the bedrooms make decorating a breeze!
Colbey Mason RYNTAL
$2,350 per month
4209 Expedition Way Unit 102, Osprey, FL 34229
This lovely 3 bedroom, 2 1⁄2 bath townhome. This unfurnished unit has (2) Separate Single car garages-Storage and Parking. Located Close to Beaches, Shopping and Dining. Like New, Freshly Painted, Built in 2016. The kitchen has granite, nice cabinets, and stainless appliances. Beautiful Water View w/ fountain! Large open kitchen, dining and living room. All bedrooms are upstairs and are great
Tim Weller EXIT KING REALTY
$4,000 per month
14041 Bellagio Way Unit 214, Osprey, FL 34229
One or more photo(s) has been virtually staged. ANNUAL or Short Term (3 Months Minimum) CONDO/VILLA AVAILABLE FOR LEASE with Option to Purchase! Short Term Rent is $6000 /month. Annual Lease is $4000/Month. Villas at the Harbor Village boasts luxurious amenities and waterfront living on Little Sarasota Bay with access to the Intracoastal Waterway and the Gulf, just across from Casey Key. Enjoy
Veronica Lee FINE PROPERTIES
$7,000 per month
5100 Jessie Harbor Dr Unit 504, Osprey, FL 34229
This beautiful 5th Floor condo located in Blackburn Harbor Residences is now available for Season 2026! There are 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 2 bathrooms. As you step inside the
Chrissie Cummings JENNETTE PROPERTIES INC
$6,000 per month
14041 Bellagio Way Unit 218, Osprey, FL 34229
If you're looking for a place that offers a rent to own opportunity, now is your chance! Welcome to your coastal sanctuary in the gated community of Villas at Osprey Harbor Village. Located just minutes from the newly reopened Midnight Pass beach, and walking distance to Casey Key fish house. This impeccably remodeled 3 bedroom, 2 bathroom residence offers an elegant, light-filled living space
Kelli Eggen COLDWELL BANKER REALTY
$2,400 per month
4214 Frontier Ln Unit 102, 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! Welcome to this lovely, fully furnished, 2-bedroom, 2-bathroom condo in Osprey! This condo is ready to welcome your entire family, complete with bright and airy spaces, spacious bedrooms, and a coastal vibe perfect for the ideal Florida lifestyle! Not
Colbey Mason RYNTAL
$2,200 per month
184 Explorer Dr, Osprey, FL 34229
The unit is available for rent from August 1 ,2025.The minimum rental period is 2months. The monthly rent is $2200. The tenant is responsible for electricity and internet costs. NO PETS! 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
Claudia Dybala DALTON WADE 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
$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
$7,900 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
$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 NOVEMBER 2025 THRU JANUARY 2026*** 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
$5,000 per month
293 Hidden Bay Dr Unit 203, Osprey, FL 34229
RENTED JANUARY TILL MARCH 2026. TURNKEY FURNISHED RENTAL! GATED, WATER VIEWS! WATERFRONT COMMUNITY IN OSPREY! 2 Bedroom 2 bath plus den. Den has French doors. Lots of light from this second-floor end unit condo. Front door has disappearing screen for fresh Air. TURNKEY FURNISHED. Completely renovated. NO CARPET. Porcelain tile thru out. Granite counters and high ceilings. Front loading washer &
Alba Lange WAGNER REALTY
$6,500 per month
1899 Vamo Way, Sarasota, FL 34231
The property can be rented for a short or long term. Property AVAILABLE from SEPTEMBER 1,2025. Rent per month as follows: $6500 for September 1- October 31,2025 and $10,500 for November 1,2025 -April 30, 2026.***Please ask the Listing Agent for more details***Beautifully crafted and maintained, this remarkable Sarasota custom-built home! FULLY FURNISHED by MM Modern Miami, there’s
Claudia Dybala DALTON WADE INC
$4,500 per month
5305 Bartolomeo St, Sarasota, FL 34238
Annual lease (no short term) turn-key furnished 3 bedroom two bath w/private heated pool and spa. Life-style community with all the resort amenities and activities: Clubhouse, pickleball, tennis courts, fitness gym, exercise rooms, day spa, Bahama Bar, resort pool, resistance pool, pool side spa, trails, & direct access to the Legacy Bike Trail.Primary suite is a peaceful retreat with a tray
Leonard Giarrano RE/MAX ALLIANCE GROUP