$6,000 Per Month
- 3 Beds
- 2 Baths
- 1,799 Sq Ft
- Condo for Rent
14041 Bellagio Way Unit 214, Osprey, FL 34229
14041 Bellagio Way Unit 214, Osprey, FL 34229$6,000 Per Month
14041 Bellagio Way Unit 214, Osprey, FL 34229
14041 Bellagio Way Unit 214, Osprey, FL 34229$5,157
Total Monthly Price
111 Tina Island Dr Unit SI ID1591462P, Osprey, FL 34229
The advertised rate of $5,157/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 28, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
$2,500 Per Month
51 Mac Ewen Dr Unit 1, Osprey, FL 34229
51 Mac Ewen Dr Unit 1, Osprey, FL 34229$5,157
Total Monthly Price
111 Tina Island Dr Unit SI ID1591462P, Osprey, FL 34229
The advertised rate of $5,157/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 28, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be
$5,000 Per Month
293 Hidden Bay Dr Unit 203, Osprey, FL 34229
293 Hidden Bay Dr Unit 203, Osprey, FL 34229$1,900 Per Month
236 Woodland Dr, Osprey, FL 34229
Property Id: 310276 IN 2026, AVAILABLE SEP 10 to OCT 10. IN 2027, AVAILABLE BEGINNING MAY 15. 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,
$775 Per Month
8 Bay Ave, Osprey, FL 34229
Property Id: 1524644 Unfurnished Room with private bath for rent, for 1 person, utilities included. No pets, no alcohol drinks, no drugs, no visitors allowed inside the house. House rules to follow, NO EXCEPTIONS Landlord requires 1st, last month rent plus $455 security deposit due at the sign of the lease. Information to verify employment, references from previous landlord and
$1,900 Per Month
236 Woodland Dr, Osprey, FL 34229
Property Id: 310276 IN 2026, AVAILABLE SEP 10 to OCT 10. IN 2027, AVAILABLE BEGINNING MAY 15. 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,
$1,600 Per Month
51 Mac Ewen Dr Unit 8, Osprey, FL 34229
Come lounge around in one of the finest golf communities where everyday can feel like a vacation. This elegant loft has a lovely view of the lake with the rolling green right behind it. Enjoy endless summer days basking in the sun at the pool which is only steps away! This loft is equipped with granite countertops, a full size washer and dryer, stainless steel appliances, fixtures and fittings, a
Deserea Hardy ROSSI & COMPANY INC
$4,800 Per Month
956 Scherer Way, Osprey, FL 34229
This FULLY FURNISHED 4 bedroom, 3 bathroom rental home is available for an ANNUAL LEASE in a quiet HOA community with a PRIVATE HEATED POOL, HOT TUB, 3-CAR GARAGE, and great access to everything Sarasota/Osprey has to offer!- This home has the perfect Florida living setup with a backyard overlooking natural Florida views that you can enjoy from your SCREENED-IN LANAI.- Inside, enjoy
$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
$13,000 Per Month
854 MacEwen Dr, Osprey, FL 34229
Set on a quiet private cul-de-sac in The Oaks, this beautifully revitalized estate embodies the elegance of refined Florida living. Bright, open interiors and thoughtful updates create a welcoming flow from the chefs kitchen through the main living areas and out to the lanai, where sweeping golf course views frame the heated pool, spa, and fully equipped outdoor kitchen perfect for year-round
$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
$2,599 Per Month
2090 S Tamiami Trail Unit 303, Osprey, FL 34229
Stunningly updated and professionally curated and designed 2 Bed 2 Bath condominium with over 1500 sq ft, sparkling pool view, tennis courts, and ample open space on Blackburn Bay. Oversized Master EnSuite with King sized bed, walk in closet, and private access to enlarged screened patio. Dedicated garage parking space in building with direct access to elevators. Enjoy exquisite finishes in this
$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
$2,599 Per Month
2090 S Tamiami Trail Unit 303, Osprey, FL 34229
Stunningly updated and professionally curated and designed 2 Bed 2 Bath condominium with over 1500 sq ft, sparkling pool view, tennis courts, and ample open space on Blackburn Bay. Oversized Master EnSuite with King sized bed, walk in closet, and private access to enlarged screened patio. Dedicated garage parking space in building with direct access to elevators. Enjoy exquisite finishes in this
$6,950 Per Month
101 Woodland Place, Osprey, FL 34229
Now AVAILABLE FOR LEASE PINE RUN Condominiums in OSPREY, Florida! 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 light and color with vaulted ceiling in the main Great Room. Custom designed
Patrice Ivan WAGNER REALTY
$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
Cody Smith RENT SARASOTA
$4,395 Per Month
260 Hidden Bay Dr Unit B 401, Osprey, FL 34229
Flexible Lease Terms Available 6-12 monthsExperience the best of Florida’s Gulf Coast from this spacious, fully furnished 3-bedroom, 2.5-bath waterfront condominium overlooking beautiful Little Sarasota Bay. Designed for comfort, convenience, and coastal living, this inviting residence features a private den/home office, in-unit laundry, and generous living areas ideal for relaxing or
Jaime Barcelo GULF COAST REALTY & MANAGEMENT
$2,250 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
$3,295 Per Month
4401 Conchfish Ln, Osprey, FL 34229
Welcome to this beautifully maintained 4-bedroom, 3-bathroom home with a 2-car garage, ideally situated on a desirable corner lot in The Palms of Casey Key, just a short walk to the nationally ranked Pine View School. Built in 2018, this residence offers thoughtful upgrades throughout, including updated flooring in every room, custom window treatments, and elegant light fixtures. The open-concept
Klara Mrcela COMPASS FLORIDA, LLC
$5,500 Per Month
6100 Jessie Harbor Dr Unit 202, Osprey, FL 34229
Experience elevated coastal living in this beautifully furnished waterfront residence, available for seasonal (DEC-APR - $8500) or long-term rental (off-season rental $5500 MAY-NOV) in the exclusive Blackburn Harbor community. Located on the second floor with elevator access, this spacious 3-bedroom plus den, 3-bath condominium offers over 3,700 square feet of elegant living space with
Angelic Tassos CORCORAN DWELLINGS REALTY
$2,150 Per Month
184 Explorer Dr, Osprey, FL 34229
The unit is available for rent from June 15 till December 15, 2026. The minimum rental period is 3 month. The monthly rent is $2150. The tenant is responsible for electricity and internet costs. 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
$3,500 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 Rivas PREFERRED SHORE LLC
$2,200 Per Month
4219 Frontier Ln Unit 105, Osprey, FL 34229
Welcome to this immaculate 2-bedroom, 2-bathroom condo with a private 1-car garage, offering beautiful pond views from every window and a peaceful, resort-style setting. Ideally located just minutes from some of Florida’s most beautiful Gulf Coast beaches: 10 minutes to Nokomis Beach and Casey Key15 minutes to the world-famous Siesta Key BeachOutdoor enthusiasts will love the easy access
Tim Weller EXIT KING REALTY
$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
$5,900 Per Month
521 Habitat Blvd, Osprey, FL 34229
Stylish 3BR Pool Home w/ Office – 10 Mins to Beach -- 90 Day minimum stay, Peak Season at $7,900/mo plus taxes and fees; Off Season at $5,900/mo plus taxes and fees. NOTE: Jan, Feb and March 2027 are Not Available. 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
$3,800 Per Month
534 Oak Bay Dr Unit 1, Osprey, FL 34229
AVAILABLE AUGUST 25, 2026 AS UNFURNISHED RENTAL. 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. New interior paint and new ceiling fans throughout. Enjoy this great home and the private pool in your spare time as the pool care and lawn and landscaping
Brian ODonnell,PLLC REALTY BY DESIGN LLC
$7,500 Per Month
5100 Jessie Harbor Dr Unit 504, Osprey, FL 34229
CLOSE TO NOKOMIS BEACH! BOOKED JAN/FEB/MAR 2027. AVAILABLE APR 2027 $7,000/MONTH. Beautiful direct 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
Chrissie Cummings JENNETTE PROPERTIES INC