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BAY STREET VILLAGE - A4695211 - 4212 EXPEDITION WAY, OSPREY, FL 34229 1 Day on yellowkey
$2,390 | Townhouse 3 bedrooms, 2.0 bathroom, 1 car garage
The property is available for rent starting JULY 1,2026. IMMACULATE, FURNISHED , POOL AND PALM TREES VIEW** Welcome to life in paradise! Here's your best opportunity yet! TURN-KEY FURNISHED "Ibis" floor plan at desirable Bay Street Village!This charming Florida condo is perfect for anyone seeking a full-time residence. This 3 Bedroom/2 Bathroom, modern, second story condo is impressive! The OPEN CONCEPT offers a spacious feel, yet the split bedroom design allows for privacy when your guests are visiting. Quality features include designer kitchen with great quality cabinets, granite counters, IMPACT windows, tile roofs, paver driveways, and solid BLOCK construction. Picture yourself at the RESORT STYLE POOL... or Relaxing on your SCREENED LANAI overlooking the pool and palm trees. Water and Sewer included in the very reasonable monthly rent. Bay Street Village is a maintenance-free gated community that includes a resort-style heated pool, fitness room, and club room. Close to shopping, dining, beaches, and and A+ Pine View School, a Niche, National, Top Ranked.! Easy access to 41 and I-75. Bay Street Village is also a Pet friendly community and is located directly across from the NEW Bay Street Dog Park and Bay Street Park/Playground. Schedule your showing today!!!
This listing is courtesy of: DALTON WADE INC
BAY ACRES - RESUB - N6144418 - 341 BAYSHORE DR, OSPREY, FL 34229 10 Days on yellowkey
$3,200 | Single Family Home 3 bedrooms, 2.0 bathroom, 2 car garage
This fully renovated classic-style residence blends Old Florida charm with modern finishes and spacious living areas throughout. Featuring 3 Bedrooms and 2 Bathrooms, the home offers a functional layout designed for comfort and privacy. Conveniently located near Blackburn Boat Ramp with plenty of on-site parking. Just under 1900 sqft of living space, the kitchen flows seamlessly into the dining and living areas, creating an ideal space for everyday living and entertaining. A rear door leads to a fenced yard with ample space for boat parking. Two Guest Bedrooms are located on the first floor and are nicely situated to the Guest Bathroom that features a walk-in shower. The expansive Primary Suite occupies the second floor that features a walk-in closet and access to the spacious balcony. The private Master Bathroom is equipped a large soaking tub, dual vanities, and a walk-in shower. Additional features include a private 2-car garage, generous storage space, and a peaceful patio area perfect for relaxing outdoors. Ideally located just 15 minutes from Siesta Beach, Nokomis Beach, and Historic Downtown Venice, residents enjoy convenient access to shopping, dining, entertainment, and some of the Gulf Coast’s most desirable beaches. This property offers a unique opportunity to enjoy Florida living in a highly sought-after and private community. ~Included in rent: Lawn Care. ~Pets: a Small Dog under 35lbs is considered.
This listing is courtesy of: COMPASS PROPERTY MANAGEMENT LLC
EDGEWATER/HIDDEN BAY BLDG B PH - A4693277 - 260 HIDDEN BAY DR #401, OSPREY, FL 34229 19 Days on yellowkey
$4,850 | Condo 3 bedrooms, 2.5 bathroom, 2 car garage
6 Month Minimum Lease Available. Experience the beauty of Florida’s Gulf Coast from this spacious, fully furnished 3-bedroom, 2.5-bath waterfront condominium overlooking Little Sarasota Bay. Thoughtfully designed for both comfort and flexibility, the home includes a private den or home office, convenient in-unit laundry, and generous living spaces perfect for relaxing or entertaining. Nestled within Hidden Bay, a private 14-acre waterfront community, residents enjoy a peaceful coastal setting directly on the bay—just across from the pristine beaches of Casey Key and the Gulf of Mexico. At the heart of the community is a beautifully renovated clubhouse featuring elegant gathering spaces, a catering kitchen, fitness center, reading library, and dining room. Outside, unwind by the heated pool and spa, gather with friends at the Tiki hut grilling area, or relax beside the tranquil pond with cascading water features. For recreation and adventure, Hidden Bay offers tennis and pickleball courts, a kayak launch, pet park, and car wash station. A scenic elevated boardwalk winds through lush mangrove preserves, leading to a long fishing pier where residents can enjoy peaceful water views, cast a line, or simply take in the area’s breathtaking sunsets. Hidden Bay offers more than a home—it offers a true waterfront lifestyle. Rental rate includes basic cable, internet (expanded services available), water, trash, and pest control. Call for a private tour today. 6-12 month lease period
This listing is courtesy of: GULF COAST REALTY & MANAGEMENT
BAY STREET VILLAGE - N6144275 - 4219 FRONTIER WAY #105, OSPREY, FL 34229 20 Days on yellowkey
$2,400 | Condo 2 bedrooms, 2.0 bathroom, 1 car garage
2 bedrooms. 2 baths, 1 car garage. Condo Unfurnished. Available July 1, 2026. Tenant Occupied until June 22, 2026. 2nd floor. Close to Beaches! Located 10 minutes to Nokomis Beach/Casey Key Beach or 15 minutes to Siesta Key Beach. Minutes by bike to Legacy Trail and Casey Key. Water, Sewer & trash included in the rent. This maintenance free community includes gated entry, resort style community pool, cabana, fitness room, and club room. The construction is concrete block, impact resistant glass windows, tile roof, and paver driveway. The community is conveniently located to Sarasota, Venice, Casey Key, the beaches, dining, shopping, the Legacy Trail, Oscar Scherer Park, and A+ Pineview School! Beautiful unit! $2400 per month 12 month minimum. Tenant Occupied until June 22, 2026.
This listing is courtesy of: EXIT KING REALTY
- A4692034 - 254 BURNEY RD, OSPREY, FL 34229 29 Days on yellowkey
$4,500 | Single Family Home 5 bedrooms, 4.5 bathroom, 2 car garage
Brand-new construction single-family home available for rent in a prime Osprey location! This spacious residence offers 5 bedrooms + 2 dedicated office/study rooms + 4.5 bathrooms + a 2-car garage, also All windows are impact-rated, eliminating the hassle of putting up hurricane shutters while providing extra security, energy efficiency, and storm protection. and ideal for large families or those working from home. Enjoy an open-concept layout with a modern kitchen, high-end finishes, and abundant natural light throughout. The flexible floor plan provides ample space for living, working, and entertaining. Conveniently located just minutes from Pine View School, shopping, dining, and the beautiful Gulf beaches including Siesta Key Beach. Easy access to U.S. Route 41 and I-75 makes commuting simple. Move-in ready. Don’t miss this exceptional rental opportunity!
This listing is courtesy of: FLORIDA MORNING REALTY LLC
- A4692030 - 246 BURNEY RD, OSPREY, FL 34229 29 Days on yellowkey
PINE RUN I - A4691525 - 354 PINE RUN DR, OSPREY, FL 34229 33 Days on yellowkey
$1,695 | Condo 2 bedrooms, 2.0 bathroom
This is an unfurnished 2 bedroom, 2 bathroom condo located in the Pine Run community in Osprey! This upper-level unit features vaulted ceilings, a mix of hardwood and tile flooring, and a distinctive courtyard-style layout that brings the outdoors inside. The kitchen features granite countertops, maple shaker-style cabinets with glass-front uppers, stainless steel appliances, a tile backsplash, and a peninsula with additional counter space. An eat-in area sits adjacent to a sliding glass door that opens to the private courtyard. The living room has wood-grain flooring, vaulted ceilings, and sliding glass doors opening to a balcony with treetop views. The dining area is open to the living room and shares the same vaulted ceiling. A hallway lined with sliding glass doors overlooks the private courtyard, filling the interior with natural light. The master bedroom has vaulted ceilings, sliding glass doors to a balcony, and a walk-in closet with built-in shelving. The master bathroom has a single vanity with a granite countertop and a tub/shower combination. The spare bedroom also features vaulted ceilings, sliding glass doors to a balcony, and custom built-in cabinetry with dresser drawers and upper storage. The spare bathroom has a pedestal sink and a walk-in shower. A laundry closet contains a stacked washer and dryer. The condo also features a private enclosed courtyard with a wood deck, accessible from both the kitchen and the hallway via sliding glass doors. Pine Run is set on over 20 acres of native Florida landscape in Osprey. Community amenities include two heated swimming pools, four tennis courts, pickleball courts, a fitness center, a clubhouse, and shell-covered walking trails that wind through the grounds. A community grilling area and fire pit overlooking a lake provide additional gathering spaces. Pine Run is located on Blackburn Point Road just west of U.S. 41, situated between Sarasota and Venice. The Legacy Bike Trail and Oscar Scherer State Park are nearby, and Blackburn Point Park with a kayak launch is close by. Casey Key and Nokomis Beach are a short drive away, and restaurants such as the Casey Key Fish House are nearby. Downtown Sarasota and downtown Venice are both easily accessible for shopping, dining, and cultural attractions. Please allow up to 30 days after lease signing for community approval before move-in. We score every application. If an application doesn't score high enough, the resident may be required to place the equivalent of two months' rent in a security deposit. Please be aware that leasing this property includes a non-optional Home Assistant Services Package that will cost an additional $39 per month. These services and their cost are separate from Tenant's monthly rent payment and all other payments described in the Lease or any separate Lease addendums. The Home Assistant Services offered are described in the Resident Welcome Packet which can be viewed on Sarasota Management's website.
This listing is courtesy of: SARASOTA MANAGEMENT & LEASING
BAYSIDE - A4686669 - 3929 WAYPOINT AVE, OSPREY, FL 34229 73 Days on yellowkey
$4,500 | Single Family Home 3 bedrooms, 3.5 bathroom, 2 car garage
ANNUAL RENTAL - Pristine Single family home in the highly sought after community of Bayside in Osprey. The beautiful heated pool home features three bedrooms and three baths as well a private office space. Master bedroom offers an en suite bathroom with dual vanities, walk in shower, oversized walk in closet with built ins. Kitchen is complete with Gas Range, Oversized Island, Quartz Countertops and walk in pantry. Guest bedrooms each have en suite bathrooms too along with one powder bath! Outdoor space is remarkable from the heated pool and spa with southern exposure plus a bonus outdoor kitchen with built in Gas fireplace. Tandem 3 car garage will allow for ample storage for bikes and kayaks. Bayside is a fabulous place to be with opportunity to kayak and paddle board everyday. Bayside also has sunset lovers in mind with a private dock and waterfront sitting area perfect for evening romance. Minutes away from shopping, Venice Beach, Siesta Key Beach, Nokomis Beach and Casey Key Beach. Lots of time to go biking with the new Legacy trail and Oscar Scherer Park. Unfurnished*No smoking* 1st, last & Security for move in!
This listing is courtesy of: RE/MAX ALLIANCE GROUP
OAKS - A4686127 - 51 MACEWEN DR #12, OSPREY, FL 34229 78 Days on yellowkey
$2,250 Reduced | Condo 1 bedrooms, 1.0 bathroom
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 combined bedroom/living room, new kitchenette with quartz countertop, dining nook, office/dressing room, well designed bathroom with walk-in shower, office/dressing room, and stacked washer/dryer. Lobby elevator provides access to the second floor. Windsor Lodge Residents have their own private swimming pool and club house. Centrally located and 15 minutes to Siesta Key Beach. Note: Residents of Windsor Lodge do not have access to The Oak Club amenities. Available now for an seven plus month lease at $2250 month.
This listing is courtesy of: WAGNER REALTY
EMERALD WOODS AT OAKS 03 PH 02 - A4682290 - 124 TURQUOISE LN, OSPREY, FL 34229 108 Days on yellowkey
$4,999 Reduced | Single Family Home 3 bedrooms, 2.0 bathroom, 2 car garage
**RENT JUST LOWERED**Impressive three-bedroom, two-bathroom home with heated pool designed for both comfortable family living and grand-scale entertaining. High-speed internet is now included. Ideally situated on a quiet cul-de-sac in Emerald Woods at The Oaks, this gated, beautifully landscaped community features serene lakes throughout and offers a prime location just minutes from Siesta Key and the Gulf of Mexico. This exceptional home showcases spacious, well-appointed rooms highlighted by elegant architectural details, custom built-ins, and abundant natural light. The expansive primary suite is a private retreat featuring rich wood flooring, a relaxing sitting area, and a luxurious en-suite bathroom complete with a soaking tub, walk-in shower, double vanities, private water closet, and three large, professionally organized closets. The chef-inspired kitchen is both functional and elegant, featuring stainless steel appliances, solid wood cabinetry, slab granite countertops, a wine cellar, breakfast bar, butler’s pantry, and a charming breakfast nook overlooking the pool and waterfall. Step outside to your private outdoor oasis. The screened lanai includes a fully equipped outdoor kitchen with a gas grill, refrigerator, and sink — perfect for entertaining. The resort-style heated pool and spa feature a stunning cascading waterfall, creating a relaxing and luxurious atmosphere. Beyond the lanai, the tropical backyard showcases a beautifully designed rock-paved pathway leading to additional patio areas, surrounded by lush landscaping and enhanced by enchanting evening lighting that transforms the yard into a magical retreat. This home is also located close to several excellent schools, including Pine View School for the Gifted, Laurel Nokomis School, and Venice High School. Schedule your private tour today and experience luxury Florida living at its finest. This community is governed by a homeowners' association (HOA). The HOA charges fees for lease applicants, which may include application processing, background screening, and common area deposits. Please contact the agent for specific HOA fee details.
This listing is courtesy of: RENT SARASOTA
EDGEWATER/HIDDEN BAY PH 3 - A4680486 - 280 HIDDEN BAY DR #203, OSPREY, FL 34229 121 Days on yellowkey
$3,795 | Condo 3 bedrooms, 2.0 bathroom
This second-story unit in Edgewater at Hidden Bay is ready for move-in and is offered furnished or unfurnished. The apartment includes 3 bedrooms, 2 bathrooms, modern finishes, and steady natural light throughout. The kitchen provides ample cabinet storage, a breakfast bar, quartz countertops, and all major appliances, including a stainless-steel refrigerator, microwave, dishwasher, and range. The open living area connects to a screened balcony for additional usable space! The primary bedroom also includes access to the screened balcony, with additional details including dual walk-in closets and an en suite bathroom for added privacy. Two additional bedrooms are included in this unit, complete with spacious closet space for all your wardrobe needs. A guest bathroom down the hall and a laundry room with additional storage complete the rest of this apartment! Underbuilding covered and secured parking provides each unit with one assigned space, and locked storage units across the main building includes additional storage for its residents. Sorry, no pets for renters. Welcome to Edgewater at Hidden Bay! Located in Osprey, Florida on the shores of Little Sarasota Bay, you'll find a vibrant, gated, waterfront condominium community that's rich with amenities such as a newly renovated clubhouse with catering kitchen and fitness room, a resort-style pool and spa, tennis and pickleball courts, a Tiki hut for grilling and entertaining, a kayak launch and meandering boardwalks that access a pond with water features and a fishing pier that allows you to watch nightly sunsets. ADDITIONAL FEES AND RENTAL INFORMATION: Move-In Funds: Minimum 1st month rent, 1 month security deposit. Application fee: $100 Application fee. Water: $120/ month Electric: Tenant Responsibility Included: Basic cable and internet are included. Laundry: In unit Washer/Dryer THIRD PARTY PET SCREENING SERVICE: ALL applicants must complete pet screening. Create a pet and/or animal profile or "no pet" profile. You will receive a separate email to connect with our service provider and to complete your pet application (note: there is cost of $30/$25 for the first pet and $25/$20 for each additional pet.) This pet profile must be completed for your application to be considered completed. Medically necessary animals for the benefit of the occupant(s) are permitted with valid documentation from a medical or mental healthcare provider. Fees and deposits are waived for medically necessary animals. THE ESA APPROVAL MUST BE OBTAINED WITH OUR PET SCREENING SERVICE. PMI SWFL does not review/evaluate ESA documents for approval. Qualifications: We run a complete background check that includes credit, income verification, prior landlord and eviction history. In terms of credit, we look at the entire picture as opposed to just the credit score, but in general, we do require a score over 550. This property is professionally managed by PMI Southwest Florida.
This listing is courtesy of: PMI SOUTHWEST FLORIDA
EDGEWATER/HIDDEN BAY PH 3 - A4680472 - 280 HIDDEN BAY DR #202, OSPREY, FL 34229 121 Days on yellowkey
$3,595 | Condo 3 bedrooms, 2.0 bathroom
Be the first to call this brand-new condo in Edgewater at Hidden Bay home. The kitchen showcases a sleek, modern design, complemented by solid wood cabinetry and quartz countertops, creating an ideal space for both everyday living and effortless entertaining. Appliances include a stainless-steel refrigerator, microwave, range, and dishwasher. Large windows bring in an abundance of natural light and partial views of Little Sarasota Bay. All three bedrooms are thoughtfully designed for everyday comfort, with the primary suite featuring dual closets and an immaculate en suite bathroom for added convenience! A full-size washer and dryer are included for hassle-free laundry days. Underbuilding covered and secured parking provides each unit with one assigned space, and locked storage units across the main building provide additional storage for its residents. Sorry, no pets for renters. For added convenience, the condo includes a full-size washer and dryer. Under the building is a covered and secured parking lot, providing each unit with (1) assigned parking spot for added security. Locked storage units across the main building also feature additional storage! Hidden Bay offers a serene, resort-style environment surrounded by scenic waterways and lush green spaces. Residents enjoy access to a community pool, tennis and pickleball courts, a clubhouse, and a fully equipped fitness center, making it the perfect setting for those seeking comfort, convenience, and a touch of luxury. ADDITIONAL FEES AND RENTAL INFORMATION: Move-In Funds: Minimum 1st month rent, 1 month security deposit. Application fee: $100 Application fee. Association Application: Pets: Only ESA Animals allowed. Water: $120/ month Electric: Tenant Responsibility Included: Basic cable and internet are included. Laundry: In unit Washer/Dryer THIRD PARTY PET SCREENING SERVICE: ALL applicants must complete pet screening. Create a pet and/or animal profile or "no pet" profile. You will receive a separate email to connect with our service provider and to complete your pet application (note: there is cost of $30/$25 for the first pet and $25/$20 for each additional pet.) This pet profile must be completed for your application to be considered completed. Medically necessary animals for the benefit of the occupant(s) are permitted with valid documentation from a medical or mental healthcare provider. Fees and deposits are waived for medically necessary animals. THE ESA APPROVAL MUST BE OBTAINED WITH OUR PET SCREENING SERVICE. PMI SWFL does not review/evaluate ESA documents for approval. Qualifications: We run a complete background check that includes credit, income verification, prior landlord and eviction history. In terms of credit, we look at the entire picture as opposed to just the credit score, but in general, we do require a score over 550. This property is professionally managed by PMI Southwest Florida.
EDGEWATER/HIDDEN BAY PH 3 - A4679931 - 280 HIDDEN BAY DR #201, OSPREY, FL 34229 124 Days on yellowkey
$3,795 | Condo 3 bedrooms, 2.5 bathroom
Be the first to live in this brand-new stunning condo in the community of Edgewater at Hidden Bay! Sorry, no pets for renters. The kitchen features a sleek and modern look, equipped with stainless steel appliances, including a refrigerator, microwave, stove, and dishwasher, paired with solid wood cabinetry and elegant quartz countertops, creating an ideal space for both everyday living and entertaining. Expansive windows fill the interior with natural light while offering partial views of Little Sarasota Bay, enhancing the home's bright and inviting atmosphere. The spacious bedrooms and designer bathrooms provide comfort and style, while the flexible office space adds valuable functionality for work or relaxation. For added convenience, the condo includes a full-size washer and dryer. Under the building is a covered and secured parking lot, providing each unit with (1) assigned parking spot for added security. Locked storage units across the main building also feature additional storage! Hidden Bay offers a serene, resort-style environment surrounded by scenic waterways and lush green spaces. Residents enjoy access to a community pool, tennis and pickleball courts, a clubhouse, and a fully equipped fitness center, making it the perfect setting for those seeking comfort, convenience, and a touch of luxury. ADDITIONAL FEES AND RENTAL INFORMATION: Move-In Funds: Minimum 1st month rent, 1 month security deposit. Application fee: $100 Application fee. Association Application: Pets: Only ESA Animals allowed. Water: $120/ month Electric: Tenant Responsibility Included: Basic cable and internet are included. Laundry: In unit Washer/Dryer THIRD PARTY PET SCREENING SERVICE: ALL applicants must complete pet screening. Create a pet and/or animal profile or "no pet" profile. You will receive a separate email to connect with our service provider and to complete your pet application (note: there is cost of $30/$25 for the first pet and $25/$20 for each additional pet.) This pet profile must be completed for your application to be considered completed. Medically necessary animals for the benefit of the occupant(s) are permitted with valid documentation from a medical or mental healthcare provider. Fees and deposits are waived for medically necessary animals. THE ESA APPROVAL MUST BE OBTAINED WITH OUR PET SCREENING SERVICE. PMI SWFL does not review/evaluate ESA documents for approval. Qualifications: We run a complete background check that includes credit, income verification, prior landlord and eviction history. In terms of credit, we look at the entire picture as opposed to just the credit score, but in general, we do require a score over 550. This property is professionally managed by PMI Southwest Florida.
EDGEWATER/HIDDEN BAY PH II BLD - A4664275 - 260 HIDDEN BAY DR #504, OSPREY, FL 34229 266 Days on yellowkey
$5,000 | Condo 2 bedrooms, 2.5 bathroom
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 doors, and powder room in an open floor plan. The kitchen is large with solid wooden soft close, shaker style cabinetry topped with slab granite counters with a breakfast bar on peninsula with seating for 4. This room has a tray ceiling and is complimented with stainless steel appliances. The dining area will seat six comfortably and has your amazing water views. The condo also features a large laundry room with sink, granite counters for folding, hanging rack and upper and lower extra storage, as well as assigned parking garage for one with adjacent huge storage closet. This is a secure community with gated access to the community, and controlled lobby access, and for your weather concerns there are catagory 5 hurricane grade windows recently installed. The building itself is built like a tank-poured concrete floors and walls between units reinforced with rebar. The amenity package in this community is impressive, with a large clubhouse with full catering kitchen, lounge, library, fitness center, resort style pool and spa with tables and umbrella's and a covered shaded area, BBQ grills and outdoor dining area in a Tiki Hut, and a board walk leading to an island with fountains spraying! Tennis or pickleball-YES! There is also a trail at the rear of the community leading near the water on a board walk. This slice of heaven can also be rented during HIGH SEASON ( December thru April) at $6000/month + 13% tax. You will also find yourself convenient to shopping, dining, Siesta Key Beach, and downtown Sarasota with theater, opera, museums and more fun! Call today for your incredible home!
OAKS 2 PH 2 - A4659277 - 852 MACEWEN DR, OSPREY, FL 34229 314 Days on yellowkey
$7,000 | Single Family Home 3 bedrooms, 3.5 bathroom, 3 car garage
**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 Wetbar, 3-CAR GARAGE, etc. Premium features abound including Crown moldings, Marble and wood floors, Coffered ceiling, Custom built-ins, a well-equipped kitchen with Granite countertops, Stainless Steel Appliances including KitchenAid and Fisher & Paykel, and much more! An Expansive Primary Bedroom Suite features a Bonus Room, Walk-In Closet, dual vanities, soaking tub and custom-tiled shower. Enjoy OUTDOOR LIVING at its FINEST in an Expansive, Screened Lanai with PEBBLETEC Pool & Spa and Outdoor Kitchen in a serene setting. NEW HURRICANE IMPACT SLIDING DOORS and WINDOWS; ROOF (2015). THE OAKS is a distinguished country club community which boasts many accolades including: Platinum Club of America, Emerald Club of the World and Elite Distinguished Club of the World. The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. **ENJOY VIEWING THE 3D VIRTUAL TOUR**
This listing is courtesy of: GENEROUS PROPERTY
BLACKBURN HARBOR RESIDENCES - A4651384 - 5100 JESSIE HARBOR DR #504, OSPREY, FL 34229 390 Days on yellowkey
$6,950 | Condo 3 bedrooms, 2.0 bathroom
CLOSE TO NOKOMIS BEACH! BOOKED JAN/FEB/MAR 2027. AVAILABLE APR 2027 $6,950/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 converted from a den) and 2 bathrooms. As you step inside the foyer, you are met with a bright and open floor plan with a separate dining area, large living room leading onto the covered and furnished balcony with its magnificent water views! The spacious and beautifully updated kitchen has granite countertops and stainless-steel appliances and is fully equipped. The primary suite has a king-sized bed, en-suite bathroom with a large walk-in shower, a separate soaking tub, and dual sinks. There are two additional guest rooms, one with a queen-sized bed and the other has 2 twin beds, plus a separate guest bathroom with walk-in shower, large granite vanity area with a single sink, and a separate laundry room with full-size side-by-side washer and dryer. The condo has an assigned parking space in the underground garage. Blackburn Harbor is a gated community and offers many amenities, which include a heated pool, fitness center, clubhouse, pickleball and tennis courts, shuffleboard, kayak launch, boat dock and fishing pier. In addition, there is a gazebo, outdoor grills and walking trails. The waterway leads out to the Intracoastal Waterway, with access to the Gulf of Mexico. You are in walking distance to Oscar Scherer Park, a short drive to the beautiful gulf beaches of Nokomis Beach, Casey Key, South and North Jetty, Venice Beach, Caspersen Beach, and the famous Siesta Key Beach! Plus, there is an abundance of shopping and dining, from the beautiful Historic Venice to Downtown Sarasota which is full of entertainment of all kinds! Np pets allowed.
This listing is courtesy of: JENNETTE PROPERTIES INC
PINE RUN II - A4644465 - 101 WOODLAND PL, OSPREY, FL 34229 439 Days on yellowkey
$6,950 | Townhouse 3 bedrooms, 2.5 bathroom , 1 car carport
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 Kitchen is EAT-IN. Main Bedroom Suite is on the first floor and two second story bedrooms. Private screened patio lanai to relax in paradise with a nature view and birdsong. Carport parking. Pine Run is a friendly community. Amenities two heated pools, tennis courts, three pickle ball courts, canopy tree lined walking trails, brick patio with fire pit and grill, kayak storage and Club House. Located less than a half mile from the Gulf of Mexico and the inland waterway. Pine Run sits halfway between Sarasota and Venice on Blackburn Point Road. Less than 15 minutes drive and you are on Nokomis Beach with plenty of parking available. Oscar Scherer State Park is less than a mile south and the Legacy Bike Trail from Venice to Sarasota runs just east of Pine Run. Great walking neighborhood; Publix, CVS, stores, services and restaurants conveniently located. Rates for December through April $6950 and May through November $3600 monthly + 13% tax. Additional charges Sales and Resort Taxes (13%) and Departure Clean. Rates include all utilities and WIFI. NO PETS / NO SMOKING
MERIDIAN AT THE OAKS PRESERVE - A4640065 - 3603 N POINT RD #602, OSPREY, FL 34229 466 Days on yellowkey
$5,900 | Condo 3 bedrooms, 3.0 bathroom, 1 car garage
**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 counter and Stainless-Steel appliances, etc. The Owner’s Bedroom Suite features a Walk-in Closet, Dual Vanities, Soaking Tub and Stunning, Custom Tiled Shower. The Spacious, Screened Balcony offers a PRIVATE and serene setting where you can view wonderful wildlife and Gorgeous Sunsets! This residence includes a single, covered parking space and climate-controlled storage unit. The adjacent Amenity Center offers exclusive access to Meridian Condo residents and features a Heated Pool & Spa, Fitness facility and Outdoor Grilling area. The Oaks-Preserve is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, Area Beaches including #1 Rated Siesta Key and all that Gulf Coast living has to offer.
VILLAS AT BELLAGIO HARBOR VILLAGE - A4622973 - 14041 BELLAGIO WAY #316, OSPREY, FL 34229 627 Days on yellowkey
$8,000 Increased | Condo 3 bedrooms, 2.0 bathroom, 2 car garage
AVAILABLE FOR SEASON 2027 - 2 MONTH MIN REQUIRED. MINUTES TO CASEY KEY & NOKOMIS BEACH! 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 entering, you are met with a spacious foyer which leads to the nicely appointed rooms. The kitchen has wood cabinets and granite counters, stainless steel appliances and comes fully equipped. Off of the kitchen is the living/dining area with sliding glass doors opening onto the large, spacious balcony overlooking the bay/harbor. The master suite has a king-sized bed, large walk-in closet, en-suite bathroom with separate shower and soaking tub, and private water closet. Enjoy more water views from the master bedroom with sliders opening onto the balcony. The 2nd bedroom is nicely furnished with a queen-sized bed, bedroom 3 has 2 twin beds, and guest bathroom has a walk-in shower and single vanity. There is a large separate laundry room with washer, dryer, a sink and plenty of storage cupboards. Wake up to the amazing waterfront views and enjoy your morning coffee on the furnished balcony. Osprey Harbor Village has it all! The Community has a resort-style bay-front heated pool and spa, sauna room, state-of-the-art fitness facility and a clubhouse with flat-screen TV's, kitchen, BBQ grills, fishing pier, boat docks, kayak launch, boat storage, on-site full-service marina and waterfront restaurant. covered under building garage parking for two cars, with elevators leading to your condo. Only minutes to the incredible Nokomis Beach, Siesta Key, and Venice Beach, shopping, dining, including the renowned Casey Key Fish House and Deep Lagoon, and walking distance to Blackburn Point Park! Easy access to I75 to University Town Center and Mall where there is an abundance of shops and restaurants.
OAKS - A4594860 - 293 TURQUOISE LN, OSPREY, FL 34229 871 Days on yellowkey
$5,750 | Single Family Home 3 bedrooms, 2.0 bathroom, 2 car garage
**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, Plantation Shutters, an Oversized, Owner’s Bedroom Suite with Multiple walk-in closets and sitting area and much more! Enjoy the expansive and private outdoor living area in a screened lanai with wet bar and southern exposure overlooking a Garden and Tranquil Preserve. Mostly NEW Hurricane Impact Windows/Door. The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer.
BAY STREET VILLAGE - A4517611 - 152 NAVIGATION CIR #107, OSPREY, FL 34229 1661 Days on yellowkey
$4,500 | Condo 3 bedrooms, 2.0 bathroom
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 solid wooden cabinetry, topped with slab granite counters and breakfast bar and complemented with stainless steel appliances. The master suite is spacious with a king bed, walk in closet and en suite bathroom with walk in shower and double vanity. There are two additional bedrooms-one with a queen size bed and one set up as a den with a pull out couch. The amenity package features a resort style heated pool, club room, fitness center and BBQ grills. Bay Street Park is right across the street and you'll find yourself close to the beach, downtown Sarasota or Venice, the Legacy Trail, shopping, dining and museums. Available NOW AND DURING HIGH SEASON (DECEMBER THRU APRIL). This community is governed by a homeowners association. Approval may include an application, background screening, fees, and an approval process. Contact the agent for details. Call now for your next vacation in the Florida sunshine!
HIDDEN BAY - A4410764 - 293 HIDDEN BAY DR #203, OSPREY, FL 34229 2848 Days on yellowkey
$5,000 | Condo 2 bedrooms, 2.0 bathroom, 1 car garage
AVAILABLE 2027 SEASON. 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 & dryer inside unit. Nicely renovated with closet barn doors. Stainless appliances. Detached one car garage immediately in front of condo and plenty of parking. PET OKAY with owner approval and nonrefundable pet fee. Resort style community pool, heated spa, fitness room, tennis courts, reading room, BBQ area with covered bar for guests, community clubhouse with kitchen. Short distance to shores of Little Sarasota Bay, Casey Key, Siesta Key. Fishing pier. Easy commute to shopping, restaurants and more. NO CATS. OWNER HAS ALLERGIES. CALL AGENT FOR MORE INFORMATION. Rentals under 6 months are subject to Sales and Tourist tax(13%). Note that rates are subject to change without notice and reservations are not guaranteed until initial reservation deposit is received.