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BAY STREET VILLAGE - A4695211 - 4212 EXPEDITION WAY, OSPREY, FL 34229 1 Day on yellowkey
$2,390 | Townhouse | 3 beds | 2.0 baths | 1 gar
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!!!
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 beds | 2.0 baths | 2 gar
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.
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 beds | 2.5 baths | 2 gar
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
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 beds | 2.0 baths | 1 gar
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.
Listing is courtesy of: EXIT KING REALTY
- A4692034 - 254 BURNEY RD, OSPREY, FL 34229 29 Days on yellowkey
$4,500 | Single Family Home | 5 beds | 4.5 baths | 2 gar
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!
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 beds | 2.0 baths
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.
Listing is courtesy of: SARASOTA MANAGEMENT & LEASING