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BAY OAKS ESTS UNIT 1 - A4699469 - 534 OAK BAY DR, OSPREY, FL 34229 7 Days on yellowkey
$3,800 | Single Family Home | 4 beds | 3.0 baths | 2 gar
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 are done for you and included in the rent. This home is located in a very nice neighborhood with easy access to many restaurants, shopping and the Florida lifestyle including the Legacy Trail for biking, walking or jogging. Only 10 minutes to two of the finest beaches on the Gulf Coast at Siesta key and Nokomis beach. First and last months rent and security deposit due upfront. pets are possible and are considered on a case by case basis.
Listing is courtesy of: REALTY BY DESIGN LLC
RIVENDELL THE WOODLANDS - N6144906 - 919 SCHERER WAY, OSPREY, FL 34229 13 Days on yellowkey
$4,200 Reduced | Single Family Home | 4 beds | 3.0 baths | 3 gar
Perfect Family Pool Home in a Location you can't ignore. Just a few blocks from The Oaks, one of the most exclusives areas in Sarasota, this impeccable home has 4 bedrooms and 3 bathrooms, 3 car garage, with just under 2,300 square feet of living area for your quiet enjoyment or entertaining friends and family. The home offers a designer pool and spa with lake and preserve views, located in the desirable Rivendell neighborhood, blocks from Pine View School - one of the top-rated schools in Florida! This home offers upgrades by design and include 10’ ceilings, rich engineered hardwood floors and tile throughout living areas, a formal living room and dining room that open to the pool and lanai, accenting arches throughout, great room opening to pool with the kitchen providing a breakfast bar and nook. A sizable Master Suite with a convenient door to the pool area, Master Bath includes a large glass enclosed shower, two walk-in closets, dual sinks and soaking tub. Enjoy the Florida living with the screen enclosed pool with a swim out for the little ones -or- visit the heated community pool, playground, and nature trails. Close proximity to Shopping, Beaches, Oscar Scherer State Park, and just 20 minutes to all of the amenities of Sarasota! ~Included in Rent: Landscaping and Pool Maintenance. ~Association: Application is required.
Listing is courtesy of: COMPASS PROPERTY MANAGEMENT LLC
BLACKBURN HARBOR RESIDENCES - A4698732 - 6100 JESSIE HARBOR DR #202, OSPREY, FL 34229 14 Days on yellowkey
$5,500 | Condo | 3 beds | 3.5 baths | 1 gar
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 breathtaking water views. Designed for both comfort and entertaining, the open-concept floor plan features expansive living and dining areas filled with natural light. Sliding glass doors open to a generous wraparound lanai where you can relax with morning coffee, enjoy coastal breezes, watch spectacular sunsets and take in peaceful waterfront scenery. The gourmet kitchen is fully equipped with rich wood cabinetry, granite countertops, stainless steel appliances, a center island and a charming dinette, making meal preparation and entertaining effortless. The luxurious primary suite offers a private retreat with generous closet space and a spa-inspired en-suite bath. Each guest bedroom includes its own en-suite bathroom and walk-in closet, providing exceptional comfort and privacy. Tenants enjoy an exceptional collection of resort-style amenities, including a heated waterfront pool, fitness center, clubhouse, tennis and pickleball courts, kayak storage and launch, and a waterfront gazebo with grilling areas. Boating enthusiasts will appreciate protected deep-water dockage with power and water, plus direct access to the Intracoastal Waterway with no bridges to the Gulf. Ideally situated across from Oscar Scherer State Park, you'll enjoy easy access to hiking, biking, kayaking, and abundant Florida wildlife. Located just 10 minutes from Venice, 15 minutes to Siesta Key & Casey Key Beaches and 25 minutes from downtown Sarasota. Close to shopping, dining, golf and cultural attractions. 13% (6% Sarasota County Tourist Development Tax (TDT) and 7% Florida State Sales Tax) will be added to all short-term leases 6 months or less . Owner will pay up to $100 in electric on short-term leases (4 months or less). Tenant responsible for Electric on all long term leases (5 months or more). 1 DOG Allowed with non refundable deposit. CONDO IS FOR SALE - TENANT WOULD HAVE TO ALLOW SHOWINGS
Listing is courtesy of: CORCORAN DWELLINGS REALTY
BAY STREET VILLAGE - N6144854 - 4304 EXPEDITION WAY WAY #105, OSPREY, FL 34229 15 Days on yellowkey
$2,250 | Condo | 3 beds | 2.0 baths | 1 gar
Virtually Staged. Spectacular water views from most windows in this immaculate, lightly used 3BR/2BA condo, built in 2018 and located in the gated community of Bay Street Villages. The popular Ibis floor plan offers an open-concept kitchen, dining, and great room with designer finishes, including white 42” cabinetry, light granite countertops, custom backsplash and stainless-steel appliances. Enjoy peaceful pond views with birds and wildlife from the screened lanai. Quality construction and peace of mind are provided by hurricane-impact windows and doors, concrete block construction, tile roof, and a paver driveway. The primary suite features plantation shutters, a custom ceiling fan with light, custom closet system, linen closet, lighted 10× makeup mirror, and a bidet-ready outlet. The second and third bedrooms also include custom ceiling fans and 2" blinds. The dining area is accented by a custom light fixture and accordion blinds on the balcony sliding doors. The balcony is enhanced with a tropical palm-leaf ceiling fan and outdoor curtains for added shade and comfort. The great room is fitted with plantation shutters for added elegance. A spacious laundry room includes a washer and dryer. Added features-Ring Doorbell, Keyless Entry on Front Door as well as an Exterior Garage door keypad. The Rent includes water, sewer, exterior and grounds maintenance, gated entry, heated resort-style pool, cabana, fitness center, and club room. Ideally located near Nokomis Beach, Casey Key, Siesta Key Beach, the Legacy Trail, Sarasota and Venice dining and shopping, Oscar Scherer Park, and A-rated Pine View School. Maintenance-free Florida living at its best. Landlord will consider 1 small dog.
Listing is courtesy of: EXIT KING REALTY
WINDSOR LODGE AT THE OAKS - A4695928 - 51 MAC EWEN DR #8, OSPREY, FL 34229 41 Days on yellowkey
$2,250 | Condo | 1 beds | 1.0 baths
Available NOW! 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 walk in shower, and a king size bed. It is fully furnished and available for viewing now! Seeking annual rental; rent includes water, sewer, internet, basic cable & pest control.. Don't miss out on this one of a kind place to call home!
Listing is courtesy of: ROSSI & COMPANY INC
BAY STREET VILLAGE - A4695420 - 184 EXPLORER DR, OSPREY, FL 34229 45 Days on yellowkey
$2,150 | Townhouse | 2 beds | 2.0 baths | 1 gar
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 two-bedroom, two-bath, impeccably maintained, property move-in ready. Located on the second floor with a one-car garage, this 2016 built condominium features a light and bright feel and has an open great room floor plan with screened lanai. Spacious “Heron” floor plan makes great use of space with two bedrooms, two baths, Attached one car garage. Kitchen features a large center island that any chef will love. Stylish design elements including 42” Scottsdale Cherry Spice, Beautiful Firenze Granite kitchen countertops, and GE stainless steel appliance package including a washer and dryer. Double slider opens to screened corner balcony. Master suite features large walk-in closet, tiled walk-in shower, and double vanity. 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 Pine View school. Please schedule your private showing today. You will not be disappointed.
Listing is courtesy of: DALTON WADE INC
EDGEWATER/HIDDEN BAY BLDG B PH - A4693277 - 260 HIDDEN BAY DR #401, OSPREY, FL 34229 65 Days on yellowkey
$4,850 | Condo | 3 beds | 2.5 baths | 2 gar
3, 6, 9 or 12 month 6 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