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RIVENDELL THE WOODLANDS - A4700530 - 956 SCHERER WAY, OSPREY, FL 34229 3 Days on yellowkey
$4,800 | Single Family Home | 4 beds | 3.0 baths | 3 gar
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 HIGH/VAULTED CEILINGS, tile & hardwood flooring and a comfortable layout that includes a DINING ROOM and BREAKFAST NOOK and plenty of natural light. The kitchen features MARBLE COUNTERTOPS, a KITCHEN ISLAND, PREMIUM GE CAFE STAINLESS STEEL APPLIANCES, and great cabinet/counter space. The laundry room also includes MARBLE COUNTERS. Fully stocked and TRULY TURN-KEY with cookware, linens, towels, and more The primary suite includes a WALK-IN CLOSET, DOUBLE VANITIES, a separate TUB, walk-in SHOWER, and plenty of space to feel comfortable at home. Enjoy extra features like an electric car/TESLA CHARGING STATION, ALARM SYSTEM, HURRICANE SHUTTERS, and an EXTRA FRIDGE IN THE GARAGE. NO PETS ALLOWED. No Cats. No Dogs. Lawn Care and Pool Maintenance INCLUDED! distance to Pine View School and Legacy Trail * Direct access to I-75 and medical offices * 1 mile from Walmart, gas stations, and everyday essentials * 5 minute drive to Costco, Total Wine, Sprouts, Ulta, Hidden Harbor Marina, and more! * 10-12 minute drive to Casey Key and Siesta Key BEACHES * Easy access to Downtown Venice and Downtown Sarasota
Listing is courtesy of: KEYRENTER SARASOTA PROPERTY MANAGEMENT
PALMS/CASEY KEY - A4700255 - 4401 CONCHFISH LN, OSPREY, FL 34229 4 Days on yellowkey
$3,595 | Single Family Home | 4 beds | 3.0 baths | 2 gar
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 floor plan is designed for both everyday living and effortless entertaining. The gourmet kitchen features a large granite island, stainless steel appliances, a pantry, and seamlessly connects to the great room and dining area. The spacious primary suite overlooks the private, tree-lined backyard and offers dual vanities, a generous walk-in closet, and convenient access to the laundry room. Three additional bedrooms and two full bathrooms provide flexibility for family, guests, or a home office. Step outside to the screened lanai and enjoy peaceful views of the lush natural surroundings. The backyard features a paved patio and a variety of mature fruit trees, including mango and dragon fruit, creating a private outdoor retreat. Additional highlights include a whole-house water filtration and softener system, an electric vehicle charging station in the oversized garage, and a paved walkway surrounding the home. Ideally located near the Legacy Trail, Historic Spanish Point, Oscar Scherer State Park, shopping, dining, and Gulf Coast beaches, this home also offers the rare convenience of being able to walk to and from Pine View School, combining comfort, functionality, and an exceptional location.
Listing is courtesy of: COMPASS FLORIDA, LLC
BAY STREET VILLAGE - A4699974 - 137 NAVIGATION CIR, OSPREY, FL 34229 9 Days on yellowkey
$1,950 | Condo | 3 beds | 2.0 baths | 1 gar
Don't miss this 3BR, 2BA fully furnished condo in Osprey, offering comfort, style, and stunning lake views! The spacious kitchen is designed for both functionality and entertaining, featuring granite countertops, a breakfast bar, solid wood cabinetry, and stainless steel appliances, including a refrigerator, microwave, dishwasher, and range. The open living and dining area offers lake views and access to a screened balcony. The primary suite is conveniently located off the main living area and features a walk-in closet and a private en suite bathroom. Two additional guest bedrooms and a full guest bathroom are situated on the opposite side of the condo, providing added privacy for family members or visitors. Additional conveniences include a laundry room with a full-size washer and dryer and an attached one-car garage for secure parking and extra storage. Enjoy maintenance-free living in Bay Street Village, featuring a clubhouse, swimming pool, and fitness center! Conveniently located between Venice and Sarasota, the community offers easy access to restaurants, entertainment, beaches, shopping, and more. PMI Southwest Florida has partnered with Obligo to provide a security deposit alternative for qualified renters. ADDITIONAL FEES AND RENTAL INFORMATION: Move-In Funds: Minimum 1st month rent, 1 month security deposit. Application: $100 Application fee Association Application: $150 application fee Pets: (2) pets considered, 35lbs max. $250 Refundable pet fee and $25/mo. pet rent Utilities: Water is $80 single and $100 double occupancy. Electric tenant responsible. Included: Trash, Lawn and Pest Control 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.
Listing is courtesy of: PMI SOUTHWEST FLORIDA
BAY OAKS ESTS UNIT 1 - A4699469 - 534 OAK BAY DR, OSPREY, FL 34229 15 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 21 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 22 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
WINDSOR LODGE AT THE OAKS - A4695928 - 51 MAC EWEN DR #8, OSPREY, FL 34229 49 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 53 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