Location: Osprey
Keyword(s): Laurel Nokomis Middle
Keyword(s) Middle School: Laurel Nokomis Middle
Do Not Show Listings
521 HABITAT BLVD, OSPREY, FL 34229
$5,900343 Days on yellowkey MLS ID: A4661768
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2266 Built: 2003Community: Willowbend Ph 1Spa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Tax Year:
Middle School: Laurel Nokomis Middle
Remarks: 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 retreat features a private screened-in pool, open-concept living, and a dedicated office workspace—perfect for remote work and extended relaxation. The fully equipped kitchen boasts granite countertops and stainless steel appliances, flowing into a bright living area and a covered lanai for outdoor dining and lounging. The master suite offers direct pool access and a spa-like bath for ultimate comfort. Beach gear provided: chairs, umbrella, cooler, and towels Dedicated home office setup with desk, chair, and fast Wi-Fi Distance to beaches: - Nokomis Beach – 10 minutes - Casey Key – 12 minutes - Siesta Key – 20 minutes Guests enjoy full access to Willowbend’s resort-style amenities: a heated pool and spa, fitness center, pickleball and basketball courts, and peaceful walking trails. Please Note: This home is part of an HOA that requires guest registration. After booking, we will request basic information to complete and submit the application. All HOA application fees are included in the rental cost—no surprises.
Listing is courtesy of: PMI SOUTHWEST FLORIDA (941-237-0011)
Listing Agent: David Holt (941-677-8090)
137 NAVIGATION CIR, OSPREY, FL 34229
$1,9509 Days on yellowkey MLS ID: A4699974
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1430 Built: 2014Community: Bay Street VillageSpa: NoCondo
Remarks: 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 Agent: Alexandra Stella (941-600-4333)
4219 FRONTIER WAY #105, OSPREY, FL 34229
$2,25074 Days on yellowkey MLS ID: N6144275
REDUCED by $50 (2.2%) on 06/29/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1244 Built: 2017Community: Bay Street VillageSpa: NoCondo
Remarks: 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 Key 15 minutes to the world-famous Siesta Key Beach Outdoor enthusiasts will love the easy access to the Legacy Trail, perfect for biking, walking, and jogging. This maintenance-free, gated community offers exceptional amenities, including: Resort-style swimming pool with cabana Fitness center Clubhouse Built for quality and peace of mind, the condo features: Solid concrete block construction Impact-resistant windows Tile roof Paver driveway Enjoy a convenient location between Sarasota and Venice, just minutes from shopping, restaurants, parks, medical facilities, and the highly acclaimed Pine View School. Water, sewer, and trash service are included in the rent. Rent: $2,250 per month
Listing is courtesy of: EXIT KING REALTY (941-497-6060)
Listing Agent: Tim Weller (941-221-0155)
534 OAK BAY DR, OSPREY, FL 34229
$3,80015 Days on yellowkey MLS ID: A4699469
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2077 Built: 1996Community: Bay Oaks Ests Unit 1Spa: NoSingle Family
Remarks: 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 (941-779-4509)
Listing Agent: Brian Odonnell (941-779-4509)
152 NAVIGATION CIR #107, OSPREY, FL 34229
$4,5001715 Days on yellowkey MLS ID: A4517611
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1528 Built: 2016 Tax: $3,006 (2021)Community: Bay Street VillageCondo
Taxes:$3,006
Tax Year: 2021
Remarks: 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. RENTED FEB-MARCH 2027. 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!
Listing is courtesy of: RENT SARASOTA (941-328-8999)
Listing Agent: Cody Smith (404-991-0209)
293 HIDDEN BAY DR #203, OSPREY, FL 34229
$5,0002902 Days on yellowkey MLS ID: A4410764
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1568 Built: 2000 Tax: $3,620 (2021)Community: Hidden BayCondo
Taxes:$3,620
Remarks: 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.
Listing is courtesy of: WAGNER REALTY (941-756-7800)
Listing Agent: Alba Lange (941-704-3026)
852 MACEWEN DR, OSPREY, FL 34229
$7,000368 Days on yellowkey MLS ID: A4659277
Bed: 3 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4519 Built: 1992Community: Oaks 2 Ph 2Spa: YesSingle Family
Remarks: **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**
Listing is courtesy of: GENEROUS PROPERTY (941-275-9399)
Listing Agent: Mark Lyda (941-586-2670)
293 TURQUOISE LN, OSPREY, FL 34229
$5,750925 Days on yellowkey MLS ID: A4594860
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2271 Built: 2001Community: OaksSpa: NoSingle Family
Remarks: **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.
51 MACEWEN DR #12, OSPREY, FL 34229
$2,250132 Days on yellowkey MLS ID: A4686127
REDUCED by $150 (6.3%) on 04/01/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 623 Built: 1990Community: OaksCondo
Remarks: 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.
Listing is courtesy of: WAGNER REALTY (941-955-1500)
Listing Agent: Patrice Ivan (941-993-0823)
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