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WILLOWBEND PH 3 - A4689938 - 531 LATITUDE LN, OSPREY, FL 34229 Just Added on 04/14/2026 8:43AM
$2,950 | Single Family Home 2 bedrooms, 2.0 bathroom, 2 car garage
Annual unfurnished single-family home is available in the Willowbend community of Osprey! With some of the best lake views in Willowbend, this two-bedroom plus den, two-bath home features a large primary bedroom with dual sink main bath, walk-in shower and separate soaking tub. Additional features include stainless steel kitchen appliances, gas range, pantry and laundry room with utility sink. The Willowbend community features a community pool and spa, gym and pickleball. The excellent location in Osprey gives you easy access to Sarasota and Venice, including Siesta Key Beach, Nokomis Beach, shopping and dining. Also nearby are top-rated Pine View School, the Intracoastal Waterway, beaches and Legacy Trail. High-speed internet, direct TV streaming, and lawn maintenance are all included.
This listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY
BISHOPSCOURT TOWNHOME ONE - A4689198 - 76 BISHOPS COURT RD #116, OSPREY, FL 34229 7 Days on yellowkey
$3,995 | Villa 2 bedrooms, 2.0 bathroom , 1 car carport
Rental Available now only thru October, 2026. Luxury turnkey furnished Georgian Style Villa in beautiful, secure, gated Oaks Preserve within The Oaks Club in Osprey FL. Nestled among the live oaks and palms and native vegetation with lovely flowering annuals and perennials, this villa is one of twelve townhome and villa condominium units of the Bishopscourt Townhomes. Both en-suite bedrooms are separated by the living/dining room with wet bar and wine/beverage cooler. Bishopscourt community pool & clubhouse is a few steps thru the woods across the street. Both buildings just painted and new roofs in place. This quiet and convenient community has 24 hour attended gate, secure walking and close proximity to the Legacy Trail for cycling to either Sarasota or Venice. Siesta Key and Casey Key/Nokomis Beaches are 15 min. drive. Publix, Target, Walmart, Lowes, Fitness Centers within 3 minutes. 1-75 is 12 minutes away.
This listing is courtesy of: CAPITAL REAL ESTATE ENTERPRISE
SOUTHBAY YACHT & RACQUET CLUB - A4688034 - 221 LOOKOUT POINT DR, OSPREY, FL 34229 15 Days on yellowkey
$3,750 | Single Family Home 3 bedrooms, 2.5 bathroom, 2 car garage
Southbay Yacht & Racquet club-Osprey Florida.$3750/mo Furnished/3Bed/2,5 Bath/Prime Bayside Location.Welcome to your tropical retreat in Southbay yacht and Racquet Club!This Beautiful single-family home sits on a spacious lot with lush landscaping,offering privacy and a relaxed coastal lifestyle just minutes from the beaches.3 Bedrooms/ 2.5 Bathrooms,Fully furnished with upscale Tommy Bahama Style decor.Newly upgraded Kitchen with granite countertops & new appliances.Renovated bathrooms with high-quality finishes.Bright open spaces with a modern tropical feel.Spacious lanai perfect for outdoor living and entertaintment.Large lot with beautiful tropical landscaping. Private Marina with boat slips & direct access to Little Sarasota Bay & Intracoastal Waterway.Newly remodeled clubhouse overlooks the marina and includes a ballroom with catering kitchen and dance floor,community room with kitchen and piano,entertaintment area,fitness center with aerobic and strenght-training equipment,card room,library and meeting room. Additional amenities include:Geomethermal heated pool and youth pool,covered outdoor patio and waterfront park ,3 tennis courts,4 pickleball courts,2 shufflelboards courts ,youth basketball court and playground ,kayac storage ,scenic walking trails and biking paths Southbay ideally located between Sarasota and Venice.Close to top-rated Pine View School,minutes to Gulf Coast Beaches. Enjoy Resort Style living in one of South Sarasota's most desirable waterfront communities.Schedule your showing today !Available May 15th-2026. An Exceptional opportunity to experience the best of Florida waterfront living.
This listing is courtesy of: KELLER WILLIAMS ON THE WATER S
BAYSIDE - A4686669 - 3929 WAYPOINT AVE, OSPREY, FL 34229 27 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 32 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 62 Days on yellowkey
$5,600 | Single Family Home 3 bedrooms, 2.0 bathroom
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 - A4680472 - 280 HIDDEN BAY DR #202, OSPREY, FL 34229 75 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 ha partial views of Little Sarasota Bay. Located down the hall is a 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 additional storage. Basic cable and internet are included. 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. Submit all applications to Ryntal Property Management ONLY! 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 listing is courtesy of: PMI SOUTHWEST FLORIDA
EDGEWATER/HIDDEN BAY PH 3 - A4679931 - 280 HIDDEN BAY DR #201, OSPREY, FL 34229 78 Days on yellowkey
$3,795 | Condo 3 bedrooms, 2.5 bathroom
WOW WOW WOW. This is a must see. Impressive upscale living!! Be the first to live in this brand-new stunning condo in the community of Edgewater at Hidden Bay! 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! Basic cable and internet are included. Sorry, no pets for renters. 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. Qualifications: We run a complete background check that includes credit, income verification, prior landlord, and eviction history.
TOWNS-END SHORES - A4678223 - 1755 HIGHLAND RD, OSPREY, FL 34229 91 Days on yellowkey
$1,995 | Half Duplex 3 bedrooms, 2.0 bathroom
Spacious duplex in Osprey with a bonus room! This Townhouse boasts 2 bedrooms and a bonus room downstairs that can be used as an office, playroom or even additional bedroom. The unit features a single car garage, washer and dryer hook ups, a screened in patio out front, an oversized living room. This community is located off us highway 41 south, right across the street from beautiful Oscar Scherer State Park. Pet friendly!
This listing is courtesy of: STOCKTON REALTY ADVISORS LLC
EDGEWATER/HIDDEN BAY PH II BLD - A4664275 - 260 HIDDEN BAY DR #504, OSPREY, FL 34229 220 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!
BLACKBURN HARBOR RESIDENCES - A4651384 - 5100 JESSIE HARBOR DR #504, OSPREY, FL 34229 344 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
BISHOPSCOURT TOWNHOME ONE - A4648193 - 60 BISHOPS COURT RD #114, OSPREY, FL 34229 369 Days on yellowkey
$2,595 | Townhouse 2 bedrooms, 3.5 bathroom , 1 car carport
This is a rare opportunity to rent a luxury, unfurnished townhome located in the heart of the Oaks Preserve. Showcasing charming architectural details and quality finishes, this traditional-style home offers an inviting floor plan with two bedrooms, each featuring its own en-suite bath. The gracious living and dining areas flow seamlessly into a spacious and private outdoor living space that overlooks a serene preserve, creating a perfect setting for relaxation. Set within a small, exclusive enclave of just 12 townhomes, residents also enjoy access to a quiet community pool ideal for social gatherings. Conveniently situated near shopping, dining, the white sands of Siesta Key Beach, and the vibrant cultural arts scene of downtown Sarasota, this home offers both comfort and an exceptional lifestyle.
This listing is courtesy of: STRINGER MANAGEMENT INC
VILLAS AT BELLAGIO HARBOR VILLAGE - A4622973 - 14041 BELLAGIO WAY #316, OSPREY, FL 34229 581 Days on yellowkey
$8,000 Increased | Condo 3 bedrooms, 2.0 bathroom, 2 car garage
AVAILABLE FOR SEASON 2027 - 3 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.
BAY STREET VILLAGE - A4517611 - 152 NAVIGATION CIR #107, OSPREY, FL 34229 1615 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!
EDGEWATER/HIDDEN BAY PH 3 - A4680486 - 280 HIDDEN BAY DR #203, OSPREY, FL 34229
$3,795 | Condo 3 bedrooms, 2.0 bathroom
This second-story unit in Edgewater at Hidden Bay is ready for move-in and is 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 additional storage. Basic cable and internet are included. 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. Submit all applications to Ryntal Property Management ONLY! 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.
BAY STREET VILLAGE - A4685905 - 80 NAVIGATION CIR, OSPREY, FL 34229
$2,500 | Townhouse 3 bedrooms, 2.0 bathroom
Turnkey fully furnished newer built 3 bedroom 2 bathroom one car garage townhouse on the second floor. Hurricane windows, gated community, with community pool, club house and gym room. 15-20 minutes to Siesta Key and about 10-15 to Nokomis Beach, Legacy Trail at the end of the street, Dogpark across the street. Walking distance to 4-5 Restaurants. Walmart across the street 3 Publixes and a Target within 3 miles. HOA application and acceptance is required. Please reach out for any questions. 6 month minimum lease is $2600 a month furnished. 12 month minimum lease is $2500 furnished. Maybe would be interested renting it unfurnished or for shorter terms. Not leasing for 2027 season yet.
This listing is courtesy of: M&M PROPERTY MANAGEMENT GROUP