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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 beds | 2.0 baths | 2 gar
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.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY
BISHOPSCOURT TOWNHOME ONE - A4689198 - 76 BISHOPS COURT RD #116, OSPREY, FL 34229 8 Days on yellowkey
$3,995 | Villa | 2 beds | 2.0 baths | 1 car
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.
Listing is courtesy of: CAPITAL REAL ESTATE ENTERPRISE
SOUTHBAY YACHT & RACQUET CLUB - A4688034 - 221 LOOKOUT POINT DR, OSPREY, FL 34229 16 Days on yellowkey
$3,750 | Single Family Home | 3 beds | 2.5 baths | 2 gar
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.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S
BAYSIDE - A4686669 - 3929 WAYPOINT AVE, OSPREY, FL 34229 28 Days on yellowkey
$4,500 | Single Family Home | 3 beds | 3.5 baths | 2 gar
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!
Listing is courtesy of: RE/MAX ALLIANCE GROUP
OAKS - A4686127 - 51 MACEWEN DR #12, OSPREY, FL 34229 33 Days on yellowkey
$2,250 Reduced | Condo | 1 beds | 1.0 baths
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
EMERALD WOODS AT OAKS 03 PH 02 - A4682290 - 124 TURQUOISE LN, OSPREY, FL 34229 63 Days on yellowkey
$5,600 | Single Family Home | 3 beds | 2.0 baths
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.
Listing is courtesy of: RENT SARASOTA