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PRIVATEER SOUTH - A4691368 - 1000 LONGBOAT CLUB RD #406, LONGBOAT KEY, FL 34228 Just Added on 04/24/2026 5:58PM
$4,000 | Condo | 1 beds | 1.5 baths | 1 car
Seasonal Rental – Beachfront Living at The Privateer on Longboat Key / Escape the cold and enjoy a relaxing winter retreat in this beautifully maintained 1-bedroom, 1-bathroom condo located on the 4th floor of the highly sought-after The Privateer on Longboat Key. This inviting residence offers a bright and open layout, a well-equipped kitchen, and a comfortable, spacious bedroom designed for easy seasonal living, along with a private balcony overlooking the Gulf—perfect for enjoying morning coffee or taking in breathtaking sunset views. Whether you're starting your day or winding down after time on the beach, you'll appreciate the peaceful atmosphere and coastal charm throughout. The Privateer provides true resort-style living with private beach access, a heated beachfront pool and spa, tennis courts, a fitness center, clubhouse, grilling areas, covered parking, 24-hour gated security, and the added convenience of on-site guest suites available for visiting friends and family, creating the perfect setting for a stress-free and enjoyable stay. Ideally located just minutes from St. Armands Circle, you’ll have convenient access to some of the area’s best restaurants, boutique shopping, and entertainment, along with nearby local cafes and waterfront dining options that make Longboat Key such a desirable seasonal destination. This property is available beginning in December, with a high season rate of $4,000 per month and an off-season rate of $2,200 per month. The community is governed by a homeowners association, and all tenants must comply with HOA rules and regulations, including any application and approval requirements prior to occupancy.
Listing is courtesy of: RENT SARASOTA
BEACH HARBOR CLUB - A4691384 - 3802 GULF OF MEXICO DR #A204, LONGBOAT KEY, FL 34228 Just Added on 04/24/2026 5:40PM
$2,500 | Condo | 1 beds | 1.5 baths | 1 car
AVAILABLE FOR SEASONAL OR ANNUAL RENTAL. 3 MONTH MINIMUM. Beach Harbor Club – Turnkey Furnished Gulf-View Condo. Welcome to your seasonal coastal retreat at the highly desirable Beach Harbor Club on Longboat Key. This beautifully appointed 1-bedroom, 1.5-bath furnished condo offers the perfect blend of comfort, convenience, and island living just steps from the Gulf of Mexico. Inside, you’ll find a bright and inviting floor plan featuring a well-equipped kitchen, spacious living area, and a private bedroom suite designed for relaxation. The unit includes the added convenience of an in-unit washer and dryer, making extended stays effortless. Enjoy your morning coffee or evening unwind with a Gulf view, while being just moments from the community’s private beach access—only a short walk across Gulf of Mexico Drive. Beach Harbor Club offers resort-style amenities including: Large heated community pool Fitness center Clubhouse for social gatherings Marina and bayfront dock access Community grills and outdoor seating areas Covered parking and bike storage Located in the heart of Longboat Key, you are minutes from Publix, CVS, St. Armands Circle, downtown Sarasota, and Anna Maria Island, giving you easy access to dining, shopping, and entertainment while still enjoying a peaceful beachside setting. Seasonal rental (3-month minimum per HOA) Non-smoking unit No pets allowed Experience true Florida island living in this fully furnished, move-in ready Gulf-side getaway—perfect for seasonal residents or extended stays.
Listing is courtesy of: NEXTHOME EXCELLENCE
ST. REGIS LONGBOAT KEY - A4691168 - 1591 GULF OF MEXICO DR #515, LONGBOAT KEY, FL 34228 1 Day on yellowkey
$17,000 | Condo | 1 beds | 2.0 baths | 2 gar
Long Term Unfurnished Rental. Experience elevated coastal living in this exceptional unfurnished annual residence at The St. Regis Longboat Key Resort. Accessed via a private elevator, this sophisticated home opens into a dramatic living space defined by soaring ceilings and walls of glass that frame breathtaking views of Sarasota Bay. The expansive living area flows seamlessly to a generous outdoor terrace—ideal for entertaining or simply enjoying the serene waterfront setting. Inside, the chef-inspired kitchen showcases sleek Poggenpohl cabinetry and a full suite of premium Wolf and Sub-Zero appliances, including a gas cooktop, double ovens, microwave, full-size refrigerator, and beverage center. Designed with timeless elegance, the interiors feature curated earth-tone finishes by Marc-Michaels Interior Design. The luxurious owner’s suite offers direct terrace access—perfect for morning coffee with a view—along with a spa-inspired bath complete with dual vanities, soaking tub, oversized glass-enclosed shower, and a Toto bidet water closet. The thoughtfully modified floor plan includes two full bathrooms and comfortably accommodates guests. Set within the exclusive Residences at The St. Regis, this property offers access to over 17 acres of meticulously maintained grounds and 800 feet of pristine Gulf-front shoreline. Residents enjoy an unmatched lifestyle with access to world-class amenities, including personalized butler and concierge services, a renowned spa, in-residence dining, and private resident-only offerings such as a clubhouse, fitness center, pool, spa, and dedicated beach area. Don't miss this rare opportunity to live where others vacation.
Listing is courtesy of: GULF COAST REALTY & MANAGEMENT
THE SHORE - A4690373 - 5757 GULF OF MEXICO DR #202, LONGBOAT KEY, FL 34228 8 Days on yellowkey
$5,500 | Condo | 2 beds | 2.0 baths
Pristine Gulf Beachfront on Longboat Key Welcome to this beautifully updated 2-bedroom, 2-bathroom luxury beachside retreat located in The Shore on mid-Longboat Key. This inviting second-floor condo offers stunning Gulf views and is just steps from the powdery white sand and crystal-clear waters—an ideal setting for a relaxed island getaway. Highlights -Sweeping Gulf views from living room and master bedroom -Thoughtfully remodeled with an airy, open-concept layout and generous living spaces -Modern kitchen featuring granite countertops and a spacious island, perfect for dining and entertaining -Fully furnished and well-appointed for a turnkey, stress-free stay -Breathtaking Gulf views from the main living area, showcasing unforgettable sunrises and sunsets Configuration - Primary Bedroom: King bed - Walk-in closet - En-suite bathroom with double sinks and walk-in shower - Direct access to the patio for refreshing Gulf breezes - Second Bedroom - Two Queen-size beds Additional Conveniences & Amenities - In-unit washer and dryer - Watch dolphins, manatees, turtles, birds, and passing boats right from your retreat - Beachside heated pool and hot tub - Fitness center and sauna - Large social room with catering kitchen - 1 Covered parking spot, plus guest parking - Bicycle and kayak storage - Beautifully maintained grounds with lush tropical landscaping and mature trees - Weber grill on your private patio - perfect for cooking and dining while taking in breathtaking Gulf views Note: 60-Day Minimum Rental (January through April are not available) Please call or text listing agent for questions or showings 2nd Floor Unit - Elevator and/or stairs available Association Application Required No Pets
Listing is courtesy of: DARAK GROUP INCORPORATED
BEACH HARBOR CLUB - R4911069 - 3806 GULF OF MEXICO DR #C310, LONGBOAT KEY, FL 34228 8 Days on yellowkey
$4,300 | Condo | 2 beds | 2.0 baths | 1 car
Lease/Option - Owner looking to lease 6 Months $4300 a Month of Longboat's Beach Harbor club is situated on 5 Acres along the most beautiful stretch of Longboat Key Shoreline. Sugary sand and flowing seeds oats beside the azure blue Gulf of Mexico. The beach Harbor club offers 133 condo units, deeded beach access with showers, umbrellas and beach chairs. Amenities also include newly constructed boat slips, rooftop decks, outdoor cook areas, heated oversized swimming pool, community area for kayaks, clubhouse, and shuffle board. Longboat Beach Harbor is a friendly community with group events and many fun times to build relationships and enjoy sense of community living. Close to Bayfront Park with Tennis, Publix/CVS shopping. This renovated condo is situated on the 3rd floor not requiring flood insurance. Air conditioned indoor hall-way with security entrance. Newly appointed appliances, bathrooms, HVAC, luxury flooring and trim. Up-scale appointed fixtures and details throughout
Listing is courtesy of: LEN SCAVRON
- A4687628 - 6980 POINSETTA, LONGBOAT KEY, FL 34228 8 Days on yellowkey
$4,650 | Single Family Home | 1 beds | 1.0 baths
Tucked away in a quiet fisherman’s village on Longboat Key, this elegant one-bedroom cottage blends classic island charm with modern luxury. The bright, open living space features soaring vaulted ceilings and a sleek, contemporary kitchen. Premium comforts include high-speed internet, in-unit laundry, a reverse osmosis water filtration system, and UV air purification. Perfect for couples seeking a tranquil seaside getaway, the property offers boat parking and convenient access to a nearby boat launch. Whitney Beach is just a short stroll away, making this an ideal private retreat with easy access to the Gulf of Mexico.
Listing is courtesy of: LPT REALTY, LLC
TRITON COVE - A4689772 - 3020 GULF OF MEXICO DR #2, LONGBOAT KEY, FL 34228 9 Days on yellowkey
$6,500 | Single Family Home | 3 beds | 3.0 baths | 2 gar
Discover your own slice of paradise in this exquisite three-story home located on the beautiful Longboat Key, Florida. This spacious, fully furnished rental is available for a year-long lease, offering the perfect blend of luxury, comfort, and convenience just a short 3-minute walk from the pristine Gulf beaches.The first floor of the home is thoughtfully designed with additional storage rooms, ensuring that you have plenty of space to keep your belongings organized. Whether it’s beach gear, seasonal items, or extra household supplies, this home has you covered. Embrace the Florida lifestyle with your own private pool. This inviting outdoor space is perfect for sunbathing, enjoying morning coffee, or hosting summer barbecues with family and friends. The pool area is surrounded by lush landscaping, creating a tranquil atmosphere for relaxation and leisure.One of the standout features of this property is its proximity to the beach. With just a short 3-minute walk, you can easily enjoy the sun, surf, and sand whenever you want. Spend your days swimming, sunbathing, or taking long walks along the shoreline.
Listing is courtesy of: KW COASTAL LIVING III
BAYPORT BCH & TEN PH F - A4689796 - 842 BAYPORT WAY #842, LONGBOAT KEY, FL 34228 10 Days on yellowkey
$4,800 | Condo | 2 beds | 2.0 baths | 1 car
Available June through December or as an 18-month rental. Nicely furnished and fully equipped for a comfortable stay, this first floor corner residence offers extra privacy and added natural light. A spacious dining and living area opens out to a screened lanai and large outdoor brick patio overlooking landscaped grounds. The primary bedroom has a king bed, large walk-in closet, and an alcove with a desk overlooking the garden. The guest bedroom can be configured as a king or two twins. A large kitchen is fully equipped for easy meal prep. There is under building parking for one car, outside locked storage and plenty of guest parking. Bayport Beach and Tennis Club is a true Gulf to Bay community, with a fishing pier and kayak launch out to Sarasota Bay, and access to 1200 feet of private beach with beach chairs and umbrellas, just 2-3 minutes from your front door. Enjoy a swim in the heated Jr olympic pool, tennis on 4 har-tru courts, a club house, fitness room, and shelled walking paths along tropical landscaped grounds. Groceries, parks and conveniences are within 2 miles, with shopping and terrific dining dotted along the Key. Sarasota's entertainment and cultural attractions are a short drive away. Condo may be rented long term.
Listing is courtesy of: COLDWELL BANKER REALTY