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BAYPORT BCH & TEN PH F - A4694333 - 840 BAYPORT WAY #840, LONGBOAT KEY, FL 34228 7 Days on yellowkey
$4,200 | Condo | 2 beds | 2.0 baths | 1 car
This stunningly appointed ground floor 2-bedroom 2 bath condo with lots of open living space is the ideal place to spend your summer vacation. Relax on screened lanai and enjoy the gentle breezes of this tropical oasis. Situated between Sarasota Bay and the Gulf of Mexico and surrounded by lush landscaping, you will truly find the private patio a great place to spend your afternoons. The beautiful upgrades to the kitchen and baths go hand in hand with the elegant decor of this property. Fully furnished and fully equipped and ready for your arrival, covered parking for one vehicle and guest parking is available as well. The clubhouse has a full kitchen facility and is large enough for meetings, private parties, and social functions, The exercise room is well equipped with machines and free weights. Classes in water Aerobics are held several times a week during the winter at a nominal cost, Available May to December at OFF Season rate of $4,200 per month plus 13% tourist tax. The property is a NO smoking/NO pet unit.
Listing is courtesy of: REALTY SERVICES INC
PRIVATEER NORTH - L4961980 - 1050 LONGBOAT CLUB RD #803, LONGBOAT KEY, FL 34228 8 Days on yellowkey
$6,000 | Condo | 2 beds | 2.0 baths | 1 car
AVAILABLE 9/1/2026 to 12/31/2026. Oceanfront 2 bed/2 bath luxury condo on the 8th floor with beach and golf course views, two private balconies, and resort-style amenities just steps from the sand.The open-concept living and dining area features a custom bar and stylish decor, creating an inviting space to relax or entertain. A dedicated office makes working remotely effortless, while the sleek bar with wine refrigerator is perfect for evening cocktails at home. The fully equipped kitchen with built-in pantry offers everything you need, and the two serene bedrooms with King beds each enjoy convenient access to a full bath.This private, gated resort community offers a true coastal club experience. Host gatherings in the large community room, then move outdoors to the oceanfront pool, jacuzzi, fire pit, and grilling patio. Stay active with a swimming pool, workout room, pickleball, and shuffleboard courts on-site, then stroll directly onto the beach for a swim or sunset walk along the shoreline. 3 MONTH MINIMUM. Rental includes all furniture, appliances, dishes, cookware, and linens. Covered Parking spot #10 included with additional guest parking, seperate storage area for beach/pool items.
Listing is courtesy of: XCELLENCE
ISLANDER CLUB OF LONGBOAT - A4693849 - 2295 GULF OF MEXICO DR #54S, LONGBOAT KEY, FL 34228 11 Days on yellowkey
$6,000 | Condo | 2 beds | 2.0 baths
Now available FOR LEASE at The Islander Club on Longboat Key, this updated 2-bedroom, 2-bath residence offers exceptional value in a true beachfront community. Turnkey and move-in ready, the unit features an open layout with quality finishes, an updated kitchen with stainless steel appliances, wood flooring, refreshed bathrooms, and a spacious 38-foot terrace for outdoor living. The primary suite includes an ensuite bath and walk-in closet, while the guest bedroom offers comfort and privacy for visitors. Residents at THE ISLANDER on LONGBOAT KEY enjoy direct BEACHFRONT access along with resort-style amenities including a private beach, heated pool, fitness center, sauna, tennis, pickleball, and on-site management. Offered at $6,000/month May through December and $10,000/month January through April. AVAILABLE NOW for immediate occupancy. Contact listing agent for showing requests. OPEN FOR 2027 SEASON RESERVATIONS - 3 MONTH MINIMUM
Listing is courtesy of: WAGNER REALTY
GRAND BAY 1 - A4690978 - 3060 GRAND BAY BLVD #172, LONGBOAT KEY, FL 34228 15 Days on yellowkey
$7,850 | Condo | 3 beds | 3.0 baths | 1 gar
LOCATION AT IT'S BEST!!!!! LUXURY RENTAL in Paradise on LONGBOAT KEY at GRAND BAY. This STUNNING 7th floor condominium has both sweeping WATER VIEWS of SARASOTA BAY and of the spectacular SUNSETS ON THE GULF of MEXICO. Open for a three month or longer stay July through November. Like NEW, this beautifully designed and remodeled this three bedroom luxury residence has recently completed a major updating, with all new designer furniture and furnishings, new custom kitchen and bathrooms. Floor to ceiling glass with panoramic views from every room in the house. MOVE-In and enjoy the Luxury lifestyle and amenities that abound at Grand Bay. GRAND BAY is a 24-hour-manned, GATED community where residents can enjoy two heated swimming pools, hot tub spa, fitness center, tennis, private garage, large clubhouse, many on site activities. Residents can enjoy the Bay Isles Beach Club private beach access to the world famous beach on the Gulf of Mexico. Close to St. Armand's Circle, Downtown Sarasota, and Ana Maria Island. OPEN FOR RESERVATION May through December 2026 for a THREE MONTH or longer stay. There is a 30 day tenant application process with the Grand Bay COA. NO PETS/No Smoking. Additional charges 13% sales/resort tax to be paid by tenants. May through November $7,850. Reservation Confirmed for February through March 2027.
THE SHORE - A4692913 - 5757 GULF OF MEXICO DR #305, LONGBOAT KEY, FL 34228 20 Days on yellowkey
$5,500 | Condo | 2 beds | 2.0 baths | 1 car
Available starting July 15, 2026! 60 Day Minimum Lease, not available Jan 1, 2027-March 31, 2027. Fully remodeled and impeccably furnished with Gulf views on Longboat Key, this top-floor 2-bedroom, 2-bath residence offers breathtaking views of the beach and Gulf of Mexico. The clear Caribbean-blue waters and white sand beaches are perfectly complemented by the beautifully redesigned interior and thoughtfully updated floor plan. The gathering room opens to the extended kitchen to create continuity in the main living area, perfect for entertaining. Custom imported cabinetry with frosted glass accents, pantry storage, complementary upper and lower cabinetry, solid surface countertops, and a waterfall-edge peninsula with seating for four elevate the space. Premium KitchenAid appliances include a French door refrigerator, dishwasher, double oven, and cooktop. A skylight fills the home with natural light alongside LED, recessed, and drop lighting throughout. Imported marble flooring, porcelain tile, and neutral Berber carpet complete the interior finishes. Both bathrooms have been beautifully modernized with Corinthian Fossil showers, frameless glass doors, floating vanities, and Quartz countertops. The primary en suite features a walk-in closet and sitting area. Multiple sets of sliding glass doors open to the covered balcony, creating the perfect place to enjoy our million dollar sunsets. Residents can unwind seaside along more than 500 feet of shoreline, stroll the lushly landscaped grounds and paver pathways, or enjoy the private community pool and spa. All lease terms shorter than 6 months are subject to 13% tourism tax.
Listing is courtesy of: TNG PROPERTY MANAGEMENT
HARBOUR LINKS - A4692261 - 2013 HARBOUR LINKS DR #2013, LONGBOAT KEY, FL 34228 25 Days on yellowkey
$6,950 | Condo | 2 beds | 2.5 baths | 1 gar
Luxury Furnished Longboat Key Retreat with Private Beach Club Access & Golf Course Views. Remodeled 2BR Residence with Elevator, Designer Finishes & Resort-Style Living. Step into elevated coastal living at 2013 Harbour Links Drive, a recently remodeled and beautifully curated 2-bedroom, 2-bathroom residence offering 2,369 square feet of beautifully designed living space on Longboat Key. Offered fully furnished and ready for immediate enjoyment, this home is perfectly positioned on a quiet cul-de-sac with extra guest parking, combining privacy, luxury, and convenience—ideal for both long-term living or a seasonal retreat. Inside, you’ll find soaring high ceilings and a bright, open layout highlighted by a stunning floating staircase and the added convenience of a private elevator, providing effortless access to every level of the home. All-new furnishings and thoughtfully selected artwork create a refined yet relaxed island feel throughout. Designed for both comfort and entertaining, the home features four TVs—including one on the screened patio—WiFi included, and a fully equipped kitchen complete with a wine refrigerator, Nespresso and Keurig machines, and everything needed from cookware to linens for a seamless, turnkey experience. The spacious primary suite offers a true spa-like retreat with a large custom bathroom, double vanities, and a separate walk-in shower. An attached garage adds everyday convenience, while the thoughtful layout ensures both comfort and functionality. Outdoor living is where this home truly stands out. Enjoy a large screened deck with sweeping views of Hole 4 and a tranquil water backdrop, creating the perfect setting for morning coffee, outdoor dining, or relaxing evenings. A dedicated BBQ deck just off the kitchen makes entertaining effortless, while just steps away you’ll find a heated pool and large hot tub, offering a true resort-style extension of your living space. One of the most sought-after features of this home is exclusive access to the private Bay Isles Beach Club. This gated, resident-only beachfront retreat offers a rare level of privacy and comfort on Longboat Key. Enjoy pristine Gulf-front beaches, convenient parking, shaded picnic areas, pavilions, and a relaxed, uncrowded atmosphere that feels worlds away from public beach access. Whether you're enjoying a full day at the beach or catching sunset over the Gulf, this private club experience truly sets the property apart. Located behind the 24/7 manned gates of Bay Isles, this home also places you close to everything you need—Publix, dining, EMS services, and miles of scenic walking and biking paths near the golf course and harbor. Just minutes away, you’ll find the vibrant energy of St. Armands Circle, the luxury of the St. Regis, and the laid-back charm of Anna Maria Island. Available as a 12-month rental or seasonal lease with a minimum 3-month stay, this is a rare opportunity to enjoy turnkey island living with true resort-style amenities in one of Longboat Key’s most desirable communities.
Listing is courtesy of: SECURE DOOR PROPERTY MANAGEMENT
ISLANDER CLUB OF LONGBOAT - A4692071 - 2301 GULF OF MEXICO DR #102N, LONGBOAT KEY, FL 34228 26 Days on yellowkey
$16,000 Increased | Condo | 2 beds | 2.0 baths | 1 car
Wake up to breathtaking Gulf of Mexico views from this beautifully remodeled 2-bedroom, 2-bath oceanfront residence at The Islander Club. Spanning approximately 1,233 sq ft, this turnkey condo offers sweeping panoramic views of the Gulf from the spacious living room and both bedrooms. Step inside to find a thoughtfully updated interior featuring modern finishes, a fully equipped kitchen with stainless steel appliances, and a bright, open living and dining area that flows seamlessly onto a private balcony—perfect for morning coffee while watching dolphins play or enjoying spectacular sunsets. The primary bedroom boasts an en-suite bath, while the guest bedroom provides comfort and privacy. Both bedrooms, along with the living room, deliver direct, unobstructed ocean views. This residence comes fully furnished. Additional features include impact-resistant windows and doors, covered parking, and access to the Islander Club’s exceptional amenities: a 24-hour fitness center with Har-Tru tennis courts, an oversized beachfront swimming pool, billiards, a library, and a vibrant community atmosphere just steps from the sugar-sand beach. Located in the heart of Longboat Key on St. Armands Circle and downtown Sarasota, this property offers the perfect blend of coastal luxury and relaxed island living. Whether you're seeking a seasonal rental or a long-term retreat, this oceanfront gem is move-in ready and delivers the best of island living with direct beach access and unforgettable Gulf vistas.
Listing is courtesy of: PREFERRED SHORE LLC